Blue-/near-infrared light-triggered photochromism in a reinforced acceptor-acceptor type dithienylethene with aggregation-induced emission

Jinzhao Song; Qilian Wang; Yongliang Feng; Keyu Liu; Aodi Guo; Xingrui Gao; Hemin Xu; Qianqian Nie; Jucai Wang; Haining Zhang; Hui Guo; Ziyong Li

doi:10.1016/j.saa.2024.125454

Blue-/near-infrared light-triggered photochromism in a reinforced acceptor-acceptor type dithienylethene with aggregation-induced emission

Spectrochim Acta A Mol Biomol Spectrosc. 2024 Nov 19:328:125454. doi: 10.1016/j.saa.2024.125454. Online ahead of print.

Authors

Jinzhao Song¹, Qilian Wang¹, Yongliang Feng¹, Keyu Liu¹, Aodi Guo¹, Xingrui Gao¹, Hemin Xu¹, Qianqian Nie¹, Jucai Wang¹, Haining Zhang², Hui Guo³, Ziyong Li⁴

Affiliations

¹ Luoyang Key Laboratory of Organic Functional Molecules, College of Food and Drug, College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471934, PR China.
² Luoyang Key Laboratory of Organic Functional Molecules, College of Food and Drug, College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471934, PR China. Electronic address: zhanghaining@lynu.edu.cn.
³ Luoyang Key Laboratory of Organic Functional Molecules, College of Food and Drug, College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471934, PR China. Electronic address: guohui@lynu.edu.cn.
⁴ Luoyang Key Laboratory of Organic Functional Molecules, College of Food and Drug, College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471934, PR China. Electronic address: liziyong@mails.ccnu.edu.cn.

PMID: 39579729
DOI: 10.1016/j.saa.2024.125454

Abstract

The development of photochromic dithienylethene (DTE) derivatives activated by visible light, particularly those exhibiting aggregation-induced emission (AIE) properties, is highly sought after for applications in photoelectric functional materials and biological systems. In this study, we rationally designed and successfully synthesized a novel cyanostilbene- and nitro-functionalized DTE derivative (6) featuring a reinforced acceptor (A)-DTE-acceptor (A) structural motif. Each of the two cyanostilbene fragments bearing nitrobenzene groups imparts both electron-withdrawing effects and AIE characteristics, thereby ensuring efficient visible light-driven photochromic performance. The chemical structure of compound 6 was characterized using standard techniques, including ¹H NMR, ¹³C NMR, and HRMS. As anticipated, the resulting DTE (6) demonstrates efficient photochromism in various solvents when alternately irradiated with blue light (λ = 460-470 nm) and near-infrared (NIR) light (λ = 730-740 nm). Prior to blue light irradiation, the AIE performance and solid-state luminescence behavior were assessed. Furthermore, DTE (6) exhibits enhanced photoswitching behavior within a poly(methyl methacrylate) (PMMA) film. The experimental findings are corroborated by density functional theory (DFT) calculations. Ultimately, this derivative has been successfully employed for information recording and erasing, thereby demonstrating its potential for information storage and encryption.

Keywords: Acceptor–acceptor; Aggregation-induced emission (AIE); Cyanostilbene; Dithienylethene; PMMA; Photochromism.