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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">PTCDA</span></h1>
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<div id="mw-content-text" class="mw-body-content mw-content-ltr" lang="de" dir="ltr"><div class="mw-content-ltr mw-parser-output" lang="de" dir="ltr"><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>
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<th colspan="2" style="background:#FFDEAD; color:#202122;">Allgemeines
</th></tr>
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<td style="width:33%;">Name
</td>
<td>PTCDA
</td></tr>
<tr>
<td>Andere Namen
</td>
<td>
<ul><li>3,4,9,10-Perylen-tetracarbonsäure-dianhydrid</li>
<li>Perylen-3,4:9,10-tetracarbonsäuredianhydrid</li>
<li><a href="Colour_Index" title="Colour Index">C.I.</a> 71127</li>
<li>C.I. Pigment Red 224</li></ul>
</td></tr>
<tr>
<td><a href="Summenformel" title="Summenformel">Summenformel</a>
</td>
<td>C<sub>24</sub>H<sub>8</sub>O<sub>6</sub>
</td></tr>
<tr>
<td>Kurzbeschreibung
</td>
<td>
<p>dunkelroter Feststoff<sup id="cite_ref-sigma_1-0" class="reference"><a href="#cite_note-sigma-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=128-69-8">128-69-8</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">204-905-3
</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/100.004.461">100.004.461</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/67191">67191</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/Q905520" class="extiw external" title="d:Q905520">Q905520</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>392,32 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
</p>
</td></tr>
<tr>
<td><a href="Schmelzpunkt" title="Schmelzpunkt">Schmelzpunkt</a>
</td>
<td>
<p>>300 <a href="Grad_Celsius" title="Grad Celsius">°C</a><sup id="cite_ref-roempp_2-0" class="reference"><a href="#cite_note-roempp-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="L%C3%B6slichkeit" title="Löslichkeit">Löslichkeit</a>
</td>
<td>
<ul><li>sehr schlecht löslich in Wasser (0,87 g·l<sup>−1</sup> bei 20 °C)<sup id="cite_ref-roempp_2-1" class="reference"><a href="#cite_note-roempp-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li>
<li>löslich in <a href="N-Methyl-2-pyrrolidon" title="N-Methyl-2-pyrrolidon">NMP</a> und <a href="Dimethylformamid" title="Dimethylformamid">DMF</a><sup id="cite_ref-Jiao_3-0" class="reference"><a href="#cite_note-Jiao-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></li>
<li>nahezu unlöslich in kaltem, aber löslich in heißem <a href="Tetrahydrofuran" title="Tetrahydrofuran">THF</a><sup id="cite_ref-Jiao_3-1" class="reference"><a href="#cite_note-Jiao-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></li>
<li>nahezu unlöslich in <a href="Chloroform" title="Chloroform">Chloroform</a> und <a href="Dichlormethan" title="Dichlormethan">Dichlormethan</a><sup id="cite_ref-Jiao_3-2" class="reference"><a href="#cite_note-Jiao-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></li></ul>
</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-GESTIS_4-0" class="reference"><a href="#cite_note-GESTIS-4"><span class="cite-bracket">[</span>4<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-GESTIS_4-1" class="reference"><a href="#cite_note-GESTIS-4"><span class="cite-bracket">[</span>4<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>3,4,9,10-Perylentetracarbonsäuredianhydrid</b> (<b>PTCDA</b>) ist ein <a href="Pigment" class="mw-redirect" title="Pigment">Pigment</a>, das in der Entwicklung <a href="Organische_Verbindung" class="mw-redirect" title="Organische Verbindung">organischer</a> <a href="Halbleiter" title="Halbleiter">Halbleiter</a>-Bauelemente verwendet und von der <a href="Farbmittel" title="Farbmittel">Farbmittel</a>-Industrie für kommerzielle Anwendungen hergestellt wird.
</p>
<div class="mw-heading mw-heading2"><h2 id="Struktur">Struktur</h2></div>
<p>Es basiert in seiner molekularen Struktur auf dem <a href="Polycyclische_aromatische_Kohlenwasserstoffe" title="Polycyclische aromatische Kohlenwasserstoffe">polycyclischen aromatischen Kohlenwasserstoff</a> <a href="Perylen" title="Perylen">Perylen</a>.
