Photochemical Properties and Stability of BODIPY Dyes
| Autor: | Szymon Bocian, Marta Ziegler-Borowska, Jaroslaw Piskorz, Dariusz Kędziera, Anna Kaczmarek-Kedziera, Aleksander Smolarkiewicz-Wyczachowski, Patryk Rybczynski |
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| Rok vydání: | 2021 |
| Předmět: |
Boron Compounds
Materials science Absorption spectroscopy QH301-705.5 Molecular Conformation DFT calculations 010402 general chemistry Photochemistry 01 natural sciences Article Catalysis Inorganic Chemistry chemistry.chemical_compound BODIPY Molecule Emission spectrum Biology (General) Physical and Theoretical Chemistry Absorption (electromagnetic radiation) Photodegradation QD1-999 Molecular Biology Density Functional Theory Spectroscopy Fluorescent Dyes absorption spectrum Photolysis 010405 organic chemistry Organic Chemistry Intermolecular force General Medicine 0104 chemical sciences Computer Science Applications Chemistry Spectrometry Fluorescence chemistry Absorption band Solvents Spectrophotometry Ultraviolet photodegradation Iodine |
| Zdroj: | International Journal of Molecular Sciences, Vol 22, Iss 6735, p 6735 (2021) International Journal of Molecular Sciences Volume 22 Issue 13 |
| ISSN: | 1422-0067 |
| DOI: | 10.3390/ijms22136735 |
| Popis: | 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 BF2 moiety, this result can be attributed to the significant cleavage of the BF2 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. |
| Databáze: | OpenAIRE |
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