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Circulene - Wikipedia
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href="#[8]Circulenes"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>[8]Circulenes</span> </div> </a> <ul id="toc-[8]Circulenes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Heterocyclic_circulenes" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Heterocyclic_circulenes"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Heterocyclic circulenes</span> </div> </a> <ul id="toc-Heterocyclic_circulenes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Gallery" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Gallery"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Gallery</span> </div> </a> <ul id="toc-Gallery-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">5</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet 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href="https://de.wikipedia.org/wiki/Circulene" title="Circulene – German" lang="de" hreflang="de" data-title="Circulene" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Circul%C3%A8ne" title="Circulène – French" lang="fr" hreflang="fr" data-title="Circulène" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Circuleni" title="Circuleni – Italian" lang="it" hreflang="it" data-title="Circuleni" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Circuleen" 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searchaux" style="display:none">Class of chemical</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:-7-circulene.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/-7-circulene.svg/110px--7-circulene.svg.png" decoding="async" width="110" height="107" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/-7-circulene.svg/165px--7-circulene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d4/-7-circulene.svg/220px--7-circulene.svg.png 2x" data-file-width="231" data-file-height="225" /></a><figcaption>[7]circulene</figcaption></figure> <p>A <b>circulene</b> is a <a href="/wiki/Macrocyclic" class="mw-redirect" title="Macrocyclic">macrocyclic</a> <a href="/wiki/Arene" class="mw-redirect" title="Arene">arene</a> in which a central <a href="/wiki/Polygon" title="Polygon">polygon</a> is surrounded and <a href="/wiki/Annulation" title="Annulation">fused</a> by <a href="/wiki/Benzene" title="Benzene">benzenoids</a>.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Nomenclature within this class of molecules is based on the number of benzene rings surrounding the core, which is equivalent to the size of the central polygon. Examples which have been <a href="/wiki/Synthetic_chemistry" class="mw-redirect" title="Synthetic chemistry">synthesized</a> include [5]circulene (<a href="/wiki/Corannulene" title="Corannulene">corannulene</a>), [6]circulene (<a href="/wiki/Coronene" title="Coronene">coronene</a>), [7]circulene,<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><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><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 [12]circulene (<a href="/wiki/Kekulene" title="Kekulene">kekulene</a>) These compounds belong to a larger class of <a href="/wiki/Geodesic_polyarene" title="Geodesic polyarene">geodesic polyarenes</a>. Whereas [5]circulene is bowl-shaped and [6]circulene is planar, [7]circulene has a unique <a href="/wiki/Saddle" title="Saddle">saddle</a>-shaped structure (compare to cones and partial cones in <a href="/wiki/Calixarene" title="Calixarene">calixarenes</a>). The <a href="/wiki/Helicene" title="Helicene">helicenes</a> are a conceptually related class of structures in which the array of benzene rings form an open <a href="/wiki/Helix" title="Helix">helix</a> rather than a closed ring. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Quadrannulene_([4]circulene)"><span id="Quadrannulene_.28.5B4.5Dcirculene.29"></span>Quadrannulene ([4]circulene)</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Circulene&action=edit&section=1" title="Edit section: Quadrannulene ([4]circulene)"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The simple [4]circulene compound itself has not been synthesized, but a derivative, tetrabenzo[4]circulene, also called <b>quadrannulene</b>, has.