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 ArylatedBorondipyrromethene (BODIPY) compounds was applied that synthesis yields found to behigher than classical alkyl substituted analogues. Arylated chromophores exhibited the broaderred-shifted absorption and fluorescence bands with higher stokes shifts with regard toreference 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 compoundBDPNH2 which has amine subunit to alkyl substituted reference. The fluorescence enhancementof this compound in acidic media was associated with the inactivation of the acceptor typephotoinduced electron transfer mechanism by fluorimetric measurements. Our results arehelpful for designing new photosensitizers and for applications in the study of the molecularphotochemistry.