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

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

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.