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class="vector-toc-link" href="#Fullerene_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Fullerene reactions</span> </div> </a> <button aria-controls="toc-Fullerene_reactions-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Fullerene reactions subsection</span> </button> <ul id="toc-Fullerene_reactions-sublist" class="vector-toc-list"> <li id="toc-Nucleophilic_additions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Nucleophilic_additions"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Nucleophilic additions</span> </div> </a> <ul id="toc-Nucleophilic_additions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pericyclic_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pericyclic_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Pericyclic reactions</span> </div> </a> <ul id="toc-Pericyclic_reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Hydrogenations" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Hydrogenations"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Hydrogenations</span> </div> </a> <ul id="toc-Hydrogenations-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Halogenation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Halogenation"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.4</span> <span>Halogenation</span> </div> </a> <ul id="toc-Halogenation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Hydroxylations" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Hydroxylations"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.5</span> <span>Hydroxylations</span> </div> </a> <ul id="toc-Hydroxylations-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Electrophilic_additions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Electrophilic_additions"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.6</span> <span>Electrophilic additions</span> </div> </a> <ul id="toc-Electrophilic_additions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Eliminations" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Eliminations"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.7</span> <span>Eliminations</span> </div> </a> <ul id="toc-Eliminations-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Carbene_additions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Carbene_additions"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.8</span> <span>Carbene additions</span> </div> </a> <ul id="toc-Carbene_additions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Radical_additions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Radical_additions"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.9</span> <span>Radical additions</span> </div> </a> <ul id="toc-Radical_additions-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Fullerenes_as_ligands" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Fullerenes_as_ligands"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Fullerenes as ligands</span> </div> </a> <ul id="toc-Fullerenes_as_ligands-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Variants" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Variants"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Variants</span> </div> </a> <button aria-controls="toc-Variants-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Variants subsection</span> </button> <ul id="toc-Variants-sublist" class="vector-toc-list"> <li id="toc-Open-cage_fullerenes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Open-cage_fullerenes"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Open-cage fullerenes</span> </div> </a> <ul id="toc-Open-cage_fullerenes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Heterofullerenes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Heterofullerenes"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Heterofullerenes</span> </div> </a> <ul id="toc-Heterofullerenes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Fullerene_dimers" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Fullerene_dimers"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Fullerene dimers</span> </div> </a> <ul id="toc-Fullerene_dimers-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Synthesis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Synthesis</span> </div> </a> <button aria-controls="toc-Synthesis-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Synthesis subsection</span> </button> <ul id="toc-Synthesis-sublist" class="vector-toc-list"> <li id="toc-Multistep_fullerene_synthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Multistep_fullerene_synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Multistep fullerene synthesis</span> </div> </a> <ul id="toc-Multistep_fullerene_synthesis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Purification" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Purification"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Purification</span> </div> </a> <button aria-controls="toc-Purification-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Purification subsection</span> </button> <ul id="toc-Purification-sublist" class="vector-toc-list"> <li id="toc-Experimental_purification_strategies" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Experimental_purification_strategies"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Experimental purification strategies</span> </div> </a> <ul id="toc-Experimental_purification_strategies-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> 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class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Qu%C3%ADmica_de_fullerenos" title="Química de fullerenos – Spanish" lang="es" hreflang="es" data-title="Química de fullerenos" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%B4%DB%8C%D9%85%DB%8C_%D9%81%D9%88%D9%84%D8%B1%D9%86" title="شیمی فولرن – Persian" lang="fa" hreflang="fa" data-title="شیمی فولرن" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Chimie_des_fuller%C3%A8nes" title="Chimie des fullerènes – French" lang="fr" hreflang="fr" data-title="Chimie des fullerènes" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Kimia_fulerena" title="Kimia fulerena – Indonesian" lang="id" hreflang="id" data-title="Kimia fulerena" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A4%D1%83%D0%BB%D0%B5%D1%80%D0%B5%D0%BD%D1%81%D0%BA%D0%B0_%D1%85%D0%B5%D0%BC%D0%B8%D1%98%D0%B0" title="Фулеренска хемија – Macedonian" lang="mk" hreflang="mk" data-title="Фулеренска хемија" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Fulleren_kimyosi" title="Fulleren kimyosi – Uzbek" lang="uz" hreflang="uz" data-title="Fulleren kimyosi" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Qu%C3%ADmica_dos_fulerenos" title="Química dos fulerenos – Portuguese" lang="pt" hreflang="pt" data-title="Química dos fulerenos" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Hemija_fulerena" title="Hemija fulerena – Serbian" lang="sr" hreflang="sr" data-title="Hemija fulerena" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a 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class="mw-halign-right" typeof="mw:File"><a href="/wiki/File:Buckminsterfullerene-2D-skeletal.png" class="mw-file-description" title="Fullerene C60"><img alt="Fullerene C60" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Buckminsterfullerene-2D-skeletal.png/200px-Buckminsterfullerene-2D-skeletal.png" decoding="async" width="200" height="201" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Buckminsterfullerene-2D-skeletal.png/300px-Buckminsterfullerene-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Buckminsterfullerene-2D-skeletal.png/400px-Buckminsterfullerene-2D-skeletal.png 2x" data-file-width="1078" data-file-height="1081" /></a><figcaption>Fullerene C<sub>60</sub></figcaption></figure> <p><b>Fullerene chemistry</b> is a field of <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a> devoted to the chemical properties of <a href="/wiki/Fullerene" title="Fullerene">fullerenes</a>.