Enhancing photochromic properties of triphenylethylene derivatives via the modulation of intermolecular interactions

IF 3.9 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments Pub Date : 2026-05-01 Epub Date: 2026-01-11 DOI:10.1016/j.dyepig.2026.113565

Mingyao Shen , Jiamin Wu , Simin Zhang , Jindou Zou , Yi Zhou , Heyang Li , Tao Yu

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Abstract

Organic photochromic materials undergo reversible color changes upon exposure to specific wavelengths of light and have found numerous applications, including photoswitches and information storage. Triarylethylene derivatives are a promising class of organic photochromic systems due to their simple synthesis and impressive performance. However, the relationships between the construction of intermolecular interactions and photochromic properties remain unclear. Herein, three triarylethylene derivatives with different electron-withdrawing groups, namely TrPE-o-Ph, TrPE-o-PhF, and TrPE-o-PhCF₃, were designed and synthesized. Detailed photochromic studies show that all three compounds display rapid photoresponse, high photobleaching rates, and good fatigue resistance in both crystalline and amorphous powders. Notably, TrPE-o-PhCF₃ demonstrates superior saturated absorption and much longer thermal decoloration time compared to the other two derivatives. Single-crystal analysis shows that TrPE-o-PhCF₃ adopts two distinct conformations in the packing patterns, with unique dimers formed via C–H⋯F intermolecular hydrogen bonds, providing increased space for conrotatory cyclization and stability of the closed form during coloration. This design strategy of modulating intermolecular interactions to enhance photochromic properties offers a new approach to developing advanced triarylethylene photochromic materials.

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通过调节分子间相互作用增强三苯基乙烯衍生物的光致变色性能

有机光致变色材料在暴露于特定波长的光时发生可逆的颜色变化，并已发现许多应用，包括光开关和信息存储。三芳烯衍生物合成简单，性能优异，是一类很有前途的有机光致变色体系。然而，分子间相互作用的构建与光致变色性能之间的关系尚不清楚。本文设计并合成了三种具有不同吸电子基团的三芳基乙烯衍生物TrPE-o-Ph、TrPE-o-PhF和TrPE-o-PhCF3。详细的光致变色研究表明，这三种化合物在结晶和非晶粉末中都表现出快速的光响应、高的光漂白率和良好的抗疲劳性能。值得注意的是，与其他两种衍生物相比，TrPE-o-PhCF3具有更好的饱和吸收和更长的热脱色时间。单晶分析表明，TrPE-o-PhCF3在填充模式中采用两种不同的构象，通过C-H⋯F分子间氢键形成独特的二聚体，为控制环化提供了更大的空间，并在着色过程中保持了封闭形式的稳定性。这种调节分子间相互作用以增强光致变色性能的设计策略为开发先进的三芳基乙烯光致变色材料提供了新的途径。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Dyes and Pigments 工程技术-材料科学：纺织

CiteScore

8.20

自引率

13.30%

发文量

933

审稿时长

33 days

期刊介绍： Dyes and Pigments covers the scientific and technical aspects of the chemistry and physics of dyes, pigments and their intermediates. Emphasis is placed on the properties of the colouring matters themselves rather than on their applications or the system in which they may be applied. Thus the journal accepts research and review papers on the synthesis of dyes, pigments and intermediates, their physical or chemical properties, e.g. spectroscopic, surface, solution or solid state characteristics, the physical aspects of their preparation, e.g. precipitation, nucleation and growth, crystal formation, liquid crystalline characteristics, their photochemical, ecological or biological properties and the relationship between colour and chemical constitution. However, papers are considered which deal with the more fundamental aspects of colourant application and of the interactions of colourants with substrates or media. The journal will interest a wide variety of workers in a range of disciplines whose work involves dyes, pigments and their intermediates, and provides a platform for investigators with common interests but diverse fields of activity such as cosmetics, reprographics, dye and pigment synthesis, medical research, polymers, etc.