Homochiral Supramolecular Thin Film from Self-Assembly of Achiral Triarylamine Molecules by Circularly Polarized Light

Molecules. 2020 Jan 18;25(2):402. doi: 10.3390/molecules25020402.

Abstract

Here, we report the formation of homochiral supramolecular thin film from achiral molecules, by using circularly polarized light (CPL) only as a chiral source, on the condition that irradiation of CPL does not induce a photochemical change of the achiral molecules. Thin films of self-assembled structures consisting of chiral supramolecular fibrils was obtained from the triarylamine derivatives through evaporation of the self-assembled triarylamine solution. The homochiral supramolecular helices with the desired handedness was achieved by irradiation of circularly polarized visible light during the self-assembly process, and the chiral stability of supramolecular self-assembled product was achieved by photopolymerization of the diacetylene moieties at side chains of the building blocks, with irradiation of circularly polarized ultraviolet light. This work provides a novel methodology for the generation of homochiral supramolecular thin film from the corresponding achiral molecules.

Keywords: circularly polarized light; helical systems; homochirality; self-assembly; spontaneous symmetry breaking; triarylamine.

MeSH terms

  • Amines / chemical synthesis
  • Amines / chemistry*
  • Chemistry Techniques, Synthetic*
  • Density Functional Theory
  • Light*
  • Molecular Structure
  • Polymerization

Substances

  • Amines