The synthesis of new aryl boron-dipyrromethene compounds: Photophysical and pH responsive properties

Abstract

In this work, a convenient protocol enabled the synthesis of novel Arylated Borondipyrromethene (BODIPY) compounds was applied that synthesis yields found to be higher than classical alkyl substituted analogues. Arylated chromophores exhibited the broader red-shifted absorption and fluorescence bands with higher stokes shifts with regard to reference Borondipyrromethene compound (4,4’-difluoro-8-phenyl-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene). We were interested in the electron transfer mechanism of compound BDPNH2 which has amine subunit to alkyl substituted reference. The fluorescence enhancement of this compound in acidic media was associated with the inactivation of the acceptor type photoinduced electron transfer mechanism by fluorimetric measurements. Our results are helpful for designing new photosensitizers and for applications in the study of the molecular photochemistry. © 2018, Turkish Chemical Society. All rights reserved.