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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">(2.2)Paracyclophan</span></h1>
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<table class="wikitable infobox float-right" id="Vorlage_Infobox_Chemikalie" style="font-size:90%; margin-top:0; width:350px;" summary="Infobox Chemikalie">
<tbody><tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Strukturformel
</th></tr>
<tr>
<td colspan="2" class="hintergrundfarbe-basis skin-invert-image" style="text-align:center;"><span typeof="mw:File"></span>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Allgemeines
</th></tr>
<tr>
<td style="width:33%;">Name
</td>
<td>(2.2)Paracyclophan
</td></tr>
<tr>
<td>Andere Namen
</td>
<td>
<ul><li>Di-<i>p</i>-xylylen</li>
<li>Tricyclo[8.2.2.2<sup>4,7</sup>]hexadeca-4,6,10,12,13,15-hexaen</li></ul>
<ul><li>[2.2]-<i>p</i>-Cyclophan</li></ul>
</td></tr>
<tr>
<td><a href="Summenformel" title="Summenformel">Summenformel</a>
</td>
<td>C<sub>16</sub>H<sub>16</sub>
</td></tr>
<tr>
<td>Kurzbeschreibung
</td>
<td>
<p>weißer Feststoff<sup id="cite_ref-TCI_1-0" class="reference"><a href="#cite_note-TCI-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Externe Identifikatoren/Datenbanken
</th></tr>
<tr>
<td colspan="2" style="padding:0;">
<table class="mw-collapsible mw-collapsed wikitable" data-expandtext="+" data-collapsetext="−" style="border-top:none; margin:-1px; width:calc(100% + 2px);">
<tbody><tr>
<td style="width:33%;"><a href="CAS-Nummer" title="CAS-Nummer">CAS-Nummer</a>
</td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=1633-22-3">1633-22-3</a><span class="editoronly" style="display:none;"></span>
</td>
<td style="background:#FFDEAD; color:#202122; border-top:1px solid #FFDEAD; padding:0.2em 0; vertical-align:bottom; width:5%;">
</td></tr>
<tr>
<td><a href="EG-Nummer" title="EG-Nummer">EG-Nummer</a>
</td>
<td colspan="2">216-644-2
</td></tr>
<tr>
<td><a href="Europ%C3%A4ische_Chemikalienagentur" title="Europäische Chemikalienagentur">ECHA</a>-InfoCard
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://www.echa.europa.eu/de/substance-information/-/substanceinfo/100.015.132">100.015.132</a>
</td></tr>
<tr>
<td><a href="PubChem" title="PubChem">PubChem</a>
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/74210">74210</a>
</td></tr>
<tr>
<td><a href="ChemSpider" title="ChemSpider">ChemSpider</a>
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.66818.html">66818</a>
</td></tr>
<tr>
<td style="border-right:1px solid #a2a9b1;"><a href="Wikidata" title="Wikidata">Wikidata</a>
</td>
<td colspan="2"><a href="https://www.wikidata.org/wiki/Q72499536" class="extiw external" title="d:Q72499536">Q72499536</a>
</td></tr></tbody></table>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Eigenschaften
</th></tr>
<tr>
<td><a href="Molare_Masse" title="Molare Masse">Molare Masse</a>