<sup id="cite_ref-full_1-0" class="reference"><a href="#cite_note-full-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Research in this field is driven by the need to functionalize fullerenes and tune their properties. For example, fullerene is notoriously insoluble and adding a suitable group can enhance solubility.<sup id="cite_ref-full_1-1" class="reference"><a href="#cite_note-full-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> By adding a polymerizable group, a fullerene polymer can be obtained. Functionalized fullerenes are divided into two classes: <a href="/wiki/Exohedral_fullerenes" class="mw-redirect" title="Exohedral fullerenes">exohedral fullerenes</a> with substituents outside the cage and <a href="/wiki/Endohedral_fullerenes" class="mw-redirect" title="Endohedral fullerenes">endohedral fullerenes</a> with trapped molecules inside the cage. </p><p>This article covers the chemistry of these so-called "buckyballs," while the chemistry of <a href="/wiki/Carbon_nanotubes" class="mw-redirect" title="Carbon nanotubes">carbon nanotubes</a> is covered in <a href="/wiki/Carbon_nanotube_chemistry" title="Carbon nanotube chemistry">carbon nanotube chemistry</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Chemical_properties_of_fullerenes">Chemical properties of fullerenes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fullerene_chemistry&action=edit&section=1" title="Edit section: Chemical properties of fullerenes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Endohedral_fullerenes" class="mw-redirect" title="Endohedral fullerenes">Endohedral fullerenes</a></div> <p>Fullerene or C<sub>60</sub> is <a href="/wiki/Truncated_icosahedron" title="Truncated icosahedron">soccer-ball-shaped</a> or <i>I<sub>h</sub></i> with 12 pentagons and 20 hexagons. According to <a href="/wiki/Euler_characteristic" title="Euler characteristic">Euler's theorem</a> these 12 pentagons are required for closure of the carbon network consisting of <i>n</i> hexagons and C<sub>60</sub> is the first stable fullerene because it is the smallest possible to obey this rule. In this structure none of the pentagons make contact with each other. Both C<sub>60</sub> and its relative C<sub>70</sub> obey this so-called isolated pentagon rule (IPR). The next homologue C<sub>84</sub> has 24 IPR isomers of which several are isolated and another 51,568 non-IPR isomers. Non-IPR fullerenes have thus far only been isolated as endohedral fullerenes such as Tb<sub>3</sub>N@C<sub>84</sub> with two fused pentagons at the apex of an egg-shaped cage.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> or as fullerenes with exohedral stabilization such as C<sub>50</sub>Cl<sub>10</sub> <sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> and reportedly C<sub>60</sub>H<sub>8</sub>.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Fullerenes with fewer than 60 carbons do not obey isolated pentagon rule (IPR). </p><p>Because of the molecule's spherical shape the carbon atoms are highly <a href="/wiki/Pyramidalization" class="mw-redirect" title="Pyramidalization">pyramidalized</a>, which has far-reaching consequences for reactivity. It is estimated that <a href="/wiki/Strain_energy" title="Strain energy">strain energy</a> constitutes 80% of the <a href="/wiki/Heat_of_formation" class="mw-redirect" title="Heat of formation">heat of formation</a>. The conjugated carbon atoms respond to deviation from planarity by <a href="/wiki/Orbital_hybridization" class="mw-redirect" title="Orbital hybridization">orbital rehybridization</a> of the sp² <a href="/wiki/Molecular_orbital" title="Molecular orbital">orbitals</a> and <a href="/wiki/Pi_orbital" class="mw-redirect" title="Pi orbital">π orbitals</a> to a sp<sup>2.27</sup> orbital with a gain in p-character. The p lobes extend further outside the surface than they do into the interior of the sphere and this is one of the reasons a fullerene is <a href="/wiki/Electronegative" class="mw-redirect" title="Electronegative">electronegative</a>. The other reason is that the empty low-lying π<sup>*</sup> orbitals also have a high s character. </p><p>The double bonds in fullerene are not all the same. Two groups can be identified: 30 so-called [6,6] double bonds connect two hexagons and 60 [5,6] bonds connect a hexagon and a pentagon. Of the two the [6,6] bonds are shorter with more double-bond character and therefore a hexagon is often represented as a <a href="/wiki/Cyclohexatriene" title="Cyclohexatriene">cyclohexatriene</a> and a pentagon as a pentalene or [5]<a href="/wiki/Radialene" title="Radialene">radialene</a>. In other words, although the carbon atoms in fullerene are all conjugated the superstructure is not a <a href="/wiki/Superaromaticity" class="mw-redirect" title="Superaromaticity">super</a> <a href="/wiki/Aromatic_compound" title="Aromatic compound">aromatic compound</a>. The <a href="/wiki/X-ray_diffraction" title="X-ray diffraction">X-ray diffraction</a> <a href="/wiki/Bond_length" title="Bond length">bond length</a> values are 139.1 <a href="/wiki/Picometer" class="mw-redirect" title="Picometer">pm</a> for the [6,6] bond and 145.5 pm for the [5,6] bond. </p><p>C<sub>60</sub> fullerene has 60 π electrons but a <a href="/wiki/Closed_shell_configuration" class="mw-redirect" title="Closed shell configuration">closed shell configuration</a> requires 72 electrons. The fullerene is able to acquire the missing electrons by reaction with <a href="/wiki/Potassium" title="Potassium">potassium</a> to form first the <span class="chemf nowrap">K<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">6</sub></span></span>C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">6−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">60</sub></span></span></span> salt and then the <span class="chemf nowrap">K<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span>C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">12−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">60</sub></span></span></span> In