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compounds">Graphite intercalation compounds</a>)</span></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Class of chemical compounds</div> <style data-mw-deduplicate="TemplateStyles:r1237032888/mw-parser-output/.tmulti">.mw-parser-output .tmulti .multiimageinner{display:flex;flex-direction:column}.mw-parser-output .tmulti .trow{display:flex;flex-direction:row;clear:left;flex-wrap:wrap;width:100%;box-sizing:border-box}.mw-parser-output .tmulti .tsingle{margin:1px;float:left}.mw-parser-output .tmulti .theader{clear:both;font-weight:bold;text-align:center;align-self:center;background-color:transparent;width:100%}.mw-parser-output .tmulti .thumbcaption{background-color:transparent}.mw-parser-output .tmulti .text-align-left{text-align:left}.mw-parser-output .tmulti .text-align-right{text-align:right}.mw-parser-output .tmulti .text-align-center{text-align:center}@media all and (max-width:720px){.mw-parser-output .tmulti .thumbinner{width:100%!important;box-sizing:border-box;max-width:none!important;align-items:center}.mw-parser-output .tmulti .trow{justify-content:center}.mw-parser-output .tmulti .tsingle{float:none!important;max-width:100%!important;box-sizing:border-box;text-align:center}.mw-parser-output .tmulti .tsingle .thumbcaption{text-align:left}.mw-parser-output .tmulti .trow>.thumbcaption{text-align:center}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .tmulti .multiimageinner img{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .tmulti .multiimageinner img{background-color:white}}</style><div class="thumb tmulti tright"><div class="thumbinner multiimageinner" style="width:292px;max-width:292px"><div class="trow"><div class="tsingle" style="width:113px;max-width:113px"><div class="thumbimage" style="height:132px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:Potassium-graphite-xtal-3D-SF-A.png" class="mw-file-description"><img alt="KC8 (side view)" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ae/Potassium-graphite-xtal-3D-SF-A.png/111px-Potassium-graphite-xtal-3D-SF-A.png" decoding="async" width="111" height="132" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ae/Potassium-graphite-xtal-3D-SF-A.png/167px-Potassium-graphite-xtal-3D-SF-A.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ae/Potassium-graphite-xtal-3D-SF-A.png/222px-Potassium-graphite-xtal-3D-SF-A.png 2x" data-file-width="922" data-file-height="1100" /></a></span></div><div class="thumbcaption">(side view)</div></div><div class="tsingle" style="width:175px;max-width:175px"><div class="thumbimage" style="height:132px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:Potassium-graphite-xtal-3D-SF-B.png" class="mw-file-description"><img alt="KC8 (top view)" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/Potassium-graphite-xtal-3D-SF-B.png/173px-Potassium-graphite-xtal-3D-SF-B.png" decoding="async" width="173" height="132" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/Potassium-graphite-xtal-3D-SF-B.png/260px-Potassium-graphite-xtal-3D-SF-B.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/55/Potassium-graphite-xtal-3D-SF-B.png/346px-Potassium-graphite-xtal-3D-SF-B.png 2x" data-file-width="1100" data-file-height="838" /></a></span></div><div class="thumbcaption">(top view)</div></div></div><div class="trow" style="display:flex"><div class="thumbcaption">Space-filling model of potassium graphite KC<sub>8</sub>.</div></div></div></div> <p>In the area of <a href="/wiki/Solid_state_chemistry" class="mw-redirect" title="Solid state chemistry">solid state chemistry</a>, <b>graphite intercalation compounds</b> are a family of materials prepared from graphite. In particular, the sheets of carbon that comprise graphite can be pried apart by the insertion (<a href="/wiki/Intercalation_(chemistry)" title="Intercalation (chemistry)">intercalation</a>) of ions. The <a href="/wiki/Graphite" title="Graphite">graphite</a> is viewed as a host and the inserted ions as <a href="/wiki/Host%E2%80%93guest_chemistry" title="Host–guest chemistry">guests</a>. The materials have the formula <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">(guest)C<sub class="template-chem2-sub"><i>n</i></sub></span> where <i>n</i> ≥ 6. The insertion of the guests increases the distance between the carbon sheets. Common guests are <a href="/wiki/Reducing_agent" title="Reducing agent">reducing agents</a> such as <a href="/wiki/Alkali_metal" title="Alkali metal">alkali metals</a>. Strong oxidants also intercalate into graphite. Intercalation involves <a href="/wiki/Electron_transfer" title="Electron transfer">electron transfer</a> into or out of the carbon sheets. So, in some sense, graphite intercalation compounds are salts. Intercalation is often reversible: the inserted ions can be removed and the sheets of carbon collapse to a graphite-like structure. </p><p>The properties of graphite intercalation compounds differ from those of the parent graphite.