<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> </p> <div class="mw-heading mw-heading2"><h2 id="[8]Circulenes"><span id=".5B8.5DCirculenes"></span>[8]Circulenes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Circulene&action=edit&section=2" title="Edit section: [8]Circulenes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The isolation of the <b>[8]circulene</b> derivative 2,5,6,9,10,13,14-octamethyl-3,4,7,8,11,12,15,16-octa(4-tolyl)[8]circulene has been reported.<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> Tetrabenzo[8]circulene (TB8C), a functionally stable form of the parent molecule [8]circulene has also been reported.<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><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><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-heading2"><h2 id="Heterocyclic_circulenes">Heterocyclic circulenes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Circulene&action=edit&section=3" title="Edit section: Heterocyclic circulenes"><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:Sulflower-from-xtal-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/84/Sulflower-from-xtal-3D-balls.png/220px-Sulflower-from-xtal-3D-balls.png" decoding="async" width="220" height="216" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/84/Sulflower-from-xtal-3D-balls.png/330px-Sulflower-from-xtal-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/84/Sulflower-from-xtal-3D-balls.png/440px-Sulflower-from-xtal-3D-balls.png 2x" data-file-width="1100" data-file-height="1079" /></a><figcaption><a href="/wiki/Sulflower" title="Sulflower">Sulflower</a>, an octacirculene</figcaption></figure> <p>A <a href="/wiki/Heterocycle" class="mw-redirect" title="Heterocycle">heterocyclic</a> circulene is one in which the fused rings around the periphery are not simple hydrocarbons, but instead contain at least one other element. <a href="/wiki/Sulflower" title="Sulflower">Sulflower</a> is a stable heterocyclic octacirculene based on <a href="/wiki/Thiophene" title="Thiophene">thiophene</a>. </p> <div style="clear:both;" class=""></div> <div class="mw-heading mw-heading2"><h2 id="Gallery">Gallery</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Circulene&action=edit&section=4" title="Edit section: Gallery"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul class="gallery mw-gallery-traditional"> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Corannulene.svg" class="mw-file-description" title="Corannulene ([5]circulene)"><img alt="Corannulene ([5]circulene)" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/23/Corannulene.svg/120px-Corannulene.svg.png" decoding="async" width="120" height="112" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/23/Corannulene.svg/180px-Corannulene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/23/Corannulene.svg/240px-Corannulene.svg.png 2x" data-file-width="150" data-file-height="140" /></a></span></div> <div class="gallerytext"><a href="/wiki/Corannulene" title="Corannulene">Corannulene</a> ([5]circulene)</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Coronene_200.svg" class="mw-file-description" title="Coronene ([6]circulene)"><img alt="Coronene ([6]circulene)" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/03/Coronene_200.svg/120px-Coronene_200.svg.png" decoding="async" width="120" height="116" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/03/Coronene_200.svg/180px-Coronene_200.