Diestervinyl-functionalized acceptor-acceptor type dithienylethenes with efficient photochromic performance

Exploring novel dithienylethenes (DTEs) with efficient photochromism has drawn increasing attention in virtue of the potential applications for photoelectric functional materials. In this contribution, we presented two novel acceptor-acceptor (A-A) type DTE derivatives (4a and 4b) by incorporating the diestervinyl moieties with strong electron-withdrawing capacity into two sides of DTE skeleton. The corresponding structures were well confirmed by the NMR (1H and 13C) and HRMS. When irradiated alternately with ultraviolet and visible light, 4a and 4b showed efficient photochromism in toluene, chloroform and DMSO, clearly implying a solvent-dependence feature. Moreover, excellent photoswitching behaviors were also observed in the poly(methyl methacrylate) (PMMA) film. The density functional theory (DFT) calculations suggested that strong Acceptor-Acceptor effect plays a dominative role in the efficient photochromic performance. Hence, this study will provide a useful guidance for developing high-performance DTE derivatives in multi-media.

Automated summary

Two novel acceptor-acceptor (A-A) type DTE derivatives (4a and 4b) were synthesized with efficient photochromism. The molecules showed solvent-dependence and excellent photoswitching behaviors in different solvents and polymer films. The study also revealed the dominant role of strong acceptor effects in the photochromic performance.