Methoxylated bis(pentafluorophenyl)boron-β-diketonates: Synthesis, Optical Properties and Hydrolytic Stability

IF 3 4区化学 Q3 CHEMISTRY, PHYSICAL

ChemPhotoChem Pub Date : 2024-04-23 DOI:10.1002/cptc.202300317

Maxim V. Filippov, Yuriy N. Kononevich, Dmitry S. Ionov, Andrey A. Safonov, Anastasia I. Karnaeva, Viacheslav A. Sazhnikov, Mikhail V. Alfimov, Aziz M. Muzafarov

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Abstract

A series of methoxylated bis(pentafluorophenyl)boron-β-diketonates (dkB(C₆F₅)₂) with intense emission has been synthesized and characterized by a variety of physicochemical methods. The photophysical properties of the synthesized compounds were thoroughly investigated by electronic absorption, steady-state, and time-resolved fluorescence spectroscopy in both solution and solid state. The studied compounds exhibit solvatochromic behavior attributed to the intramolecular charge transfer (ICT) nature of the first excited state. The formation of exciplexes between DBMB(C₆F₅)₂ and benzene derivatives was also studied. Notably, the studied compounds display a complex luminescence profile in the solid state, featuring fluorescence, delayed fluorescence and phosphorescence emission. Furthermore, the hydrolytical stability of the complexes was assessed, demonstrating excellent resistance to hydrolysis. Estimated rate constants, determined at 60 °C, are significantly lower (90-2000 times) than those observed for the well-studied dibenzoylmethanatoboron difluoride (DBMBF₂). The incorporation of pentafluorophenyl substituents at the boron atom enables the synthesis of highly fluorescent and hydrolytically stable boron chelate complexes, suitable for sensing and bioimaging applications in water-containing environments.

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甲氧基化双（五氟苯基）硼-β-二酮：合成、光学特性和水解稳定性

通过多种物理化学方法合成并表征了一系列具有强烈发射的甲氧基化双（五氟苯基）硼-β-二酮酸盐（dkB(C6F5)2）。通过电子吸收、稳态和时间分辨荧光光谱，对合成化合物在溶液和固体状态下的光物理特性进行了深入研究。所研究的化合物表现出溶解变色行为，这归因于第一激发态的分子内电荷转移（ICT）性质。此外，还研究了 DBMB(C6F5)2 与苯衍生物之间形成的共混物。值得注意的是，所研究的化合物在固态下显示出复杂的发光特征，包括荧光、延迟荧光和磷光发射。此外，还对复合物的水解稳定性进行了评估，结果表明其具有出色的抗水解性。在 60 °C 温度下测定的估计速率常数（90-2000 倍）明显低于已被广泛研究的二苯甲酰基甲硼二氟化物（DBMBF2）。在硼原子上加入五氟苯基取代基能够合成高荧光和水解稳定的硼螯合物，适用于含水环境中的传感和生物成像应用。

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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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