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Aggregation behavior and spectroscopic properties of red-emitting distyryl-BODIPY in aqueous solution, Langmuir-Schaefer films and Pluoronic® F127 micelles
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy ( IF 4.3 ) Pub Date : 2022-05-11 , DOI: 10.1016/j.saa.2022.121366
Lubov A Antina 1 , Natalia A Bumagina 1 , Valeria A Kalinkina 2 , Michail M Lukanov 2 , Alexander A Ksenofontov 1 , Alexander V Kazak 3 , Mikhail B Berezin 1 , Elena V Antina 1
Affiliation  

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).



中文翻译:

红色发光二苯乙烯基-BODIPY在水溶液、Langmuir-Schaefer 薄膜和 Pluoronic® F127 胶束中的聚集行为和光谱特性

发红光的二苯乙烯基取代的 BODIPY 染料是生物成像和光学应用中最有前途的发光体之一。然而,BODIPYs 的实际应用受到限制,因为它们具有高疏水性以及在水性有机溶液和固相中聚集的倾向。在本文中,我们提出了一个优雅的解决方案来解决这个问题。为此,我们对BF 2 - ms的结构和光谱特征进行了详细的实验和量子化学研究。-苯基-5,5'-双(4-二甲基氨基苯乙烯基)-3,3'-二甲基-2,2'-二吡咯亚甲基(二苯乙烯基-BDP)。特别注意分析二苯乙烯基-BDP光谱特征对溶剂性质的高灵敏度,以及水-有机介质和单层和多层Langmuir-Schaefer薄膜中的聚集行为特征。我们选择了最佳条件来获得具有高效染料溶解的 Pluronic® F127 的二苯乙烯基-BDP 的亲水胶束结构。这种增加溶解度的方法提高了二苯乙烯基-BDP 在生理水介质中的转运效率。二苯乙烯基-BDP-Pl 胶束的水溶液在光疗窗口区域(λ fl  = 739 nm)显示出强烈的荧光。

更新日期:2022-05-16
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