Multi-component synthesis and enhanced photophysical study of novel azolo[1,5-a]pyrimidine based dyes

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments Pub Date : 2024-09-11 DOI:10.1016/j.dyepig.2024.112447

Semen V. Aminov , Victor V. Fedotov , Konstantin V. Savateev , Evgeny N. Ulomsky , Grigory A. Kim , Alexander S. Novikov , Albert F. Khasanov , Olga S. Taniya , Ekaterina S. Starnovskaya , Vasily A. Medvedev , Alexey A. Kalinichev , Artem S. Minin , Grigory V. Zyryanov , Vladimir L. Rusinov

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Abstract

A series of novel fluorophores were obtained based on azolo[1,5-a]pyrimidines (APs) through multicomponent and oxidation reactions, starting from aminoazoles, morpholineacrylonitrile, and 4-(dimethylamino)benzaldehyde. Photophysical studies, as well as DFT calculations have been performed for the obtained APs. Aggregation-induced emission (AIE) phenomenon was demonstrated for fluorophores containing an aromatic substituent at the C-2 position of the azolo[1,5-a]pyrimidine core. It was observed that fluorophore 6d exhibited reversible mechanochromic luminescence. Two-photon absorption cross-section was measured for all obtained APs. In addition, cell staining resulted in identical intracellular distribution under excitation at 405 nm, 488 nm and 561 nm.

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新型偶氮并[1,5-a]嘧啶基染料的多组分合成与增强光物理研究

以氨基唑、吗啉丙烯腈和 4-(二甲基氨基)苯甲醛为起点，通过多组分反应和氧化反应，获得了一系列基于偶氮并[1,5-a]嘧啶（APs）的新型荧光团。对获得的 AP 进行了光物理研究和 DFT 计算。对于在偶氮并[1,5-a]嘧啶核心的 C-2 位含有芳香取代基的荧光团，聚合诱导发射（AIE）现象得到了证实。据观察，荧光团 6d 显示出可逆的机械变色发光。对所有获得的 AP 进行了双光子吸收截面测量。此外，在 405 nm、488 nm 和 561 nm 的激发下，细胞染色结果显示出相同的细胞内分布。

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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.