Triindolo‐Truxene Derivatives: Design, Synthesis, and Fine‐Tuning of Electronic Properties and Molecular Assembly through Molecular Engineering,Chemistry - A European Journal

当前位置： X-MOL 学术 › Chem. Eur. J. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Triindolo‐Truxene Derivatives: Design, Synthesis, and Fine‐Tuning of Electronic Properties and Molecular Assembly through Molecular Engineering
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2018-12-18 , DOI: 10.1002/chem.201804457
Jun-Bo Chen ₁ , Cen Zhou ₁ , Ru-Qiang Lu ₁ , Xin-Chang Wang ₁ , Hang Qu ₁ , Mithu Saha ₁ , Hao-Liang Liu ₁ , Hui Zhang ₁ , Xiao-Yu Cao ₁

Affiliation

Triindolo‐truxene, a C₃‐symmetric molecule with a large π‐conjugated plane, has six methylene carbon atoms and three aromatic carbon atoms that can be facilely functionalized. Herein, butyl, carbonyl, cyano, and/or malononitrile groups were introduced at six methylene carbon atoms (6‐, 14‐, 22‐ or 8‐, 16‐, 24‐positions) and/or three aromatic carbon atoms (2‐, 10‐, and 18‐positions) of triindolo‐truxene to produce eight derivatives. Their photophysical properties, electrochemical properties, and molecular assembly can be effectively modulated by substituents and substitution patterns. Incorporation of electron‐deficient groups led to redshifts in both the absorption and emission of these derivatives and also lowered their HOMO and LUMO levels. Different substitution patterns resulted in the different intramolecular donor–acceptor interactions. Electron‐deficient substituents at the methylene carbon atoms in the 6‐, 14‐, and 22‐positions led to intramolecular charge transfer from the fluorene arms to the truxene core, whereas the corresponding substitutions at the methylene carbon atoms in the 8‐, 16‐, and 24‐positions resulted in intramolecular charge transfer from the truxene core to the fluorene arms. The molecular packing in single crystals and molecular aggregation in solution are also influenced by the substituents and substitution patterns. This work provides a straightforward strategy to alter the properties of triindolo‐truxene.

中文翻译：

Triindolo-Truxene衍生物：通过分子工程学设计，合成和微调电子性质和分子组装

Triindolo-truxene，C ₃具有大π共轭面的对称分子具有6个亚甲基碳原子和3个可以容易地官能化的芳族碳原子。在此，丁基，羰基，氰基和/或丙二腈基团在六个亚甲基碳原子（6-，14-，22-或8-，16-，24位）和/或三个芳族碳原子（2-三吲哚-曲烯的10位和10位）生成八种衍生物。它们的光物理性质，电化学性质和分子组装可以通过取代基和取代模式有效地调节。缺电子基团的引入导致这些衍生物的吸收和发射均发生红移，并降低了它们的HOMO和LUMO水平。不同的取代方式导致分子内的供体-受体相互作用不同。在6位，14位和22位的亚甲基碳原子上缺乏电子的取代基导致分子内电荷从芴臂转移至戊烯核，而在8位，16位的亚甲基碳原子处有相应的取代基位置和24位位置导致分子内电荷从tr烯核转移到芴臂。单晶中的分子堆积和溶液中的分子聚集也受取代基和取代方式的影响。这项工作提供了一种简单的策略来改变triindolo-truxene的特性。和24位导致分子内电荷从from烯核转移至芴臂。单晶中的分子堆积和溶液中的分子聚集也受取代基和取代方式的影响。这项工作提供了一种简单的策略来改变triindolo-truxene的特性。和24位导致分子内电荷从from烯核转移至芴臂。单晶中的分子堆积和溶液中的分子聚集也受取代基和取代方式的影响。这项工作提供了一种简单的策略来改变triindolo-truxene的特性。

更新日期：2018-12-18

点击分享查看原文

点击收藏

阅读更多本刊最新论文