Achiral substituent- and stoichiometry-controlled inversion of supramolecular chirality and circularly polarized luminescence in ternary co-assemblies

Handedness inversion of supramolecular chirality and circularly polarized luminescence (CPL) in assembled systems containing more than two components with higher complexity is of prominent importance to simulate biological multicomponent species and design advanced chiral materials, but it remains a considerable challenge. Herein, we have successfully developed ternary co-assembly systems based on aromatic amino acids, vinylnaphthalene derivatives and 1,2,4,5-tetracyanobenzene with effective chirality transfer. Notably, the handedness of supramolecular chirality and CPL can be readily inverted by changing the residues of amino acids, the substituents of achiral vinylnaphthalene derivatives, or by adjusting the stoichiometric ratio. The hydrogen bonds, charge transfer interactions, and steric hindrance are proved to be the crucial factors for the chirality inversion. This flexible control over chirality not only offers insights into developing multicomponent chiral materials with desirable handedness from simple molecular building blocks, but also is of practical value for use in chiroptics, chiral sensing, and photoelectric devices. Supramolecular chirality and CPL handedness of the ternary co-assemblies can be inverted flexibly by adjusting the stoichiometric ratio or by changing the achiral substituents including the amino acid residues and the substituted ethylene groups.