Von der Kristallstruktur<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> sind zwei Modifikationen bekannt (alpha und beta).<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> Die zweidimensionale Struktur von PTCDA-Schichten, die sich durch <a href="Molekularstrahlepitaxie" title="Molekularstrahlepitaxie">Molekularstrahlepitaxie</a> erzeugen lässt, wurde auf verschiedenen Substraten mittels <a href="Rastertunnelmikroskop" title="Rastertunnelmikroskop">Rastertunnelmikroskopie</a> eingehend untersucht, darunter <a href="Graphit" title="Graphit">Graphit</a>, <a href="Molybd%C3%A4n" title="Molybdän">Molybdändisulfid</a> (MoS<sub>2</sub>)<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>, <a href="Kupfer" title="Kupfer">Kupfer</a><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> und Silber.<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> Neben diesen metallischen Substraten wurde auch die Epitaxie auf verschiedenen Isolatoroberflächen wie NaCl<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><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>, KCl<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><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> und KBr<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> untersucht.
</p>
<div class="mw-heading mw-heading2"><h2 id="Eigenschaften">Eigenschaften</h2></div>
<p>PTCDA ist ein planares Molekül mit einem zweidimensional konjugierten π-Elektronensystem, welches über das gesamte Perylengerüst delokalisiert ist.<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> Das <a href="Anhydrid" class="mw-redirect" title="Anhydrid">Anhydrid</a> ist ein <a href="Organische_Halbleiter" title="Organische Halbleiter">organischer Halbleiter</a> (n-Leiter)<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> aus der Gruppe der zweidimensional kondensierten Ringsysteme.
</p>
<div class="mw-heading mw-heading2"><h2 id="Verwendung">Verwendung</h2></div>
<p>Als <a href="Organische_Halbleiter" title="Organische Halbleiter">organischer Halbleiter</a> lässt sich PTCDA z. B. für die Herstellung von <a href="Organischer_Feldeffekttransistor" title="Organischer Feldeffekttransistor">organischen Feldeffekttransistoren</a><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> verwenden. <a href="Derivat_(Chemie)" title="Derivat (Chemie)">Derivate</a> der PTCDA lassen sich als Schicht in organischen <a href="Solarzelle" title="Solarzelle">Solarzellen</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> einsetzen oder dienen als <a href="Adsorption" title="Adsorption">Adsorbat</a> zur <a href="Fluoreszenz" title="Fluoreszenz">Sensibilisierung</a> von <a href="Titandioxid" class="mw-redirect" title="Titandioxid">Titandioxid</a>-Solarzellen für sichtbares <a href="Licht" title="Licht">Licht</a>.<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> PTCDA eignet sich zudem als <a href="Photokatalyse" title="Photokatalyse">Photokatalystor</a> zur <a href="Sauerstoff" title="Sauerstoff">Sauerstoff</a>-Produktion aus <a href="Wasser" title="Wasser">Wasser</a> mittels <a href="Sonnenenergie" title="Sonnenenergie">Sonnenenergie</a>.<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><p>Als <a href="Pigment" class="mw-redirect" title="Pigment">Pigment</a> wird PTCDA vor allem in hochwertigen Industrie-<a href="Lack" title="Lack">Lacken</a>, insbesondere im <a href="Automobil" title="Automobil">Automobil</a>-Bereich, eingesetzt.<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-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
<li id="cite_note-sigma-1"><span class="mw-cite-backlink"><a href="#cite_ref-sigma_1-0">↑</a></span> <span class="reference-text">Datenblatt <span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/catalog/product/ALDRICH/P11255">Perylene-3,4,9,10-tetracarboxylic dianhydride</a></span> bei <a href="Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a>, abgerufen am 5. November 2018 (<a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/DE/de/sds/ALDRICH/P11255?userType=anonymous">PDF</a>).