Photochemical Properties and Stability of BODIPY Dyes

Patryk Rybczynski,Aleksander Smolarkiewicz-Wyczachowski,Jaroslaw Piskorz,Dariusz Kędziera,Szymon Bocian,Anna Kaczmarek-Kędziera,Marta Ziegler-Borowska

doi:10.3390/ijms22136735

Patryk Rybczynski, Aleksander Smolarkiewicz-Wyczachowski + Show 5 more

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https://doi.org/10.3390/ijms22136735

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Abstract

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.

Highlights

Published: 23 June 2021Photophysical and photochemical phenomena are nowadays indispensable and common in various fields of modern science, technology and medicine [1]
This effect is pronounced in both systems, 1 and 2, due to the evident stacking interaction between the BODIPY core and the phthalimide substituent, independently, on the iodine presence
The present study devoted to the photostability of the two BODIPY derivatives, synthesized previously for bacteria photoinactivation, combines the theoretical and chromatographic approaches

Summary

Introduction

Photophysical and photochemical phenomena are nowadays indispensable and common in various fields of modern science, technology and medicine [1] Among their applications of particular importance for everyday life comfort, the photocatalytic oxidation processes of environmental pollutants (for instance, bisphenol A, p-aminobenzoic acid, etc.) [2,3] or novel developments in photodynamic therapy (PDT) can be mentioned. Photodynamic therapy has gained large interest, due to its weak side effects, as an alternative to damaging surgical, chemo- and radiotherapeutic treatment [4,5,6]. It is applied frequently in microbial illnesses, acne, psoriasis or several malignant types of tumors. Via the intersystem crossing, the triplet state of the photosensitizer can be generated and, further on its energy, can be transferred to the oxygen present in the cells

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