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Synthesis and Spectroscopy of Benzylamine‐Substituted BODIPYs for Bioimaging
Author(s) -
Ripoll Consuelo,
Cheng Cheng,
GarciaFernandez Emilio,
Li Jin,
Orte Angel,
Do Hainam,
Jiao Lijuan,
Robinson David,
Crovetto Luis,
GonzálezVera Juan A.,
Talavera Eva M.,
AlvarezPez Jose M.,
Boens Noël,
RuedasRama María Jose
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800083
Subject(s) - bathochromic shift , chemistry , bodipy , photochemistry , fluorescence , benzylamine , nucleophilic substitution , absorption (acoustics) , spectroscopy , absorption spectroscopy , derivative (finance) , organic chemistry , physics , quantum mechanics , acoustics , financial economics , economics
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 8‐benzylaminoBODIPY derivative. The position of the benzylamino group has a significant influence on the spectral band positions, fluorescence quantum yields, and fluorescence lifetimes. The 8‐benzylaminoBODIPY emits in the blue range, whereas the 3‐substituted 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 effect of solvents 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.