Synthesis and photophysical properties of monomeric and dimeric halogenated aza-BODIPYs

Çınar H. Ş. , Özçelik Ş. , Kaya K. , Kutlu O. D. , ERDOĞMUŞ A., Gül A.

JOURNAL OF MOLECULAR STRUCTURE, cilt.1200, 2020 (SCI İndekslerine Giren Dergi) identifier identifier


In this study, the effects of incorporation of halogen atoms at different positions and dimerization on the photophysical properties of the aza-BODIPYs were investigated. Aza-BODIPY derivative carrying chlorine atoms on the para-position of the distal phenyl groups (4) and its core-brominated analogue (5) were prepared to establish the external and internal heavy atom effects. Dimerization of aza-BODIPY 4 through oxidative homocoupling with FeCl3 yielded the target homonuclear aza-BODIPY dimer (6). All of the aza-BODIPY derivatives prepared in this study were fully characterized by using UV-Vis, Fluorescence, NMR (H-1, C-13, B-11 and F-19), Mass and X-Ray spectroscopy techniques. The photophysical properties were fully characterized and compared to those of the tetra-phenyl aza-BODIPY derivative (A). Singlet oxygen generation experiments were also performed. The aza-BODIPY derivative possessing bromine atoms at the central core displayed the utmost efficiency for singlet oxygen generation. (C) 2019 Elsevier B.V. All rights reserved.