A novel pyrimido[1,6-b]indazole heterocycle as a building block for the design of low-molecular-weight fluorescent probes with large Stokes shifts

IF 4.2 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments Pub Date : 2026-05-01 Epub Date: 2025-12-19 DOI:10.1016/j.dyepig.2025.113484

Raul Marques Novais , Pedro I.P. Leite , Sem Bleus , Thanh Chung Pham , Ricardo Vessecchi , Daniel Escudero , Wim Dehaen , Flavio da Silva Emery

引用次数: 0

Abstract

A novel class of pyrimido[1,6-b]indazole fluorophores was synthesized via a concise condensation featuring a 6-endo-dig cyclization. The ring system displays large Stokes shifts (99–115 nm) and positive solvatochromism, suggesting an intramolecular charge transfer. Suzuki–Miyaura cross-coupling enables π-extension to derivatives with improved quantum yields and Stokes shifts exceeding 130 nm. TD-DFT calculations corroborate these trends, highlighting their potential for advanced fluorescence-based technologies.

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一种新型嘧啶[1,6-b]吲哚唑杂环作为设计具有大斯托克斯位移的低分子量荧光探针的基础

以6-内位环化为特征，通过缩合反应合成了一类新型的嘧啶[1,6-b]吲哚唑荧光基团。环状体系表现出较大的斯托克斯位移（99 ~ 115 nm）和正溶剂变色，表明存在分子内电荷转移。Suzuki-Miyaura交叉耦合使π扩展到衍生物，提高了量子产率和Stokes位移超过130 nm。TD-DFT计算证实了这些趋势，突出了它们在先进荧光技术方面的潜力。

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.