this compound the bond length alternation observed in the parent molecule has vanished. </p> <div class="mw-heading mw-heading2"><h2 id="Fullerene_reactions">Fullerene reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fullerene_chemistry&action=edit&section=2" title="Edit section: Fullerene reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Bingel_reaction" title="Bingel reaction">Bingel reaction</a> and <a href="/wiki/Prato_reaction" title="Prato reaction">Prato reaction</a></div> <p>Fullerenes tend to react as electrophiles. An additional driving force is relief of <a href="/wiki/Strain_(chemistry)" title="Strain (chemistry)">strain</a> when double bonds become saturated. Key in this type of reaction is the level of functionalization i.e. monoaddition or multiple additions and in case of multiple additions their topological relationships (new substituents huddled together or evenly spaced). In conformity with <a href="/wiki/IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a> rules, the terms <a href="/w/index.php?title=Methanofullerene&action=edit&redlink=1" class="new" title="Methanofullerene (page does not exist)">methanofullerene</a> are used to indicate the ring-closed (<a href="/wiki/Cyclopropane" title="Cyclopropane">cyclopropane</a>) <a href="/wiki/Fullerene" title="Fullerene">fullerene</a> derivatives, and fulleroid to ring-open (<a href="/w/index.php?title=Methanoannulene&action=edit&redlink=1" class="new" title="Methanoannulene (page does not exist)">methanoannulene</a>) structures.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Nucleophilic_additions">Nucleophilic additions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fullerene_chemistry&action=edit&section=3" title="Edit section: Nucleophilic additions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Fullerenes react as <a href="/wiki/Electrophile" title="Electrophile">electrophiles</a> with a host of nucleophiles in <a href="/wiki/Nucleophilic_addition" title="Nucleophilic addition">nucleophilic additions</a>. The intermediary formed <a href="/wiki/Carbanion" title="Carbanion">carbanion</a> is captured by another electrophile. Examples of nucleophiles are <a href="/wiki/Grignard_reagent" title="Grignard reagent">Grignard reagents</a> and <a href="/wiki/Organolithium_reagent" title="Organolithium reagent">organolithium reagents</a>. For example, the reaction of C<sub>60</sub> with <a href="/wiki/Methylmagnesium_chloride" title="Methylmagnesium chloride">methylmagnesium chloride</a> stops quantitatively at the penta-adduct with the methyl groups centered around a cyclopentadienyl anion which is subsequently protonated.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Another nucleophilic reaction is the <a href="/wiki/Bingel_reaction" title="Bingel reaction">Bingel reaction</a>. Fullerene reacts with <a href="/wiki/Chlorobenzene" title="Chlorobenzene">chlorobenzene</a> and <a href="/wiki/Aluminium_chloride" title="Aluminium chloride">aluminium chloride</a> in a <a href="/wiki/Friedel-Crafts_alkylation" class="mw-redirect" title="Friedel-Crafts alkylation">Friedel-Crafts alkylation</a> type reaction. In this hydroarylation the reaction product is the 1,2-addition adduct (Ar-CC-H).<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Pericyclic_reactions">Pericyclic reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fullerene_chemistry&action=edit&section=4" title="Edit section: Pericyclic reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The [6,6] bonds of fullerenes react as dienes or dienophiles in <a href="/wiki/Cycloaddition" title="Cycloaddition">cycloadditions</a> for instance <a href="/wiki/Diels-Alder_reaction" class="mw-redirect" title="Diels-Alder reaction">Diels-Alder reactions</a>. 4-membered rings can be obtained by [2+2]cycloadditions for instance with <a href="/wiki/Benzyne" class="mw-redirect" title="Benzyne">benzyne</a>.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> An example of a <a href="/wiki/1,3-dipolar_cycloaddition" class="mw-redirect" title="1,3-dipolar cycloaddition">1,3-dipolar cycloaddition</a> to a 5-membered ring is the <a href="/wiki/Prato_reaction" title="Prato reaction">Prato reaction</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Hydrogenations">Hydrogenations</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fullerene_chemistry&action=edit&section=5" title="Edit section: Hydrogenations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Fullerenes are easily hydrogenated by several methods. The smallest perhydrogenated fullerene known is dodecahedrane C<sub>20</sub>H<sub>20</sub>, formally derived from the smallest possible but unknown fullerene, C<sub>20</sub>, which comprises just 12 pentagonal faces. </p><p>Examples of hydrofullerenes are C<sub>60</sub>H<sub>18</sub> and C<sub>60</sub>H<sub>36</sub>. However, completely hydrogenated C<sub>60</sub>H<sub>60</sub> is only hypothetical because of large strain. Highly hydrogenated fullerenes are not stable, as prolonged hydrogenation of fullerenes by direct reaction with hydrogen gas at high temperature conditions results in cage fragmentation. At the final reaction stage this causes collapse of cage structure with formation of polycyclic aromatic hydrocarbons.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p>C<sub>60</sub> reacts with Li[BHEt<sub>3</sub>] to the weak base [HC<sub>60</sub>]<sup>−</sup>, which is isolated as Li[HC<sub>60</sub>][H<sub>2</sub>O]<sub>6-9</sub>.<sup id="cite_ref-King_14-0" class="reference"><a href="#cite_note-King-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Halogenation">Halogenation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fullerene_chemistry&action=edit&section=6" title="Edit section: Halogenation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Fullerenes can react with halogens. The preferred pattern for addition C<sub>60</sub> is calculated to be 1,9- for small groups and 1,7- for bulky groups. C<sub>60</sub>F<sub>60</sub> is a possible structure. C<sub>60</sub> reacts with Cl<sub>2</sub> gas at 250 °C to a material with average composition C<sub>60</sub>Cl<sub>24</sub>, although only C<sub>60</sub> can be detected by mass spectrometry.<sup id="cite_ref-King_14-1" class="reference"><a href="#cite_note-King-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> With liquid Br<sub>2</sub> C<sub>60</sub> yields C<sub>60</sub>Br<sub>24</sub>, in which all 24 <a href="/wiki/Bromine" title="Bromine">bromine</a> atoms are equivalent. The only characterized iodine-containing compounds are intermediates: [C<sub>60</sub>][CH<sub>2</sub>I<sub>2</sub>][C<sub>6</sub>H<sub>6</sub>] and [C<sub>60</sub>][I<sub>2</sub>]<sub>2</sub>.