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

Sujun Wang; Hui Zhou; Chunlin Xiong; Lin Zhou; Jingfang Han; Xiaohan Cao; Si Chen; Ziyong Li

doi:10.1016/j.saa.2023.122488

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

Spectrochim Acta A Mol Biomol Spectrosc. 2023 Jun 5:294:122488. doi: 10.1016/j.saa.2023.122488. Epub 2023 Feb 11.

Authors

Sujun Wang¹, Hui Zhou¹, Chunlin Xiong¹, Lin Zhou¹, Jingfang Han¹, Xiaohan Cao¹, Si Chen¹, Ziyong Li²

Affiliations

¹ Luoyang Key Laboratory of Organic Functional Molecules, College of Food and Drug, Luoyang Normal University, Luoyang 471934, PR China.
² Luoyang Key Laboratory of Organic Functional Molecules, College of Food and Drug, Luoyang Normal University, Luoyang 471934, PR China. Electronic address: liziyong@mails.ccnu.edu.cn.

PMID: 36822121
DOI: 10.1016/j.saa.2023.122488

Abstract

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.

Keywords: Acceptor–acceptor; Diestervinyl; Dithienylethene; Fluorescence switch; PMMA; Photochromism.