Synthesis and photophysical properties of 6-aryl-2,4-bis(2′-hydroxyphenyl)pyrimidines ligands and their boron fluoride complexes

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments Pub Date : 2025-01-20 DOI:10.1016/j.dyepig.2025.112660

Clément Diguet , Amparo Navarro , M. Paz Fernández-Liencres , Sonia B. Jiménez-Pulido , Nuria A. Illán-Cabeza , Julien Massue , Sébastien Gauthier , Françoise Robin-le Guen , Sylvain Achelle , Julián Rodríguez-López

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Abstract

A new family of 6-aryl-2,4-bis(2′-hydroxyphenyl)pyrimidines has been efficiently synthesized and characterized using Suzuki-Miyaura reactions, demonstrating their ability to function as rigid tridentate O^N^O chelating ligands for the preparation of four-coordinate organoboron compounds. Similar to related structures, the uncoordinated compounds do not exhibit fluorescence in either solution or the solid state. The intramolecular hydrogen bonds in their molecular structure promote an excited-state intramolecular proton transfer (ESIPT) process, leading to an excited keto tautomer that deactivates through non-radiative decay. Protonation and boron complexation can successfully inhibit the ESIPT process, resulting in fluorescence recovery, which can be finely tuned by modifying the substituents on the aryl group. Advanced techniques, including X-ray diffraction, density functional theory (DFT), and time-dependent DFT (TD-DFT), provide critical insights into the electronic structure and emission properties. This work offers a deeper understanding of the role of boron chelation in modulating emission properties, opening new avenues for the design of functional fluorescent materials.

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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.