<sup id="cite_ref-King_14-2" class="reference"><a href="#cite_note-King-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Hydroxylations">Hydroxylations</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fullerene_chemistry&action=edit&section=7" title="Edit section: Hydroxylations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Fullerenes can be hydroxylated to <b><a href="/w/index.php?title=Fullerenol&action=edit&redlink=1" class="new" title="Fullerenol (page does not exist)">fullerenols</a></b> or <b><a href="/w/index.php?title=Fullerol&action=edit&redlink=1" class="new" title="Fullerol (page does not exist)">fullerols</a></b>. Water solubility depends on the total number of hydroxyl groups that can be attached. One method is fullerene reaction in diluted <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a> and <a href="/wiki/Potassium_nitrate" title="Potassium nitrate">potassium nitrate</a> to C<sub>60</sub>(OH)<sub>15</sub>.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Another method is reaction in diluted <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">sodium hydroxide</a> catalysed by <a href="/wiki/TBAH" class="mw-redirect" title="TBAH">TBAH</a> adding 24 to 26 hydroxyl groups.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Hydroxylation has also been reported using solvent-free NaOH / <a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">hydrogen peroxide</a>.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> C<sub>60</sub>(OH)<sub>8</sub> was prepared using a multistep procedure starting from a mixed peroxide fullerene.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> The maximum number of <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> groups that can be attached (hydrogen peroxide method) stands at 36–40.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Electrophilic_additions">Electrophilic additions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fullerene_chemistry&action=edit&section=8" title="Edit section: Electrophilic additions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Fullerenes react in <a href="/wiki/Electrophilic_addition" title="Electrophilic addition">electrophilic additions</a> as well. The reaction with <a href="/wiki/Bromine" title="Bromine">bromine</a> can add up to 24 bromine atoms to the sphere. The record holder for fluorine addition is C<sub>60</sub>F<sub>48</sub>. According to <a href="/wiki/In_silico" title="In silico">in silico</a> predictions the as yet elusive C<sub>60</sub>F<sub>60</sub> may have some of the fluorine atoms in endo positions (pointing inwards) and may resemble a tube more than it does a sphere.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Eliminations">Eliminations</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fullerene_chemistry&action=edit&section=9" title="Edit section: Eliminations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Protocols have been investigated for removing substituents via eliminations after they have served their purpose. Examples are the <a href="/wiki/Retro-Bingel_reaction" class="mw-redirect" title="Retro-Bingel reaction">retro-Bingel reaction</a> and the <a href="/wiki/Retro-Prato_reaction" class="mw-redirect" title="Retro-Prato reaction">retro-Prato reaction</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Carbene_additions">Carbene additions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fullerene_chemistry&action=edit&section=10" title="Edit section: Carbene additions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Fullerenes react with <a href="/wiki/Carbene" title="Carbene">carbenes</a> to methanofullerenes.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> The reaction of fullerene with <a href="/wiki/Dichlorocarbene" title="Dichlorocarbene">dichlorocarbene</a> (created by <a href="/wiki/Sodium_trichloroacetate" title="Sodium trichloroacetate">sodium trichloroacetate</a> pyrolysis) was first reported in 1993.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> A single addition takes place along a [6,6] bond. </p> <div class="mw-heading mw-heading3"><h3 id="Radical_additions">Radical additions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fullerene_chemistry&action=edit&section=11" title="Edit section: Radical additions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Fullerenes can be considered <a href="/wiki/Radical_scavenger" class="mw-redirect" title="Radical scavenger">radical scavengers</a>.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> With a simple hydrocarbon radical such as the <a href="/wiki/T-butyl" class="mw-redirect" title="T-butyl">t-butyl</a> radical obtained by <a href="/wiki/Thermolysis" class="mw-redirect" title="Thermolysis">thermolysis</a> or <a href="/wiki/Photolysis" class="mw-redirect" title="Photolysis">photolysis</a> from a suitable precursor the tBuC60 radical is formed that can be studied. The unpaired electron does not delocalize over the entire sphere but takes up positions in the vicinity of the tBu substituent. </p> <div class="mw-heading mw-heading2"><h2 id="Fullerenes_as_ligands">Fullerenes as ligands</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fullerene_chemistry&action=edit&section=12" title="Edit section: Fullerenes as ligands"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Fullerene_ligands" class="mw-redirect" title="Fullerene ligands">Fullerene ligands</a></div> <p>Fullerene is a <a href="/wiki/Ligand" title="Ligand">ligand</a> in <a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">organometallic chemistry</a>. The organometallic chemistry of C<sub>60</sub> is dictated by its spherical geometry and localized polyalkene π-electronic structure. All reported derivatives are <i>η</i><sup>2</sup> complexe in which the metal coordinates at a six–six ring fusion with formal double bond. No analogous <i>η</i><sup>4</sup>-diene or <i>η</i><sup>6</sup>-triene complexes are prepared.<sup id="cite_ref-King_14-3" class="reference"><a href="#cite_note-King-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>C<sub>60</sub> and C<sub>70</sub> form complexes with a variety of molecules. In the solid state lattice structures are stabilized by the intermolecular interactions.<sup id="cite_ref-King_14-4" class="reference"><a href="#cite_note-King-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Charge transfer complexes are formed with weak electron donors. The [6,6] double bond is electron-deficient and usually forms metallic bonds with η = 2 <a href="/wiki/Hapticity" title="Hapticity">hapticity</a>. Bonding modes such as η = 5 or η = 6 can be induced by modification of the <a href="/wiki/Coordination_sphere" title="Coordination sphere">coordination sphere</a>. </p> <ul><li>[C<sub>60</sub>][ferrocene]<sub>2</sub>, in which the C<sub>60</sub> molecules are arranged in close-packed layers</li> <li>[C<sub>60</sub>][1,4-dihydroquinone]<sub>3</sub> has C<sub>60</sub> molecules trapped in a hydrogen-bonded of 1,4-dihydroquinone molecules</li> <li>The solvated C<sub>60</sub> compounds: [C<sub>60</sub>][C<sub>6</sub>H<sub>6</sub>]<sub>4</sub> and [C<sub>60</sub>][CH<sub>2</sub>I<sub>2</sub>][C<sub>6</sub>H<sub>6</sub>], and the intercalate [C<sub>60</sub>][I<sub>2</sub>]<sub>2</sub>, are structurally characterized.