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从同手性组装到异手性组装:联萘酚基轴向手性材料电荷传输性质的一次飞跃。

From Homochiral Assembly to Heterochiral Assembly: A Leap in Charge Transport Properties of Binaphthol-Based Axially Chiral Materials.

作者信息

Chen Ming, Jiao Xuechen, Li Jing, Wu Wenting, Xin Hanshen, McNeill Christopher R, Gao Xike

机构信息

Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences , Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , China.

Department of Materials Science and Engineering , Monash University , Clayton , Victoria 3800 , Australia.

出版信息

Langmuir. 2019 May 7;35(18):6188-6195. doi: 10.1021/acs.langmuir.9b00463. Epub 2019 Apr 25.

DOI:10.1021/acs.langmuir.9b00463
PMID:30977665
Abstract

Chirality, as a fundamental symmetry property, plays an important role in molecular assembly in the solid state, impacting upon the properties and performance of organic materials. Here, heterochiral assembly was observed upon a binaphthol-based axially chiral material in the thin film state, where the heterochiral assemblies of racemic mixtures exhibit superior crystallization behavior and film morphologies than their homochiral counterparts. Additionally, a dramatic increase (nearly 2 orders of magnitudes) in electronic mobility was obtained upon switching the active layers of organic thin-film transistors from homochiral assemblies to heterochiral assemblies. This work not only gives insights into the structure-aggregation property relationships of axially chiral self-assemblies but also offers new opportunities for novel organic soft materials.

摘要

手性作为一种基本的对称性质,在固态分子组装中起着重要作用,影响着有机材料的性质和性能。在此,在薄膜状态下观察到基于联萘酚的轴向手性材料发生了异手性组装,其中外消旋混合物的异手性组装表现出比其同手性对应物更优异的结晶行为和薄膜形态。此外,当将有机薄膜晶体管的有源层从同手性组装切换为异手性组装时,电子迁移率显著提高(近2个数量级)。这项工作不仅深入了解了轴向手性自组装的结构-聚集性质关系,还为新型有机软材料提供了新的机遇。

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