<sup id="cite_ref-greenwood_1-0" class="reference"><a href="#cite_note-greenwood-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> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Preparation_and_structure">Preparation and structure</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Graphite_intercalation_compound&action=edit&section=1" title="Edit section: Preparation and structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>These materials are prepared by treating graphite with a strong oxidant or a strong reducing agent: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C + <i>m</i> X → CX<sub class="template-chem2-sub"><i>m</i></sub></span></dd></dl> <p>The reaction is reversible. </p><p>The host (graphite) and the guest X interact by <a href="/wiki/Charge_transfer_complex" class="mw-redirect" title="Charge transfer complex">charge transfer</a>. An analogous process is the basis of commercial <a href="/wiki/Lithium-ion_battery" title="Lithium-ion battery">lithium-ion batteries</a>. </p><p>In a graphite intercalation compound not every layer is necessarily occupied by guests. In so-called <i>stage 1 compounds</i>, graphite layers and intercalated layers alternate and in <i>stage 2 compounds</i>, two graphite layers with no guest material in between alternate with an intercalated layer. The actual composition may vary and therefore these compounds are an example of <a href="/wiki/Stoichiometry" title="Stoichiometry">non-stoichiometric</a> compounds. It is customary to specify the composition together with the stage. The layers are pushed apart upon incorporation of the guest ions. </p> <div class="mw-heading mw-heading2"><h2 id="Examples">Examples</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Graphite_intercalation_compound&action=edit&section=2" title="Edit section: Examples"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Alkali_and_alkaline_earth_derivatives">Alkali and alkaline earth derivatives</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Graphite_intercalation_compound&action=edit&section=3" title="Edit section: Alkali and alkaline earth derivatives"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Potassium_graphite.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2c/Potassium_graphite.jpg/220px-Potassium_graphite.jpg" decoding="async" width="220" height="191" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2c/Potassium_graphite.jpg/330px-Potassium_graphite.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2c/Potassium_graphite.jpg/440px-Potassium_graphite.jpg 2x" data-file-width="1696" data-file-height="1476" /></a><figcaption>Potassium graphite under argon in a <a href="/wiki/Schlenk_flask" title="Schlenk flask">Schlenk flask</a>. A glass-coated magnetic stir bar is also present.</figcaption></figure> <p>One of the best studied graphite intercalation compounds, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">KC<sub class="template-chem2-sub">8</sub></span>, is prepared by melting <a href="/wiki/Potassium" title="Potassium">potassium</a> over graphite powder. The potassium is absorbed into the graphite and the material changes color from black to bronze.<sup id="cite_ref-OttmersRase1966_3-0" class="reference"><a href="#cite_note-OttmersRase1966-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> The resulting solid is <a href="/wiki/Pyrophoric" class="mw-redirect" title="Pyrophoric">pyrophoric</a>.<sup id="cite_ref-InorgChem_4-0" class="reference"><a href="#cite_note-InorgChem-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> The composition is explained by assuming that the potassium to potassium distance is twice the distance between hexagons in the carbon framework. The bond between anionic graphite layers and potassium cations is ionic. The electrical conductivity of the material is greater than that of α-graphite.<sup id="cite_ref-InorgChem_4-1" class="reference"><a href="#cite_note-InorgChem-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><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> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">KC<sub class="template-chem2-sub">8</sub></span> is a <a href="/wiki/Superconductor" class="mw-redirect" title="Superconductor">superconductor</a> with a very low critical temperature T<sub>c</sub> = 0.14 K.