Mechanochemical synthesis and optical properties of solvatochromic 2H-indazole-3,5-diones

IF 4.2 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments Pub Date : 2025-07-15 DOI:10.1016/j.dyepig.2025.113044

Sara Morasi Piperčić , Alen Bjelopetrović , Marina Juribašić Kulcsár

引用次数: 0

Abstract

Mechanochemical synthesis of 4-hydroxyazobenzene-2-carboxylic acids and their cyclization to highly-functionalized chromophores, 2-aryl-4-(arylamino)-2H-indazole-3,5-diones, is reported. Mechanism of the cyclization is suggested and supported by DFT calculations. Optical properties of azobenzenes and indazoles have been studied in solution and in the solid state using UV–vis spectroscopy, and in silico by DFT calculations. 2H-indazole-3,5-diones strongly absorb above 400 nm and show a negative solvatochromic behavior. Computational analysis of the ground-state photophysical properties for the 2H-indazole-3,5-diones showed that they are a donor-acceptor-donor (D-A-D′) system where two donor substituents (D and D’, 2-aryl and 4-arylamino groups) transfer their electron density to the central acceptor 2H-indazole unit (A).

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溶剂致变色2h -吲哚-3,5-二酮的机械化学合成及光学性质

报道了机械化学合成4-羟基偶氮苯-2-羧酸及其环化成高功能化发色团2-芳基-4-（芳基氨基）- 2h -吲哚-3,5-二酮。通过DFT计算，提出并支持了环化机理。用紫外-可见光谱法研究了偶氮苯和茚唑在溶液和固体中的光学性质，并用DFT计算了它们在硅中的光学性质。2h -吲哚-3,5-二酮在400 nm以上有很强的吸收，并表现出负的溶剂致变色行为。对2h -吲哚-3,5-二酮基态光物理性质的计算分析表明，它们是一个供体-受体-供体（D- a -D ‘）体系，两个供体取代基（D和D ’， 2-芳基和4-芳基）将它们的电子密度转移到中心受体2h -吲哚基(a)上。

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.