</td>
<td>208,30 g·<a href="Mol" title="Mol">mol</a><sup>−1</sup>
</td></tr>
<tr>
<td><a href="Aggregatzustand" title="Aggregatzustand">Aggregatzustand</a>
</td>
<td>
<p>fest<sup id="cite_ref-TCI_1-1" class="reference"><a href="#cite_note-TCI-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="Dichte" title="Dichte">Dichte</a>
</td>
<td>
<p>1,229 g·cm<sup>−3</sup><sup id="cite_ref-Kathleen_Yardley_Lonsdale_2-0" class="reference"><a href="#cite_note-Kathleen_Yardley_Lonsdale-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="Schmelzpunkt" title="Schmelzpunkt">Schmelzpunkt</a>
</td>
<td>
<p>285 <a href="Grad_Celsius" title="Grad Celsius">°C</a><sup id="cite_ref-Kathleen_Yardley_Lonsdale_2-1" class="reference"><a href="#cite_note-Kathleen_Yardley_Lonsdale-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Sicherheitshinweise
</th></tr>
<tr>
<td colspan="2">
<table cellspacing="0" cellpadding="2" style="width:100%;">
<tbody><tr>
<td colspan="2" style="text-align:center"><b><a href="Global_harmonisiertes_System_zur_Einstufung_und_Kennzeichnung_von_Chemikalien" title="Global harmonisiertes System zur Einstufung und Kennzeichnung von Chemikalien">GHS-Gefahrstoffkennzeichnung</a></b><sup id="cite_ref-TCI_1-2" class="reference"><a href="#cite_note-TCI-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
<table class="hintergrundfarbe-neutral" style="text-align:center; margin-left:auto; margin-right:auto; display:flex; justify-content:center;">
<tbody><tr>
<td><i>keine GHS-Piktogramme</i>
</td></tr></tbody></table>
<p>
</p>
</td></tr>
<tr>
<td rowspan="2" width="33%" style="border-top:1px #A7A7A7 dashed; border-right:1px #A7A7A7 dashed;"><a href="H-_und_P-S%C3%A4tze" title="H- und P-Sätze">H- und P-Sätze</a>
</td>
<td style="border-top:1px #A7A7A7 dashed;">H: <span title="Untervorlage eingebunden: H-Sätze"></span><i>keine H-Sätze</i>
</td></tr>
<tr>
<td style="border-top:1px #A7A7A7 dashed;">P: <span title="Untervorlage eingebunden: P-Sätze"></span><i>keine P-Sätze</i><sup id="cite_ref-TCI_1-3" class="reference"><a href="#cite_note-TCI-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</td></tr>
</tbody></table>
</td></tr>
<tr>
<td colspan="2" style="background:#FFDEAD; color:#202122; font-size:80%; text-align:center; line-height:150%; padding:.25em;">Wenn nicht anders vermerkt, gelten die angegebenen Daten bei <a href="Standardbedingungen" title="Standardbedingungen">Standardbedingungen</a> (0 °C, 1000 hPa).
</td></tr></tbody></table><p><span class="editoronly" style="display:none;"></span>
</p><p><b>[2.2]Paracyclophan</b> ist eine <a href="Chemische_Verbindung" title="Chemische Verbindung">chemische Verbindung</a> aus der Gruppe der <a href="Cyclophane" class="mw-redirect" title="Cyclophane">Cyclophane</a>. Strukturell ist es aus zwei Benzolringen aufgebaut, die durch zwei Ethylenbrücken verknüpft sind.