<sup id="cite_ref-cac6_6-0" class="reference"><a href="#cite_note-cac6-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Heating <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">KC<sub class="template-chem2-sub">8</sub></span> leads to the formation of a series of decomposition products as the K atoms are eliminated:<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (April 2016)">citation needed</span></a></i>]</sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">3 KC<sub class="template-chem2-sub">8</sub> → KC<sub class="template-chem2-sub">24</sub> + 2 K</span></dd></dl> <p>Via the intermediates <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">KC<sub class="template-chem2-sub">24</sub></span> (blue in color),<sup id="cite_ref-OttmersRase1966_3-1" class="reference"><a href="#cite_note-OttmersRase1966-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">KC<sub class="template-chem2-sub">36</sub></span>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">KC<sub class="template-chem2-sub">48</sub></span>, ultimately the compound <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">KC<sub class="template-chem2-sub">60</sub></span> results. </p><p>The stoichiometry <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">MC<sub class="template-chem2-sub">8</sub></span> is observed for M = K, Rb and Cs. For smaller ions M = <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Li<sup class="template-chem2-sup">+</sup></span>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Sr<sup>2+</sup></span>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ba<sup>2+</sup></span>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Eu<sup>2+</sup></span>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Yb<sup>3+</sup></span>, and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ca<sup>2+</sup></span>, the limiting stoichiometry is <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">MC<sub class="template-chem2-sub">6</sub></span>.<sup id="cite_ref-cac6_6-1" class="reference"><a href="#cite_note-cac6-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Calcium graphite <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CaC<sub class="template-chem2-sub">6</sub></span> is obtained by immersing highly oriented <a href="/wiki/Pyrolytic_graphite" class="mw-redirect" title="Pyrolytic graphite">pyrolytic graphite</a> in liquid Li–Ca alloy for 10 days at 350 °C. The crystal structure of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CaC<sub class="template-chem2-sub">6</sub></span> belongs to the R<span style="text-decoration:overline;">3</span>m space group. The graphite interlayer distance increases upon Ca intercalation from 3.35 to 4.524 Å, and the carbon-carbon distance increases from 1.42 to 1.444 Å. </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:CaC6structure.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ec/CaC6structure.jpg/220px-CaC6structure.jpg" decoding="async" width="220" height="144" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ec/CaC6structure.jpg/330px-CaC6structure.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ec/CaC6structure.jpg/440px-CaC6structure.jpg 2x" data-file-width="843" data-file-height="552" /></a><figcaption>Structure of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CaC<sub class="template-chem2-sub">6</sub></span></figcaption></figure> <p>With <a href="/wiki/Barium" title="Barium">barium</a> and <a href="/wiki/Ammonia" title="Ammonia">ammonia</a>, the cations are solvated, giving the stoichiometry (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ba(NH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2.5</sub>C<sub class="template-chem2-sub">10.9</sub></span>(stage 1)) or those with <a href="/wiki/Caesium" title="Caesium">caesium</a>, <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> and <a href="/wiki/Potassium" title="Potassium">potassium</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CsC<sub class="template-chem2-sub">8</sub>·K<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">4/3</sub>C<sub class="template-chem2-sub">8</sub></span>(stage 1)).<sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="The text near this tag may need clarification or removal of jargon. (September 2022)">clarification needed</span></a></i>]</sup> </p><p>In situ adsorption on free-standing graphene and intercalation in bilayer graphene of the alkali metals K, Cs, and Li was observed by means of low-energy electron microscopy.<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> </p><p>Different from other alkali metals, the amount of Na intercalation is very small. Quantum-mechanical calculations show that this originates from a quite general phenomenon: among the alkali and alkaline earth metals, Na and Mg generally have the weakest chemical binding to a given substrate, compared with the other elements in the same group of the periodic table.