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首页> 外文期刊>Chemistry: A European journal >Efficient Syntheses of Novel Fluoro-Substituted Pentacenes and Azapentacenes: Molecular and Solid-State Properties
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Efficient Syntheses of Novel Fluoro-Substituted Pentacenes and Azapentacenes: Molecular and Solid-State Properties

机译：新型氟取代的戊烯和氮杂戊烯的高效合成：分子和固态性质

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摘要

Non-symmetrical 6,13-disubstituted pentacenes bearing trifluoromethyl and aryl substituents have been synthesized starting from pentacenequinone. Diazapentacenes with a variety of fluorine substituents were prepared either via a Hartwig-Buchwald aryl amination route or by a SNAr strategy. As a result of a non-symmetric substitution pattern containing electron-donating substituents in combination with electron-accepting fluorine substituents, the synthesized compounds feature distinct molecular dipoles. All compounds are analyzed regarding their optoelectronic properties in solution with special focus on the frontier orbital energies as well as their molecular packing in the crystal structures. The analyses of isolated molecules are complemented by thin-film studies to examine their solid-state properties. A precise comparison between these and the molecular properties gave detailed insights into the exciton binding energies of these compounds, which are explained by means of a simple model considering the molecular packing and polarizabilities.
机译：从并五苯醌开始合成具有三氟甲基和芳基取代基的非对称6，13-二取代的戊烯。通过Hartwig-Buchwald芳基胺化路线或通过SNAr策略制备具有多种氟取代基的二氮杂戊烯。由于包含给电子取代基和电子接受氟取代基的非对称取代模式，合成的化合物具有独特的分子偶极子。分析了所有化合物在溶液中的光电特性，特别关注前沿轨道能量以及它们在晶体结构中的分子堆积。分离的分子的分析得到薄膜研究的补充，以检查其固态性质。这些和分子性质之间的精确比较给出了这些化合物的激子结合能的详细见解，这是通过考虑分子堆积和极化率的简单模型来解释的。

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