Synthesis and spectroscopy of benzylamine-substituted BODIPYs for bioimaging
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AuthorRipoll, Consuelo; Cheng, Cheng; García-Fernández, Emilio; Li, Jin; Orte, Angel; Do, Hainam; Jiao, Lijuan; Robinson, David; Crovetto, Luis; Gonzalez-Vera, Juan A.; Talavera Rodríguez, Eva María; Alvarez-Pez, Jose M.; Boens, Noël; Ruedas-Rama, Maria J.
Ripoll, Consuelo... [et al.]. Synthesis and spectroscopy of benzylamine-substituted BODIPYs for bioimaging. Eur. J. Org. Chem. 2018, 2561–2571
SponsorshipThis work has been financially supported by the National Nature Science Foundation of China (Grants Nos. 21672006) and Nature Science Foundation of Anhui Province (Grants No. 1508085J07); and grant CTQ2014-56370-R from the Spanish Ministry of Economy and Competitiveness and the European Regional Development Fund (ERDF).
Three new boron dipyrromethene (BODIPY) dyes substituted with a benzylamino group at the 3-position have been synthesized from halogenated BODIPYs by nucleophilic substitution. The spectroscopic and photophysical properties have been explored in different solvents and have been compared with an analogous 8benzylaminoBODIPY derivative. The position of the benzylamino group has a signiﬁcant inﬂuence on the spectral band positions, ﬂuorescence quantum yields, and fluorescence lifetimes. The 8benzylaminoBODIPY emits in the blue range, whereas the 3substituted shows green fluorescence. Additionally, the extension of the conjugation at the 5-position of 3-benzylaminoBODIPY produces a bathochromic shift of the absorption and emission spectra. The solvent effect on their spectroscopic features has been investigated using the generalized Catalán solvent scales. Quantum-chemical calculations have been performed to assess the effect of the position of the substitution on the spectroscopic properties. Finally, the BODIPY dyes have been employed as probes in fluorescence lifetime imaging of living cells, demonstrating their high potential for bioimaging.