A Solid-State Fluorescence Switch Based on Triphenylethene-Functionalized Dithienylethene With Aggregation-Induced Emission.

Haining Zhang,Huijuan Zhu,Ziyong Li,Xinyu Gao,Lingmei Li,Yan-Ping Zhu,Limin Shen,Congmin Liu,Xiaoxiao Hu,Xiaoman Zhang

doi:10.3389/fchem.2021.665880

Haining Zhang, Huijuan Zhu + Show 8 more

Open Access

https://doi.org/10.3389/fchem.2021.665880

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Abstract

The development of novel dithienylethene-based fluorescence switches in the aggregated state, and the solid state is highly desirable for potential application in the fields of optoelectronics and photopharmacology. In this contribution, three novel triphenylethene-functionalized dithienylethenes (1–3) have been designed and prepared by appending triphenylethene moieties at one end of dithienylethene unit. Their chemical structures are confirmed by 1H NMR, 13C NMR, and HRMS (ESI). They display good photochromic behaviors with excellent fatigue resistance upon irradiation with UV or visible light in Tetrahydrofuran (THF) solution. Before irradiation with UV light, they exhibit Aggregation Induced Emission (AIE) properties and luminescence behaviors in the solid state. Moreover, upon alternating irradiation with UV/visible light, they display effective fluorescent switching behaviors in the aggregated state and the solid state. The experimental results have been validated by the Density Functional Theory (DFT) calculations. Thus, they can be utilized as novel fluorescence switches integrated in smart, solid-state optoelectronic materials and photopharmacology.

Highlights

In recent years, fluorescence switches have received increasing attention due to their potential applications in super-resolution fluorescence microscopies and optical data storage (Irie et al, 2002; Qiang et al, 2018; Yu et al, 2018)
Most normal fluorophores suffer from fluorescence weakening or quenching at high concentration or in the aggregated state, which is known as “aggregation-caused quenching” (ACQ) caused by the strong intermolecular π–π interaction or hydrogen bonding between neighboring fluorophores (Cui et al, 2016; Ma et al, 2018; Zhou et al, 2020), limiting applications of these photoswitches in the optoelectronics and photopharmacology in the future
The cyclization and cycloreversion quantum yields of dithienylethenes 1–3 are determined by comparing the reaction yield with the known yield of the compound 2-bis(2-methyl-5-phenyl-3thienyl)perfluorocyclopentene (Irie et al, 2000)

Summary

Introduction

Fluorescence switches have received increasing attention due to their potential applications in super-resolution fluorescence microscopies and optical data storage (Irie et al, 2002; Qiang et al, 2018; Yu et al, 2018). Dithienylethene (DTE), a family of classic P-type-photochromic compounds, can be reversibly transformed between ring-open and ring-closed isomers by photoirradiation, which is appealing for optical switching of fluorescence on account of high thermal stability, rapid response, and fatigue resistance (Irie, 2000; Irie et al, 2000, 2014; Tian and Yang, 2004; Zhang et al, 2014; Pu et al, 2016; Yao et al, 2016; Lubbe et al, 2017; Zhang and Tian, 2018; Li et al, 2019a; Li Z. et al, 2020). Great progress has Fluorescent-Switching in the Solid. It will be highly desirable to develop the aggregated/solid-state fluorescence switches for potential applications

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