<sup id="cite_ref-King_14-5" class="reference"><a href="#cite_note-King-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup></li> <li>[C<sub>70</sub>][S<sub>8</sub>]<sub>6</sub></li> <li>[C<sub>60</sub>][γ-cyclodextrin]<sub>2</sub></li> <li>C<sub>60</sub> fullerene reacts with <a href="/wiki/Tungsten_hexacarbonyl" title="Tungsten hexacarbonyl">tungsten hexacarbonyl</a> W(CO)<sub>6</sub> to the (η²-C<sub>60</sub>)W(CO)<sub>5</sub> complex in a <a href="/wiki/Hexane" title="Hexane">hexane</a> solution in direct sunlight.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading2"><h2 id="Variants">Variants</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fullerene_chemistry&action=edit&section=13" title="Edit section: Variants"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Open-cage_fullerenes">Open-cage fullerenes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fullerene_chemistry&action=edit&section=14" title="Edit section: Open-cage fullerenes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A part of fullerene research is devoted to so-called <b>open-cage fullerenes</b> <sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> whereby one or more bonds are removed chemically exposing an orifice.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> In this way it is possible to insert into it small molecules such as hydrogen, helium or lithium. The first such open-cage fullerene was reported in 1995.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> In <a href="/wiki/Endohedral_hydrogen_fullerene" title="Endohedral hydrogen fullerene">endohedral hydrogen fullerenes</a> the opening, hydrogen insertion and closing back up has already been demonstrated. </p> <div class="mw-heading mw-heading3"><h3 id="Heterofullerenes">Heterofullerenes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fullerene_chemistry&action=edit&section=15" title="Edit section: Heterofullerenes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Heterofullerene" title="Heterofullerene">heterofullerene</a></div> <p>In <b>heterofullerenes</b> at least one carbon atom is replaced by another element.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> Based on <a href="/wiki/Spectroscopy" title="Spectroscopy">spectroscopy</a>, substitutions have been reported with <a href="/wiki/Boron" title="Boron">boron</a> (<b><a href="/wiki/Borafullerene" title="Borafullerene">borafullerenes</a></b>),<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a> (<b><a href="/wiki/Azafullerene" title="Azafullerene">azafullerenes</a></b>),<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Oxygen" title="Oxygen">oxygen</a>,<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Arsenic" title="Arsenic">arsenic</a>, <a href="/wiki/Germanium" title="Germanium">germanium</a>,<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Phosphorus" title="Phosphorus">phosphorus</a>,<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Silicon" title="Silicon">silicon</a>,<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Billas_40-0" class="reference"><a href="#cite_note-Billas-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Iron" title="Iron">iron</a>, <a href="/wiki/Copper" title="Copper">copper</a>, <a href="/wiki/Nickel" title="Nickel">nickel</a>, <a href="/wiki/Rhodium" title="Rhodium">rhodium</a><sup id="cite_ref-Billas_40-1" class="reference"><a href="#cite_note-Billas-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Iridium" title="Iridium">iridium</a>.<sup id="cite_ref-Billas_40-2" class="reference"><a href="#cite_note-Billas-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> Reports on isolated heterofullerenes are limited to those based on nitrogen <sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> and oxygen.<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p><p>The fullerene oxides C<sub>60</sub>O and C<sub>70</sub>O are observed in minor in fullerene-containing soot. Only C<sub>60</sub>O is isolated as a pure compound in macroscopic amounts.<sup id="cite_ref-King_14-6" class="reference"><a href="#cite_note-King-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Fullerene_dimers">Fullerene dimers</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fullerene_chemistry&action=edit&section=16" title="Edit section: Fullerene dimers"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The C<sub>60</sub> fullerene dimerizes in a formal [2+2] <a href="/wiki/Cycloaddition" title="Cycloaddition">cycloaddition</a> to a C<sub>120</sub> bucky dumbbell in the solid state by <a href="/wiki/Mechanochemistry" title="Mechanochemistry">mechanochemistry</a> (high-speed vibration milling) with <a href="/wiki/Potassium_cyanide" title="Potassium cyanide">potassium cyanide</a> as a catalyst.<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> The trimer has also been reported using <a href="/wiki/4-aminopyridine" class="mw-redirect" title="4-aminopyridine">4-aminopyridine</a> as catalyst (4% yield) <sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> and observed with <a href="/wiki/Scanning_tunneling_microscopy" class="mw-redirect" title="Scanning tunneling microscopy">scanning tunneling microscopy</a> as a <a href="/wiki/Monolayer" title="Monolayer">monolayer</a>.<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fullerene_chemistry&action=edit&section=17" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Buckminsterfullerene#Synthesis" title="Buckminsterfullerene">Buckminsterfullerene § Synthesis</a></div> <div class="mw-heading mw-heading3"><h3 id="Multistep_fullerene_synthesis">Multistep fullerene synthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fullerene_chemistry&action=edit&section=18" title="Edit section: Multistep fullerene synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Although the procedure for the synthesis of the C<sub>60</sub> fullerene is well established (generation of a large current between two nearby graphite electrodes in an inert atmosphere) a 2002 study described an <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</a> of the compound starting from simple organic compounds.<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:MultistepFullereneSynthesisScott2002.png" class="mw-file-description" title="Multistep fullerene synthesis"><img alt="Multistep fullerene synthesis" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/MultistepFullereneSynthesisScott2002.png/400px-MultistepFullereneSynthesisScott2002.png" decoding="async" width="400" height="293" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/MultistepFullereneSynthesisScott2002.png/600px-MultistepFullereneSynthesisScott2002.