Ratiometric Singlet Oxygen Sensor Based on BODIPY-DPA Dyad

Abstract

Compounds sensitive to reactive oxygen species are widely used in the study of processes in living cells and in the development of therapeutic agents for photodynamic therapy. In the present work, we have synthesized a dyad in which the BODIPY dye is chemically bound to 9,10-diphenylanthracene (DPA). Here, DPA acts as a specific sensor of singlet oxygen and BODIPY as a reference dye. We studied the photophysical properties of the BODIPY-DPA dyad and showed that energy transfer occurs between the chromophores. As a result, the compound has excitation maxima in the absorption region of both DPA and BODIPY, but the fluorescence emission occurs mainly from BODIPY. In the presence of singlet oxygen, the excitation maximum of DPA decreases, while the intensity of the excitation maximum of BODIPY remains almost unchanged. This allows the BODIPY-DPA dyad to be used as a ratiometric sensor of singlet oxygen.

Pd and Pt Complexes of Benzo-Fused Dipyrrins: Synthesis, Structure, Electrochemical, and Optical Properties

“…Owing to their rich and diverse coordination chemistry, they form complexes with a variety of metal ions. The most popular and stable complex of dipyrrin with boron difluoride, known as BODIPY, is widely used as a fluorophore for biomedical applications, such as imaging, − sensing, − and photodynamic therapy. − On the other hand, dipyrrin complexes with transition metals can be advantageous for catalysis, , the preparation of coordination polymers, − metal–organic frameworks, − and self-assembly of supramolecules − due to the facile complexation reactions.…”