Faculty of Chemistry, Nicolaus Copernicus University in Toruń, Gagarina 7, 87-100 Toruń, Poland.
Department of Inorganic and Analytical Chemistry, University of Medical Sciences, Grunwaldzka 6, 60-780 Poznań, Poland.
Int J Mol Sci. 2021 Jun 23;22(13):6735. doi: 10.3390/ijms22136735.
The present study is devoted to the combined experimental and theoretical description of the photophysical properties and photodegradation of the new boron-dipyrromethene (BODIPY) derivatives obtained recently for biomedical applications, such as bacteria photoinactivation (Piskorz et al., Dyes and Pigments 2020, 178, 108322). Absorption and emission spectra for a wide group of solvents of different properties for the analyzed BODIPY derivatives were investigated in order to verify their suitability for photopharmacological applications. Additionally, the photostability of the analyzed systems were thoroughly determined. The exposition to the UV light was found first to cause the decrease in the most intensive absorption band and the appearance of the hypsochromically shifted band of similar intensity. On the basis of the chromatographic and computational study, this effect was assigned to the detachment of the iodine atoms from the BODIPY core. After longer exposition to UV light, photodegradation occurred, leading to the disappearance of the intensive absorption bands and the emergence of small intensity signals in the strongly blue-shifted range of the spectrum. Since the most intensive bands in original dyes are ascribed to the molecular core bearing the BF moiety, this result can be attributed to the significant cleavage of the BF ring. In order to fully characterize the obtained molecules, the comprehensive computational chemistry study was performed. The influence of the intermolecular interactions for their absorption in solution was analyzed. The theoretical data entirely support the experimental outcomes.
本研究致力于对新的硼二吡咯甲川（BODIPY）衍生物的光物理性质和光降解进行实验和理论描述，这些衍生物最近被用于生物医学应用，如细菌光灭活（Piskorz 等人，Dyes and Pigments 2020, 178, 108322）。为了验证它们在光药理应用中的适用性，研究了广泛的不同性质溶剂对分析的 BODIPY 衍生物的吸收和发射光谱。此外，还彻底确定了分析系统的光稳定性。首先发现，暴露在紫外光下会导致最强烈的吸收带的减少和具有相似强度的蓝移带的出现。基于色谱和计算研究，这种效应被归因于碘原子从 BODIPY 核心上的脱离。在更长时间的紫外线照射后，发生了光降解，导致强烈蓝移范围内的高强度吸收带消失，出现小强度信号。由于原始染料中最强的吸收带归因于带有 BF 部分的分子核心，因此该结果可以归因于 BF 环的显著断裂。为了充分表征所获得的分子，进行了全面的计算化学研究。分析了分子间相互作用对其在溶液中吸收的影响。理论数据完全支持实验结果。