</p>
<div class="mw-heading mw-heading2"><h2 id="Geschichte">Geschichte</h2></div>
<p>[2.2]Paracyclophan wurde erstmals 1949 von C. J. Brown und A. C. Farthing synthetisiert.<sup id="cite_ref-Kathleen_Yardley_Lonsdale_2-2" class="reference"><a href="#cite_note-Kathleen_Yardley_Lonsdale-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Gewinnung_und_Darstellung">Gewinnung und Darstellung</h2></div>
<p>[2.2]Paracyclophan kann durch <a href="Polymerisation" title="Polymerisation">Polymerisation</a> von <a href="Xylole" title="Xylole"><i>p</i>-Xylen</a> gewonnen werden.<sup id="cite_ref-C._J._Brown_3-0" class="reference"><a href="#cite_note-C._J._Brown-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Eigenschaften">Eigenschaften</h2></div>
<p>[2.2]Paracyclophan ist ein weißes kristallines Pulver.<sup id="cite_ref-TCI_1-4" class="reference"><a href="#cite_note-TCI-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Es besitzt eine <a href="Tetragonal" class="mw-redirect" title="Tetragonal">tetragonale</a> <a href="Kristallstruktur" title="Kristallstruktur">Kristallstruktur</a> mit der <a href="Raumgruppe" title="Raumgruppe">Raumgruppe</a> <i>P</i>4<sub>2</sub>/<i>mnm</i> (Raumgruppen-Nr. 136)<span style="display:none;">Vorlage:Raumgruppe/136</span><span class="editoronly" style="display:none;"></span>.<sup id="cite_ref-C._J._Brown_3-1" class="reference"><a href="#cite_note-C._J._Brown-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>
</p><p>Seine Formyl-, Acetyl-, Nitro- und Bromderivate können durch <a href="Elektrophile_aromatische_Substitution" title="Elektrophile aromatische Substitution">elektrophile aromatische Substitution</a> in einem Schritt erhalten werden.<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>
</p>
<dl><dd><span typeof="mw:File"></span></dd></dl>
<div class="mw-heading mw-heading2"><h2 id="Verwendung">Verwendung</h2></div>
<p>[2.2]Paracyclophan und einige seiner einfachen <a href="Derivat_(Chemie)" title="Derivat (Chemie)">Derivate</a> werden als <a href="Monomer" title="Monomer">Monomere</a> für die Herstellung aromatischer <a href="Polymere" class="mw-redirect" title="Polymere">Polymere</a> genutzt. Sie dienen auch als Modellverbindungen in der <a href="Grundlagenforschung" title="Grundlagenforschung">Grundlagenforschung</a>.<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>
</p>
<div class="mw-heading mw-heading2"><h2 id="Weblinks">Weblinks</h2></div>
<div class="sisterproject" style="margin:0.1em 0 0 0;"><div class="noresize noviewer" style="display:inline-block; line-height:10px; min-width:1.6em; text-align:center;" aria-hidden="true" role="presentation"><span class="mw-default-size" typeof="mw:File"><span title="Commons"></span></span></div><b><span class=""><a class="external text" href="https://commons.wikimedia.org/wiki/Category:Paracyclophane?uselang=de"><span lang="en">Commons</span>: (2.2)Paracyclophan</a></span></b> – Sammlung von Bildern, Videos und Audiodateien</div>
<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
<li id="cite_note-TCI-1"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-TCI_1-0">a</a></sup> <sup><a href="#cite_ref-TCI_1-1">b</a></sup> <sup><a href="#cite_ref-TCI_1-2">c</a></sup> <sup><a href="#cite_ref-TCI_1-3">d</a></sup> <sup><a href="#cite_ref-TCI_1-4">e</a></sup></span> <span class="reference-text">Eintrag zu <span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://www.tcichemicals.com/eshop/de/de/commodity/P1165">[2.2]Paracyclophane, >99.0%</a></span> bei TCI Europe, abgerufen am 27. November 2023.<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-Kathleen_Yardley_Lonsdale-2"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Kathleen_Yardley_Lonsdale_2-0">a</a></sup> <sup><a href="#cite_ref-Kathleen_Yardley_Lonsdale_2-1">b</a></sup> <sup><a href="#cite_ref-Kathleen_Yardley_Lonsdale_2-2">c</a></sup></span> <span class="reference-text">Kathleen Yardley Lonsdale, H. Judith Milledge and Krishna K. V. Rao: <cite style="font-style:italic">Studies of the structure, thermal expansion and molecular vibrations of di-p-xylylene, C16H16, at 93 and 291 °K</cite>. In: <cite style="font-style:italic">Proceedings of the Royal Society of London. Series A. Mathematical and Physical Sciences</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>255</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>1280</span>, 1960, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>82–100</span>, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1098/rspa.1960.0055">10.1098/rspa.1960.0055</a></span>.