Understanding the effect of indole as a donor in fluorophores by the localization of acceptor

IF 4.2 3区工程技术 Q2 CHEMISTRY, APPLIED Dyes and Pigments Pub Date : 2025-02-28 DOI:10.1016/j.dyepig.2025.112735

Kai Jiang , Yao Huang , Zhaodi Wang , Xiang Tian , Aihua Wu , Weihong Liang , Bo Liu

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Abstract

Indole is widely acknowledged as a donor group in molecular luminescent materials such as dyes, probes, biomarkers and organic conductors due to its electron-rich and stable chemical properties. In order to acquire the best fluorescence properties, the structural extension of indole to the construction of donor−acceptor fluorophores should consider the substitution site on the indole ring. Herein, the indole-based positional isomers (3a−3f) with stationary acceptor structures and typical push-pull feature were utilized to describe their difference on fluorescence properties. The results have shown that the C4 isomer 3c is of the longest maximal emission wavelength, while the C6 isomer 3e is of the highest fluorescence quantum yield. Structural derivatives based on the skeleton of 3c and 3e were provided for (i) a NIR fluorophore (4), and (ii) a biocompatible fluorophore (5) resulting from the enhanced solubility and the avoidance of heavy counterion, following by its application in cell imaging.

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通过受体定位了解吲哚作为荧光团供体的作用

吲哚具有丰富的电子和稳定的化学性质，被广泛认为是染料、探针、生物标志物和有机导体等分子发光材料的供体基团。为了获得最佳的荧光性质，吲哚的结构延伸到供体-受体荧光团的构建应考虑吲哚环上的取代位点。本文利用具有固定受体结构和典型推挽特征的吲哚基位置异构体（3a−3f）来描述其荧光性质的差异。结果表明，C4异构体3c的最大发射波长最长，而C6异构体3e的荧光量子产率最高。基于3c和3e骨架的结构衍生物提供了(i)近红外荧光团(4)和（ii）生物相容性荧光团(5)，这些荧光团的溶解度增强并避免了重反离子，随后将其应用于细胞成像。

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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.