<sup id="cite_ref-PNAS_2016_8-0" class="reference"><a href="#cite_note-PNAS_2016-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> The phenomenon arises from the competition between trends in the ionization energy and the ion–substrate coupling, down the columns of the periodic table.<sup id="cite_ref-PNAS_2016_8-1" class="reference"><a href="#cite_note-PNAS_2016-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> However, considerable Na intercalation into graphite can occur in cases when the ion is wrapped in a solvent shell through the process of co-intercalation. A complex magnesium(I) species has also been intercalated into graphite.<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> </p> <div class="mw-heading mw-heading3"><h3 id="Graphite_bisulfate,_perchlorate,_hexafluoroarsenate:_oxidized_carbons"><span id="Graphite_bisulfate.2C_perchlorate.2C_hexafluoroarsenate:_oxidized_carbons"></span>Graphite bisulfate, perchlorate, hexafluoroarsenate: oxidized carbons</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Graphite_intercalation_compound&action=edit&section=4" title="Edit section: Graphite bisulfate, perchlorate, hexafluoroarsenate: oxidized carbons"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The intercalation compounds graphite bisulfate and graphite perchlorate can be prepared by treating graphite with strong oxidizing agents in the presence of strong acids. In contrast to the potassium and calcium graphites, the carbon layers are oxidized in this process: </p> <dl><dd>48 C + 0. 5 ［O ］+ 3 H<sub>2</sub>SO<sub>4</sub> → [C<sub>24</sub>]<sup>+</sup>[HSO<sub>4</sub>]<sup>−</sup>·2H<sub>2</sub>SO<sub>4</sub> + 0.5 H<sub>2</sub>O<sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="The text near this tag may need clarification or removal of jargon. (September 2022)">clarification needed</span></a></i>]</sup></dd></dl> <p>In graphite perchlorate, planar layers of carbon atoms are 794 <a href="/wiki/Picometre" title="Picometre">picometers</a> apart, separated by <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">ClO<span class="template-chem2-su"><span>−</span><span>4</span></span></span> ions. Cathodic reduction of graphite perchlorate is analogous to heating <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">KC<sub class="template-chem2-sub">8</sub></span>, which leads to a sequential elimination of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">HClO<sub class="template-chem2-sub">4</sub></span>. </p><p>Both graphite bisulfate and graphite perchlorate are better conductors as compared to graphite, as predicted by using a positive-hole mechanism.<sup id="cite_ref-InorgChem_4-2" class="reference"><a href="#cite_note-InorgChem-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Reaction of graphite with <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[O<sub class="template-chem2-sub">2</sub>]<sup class="template-chem2-sup">+</sup>[AsF<sub class="template-chem2-sub">6</sub>]<sup class="template-chem2-sup">−</sup></span> affords the salt <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[C<sub class="template-chem2-sub">8</sub>]<sup class="template-chem2-sup">+</sup>[AsF<sub class="template-chem2-sub">6</sub>]<sup class="template-chem2-sup">−</sup></span>.<sup id="cite_ref-InorgChem_4-3" class="reference"><a href="#cite_note-InorgChem-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Metal_halide_derivatives">Metal halide derivatives</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Graphite_intercalation_compound&action=edit&section=5" title="Edit section: Metal halide derivatives"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A number of metal halides intercalate into graphite. The chloride derivatives have been most extensively studied. Examples include <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">MCl<sub class="template-chem2-sub">2</sub></span> (M = Zn, Ni, Cu, Mn), <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">MCl<sub class="template-chem2-sub">3</sub></span> (M = Al, Fe, Ga), <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">MCl<sub class="template-chem2-sub">4</sub></span> (M = Zr, Pt), etc.<sup id="cite_ref-greenwood_1-1" class="reference"><a href="#cite_note-greenwood-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> The materials consists of layers of close-packed metal halide layers between sheets of carbon. The derivative <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">~8</sub>FeCl<sub class="template-chem2-sub">3</sub></span> exhibits <a href="/wiki/Spin_glass" title="Spin glass">spin glass</a> behavior.<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> It proved to be a particularly fertile system on which to study phase transitions.