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9b/MultistepFullereneSynthesisScott2002.png/800px-MultistepFullereneSynthesisScott2002.png 2x" data-file-width="1030" data-file-height="754" /></a></span></dd></dl> <p>In the final step a large <a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">polycyclic aromatic hydrocarbon</a> consisting of 13 hexagons and three pentagons was submitted to <a href="/wiki/Flash_vacuum_pyrolysis" title="Flash vacuum pyrolysis">flash vacuum pyrolysis</a> at 1100 °C and 0.01 <a href="/wiki/Torr" title="Torr">Torr</a>. The three <a href="/wiki/Organochlorine" class="mw-redirect" title="Organochlorine">carbon chlorine bonds</a> served as <a href="/wiki/Free_radical" class="mw-redirect" title="Free radical">free radical</a> incubators and the ball was stitched up in a no-doubt complex series of <a href="/wiki/Radical_reaction" class="mw-redirect" title="Radical reaction">radical reactions</a>. The <a href="/wiki/Chemical_yield" class="mw-redirect" title="Chemical yield">chemical yield</a> was low: 0.1 to 1%. A small percentage of fullerenes is formed in any process which involves burning of hydrocarbons, e.g. in candle burning. The yield through a combustion method is often above 1%. The method proposed above does not provide any advantage for synthesis of fullerenes compared to the usual combustion method, and therefore, the organic synthesis of fullerenes remains a challenge for chemistry. </p><p>Continuous high-resolution transmission electron microscopic video imaging of the electron-beam-induced bottom-up synthesis of fullerene C<sub>60</sub> through cyclodehydrogenation of C<sub>60</sub>H<sub>30</sub> was reported in 2021.<sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> </p><p>A similar exercise aimed at construction of a C78 cage in 2008 (but leaving out the precursor's halogens) did not result in a sufficient yield but at least the introduction of <a href="/wiki/Stone_Wales_defect" class="mw-redirect" title="Stone Wales defect">Stone Wales defects</a> could be ruled out.<sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> C60 synthesis through a fluorinated fullerene precursor was reported in 2013 <sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Purification">Purification</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fullerene_chemistry&action=edit&section=19" title="Edit section: Purification"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><b>Fullerene purification</b> is the process of obtaining a <a href="/wiki/Fullerene" title="Fullerene">fullerene</a> compound free of contamination. In fullerene production mixtures of C<sub>60</sub>, C<sub>70</sub> and higher <a href="/wiki/Homologization" class="mw-redirect" title="Homologization">homologues</a> are always formed. Fullerene purification is key to <a href="/wiki/Fullerene" title="Fullerene">fullerene</a> science and determines fullerene prices and the success of practical applications of fullerenes. The first available purification method for C<sub>60</sub> fullerene was by <a href="/wiki/High-performance_liquid_chromatography" title="High-performance liquid chromatography">HPLC</a> from which small amounts could be generated at large expense. </p><p>A practical laboratory-scale method for purification of soot enriched in C<sub>60</sub> and C<sub>70</sub> starts with <a href="/wiki/Solvent_extraction" class="mw-redirect" title="Solvent extraction">extraction</a> in <a href="/wiki/Toluene" title="Toluene">toluene</a> followed by <a href="/wiki/Filtration" title="Filtration">filtration</a> with a paper filter. The solvent is evaporated and the residue (the toluene-soluble soot fraction) redissolved in toluene and subjected to <a href="/wiki/Column_chromatography" title="Column chromatography">column chromatography</a>. C<sub>60</sub> elutes first with a purple color and C<sub>70</sub> is next displaying a reddish-brown color.<sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </p><p>In nanotube processing the established purification method for removing amorphous carbon and metals is by competitive oxidation (often a <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a> / <a href="/wiki/Nitric_acid" title="Nitric acid">nitric acid</a> mixture). It is assumed that this oxidation creates oxygen containing groups (<a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a>, <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a>, <a href="/wiki/Carboxyl" class="mw-redirect" title="Carboxyl">carboxyl</a>) on the nanotube surface which electrostatically stabilize them in water and which can later be utilized in chemical functionalization. One report <sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> reveals that the oxygen containing groups in actuality combine with carbon contaminations absorbed to the nanotube wall that can be removed by a simple base wash. Cleaned nanotubes are reported to have reduced D/G ratio indicative of less functionalization, and the absence of oxygen is also apparent from <a href="/wiki/IR_spectroscopy" class="mw-redirect" title="IR spectroscopy">IR spectroscopy</a> and <a href="/wiki/X-ray_photoelectron_spectroscopy" title="X-ray photoelectron spectroscopy">X-ray photoelectron spectroscopy</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Experimental_purification_strategies">Experimental purification strategies</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fullerene_chemistry&action=edit&section=20" title="Edit section: Experimental purification strategies"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A recent kilogram-scale fullerene purification strategy was demonstrated by Nagata <i>et al.</i><sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> In this method C<sub>60</sub> was separated from a mixture of C<sub>60</sub>, C<sub>70</sub> and higher fullerene compounds by first adding the <a href="/wiki/Amidine" title="Amidine">amidine</a> compound <a href="/wiki/DBU_(chemistry)" class="mw-redirect" title="DBU (chemistry)">DBU</a> to a solution of the mixture in <a href="/wiki/1,2,3-trimethylbenzene" class="mw-redirect" title="1,2,3-trimethylbenzene">1,2,3-trimethylbenzene</a>. DBU as it turns out only reacts to C<sub>70</sub> fullerenes and higher which reaction products separate out and can be removed by filtration. C<sub>60</sub> fullerenes do not have any affinity for DBU and are subsequently isolated. Other diamine compounds like <a href="/wiki/DABCO" title="DABCO">DABCO</a> do not share this selectivity. </p><p>C<sub>60</sub> but not C<sub>70</sub> forms a 1:2 <a href="/wiki/Inclusion_compound" class="mw-redirect" title="Inclusion compound">inclusion compound</a> with <a href="/wiki/Cyclodextrin" title="Cyclodextrin">cyclodextrin</a> (CD). A separation method for both fullerenes based on this principle is made possible by anchoring cyclodextrin to <a href="/wiki/Colloidal_gold" title="Colloidal gold">colloidal gold</a> particles through a <a href="/wiki/Sulfur" title="Sulfur">sulfur</a>-sulfur bridge.<sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> The Au/CD compound is very stable and soluble in water and selectively extracts C<sub>60</sub> from the insoluble mixture after <a href="/wiki/Reflux" title="Reflux">refluxing</a> for several days. The C<sub>70</sub> fullerene component is then removed by simple <a href="/wiki/Filtration" title="Filtration">filtration</a>. C<sub>60</sub> is driven out from the Au/CD compound by adding <a href="/wiki/Adamantane" title="Adamantane">adamantol</a> which has a higher affinity for the cyclodextrin cavity. Au/CD is completely <a href="/wiki/Recycling" title="Recycling">recycled</a> when adamantol in turn is driven out by adding <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> and ethanol removed by evaporation; 50 <a href="/wiki/Milligram" class="mw-redirect" title="Milligram">mg</a> of Au/CD captures 5 mg of C<sub>60</sub> fullerene. </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fullerene_chemistry&action=edit&section=21" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Solubility_of_fullerenes" title="Solubility of fullerenes">Solubility of fullerenes</a></li> <li><a href="/wiki/Geodesic_polyarene" title="Geodesic polyarene">Geodesic polyarene</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fullerene_chemistry&action=edit&section=22" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width" style="column-width: 35em;"> <ol class="references"> <li id="cite_note-full-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-full_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-full_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFHirsch,_A.Bellavia-Lund,_C.1993" class="citation book cs1">Hirsch, A.; Bellavia-Lund, C., eds. 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(2005). <a rel="nofollow" class="external text" href="https://www.jstage.jst.go.jp/article/cl/34/2/34_2_178/_pdf">"Kilogram-scale [60]Fullerene Separation from a Fullerene Mixture: Selective Complexation of Fullerenes with 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)"</a>. <i>Chemistry Letters</i>. <b>34</b> (2): 178. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1246%2Fcl.2005.178">10.1246/cl.2005.178</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemistry+Letters&rft.atitle=Kilogram-scale+%5B60%5DFullerene+Separation+from+a+Fullerene+Mixture%3A+Selective+Complexation+of+Fullerenes+with+1%2C8-Diazabicyclo%5B5.4.0%5Dundec-7-ene+%28DBU%29&rft.volume=34&rft.issue=2&rft.pages=178&rft.date=2005&rft_id=info%3Adoi%2F10.1246%2Fcl.2005.178&rft.aulast=Nagata&rft.aufirst=K.&rft.au=Dejima%2C+E.&rft.au=Kikuchi%2C+Y.&rft.au=Hashiguchi%2C+M.&rft_id=https%3A%2F%2Fwww.jstage.jst.go.jp%2Farticle%2Fcl%2F34%2F2%2F34_2_178%2F_pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFullerene+chemistry" class="Z3988"></span><sup class="noprint Inline-Template"><span style="white-space: nowrap;">[<i><a href="/wiki/Wikipedia:Link_rot" title="Wikipedia:Link rot"><span title=" Dead link tagged May 2024">permanent dead link</span></a></i><span style="visibility:hidden; color:transparent; padding-left:2px">‍</span>]</span></sup></span> </li> <li id="cite_note-58"><span class="mw-cite-backlink"><b><a href="#cite_ref-58">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLiuYangChen2005" class="citation journal cs1">Liu, Y.; Yang, Y. W.; Chen, Y. (2005). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160304050618/http://supram.nankai.edu.cn/documents/cc-05-4208.pdf">"Thio[2-(benzoylamino)ethylamino]-β-CD fragment modified gold nanoparticles as recycling extractors for [60]fullerene"</a> <span class="cs1-format">(PDF)</span>. <i>Chemical Communications</i> (33): 4208–10. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2Fb507650a">10.1039/b507650a</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16100605">16100605</a>. Archived from <a rel="nofollow" class="external text" href="http://supram.nankai.edu.cn/documents/cc-05-4208.pdf">the original</a> <span class="cs1-format">(PDF)</span> on 2016-03-04<span class="reference-accessdate">. Retrieved <span class="nowrap">2015-08-29</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Communications&rft.atitle=Thio%5B2-%28benzoylamino%29ethylamino%5D-%CE%B2-CD+fragment+modified+gold+nanoparticles+as+recycling+extractors+for+%5B60%5Dfullerene&rft.issue=33&rft.pages=4208-10&rft.date=2005&rft_id=info%3Adoi%2F10.1039%2Fb507650a&rft_id=info%3Apmid%2F16100605&rft.aulast=Liu&rft.aufirst=Y.&rft.au=Yang%2C+Y.+W.&rft.au=Chen%2C+Y.&rft_id=http%3A%2F%2Fsupram.nankai.edu.cn%2Fdocuments%2Fcc-05-4208.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFullerene+chemistry" class="Z3988"></span></span> </li> </ol></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1236075235">.mw-parser-output .navbox{box-sizing:border-box;border:1px solid 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title="Spectroscopy">Spectroscopy</a></li> <li><a href="/wiki/Photochemistry" title="Photochemistry">Photochemistry</a></li> <li><a href="/wiki/Spin_chemistry" title="Spin chemistry">Spin chemistry</a></li> <li><a href="/wiki/Microwave_chemistry" title="Microwave chemistry">Microwave chemistry</a></li> <li><a href="/wiki/Equilibrium_chemistry" title="Equilibrium chemistry">Equilibrium chemistry</a></li> <li><a href="/wiki/Mechanochemistry" title="Mechanochemistry">Mechanochemistry</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Inorganic_chemistry" title="Inorganic chemistry">Inorganic</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Coordination_complex" title="Coordination complex">Coordination chemistry</a></li> <li><a href="/wiki/Magnetochemistry" title="Magnetochemistry">Magnetochemistry</a></li> <li><a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">Organometallic chemistry</a> <ul><li><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">Organolanthanide chemistry</a></li></ul></li> <li><a href="/wiki/Atom_cluster" class="mw-redirect" title="Atom cluster">Cluster chemistry</a></li> <li><a href="/wiki/Solid-state_chemistry" title="Solid-state chemistry">Solid-state chemistry</a></li> <li><a href="/wiki/Ceramic_chemistry" class="mw-redirect" title="Ceramic chemistry">Ceramic chemistry</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Organic_chemistry" title="Organic chemistry">Organic</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Stereochemistry" title="Stereochemistry">Stereochemistry</a> <ul><li><a href="/wiki/Alkane_stereochemistry" class="mw-redirect" title="Alkane stereochemistry">Alkane stereochemistry</a></li></ul></li> <li><a href="/wiki/Physical_organic_chemistry" title="Physical organic chemistry">Physical organic chemistry</a></li> <li><a href="/wiki/Organic_reactions" class="mw-redirect" title="Organic reactions">Organic reactions</a></li> <li><a href="/wiki/Organic_synthesis" title="Organic synthesis">Organic synthesis</a></li> <li><a href="/wiki/Retrosynthetic_analysis" title="Retrosynthetic analysis">Retrosynthetic analysis</a></li> <li><a href="/wiki/Enantioselective_synthesis" title="Enantioselective synthesis">Enantioselective synthesis</a></li> <li><a href="/wiki/Total_synthesis" title="Total synthesis">Total synthesis</a> / <a href="/wiki/Semisynthesis" title="Semisynthesis">Semisynthesis</a></li> <li><a class="mw-selflink selflink">Fullerene chemistry</a></li> <li><a href="/wiki/Polymer_chemistry" title="Polymer chemistry">Polymer chemistry</a></li> <li><a