Formation of supermolecular chiral gels from l-aspartic acid-based perylenebisimides and benzene dicarboxylic acids

Abstract

Herein, supramolecular gels from L-aspartic acid-based perylenebisimides (APBI) and various isomeric benzene dicarboxylic acids (o-phthalic acid, OPA; isophthalic acid, IPA and terephthalic acid, TPA) were obtained. It has been found that spatial position of carboxyl on the benzene ring plays a key role in the gelation process, and OPA or IPA could lead to gel formation while TPA could not. Intermolecular hydrogen bonding and π–π stacking interactions have been found to guide the aggregation as determined by UV-vis spectra, fluorescence spectra and FT-IR. Moreover the chirality transfer from perylene chromophores to benzene dicarboxylic acids was detected via circular dichroism spectroscopy (CD). The interesting features of the two-component gel system may give a better understanding of supramolecular chirality.