Self-assembly of luminescent twisted fibers based on achiral quinacridone derivatives

Abstract

It is a great challenge to spontaneously assemble achiral molecules into twisted nanostructures in the absence of chiral substances. Here we show that two achiral centrosymmetric quinacridone (QA) derivatives, N,N′-di(n-hexyl)-1, 3, 8, 10-tetramethylquinacridone (C6TMQA) and N,N′-di(n-decyl)-1, 3, 8, 10-tetramethylquinac ridone (C10TMQA), can be employed as building blocks to fabricate well-defined twisted nanostructures by controlling the solvent composition and concentration. Bowknot-like bundles with twisted fiber arms were prepared from C6TMQA, whilst uniform twisted fibers were generated from C10TMQA in ethanol/THF solution. Spectroscopic characterization and molecular simulation calculations revealed that the introduction of ethanol into the solution could induce a staggered aggregation of C6TMQA (or C10TMQA) molecules and the formation of twisted nanostructures. Such twisted materials generated from achiral organic functional molecules may be valuable in the design and fabrication of new materials for optoelectronic applications.