Synthesis and multi-stimuli-responsive fluorescent properties of tetraphenylethylene-armed star-shaped isomer dyes with distinct core structures

IF 4.2 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments Pub Date : 2025-09-19 DOI:10.1016/j.dyepig.2025.113257

Bingshan Zhang , Zefeng Li , Caihang Zhang, Hepeng Duan, Ping Deng, Yan Yu

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Abstract

Two isomeric star-shaped dyes (M1, M2) with tetraphenylethylene arms and distinct cores (β-enaminone vs. trimesoylamine) were synthesized via a liquid-assisted grinding mechanochemical approach. M1 was formed by Schiff base condensation, while M2 was obtained through amidation. The core structures profoundly influenced their optoelectronic properties. M2 exhibited a blueshifted absorption band and a larger optical bandgap relative to M1. Critically, M1 showed aggregation-caused quenching (ACQ), while M2 displayed aggregation-induced emission (AIE), a reversal directly driven by core isomerization. Both isomers responded to external stimuli, with M2 exhibiting exceptional Fe³⁺ sensing capability in aqueous media (THF/H₂O = 1:99, v/v), achieving a detection limit of 0.056 μM and demonstrating 1.8-fold higher sensitivity than M1. Solid-state M2 further demonstrated reversible mechanochromism, which was not observed in M1. These minor structural differences in core topology drive drastic photophysical changes, which establish a design strategy for stimuli-responsive fluorescent dyes.

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具有不同核心结构的四苯乙烯臂星形异构体染料的合成及其多刺激响应荧光特性

采用液体辅助研磨机械化学方法合成了两种具有四苯基乙烯臂和不同芯（β-胺酮和三聚氰胺）的异构体星形染料（M1, M2）。M1是席夫碱缩合生成的，M2是酰胺化生成的。核心结构深刻地影响了它们的光电性能。相对于M1， M2表现出蓝移的吸收带和更大的光带隙。关键是，M1表现为聚集引起的猝灭（ACQ），而M2表现为聚集引起的发射（AIE），这是由核心异构化直接驱动的逆转。两种异构体对外界刺激均有响应，其中M2在水介质（THF/H2O = 1:99, v/v）中表现出优异的Fe3+传感能力，检测限为0.056 μM，灵敏度比M1高1.8倍。固态M2进一步表现出可逆的机械致色性，这在M1中没有观察到。这些微小的核心拓扑结构差异驱动剧烈的光物理变化，从而建立了刺激响应荧光染料的设计策略。

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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.