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/03/Coronene_200.svg/240px-Coronene_200.svg.png 2x" data-file-width="155" data-file-height="150" /></a></span></div> <div class="gallerytext"><a href="/wiki/Coronene" title="Coronene">Coronene</a> ([6]circulene)</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:-7-circulene.svg" class="mw-file-description" title="[7]circulene"><img alt="[7]circulene" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/-7-circulene.svg/120px--7-circulene.svg.png" decoding="async" width="120" height="117" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/-7-circulene.svg/180px--7-circulene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d4/-7-circulene.svg/240px--7-circulene.svg.png 2x" data-file-width="231" data-file-height="225" /></a></span></div> <div class="gallerytext">[7]circulene</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Kekulene.svg" class="mw-file-description" title="Kekulene ([12]circulene)"><img alt="Kekulene ([12]circulene)" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Kekulene.svg/120px-Kekulene.svg.png" decoding="async" width="120" height="111" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Kekulene.svg/180px-Kekulene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Kekulene.svg/240px-Kekulene.svg.png 2x" data-file-width="512" data-file-height="474" /></a></span></div> <div class="gallerytext"><a href="/wiki/Kekulene" title="Kekulene">Kekulene</a> ([12]circulene)</div> </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=Circulene&action=edit&section=5" 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 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"General Method for the Synthesis of Functionalized Tetrabenzo[8]circulenes". <i>The Journal of Organic Chemistry</i>. <b>81</b> (23): 12005. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Facs.joc.6b02244">10.1021/acs.joc.6b02244</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/27934450">27934450</a>.</cite><span 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href="/wiki/Template:PAHs" title="Template:PAHs"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:PAHs" title="Template talk:PAHs"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:PAHs" title="Special:EditPage/Template:PAHs"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Polycyclic_aromatic_hydrocarbons" style="font-size:114%;margin:0 4em"><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">Polycyclic aromatic hydrocarbons</a></div></th></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">2 rings</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Butalene" title="Butalene">Butalene</a></li> <li><a href="/wiki/Azulene" title="Azulene">Azulene</a></li> <li><a href="/wiki/Naphthalene" title="Naphthalene">Naphthalene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">3 rings</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acenaphthene" title="Acenaphthene">Acenaphthene</a></li> <li><a href="/wiki/Acenaphthylene" title="Acenaphthylene">Acenaphthylene</a></li> <li><a href="/wiki/Anthracene" title="Anthracene">Anthracene</a></li> <li><a href="/wiki/Fluorene" title="Fluorene">Fluorene</a></li> <li><a href="/wiki/Phenalene" title="Phenalene">Phenalene</a></li> <li><a href="/wiki/Phenanthrene" title="Phenanthrene">Phenanthrene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">4 rings</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benz(a)anthracene" title="Benz(a)anthracene">Benz[<i>a</i>]anthracene</a></li> <li><a href="/wiki/Benzo(a)fluorene" title="Benzo(a)fluorene">Benzo[<i>a</i>]fluorene</a></li> <li><a href="/wiki/Benzo(c)fluorene" title="Benzo(c)fluorene">Benzo[<i>c</i>]fluorene</a></li> <li><a href="/wiki/Benzo(c)phenanthrene" title="Benzo(c)phenanthrene">Benzo[<i>c</i>]phenanthrene</a></li> <li><a href="/wiki/Chrysene" title="Chrysene">Chrysene</a></li> <li><a href="/wiki/Fluoranthene" title="Fluoranthene">Fluoranthene</a></li> <li><a href="/wiki/Pyrene" title="Pyrene">Pyrene</a></li> <li><a href="/wiki/Tetracene" title="Tetracene">Tetracene</a></li> <li><a href="/wiki/Triphenylene" title="Triphenylene">Triphenylene</a></li> <li><a href="/wiki/Tricyclobutabenzene" title="Tricyclobutabenzene">Tricyclobutabenzene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">5 rings</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benz(e)acephenanthrylene" title="Benz(e)acephenanthrylene">Benz[<i>e</i>]acephenanthrylene</a></li> <li><a href="/wiki/Benzopyrene" title="Benzopyrene">Benzopyrene</a> <ul><li><a href="/wiki/Benzo(a)pyrene" title="Benzo(a)pyrene">Benzo[<i>a</i>]pyrene</a></li> <li><a href="/wiki/Benzo(e)pyrene" title="Benzo(e)pyrene">Benzo[<i>e</i>]pyrene</a></li> <li><a