href="/wiki/Petrochemistry" class="mw-redirect" title="Petrochemistry">Petrochemistry</a></li> <li><a href="/wiki/Dynamic_covalent_chemistry" title="Dynamic covalent chemistry">Dynamic covalent chemistry</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Biochemistry" title="Biochemistry">Biological</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Biochemistry" title="Biochemistry">Biochemistry</a> <ul><li><a href="/wiki/Molecular_biology" title="Molecular biology">Molecular biology</a></li> <li><a href="/wiki/Cell_biology" title="Cell biology">Cell biology</a></li></ul></li> <li><a href="/wiki/Chemical_biology" title="Chemical biology">Chemical biology</a> <ul><li><a href="/wiki/Bioorthogonal_chemistry" title="Bioorthogonal chemistry">Bioorthogonal chemistry</a></li></ul></li> <li><a href="/wiki/Medicinal_chemistry" title="Medicinal chemistry">Medicinal chemistry</a> <ul><li><a href="/wiki/Pharmacology" title="Pharmacology">Pharmacology</a></li></ul></li> <li><a href="/wiki/Clinical_chemistry" title="Clinical chemistry">Clinical chemistry</a></li> <li><a href="/wiki/Neurochemistry" title="Neurochemistry">Neurochemistry</a></li> <li><a href="/wiki/Bioorganic_chemistry" title="Bioorganic chemistry">Bioorganic chemistry</a></li> <li><a href="/wiki/Bioorganometallic_chemistry" title="Bioorganometallic chemistry">Bioorganometallic chemistry</a></li> <li><a href="/wiki/Bioinorganic_chemistry" title="Bioinorganic chemistry">Bioinorganic chemistry</a></li> <li><a href="/wiki/Biophysical_chemistry" title="Biophysical chemistry">Biophysical chemistry</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Interdisciplinarity" title="Interdisciplinarity">Interdisciplinarity</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Nuclear_chemistry" title="Nuclear chemistry">Nuclear chemistry</a> <ul><li><a href="/wiki/Radiochemistry" title="Radiochemistry">Radiochemistry</a></li> <li><a href="/wiki/Radiation_chemistry" title="Radiation chemistry">Radiation chemistry</a></li> <li><a href="/wiki/Actinide_chemistry" title="Actinide chemistry">Actinide chemistry</a></li></ul></li> <li><a href="/wiki/Cosmochemistry" title="Cosmochemistry">Cosmochemistry</a> / <a href="/wiki/Astrochemistry" title="Astrochemistry">Astrochemistry</a> / <a href="/wiki/Stellar_chemistry" title="Stellar chemistry">Stellar chemistry</a></li> <li><a href="/wiki/Geochemistry" title="Geochemistry">Geochemistry</a> <ul><li><a href="/wiki/Biogeochemistry" title="Biogeochemistry">Biogeochemistry</a></li> <li><a href="/wiki/Photogeochemistry" title="Photogeochemistry">Photogeochemistry</a></li></ul></li></ul> <ul><li><a href="/wiki/Environmental_chemistry" title="Environmental chemistry">Environmental chemistry</a> <ul><li><a href="/wiki/Atmospheric_chemistry" title="Atmospheric chemistry">Atmospheric chemistry</a></li> <li><a href="/wiki/Ocean_chemistry" class="mw-redirect" title="Ocean chemistry">Ocean chemistry</a></li></ul></li> <li><a href="/wiki/Clay_chemistry" title="Clay chemistry">Clay chemistry</a></li> <li><a href="/wiki/Carbochemistry" title="Carbochemistry">Carbochemistry</a></li> <li><a href="/wiki/Food_chemistry" title="Food chemistry">Food chemistry</a> <ul><li><a href="/wiki/Carbohydrate_chemistry" class="mw-redirect" title="Carbohydrate chemistry">Carbohydrate chemistry</a></li> <li><a href="/wiki/Food_physical_chemistry" title="Food physical chemistry">Food physical chemistry</a></li></ul></li> <li><a href="/wiki/Agricultural_chemistry" title="Agricultural chemistry">Agricultural chemistry</a> <ul><li><a href="/wiki/Soil_chemistry" title="Soil chemistry">Soil chemistry</a></li></ul></li></ul> <ul><li><a href="/wiki/Chemistry_education" title="Chemistry education">Chemistry education</a> <ul><li><a href="/wiki/Amateur_chemistry" title="Amateur chemistry">Amateur chemistry</a></li> <li><a href="/wiki/General_chemistry" title="General chemistry">General chemistry</a></li></ul></li> <li><a href="/wiki/Clandestine_chemistry" title="Clandestine chemistry">Clandestine chemistry</a></li> <li><a href="/wiki/Forensic_chemistry" title="Forensic chemistry">Forensic chemistry</a> <ul><li><a href="/wiki/Forensic_toxicology" title="Forensic toxicology">Forensic toxicology</a></li> <li><a href="/wiki/Post-mortem_chemistry" title="Post-mortem chemistry">Post-mortem chemistry</a></li></ul></li></ul> <ul><li><a href="/wiki/Nanochemistry" title="Nanochemistry">Nanochemistry</a> <ul><li><a href="/wiki/Supramolecular_chemistry" title="Supramolecular chemistry">Supramolecular chemistry</a></li></ul></li> <li><a href="/wiki/Chemical_synthesis" title="Chemical synthesis">Chemical synthesis</a> <ul><li><a href="/wiki/Green_chemistry" title="Green chemistry">Green chemistry</a></li> <li><a href="/wiki/Click_chemistry" title="Click chemistry">Click chemistry</a></li> <li><a href="/wiki/Combinatorial_chemistry" title="Combinatorial chemistry">Combinatorial chemistry</a></li> <li><a href="/wiki/Biosynthesis" title="Biosynthesis">Biosynthesis</a></li></ul></li> <li><a href="/wiki/Chemical_engineering" title="Chemical engineering">Chemical engineering</a> <ul><li><a href="/wiki/Stoichiometry" title="Stoichiometry">Stoichiometry</a></li></ul></li> <li><a href="/wiki/Materials_science" title="Materials science">Materials science</a> <ul><li><a href="/wiki/Metallurgy" title="Metallurgy">Metallurgy</a></li> <li><a href="/wiki/Ceramic_engineering" title="Ceramic engineering">Ceramic engineering</a></li> <li><a href="/wiki/Polymer_science" title="Polymer science">Polymer science</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">See also</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/History_of_chemistry" title="History of chemistry">History of chemistry</a></li> <li><a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Nobel Prize in Chemistry</a></li> <li><a href="/wiki/Timeline_of_chemistry" title="Timeline of chemistry">Timeline of chemistry</a> <ul><li><a href="/wiki/Discovery_of_chemical_elements" title="Discovery of chemical elements">of element discoveries</a></li></ul></li> <li>"<a href="/wiki/The_central_science" title="The central science">The central science</a>"</li> <li><a href="/wiki/Chemical_reaction" title="Chemical reaction">Chemical reaction</a> <ul><li><a href="/wiki/Catalysis" title="Catalysis">Catalysis</a></li></ul></li> <li><a href="/wiki/Chemical_element" title="Chemical element">Chemical element</a></li> <li><a href="/wiki/Chemical_compound" title="Chemical compound">Chemical compound</a></li> <li><a href="/wiki/Atom" title="Atom">Atom</a></li> <li><a href="/wiki/Molecule" title="Molecule">Molecule</a></li> <li><a href="/wiki/Ion" title="Ion">Ion</a></li> <li><a href="/wiki/Chemical_substance" title="Chemical substance">Chemical substance</a></li> <li><a href="/wiki/Chemical_bond" title="Chemical bond">Chemical bond</a></li> <li><a href="/wiki/Alchemy" title="Alchemy">Alchemy</a></li> <li><a href="/wiki/Quantum_mechanics" title="Quantum mechanics">Quantum mechanics</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" 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