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (April 2015)">citation needed</span></a></i>]</sup> A stage n magnetic graphite intercalation compounds has n graphite layers separating successive magnetic layers. As the stage number increases the interaction between spins in successive magnetic layers becomes weaker and 2D magnetic behaviour may arise. </p> <div class="mw-heading mw-heading3"><h3 id="Halogen-_and_oxide-graphite_compounds">Halogen- and oxide-graphite compounds</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Graphite_intercalation_compound&action=edit&section=6" title="Edit section: Halogen- and oxide-graphite compounds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Chlorine and bromine reversibly intercalate into graphite. Iodine does not. Fluorine reacts irreversibly. In the case of bromine, the following stoichiometries are known: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub"><i>n</i></sub>Br</span> for <i>n</i> = 8, 12, 14, 16, 20, and 28. </p><p>Because it forms irreversibly, <a href="/wiki/Carbon_monofluoride" title="Carbon monofluoride">carbon monofluoride</a> is often not classified as an intercalation compound. It has the formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CF)<sub class="template-chem2-sub"><i>x</i></sub></span>. It is prepared by reaction of gaseous <a href="/wiki/Fluorine" title="Fluorine">fluorine</a> with graphitic carbon at 215–230 °C. The color is greyish, white, or yellow. The bond between the carbon and fluorine atoms is covalent. Tetracarbon monofluoride (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">4</sub>F</span>) is prepared by treating graphite with a mixture of fluorine and <a href="/wiki/Hydrogen_fluoride" title="Hydrogen fluoride">hydrogen fluoride</a> at room temperature. The compound has a blackish-blue color. Carbon monofluoride is not electrically conductive. It has been studied as a <a href="/wiki/Cathode" title="Cathode">cathode</a> material in one type of primary (non-rechargeable) <a href="/wiki/Lithium_battery" title="Lithium battery">lithium batteries</a>. </p><p><a href="/wiki/Graphite_oxide" title="Graphite oxide">Graphite oxide</a> is an unstable yellow solid. </p> <div class="mw-heading mw-heading2"><h2 id="Properties_and_applications">Properties and applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Graphite_intercalation_compound&action=edit&section=7" title="Edit section: Properties and applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Graphite intercalation compounds have fascinated materials scientists for many years owing to their diverse electronic and electrical properties. </p> <div class="mw-heading mw-heading3"><h3 id="Superconductivity">Superconductivity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Graphite_intercalation_compound&action=edit&section=8" title="Edit section: Superconductivity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Among the superconducting graphite intercalation compounds, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CaC<sub class="template-chem2-sub">6</sub></span> exhibits the highest <a href="/wiki/Superconductivity" title="Superconductivity">critical temperature</a> <i>T</i><sub>c</sub> = 11.5 K, which further increases under applied pressure (15.1 K at 8 GPa).<sup id="cite_ref-cac6_6-2" class="reference"><a href="#cite_note-cac6-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Superconductivity in these compounds is thought to be related to the role of an interlayer state, a free electron like band lying roughly 2 eV (0.32 aJ) above the <a href="/wiki/Fermi_level" title="Fermi level">Fermi level</a>; superconductivity only occurs if the interlayer state is occupied.<sup id="cite_ref-Yang_11-0" class="reference"><a href="#cite_note-Yang-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Analysis of pure <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CaC<sub class="template-chem2-sub">6</sub></span> using a high quality <a href="/wiki/Ultraviolet_light" class="mw-redirect" title="Ultraviolet light">ultraviolet light</a> revealed to conduct <a href="/wiki/Angle-resolved_photoemission_spectroscopy" title="Angle-resolved photoemission spectroscopy">angle-resolved photoemission spectroscopy</a> measurements. The opening of a superconducting gap in the π* band revealed a substantial contribution to the total electron–phonon-coupling strength from the π*-interlayer interband interaction.