Isomerically Fused Benzo[i]dithiophenephenazine and Benzo[i]diselenophenephenazine: Synthesis, Crystal Packing, and Density Functional Theory Calculations,Crystal Growth & Design

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Isomerically Fused Benzo[i]dithiophenephenazine and Benzo[i]diselenophenephenazine: Synthesis, Crystal Packing, and Density Functional Theory Calculations
Crystal Growth & Design ( IF 3.2 ) Pub Date : 2020-05-18 , DOI: 10.1021/acs.cgd.0c00290
Di Tian ₁ , Zhiying Ma ₂ , Luomeng Gu ₁ , Congsheng Zhou ₁ , Chunli Li ₂ , Zhihua Wang ₁ , Hua Wang ₂

Affiliation

Creating functional organic semiconductors with cofacial molecular packing requires balancing several competing types of noncovalent intermolecular interactions. Through the synthesis of a series of fused benzo[i]dithiophenephenazine and benzo[i]diselenophenephenazine compounds, we demonstrate that it can encourage cofacial packing and thus increase the amount of π-orbital overlap through the introduction of soft polarizable and electron-rich sulfur/selenium atoms into electron-deficient N-containing heteroaromatics. In certain isomers, the chalcogen in the correct position coupled with trimethylsilyl substituents can generate a cofacial π–π stacked lamellar motif. Density functional theory calculations demonstrate that the cofacial lamellar motif improves the charge transport properties of these compounds, providing a way to enhance electron transport in functional organic materials.

中文翻译：

异构融合的苯并[ i ]二噻吩吩嗪和苯并[ i ]二硒吩吩嗪：合成，晶体堆积和密度泛函理论计算

创建具有界面分子堆积的功能性有机半导体需要平衡几种竞争类型的非共价分子间相互作用。通过合成一系列稠合的苯并[ i ]二噻吩吩嗪和苯并[ i]]二硒吩吩嗪化合物，我们证明它可以通过将柔软的可极化和富电子的硫/硒原子引入缺电子的含氮杂芳族化合物中来促进界面堆积，从而增加π轨道重叠量。在某些异构体中，硫属元素在正确的位置与三甲基甲硅烷基取代基结合可产生π-π堆叠的层状基序。密度泛函理论计算表明，界面层状基序可改善这些化合物的电荷传输性质，从而提供一种增强功能性有机材料中电子传输的方式。

更新日期：2020-07-01

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