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Antina, Lubov A.; Bumagina, Natalia A.; Kalinkina, Valeria A.; Lukanov, Michail M.; Ksenofontov, Alexander A.; Kazak, Alexander V.; Berezin, Mikhail B.; Antina, Elena V.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 10/2022, Volume: 278Journal Article
Display omitted Red-emitting distyryl substituted BODIPY dyes are among the most promising luminophors for bioimaging and optics applications. However, the practical application of BODIPYs is limited due to their high hydrophobicity and tendency to aggregate in aqueous organic solutions and solid phase. In this article, we propose an elegant solution to this problem. To this end, we carried out the detailed experimental and quantum-chemical study of the structural and spectral features of BF2-ms-phenyl-5,5′-bis(4-dimethylaminostyryl)-3,3′-dimethyl-2,2′-dipyrromethene (distyryl-BDP). The particular attention was paid to analysis of high sensitivity of the distyryl-BDP spectral characteristics to the solvent properties, and also the aggregation behavior features both in water-organic media and in mono- and multilayer Langmuir-Schaefer films. We selected the best conditions to obtain the hydrophilic micellar structures of distyryl-BDP with Pluronic® F127 having a high efficiency of dye solubilization. This method increasing the solubility improves the distyryl-BDP transport efficiency in physiological aqueous media. The aqueous solutions of distyryl-BDP–Pl micelles show the intense fluorescence in the phototherapy window region (λfl = 739 nm).
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