Synthesis and Photophysical Study of 3-(Isoxazol-5-yl)Coumarins

IF 3 4区化学 Q3 CHEMISTRY, PHYSICAL

ChemPhotoChem Pub Date : 2025-02-17 DOI:10.1002/cptc.202400389

María-C. Ríos, Néstor-F. Bravo, Mario Macías, Bernardo A. Iglesias, Jaime Portilla

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Abstract

Herein, efficient synthesis and photophysical study of three novel dyes based on 3-(isoxazol-5-yl)coumarins were developed, and their structures were confirmed by X-ray crystallography. The access to these fluorophores implied two condensation reaction steps under microwave conditions, starting from 3-acetylcoumarins and ending with the cyclization of the respective β-enaminone intermediate with hydroxylamine hydrochloride. By investigating solvatofluorochromism, acidochromism, and properties in the solid state, it was possible to establish that the optical properties of these dyes are coumarin ring-dependent, which was supported by TD-DFT calculations. In addition, fluorescence quantum yields (Φ_F) up to 36 % with short lifetimes decay (1.40–4.60 ns) were accompanied by a redshift behavior with electro-donating coumarins. Remarkably, solid-state studies showed a higher emission of the unsubstituted coumarin (Φ_F=64 %) due to significant supramolecular interactions; in addition, acidochromism experiments using TFA were performed, finding detection limits of up to 1.03 μM.

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3-（异恶唑-5-酰基）香豆素的合成及光物理研究

本文以3-（异恶唑-5-酰基）香豆素为原料制备了三种新型染料，并对其进行了光物理研究，并通过x射线晶体学对其结构进行了表征。这些荧光团的获得意味着在微波条件下的两个缩合反应步骤，从3-乙酰香豆素开始，以相应的β-胺酮中间体与盐酸羟胺环化结束。通过研究固体状态下的溶剂致荧光性、酸致变色性和性质，可以确定这些染料的光学性质与香豆素环有关，这得到了TD-DFT计算的支持。此外，荧光量子产率（ΦF）高达36%，寿命衰减短（1.40-4.60 ns），伴有电致香豆素的红移行为。值得注意的是，固态研究表明，由于显著的超分子相互作用，未取代香豆素的发射量更高（ΦF= 64%）；此外，利用TFA进行了酸致变色实验，检测限高达1.03 μM。

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来源期刊

ChemPhotoChem Chemistry-Physical and Theoretical Chemistry

CiteScore

5.80

自引率

5.40%

发文量

165

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