href="/wiki/Olympicene" title="Olympicene">6<i>H</i>-Benzo[<i>cd</i>]pyrene(Olympicene)</a></li></ul></li> <li><a href="/wiki/Benzo(a)fluoranthene" title="Benzo(a)fluoranthene">Benzo[<i>a</i>]fluoranthene</a></li> <li><a href="/wiki/Benzo(b)fluoranthene" class="mw-redirect" title="Benzo(b)fluoranthene">Benzo[<i>b</i>]fluoranthene</a></li> <li><a href="/wiki/Benzo(j)fluoranthene" title="Benzo(j)fluoranthene">Benzo[<i>j</i>]fluoranthene</a></li> <li><a href="/wiki/Benzo(k)fluoranthene" title="Benzo(k)fluoranthene">Benzo[<i>k</i>]fluoranthene</a></li> <li><a href="/wiki/Bicalicene" title="Bicalicene">trans-Bicalicene</a></li> <li><a href="/wiki/Dibenz(a,h)anthracene" title="Dibenz(a,h)anthracene">Dibenz[<i>a</i>,<i>h</i>]anthracene</a></li> <li><a href="/wiki/Dibenz(a,j)anthracene" title="Dibenz(a,j)anthracene">Dibenz[<i>a</i>,<i>j</i>]anthracene</a></li> <li><a href="/wiki/Pentacene" title="Pentacene">Pentacene</a></li> <li><a href="/w/index.php?title=Pentaphene&action=edit&redlink=1" class="new" title="Pentaphene (page does not exist)">Pentaphene</a></li> <li><a href="/wiki/Perylene" title="Perylene">Perylene</a></li> <li><a href="/wiki/Picene" title="Picene">Picene</a></li> <li><a href="/wiki/Tetraphenylene" title="Tetraphenylene">Tetraphenylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">6 rings</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Anthanthrene" title="Anthanthrene">Anthanthrene</a></li> <li><a href="/wiki/Benzo(ghi)perylene" title="Benzo(ghi)perylene">Benzo[<i>ghi</i>]perylene</a></li> <li><a href="/wiki/Corannulene" title="Corannulene">Corannulene</a></li> <li><a href="/wiki/Dibenzopyrenes" title="Dibenzopyrenes">Dibenzopyrenes</a></li> <li><a href="/wiki/Hexacene" title="Hexacene">Hexacene</a></li> <li><a href="/wiki/Triangulene" title="Triangulene">Triangulene</a></li> <li><a href="/wiki/Zethrene" title="Zethrene">Zethrene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">7+ rings</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Coronene" title="Coronene">Coronene</a></li> <li><a href="/wiki/Dicoronylene" title="Dicoronylene">Dicoronylene</a></li> <li><a href="/wiki/Diindenoperylene" title="Diindenoperylene">Diindenoperylene</a></li> <li><a href="/wiki/Heptacene" title="Heptacene">Heptacene</a></li> <li><a href="/wiki/Hexabenzocoronene" title="Hexabenzocoronene">Hexabenzocoronene</a> (<a href="/wiki/Hexa-cata-hexabenzocoronene" title="Hexa-cata-hexabenzocoronene">Hexa-cata-</a>)</li> <li><a href="/wiki/Kekulene" title="Kekulene">Kekulene</a></li> <li><a href="/wiki/Ovalene" title="Ovalene">Ovalene</a></li> <li><a href="/wiki/Rubicene" title="Rubicene">Rubicene</a></li> <li><a href="/wiki/Rubrene" title="Rubrene">Rubrene</a></li> <li><a href="/wiki/Sumanene" title="Sumanene">Sumanene</a></li> <li><a href="/wiki/Superphenalene" title="Superphenalene">Superphenalene</a></li> <li><a href="/wiki/Trinaphthylene" title="Trinaphthylene">Trinaphthylene</a></li> <li><a href="/wiki/Truxene" title="Truxene">Truxene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">General classes</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acene" title="Acene">Acene</a></li> <li><a class="mw-selflink selflink">Circulene</a></li> <li><a href="/wiki/Cyclacene" title="Cyclacene">Cyclacene</a></li> <li><a href="/wiki/Helicene" title="Helicene">Helicene</a></li> <li><a href="/wiki/Phenacene" title="Phenacene">Phenacene</a></li></ul> </div></td></tr></tbody></table></div> <!-- NewPP limit report Parsed by mw‐api‐ext.codfw.main‐7556f8b5dd‐tpd27 Cached time: 20241122164626 Cache expiry: 2592000 Reduced expiry: false Complications: [vary‐revision‐sha1, show‐toc] CPU time usage: 0.442 seconds Real time usage: 0.628 seconds Preprocessor visited node count: 908/1000000 Post‐expand include size: 33512/2097152 bytes Template argument size: 350/2097152 bytes Highest expansion depth: 8/100 Expensive parser function count: 1/500 Unstrip recursion depth: 1/20 Unstrip post‐expand size: 46627/5000000 bytes Lua time usage: 0.291/10.000 seconds Lua memory usage: 5219108/52428800 bytes Number of Wikibase 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