Unsymmetrical photochromic bithienylethene-bridge tetraphenylethene molecular switches: Synthesis, aggregation-induced emission and information storage

Abstract

Aggregation-induced emission (AIE) active photochromic molecules have attracted growing attention for their versatile applications. Here we designed and synthesized five newly unsymmetrical photochromic diarylethene (DAE) dyads (BTE1–5) by connecting tetraphenylethene (TPE) and aromatic substituent via bithienylethene (BTE) bridge. The chemical structures of those compounds were identified by 1H NMR, 13C NMR and HRMS. The absorption and emission of these dyads were investigated by UV–vis and fluorescence spectroscopy, respectively. The results showed that all those compounds exhibited typically AIE or aggregation-induced emission enhancement (AIEE) characteristic. Particularly, when an aggregation-caused quenching (ACQ) fluorophore (triphenylamine) was grafted to the molecule, connecting with TPE via BTE-bridge, the ACQ phenomenon was dissipated and converted to an AIE luminophore, and those compounds exhibited photochromism upon irradiation with alternative UV and visible light. The solution or solid of those compounds showed distinctly fluorescence switching “ON” or “OFF” observation upon irradiation with alternative UV and visible light. It is interesting that BTE1 could be applied in recording and rewritable information storage, and the cyclization quantum yields could be affected by substituent significantly.