<sup id="cite_ref-Yang_11-1" class="reference"><a href="#cite_note-Yang-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Reagents_in_chemical_synthesis:_KC8">Reagents in chemical synthesis: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">KC<sub class="template-chem2-sub">8</sub></span></h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Graphite_intercalation_compound&action=edit&section=9" title="Edit section: Reagents in chemical synthesis: KC8"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The bronze-colored material <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">KC<sub class="template-chem2-sub">8</sub></span> is one of the strongest <a href="/wiki/Reducing_agents" class="mw-redirect" title="Reducing agents">reducing agents</a> known. It has also been used as a <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyst</a> in <a href="/wiki/Polymerization" title="Polymerization">polymerizations</a> and as a <a href="/wiki/Coupling_reaction" title="Coupling reaction">coupling reagent</a> for <a href="/wiki/Aryl_halide" title="Aryl halide">aryl halides</a> to <a href="/wiki/Biphenyl" title="Biphenyl">biphenyls</a>.<sup id="cite_ref-Chakraborty_12-0" class="reference"><a href="#cite_note-Chakraborty-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> In one study, freshly prepared <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">KC<sub class="template-chem2-sub">8</sub></span> was treated with 1-iodododecane delivering a modification (<a href="/wiki/Micrometre" title="Micrometre">micrometre</a> scale carbon platelets with long alkyl chains sticking out providing solubility) that is soluble in <a href="/wiki/Chloroform" title="Chloroform">chloroform</a>.<sup id="cite_ref-Chakraborty_12-1" class="reference"><a href="#cite_note-Chakraborty-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> Another potassium graphite compound, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">KC<sub class="template-chem2-sub">24</sub></span>, has been used as a neutron monochromator. A new essential application for potassium graphite was introduced by the invention of the <a href="/wiki/Potassium-ion_battery" title="Potassium-ion battery">potassium-ion battery</a>. Like the <a href="/wiki/Lithium-ion_battery" title="Lithium-ion battery">lithium-ion battery</a>, the <a href="/wiki/Potassium-ion_battery" title="Potassium-ion battery">potassium-ion battery</a> should use a carbon-based anode instead of a metallic anode. In this circumstance, the stable structure of potassium graphite is an important advantage. </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=Graphite_intercalation_compound&action=edit&section=10" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Buckminsterfullerene_intercalates" class="mw-redirect" title="Buckminsterfullerene intercalates">Buckminsterfullerene intercalates</a></li> <li><a href="/wiki/Covalent_superconductors" class="mw-redirect" title="Covalent superconductors">Covalent superconductors</a></li> <li><a href="/wiki/Magnesium_diboride" title="Magnesium diboride">Magnesium diboride</a>, which uses hexagonal planar <a href="/wiki/Boron" title="Boron">boron</a> sheets instead of carbon</li> <li><a href="/wiki/Pyrolytic_graphite" class="mw-redirect" title="Pyrolytic graphite">Pyrolytic graphite</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=Graphite_intercalation_compound&action=edit&section=11" 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: 30em;"> <ol class="references"> <li id="cite_note-greenwood-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-greenwood_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-greenwood_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="CITEREFGreenwoodEarnshaw1997" class="citation book cs1"><a href="/wiki/Norman_Greenwood" title="Norman Greenwood">Greenwood, Norman N.</a>; 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(2018-06-25). "Graphite Intercalation by Mg Diamine Complexes". <i>Inorganic Chemistry</i>. <b>57</b> (14). 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"Observation of spin glass state in FeCl<sub>3</sub>: intercalated graphite". <i>Journal of Physics C: Solid State Physics</i>. <b>16</b> (4): L89. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1983JPhC...16L..89M">1983JPhC...16L..89M</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1088%2F0022-3719%2F16%2F4%2F001">10.1088/0022-3719/16/4/001</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Physics+C%3A+Solid+State+Physics&rft.atitle=Observation+of+spin+glass+state+in+FeCl%3Csub%3E3%3C%2Fsub%3E%3A+intercalated+graphite&rft.volume=16&rft.issue=4&rft.pages=L89&rft.date=1983&rft_id=info%3Adoi%2F10.1088%2F0022-3719%2F16%2F4%2F001&rft_id=info%3Abibcode%2F1983JPhC...16L..89M&rft.aulast=Millman&rft.aufirst=S+E&rft.au=Zimmerman%2C+G+O&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGraphite+intercalation+compound" class="Z3988"></span></span> </li> <li