Impact of aryl extension on the proton-triggered transition switch in azaheterocycle-functionalized ESIPT fluorophores

IF 4.2 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments Pub Date : 2025-06-18 DOI:10.1016/j.dyepig.2025.112975

Timothée Stoerkler , Théo Andris , Gilles Ulrich , Adèle D. Laurent , Denis Jacquemin , Julien Massue

引用次数: 0

Abstract

This article describes the synthesis along with full photophysical characterization in both solution and solid-state of a series of 2-(2′-hydroxyphenyl)benzazole linked to an aza-heterocycle (pyridine or isoquinoline) by one or two aryl rings. The impact of the length of the spacer is investigated in the light of emission wavelength, quantum yield, sensitivity to protons and possibility of transition switch upon protonation. Correlation of first-principle calculations and experimental results help decipher the excited-state dynamics, allowing to draw and discuss hypotheses concerning the nature of the excited species.

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芳基延伸对氮杂环功能化ESIPT荧光团中质子触发跃迁开关的影响

本文描述了一系列2-（2′-羟基苯基）苯并唑的合成，并在溶液和固体中通过一个或两个芳基环连接到偶氮杂环（吡啶或异喹啉）上。从发射波长、量子产率、对质子的敏感性和质子化后跃迁开关的可能性等方面研究了间隔层长度的影响。第一性原理计算和实验结果的关联有助于破译激发态动力学，允许绘制和讨论有关激发态性质的假设。

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.