<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rfr_id=info:sid/de.wikipedia.org:%282.2%29Paracyclophan&rft.atitle=Studies+of+the+structure%2C+thermal+expansion+and+molecular+vibrations+of+di-p-xylylene%2C+C16H16%2C+at+93+and+291+%C2%B0K&rft.au=Kathleen+Yardley+Lonsdale%2C+H.+Judith+Milledge+and+Krishna+K.+V.+Rao&rft.date=1960&rft.doi=10.1098%2Frspa.1960.0055&rft.genre=journal&rft.issue=1280&rft.jtitle=Proceedings+of+the+Royal+Society+of+London.+Series+A.+Mathematical+and+Physical+Sciences&rft.pages=82-100&rft.volume=255" style="display:none"> </span></span>
</li>
<li id="cite_note-C._J._Brown-3"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-C._J._Brown_3-0">a</a></sup> <sup><a href="#cite_ref-C._J._Brown_3-1">b</a></sup></span> <span class="reference-text">C. J. Brown, A. C. Farthing: <cite style="font-style:italic">Preparation and Structure of Di-p-Xylylene</cite>. In: <cite style="font-style:italic">Nature</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>164</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>4178</span>, 1949, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>915–916</span>, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1038/164915b0">10.1038/164915b0</a></span>.<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rfr_id=info:sid/de.wikipedia.org:%282.2%29Paracyclophan&rft.atitle=Preparation+and+Structure+of+Di-p-Xylylene&rft.au=C.+J.+Brown%2C+A.+C.+Farthing&rft.date=1949&rft.doi=10.1038%2F164915b0&rft.genre=journal&rft.issue=4178&rft.jtitle=Nature&rft.pages=915-916&rft.volume=164" style="display:none"> </span></span>
</li>
<li id="cite_note-4"><span class="mw-cite-backlink"><a href="#cite_ref-4">↑</a></span> <span class="reference-text">Zahid Hassan, Eduard Spuling, Daniel M. Knoll, Stefan Bräse: <cite style="font-style:italic">Regioselective Functionalization of [2.2]Paracyclophanes: Recent Synthetic Progress and Perspectives</cite>. In: <cite style="font-style:italic">Angewandte Chemie International Edition</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>59</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>6</span>, 2020, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>2156–2170</span>, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1002/anie.201904863">10.1002/anie.201904863</a></span>, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/31283092?dopt=Abstract">PMID 31283092</a>.<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rfr_id=info:sid/de.wikipedia.org:%282.2%29Paracyclophan&rft.atitle=Regioselective+Functionalization+of+%26%2391%3B2.2%26%2393%3BParacyclophanes%3A+Recent+Synthetic+Progress+and+Perspectives&rft.au=Zahid+Hassan%2C+Eduard+Spuling%2C+Daniel+M.+Knoll%2C+...&rft.date=2020&rft.doi=10.1002%2Fanie.201904863&rft.genre=journal&rft.issue=6&rft.jtitle=Angewandte+Chemie+International+Edition&rft.pages=2156-2170&rft.pmid=31283092&rft.volume=59" style="display:none"> </span></span>
</li>
<li id="cite_note-5"><span class="mw-cite-backlink"><a href="#cite_ref-5">↑</a></span> <span class="reference-text">Henning Hopf: <cite style="font-style:italic">[2.2]Paracyclophane in Polymerchemie und Materialwissenschaften</cite>. In: <cite style="font-style:italic">Angewandte Chemie</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>120</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>51</span>, 2008, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>9954–9958</span>, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1002/ange.200800969">10.1002/ange.200800969</a></span>.<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rfr_id=info:sid/de.wikipedia.org:%282.2%29Paracyclophan&rft.atitle=%26%2391%3B2.2%26%2393%3BParacyclophane+in+Polymerchemie+und+Materialwissenschaften&rft.au=Henning+Hopf&rft.date=2008&rft.doi=10.1002%2Fange.200800969&rft.genre=journal&rft.issue=51&rft.jtitle=Angewandte+Chemie&rft.pages=9954-9958&rft.volume=120" style="display:none"> </span></span>
</li>
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