id="cite_note-Yang-11"><span class="mw-cite-backlink">^ <a href="#cite_ref-Yang_11-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Yang_11-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCsányiLittlewoodNevidomskyyPickard2005" class="citation journal cs1">Csányi; Littlewood, P. B.; Nevidomskyy, Andriy H.; Pickard, Chris J.; Simons, B. D.; et al. (2005). "The role of the interlayer state in the electronic structure of superconducting graphite intercalated compounds". <i>Nature Physics</i>. <b>1</b> (1): 42–45. <a href="/wiki/ArXiv_(identifier)" class="mw-redirect" title="ArXiv (identifier)">arXiv</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://arxiv.org/abs/cond-mat/0503569">cond-mat/0503569</a></span>. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2005NatPh...1...42C">2005NatPh...1...42C</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fnphys119">10.1038/nphys119</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:6764457">6764457</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nature+Physics&rft.atitle=The+role+of+the+interlayer+state+in+the+electronic+structure+of+superconducting+graphite+intercalated+compounds&rft.volume=1&rft.issue=1&rft.pages=42-45&rft.date=2005&rft_id=info%3Aarxiv%2Fcond-mat%2F0503569&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A6764457%23id-name%3DS2CID&rft_id=info%3Adoi%2F10.1038%2Fnphys119&rft_id=info%3Abibcode%2F2005NatPh...1...42C&rft.au=Cs%C3%A1nyi&rft.au=Littlewood%2C+P.+B.&rft.au=Nevidomskyy%2C+Andriy+H.&rft.au=Pickard%2C+Chris+J.&rft.au=Simons%2C+B.+D.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGraphite+intercalation+compound" class="Z3988"></span></span> </li> <li id="cite_note-Chakraborty-12"><span class="mw-cite-backlink">^ <a href="#cite_ref-Chakraborty_12-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Chakraborty_12-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChakraborty,_S.ChattopadhyayGuoBillups2007" class="citation journal cs1">Chakraborty, S.; Chattopadhyay, Jayanta; Guo, Wenhua; Billups, W. 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"Functionalization of Potassium Graphite". <i>Angewandte Chemie International Edition</i>. <b>46</b> (24): 4486–8. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.200605175">10.1002/anie.200605175</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/17477336">17477336</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angewandte+Chemie+International+Edition&rft.atitle=Functionalization+of+Potassium+Graphite&rft.volume=46&rft.issue=24&rft.pages=4486-8&rft.date=2007&rft_id=info%3Adoi%2F10.1002%2Fanie.200605175&rft_id=info%3Apmid%2F17477336&rft.au=Chakraborty%2C+S.&rft.au=Chattopadhyay%2C+Jayanta&rft.au=Guo%2C+Wenhua&rft.au=Billups%2C+W.+Edward&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGraphite+intercalation+compound" class="Z3988"></span></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Graphite_intercalation_compound&action=edit&section=12" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239549316">.mw-parser-output .refbegin{margin-bottom:0.5em}.mw-parser-output .refbegin-hanging-indents>ul{margin-left:0}.mw-parser-output .refbegin-hanging-indents>ul>li{margin-left:0;padding-left:3.2em;text-indent:-3.2em}.mw-parser-output .refbegin-hanging-indents ul,.mw-parser-output .refbegin-hanging-indents ul li{list-style:none}@media(max-width:720px){.mw-parser-output .refbegin-hanging-indents>ul>li{padding-left:1.6em;text-indent:-1.6em}}.mw-parser-output .refbegin-columns{margin-top:0.3em}.mw-parser-output .refbegin-columns ul{margin-top:0}.mw-parser-output .refbegin-columns li{page-break-inside:avoid;break-inside:avoid-column}@media screen{.mw-parser-output .refbegin{font-size:90%}}</style><div class="refbegin" style=""> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFT._Enoki,_M._Suzuki_and_M._Endo2003" class="citation book cs1">T. Enoki, M. Suzuki and M. Endo (2003). <i>Graphite intercalation compounds and applications</i>. Oxford University Press. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-19-512827-7" title="Special:BookSources/978-0-19-512827-7"><bdi>978-0-19-512827-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Graphite+intercalation+compounds+and+applications&rft.pub=Oxford+University+Press&rft.date=2003&rft.isbn=978-0-19-512827-7&rft.au=T.+Enoki%2C+M.+Suzuki+and+M.+Endo&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGraphite+intercalation+compound" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDresselhausDresselhaus1981" class="citation journal cs1"><a href="/wiki/Mildred_Dresselhaus" title="Mildred Dresselhaus">Dresselhaus, M.S.</a>; Dresselhaus, G. (1981). 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