<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-roempp-2"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-roempp_2-0">a</a></sup> <sup><a href="#cite_ref-roempp_2-1">b</a></sup></span> <span class="reference-text">Eintrag zu <a rel="nofollow" class="external text" href="https://roempp.thieme.de/lexicon/RD-16-01241"><i>Perylen-3,4,9,10-tetracarbonsäuredianhydrid</i></a>. In: <i><a href="R%C3%B6mpp_Online" class="mw-redirect" title="Römpp Online">Römpp Online</a>.</i> Georg Thieme Verlag, abgerufen am 28. März 2014.<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-Jiao-3"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Jiao_3-0">a</a></sup> <sup><a href="#cite_ref-Jiao_3-1">b</a></sup> <sup><a href="#cite_ref-Jiao_3-2">c</a></sup></span> <span class="reference-text">Chun Ming Jiao, Bing Jun Li, Si Li Yi, Qing Xu: <cite class="lang" lang="en" dir="auto" style="font-style:italic">Synthesis and Photoelectric Properties of Donor-Acceptor-Donor Molecule Containing Perylene Diimide</cite>. In: <cite class="lang" lang="en" dir="auto" style="font-style:italic">Asian Journal of Chemistry</cite>. 26. Jahrgang, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>23</span>, 2014, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>8049–8052</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/10.14233/ajchem.2014.17040">10.14233/ajchem.2014.17040</a></span> (englisch).<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:PTCDA&rft.atitle=Synthesis+and+Photoelectric+Properties+of+Donor-Acceptor-Donor+Molecule+Containing+Perylene+Diimide&rft.au=Chun+Ming%26%2332%3BJiao%2C%26%2332%3BBing+Jun%26%2332%3BLi%2C%26%2332%3BSi+Li%26%2332%3BYi%2C+...&rft.date=2014&rft.doi=10.14233%2Fajchem.2014.17040&rft.genre=journal&rft.issue=23&rft.jtitle=Asian+Journal+of+Chemistry&rft.pages=8049-8052&rft.volume=26.+Jahrgang" style="display:none"> </span></span>
</li>
<li id="cite_note-GESTIS-4"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-GESTIS_4-0">a</a></sup> <sup><a href="#cite_ref-GESTIS_4-1">b</a></sup></span> <span class="reference-text">Eintrag zu <span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://gestis.dguv.de/data?name=492891">Perylen-3,4:9,10-tetracarbonsäuredianhydrid</a></span> in der <a href="GESTIS-Stoffdatenbank" title="GESTIS-Stoffdatenbank">GESTIS-Stoffdatenbank</a> des <a href="Institut_f%C3%BCr_Arbeitsschutz_der_Deutschen_Gesetzlichen_Unfallversicherung" title="Institut für Arbeitsschutz der Deutschen Gesetzlichen Unfallversicherung">IFA</a>, abgerufen am 20. November 2022.<small class="noscript"><span></span> (JavaScript erforderlich)</small></span>
</li>
<li id="cite_note-5"><span class="mw-cite-backlink"><a href="#cite_ref-5">↑</a></span> <span class="reference-text">T. Ogawa et al.: <i>3,4:9,10-Perylenetetracarboxylic dianhydride (PTCDA) by electron crystallography</i>. In: <i><a href="Acta_Cryst." class="mw-redirect" title="Acta Cryst.">Acta Cryst.</a></i> B55, 1999, S. 123–130.</span>
</li>
<li id="cite_note-6"><span class="mw-cite-backlink"><a href="#cite_ref-6">↑</a></span> <span class="reference-text">H. P. Wagner et al.: <i>Exciton emission in PTCDA films and PTCDA / Alq3 multilayers</i>. In: <i><a href="Physical_Review_B" class="mw-redirect" title="Physical Review B">Physical Review B</a></i> 70, 2004, S. 235201.</span>
</li>
<li id="cite_note-7"><span class="mw-cite-backlink"><a href="#cite_ref-7">↑</a></span> <span class="reference-text">C. Ludwig et al.: <i>STM investigations of PTCDA and PTCDI on graphite and MoS2. A systematic study of epitaxy and STM image contrast</i>. In: <i><a href="Zeitschrift_f%C3%BCr_Physik" title="Zeitschrift für Physik">Z. Phys. B</a></i> 93, 1994, S. 365–373.</span>
</li>
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<li id="cite_note-10"><span class="mw-cite-backlink"><a href="#cite_ref-10">↑</a></span> <span class="reference-text">Burke et al., <a href="Phys._Rev._Lett." class="mw-redirect" title="Phys. Rev. Lett.">Phys. Rev. Lett.</a> 100, 186104 (2008).</span>
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<li id="cite_note-14"><span class="mw-cite-backlink"><a href="#cite_ref-14">↑</a></span> <span class="reference-text">Kunstmann et al., <a href="Phys._Rev._B" class="mw-redirect" title="Phys. Rev. B">Phys. Rev. B</a> 71, 121403 (2005).</span>
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