화학공학소재연구정보센터
Journal of Physical Chemistry B, Vol.117, No.18, 5533-5539, 2013
Singlet Oxygen Generation and Triplet Excited-State Spectra of Brominated BODIPY
The excited triplet-, singlet-, and ground-state properties as well as singlet oxygen generation capability of four brominated BODIPY dyes were measured in toluene with laser flash photolysis, fluorescence spectroscopy, time-correlated single-photon counting, and absorption spectroscopy. The triplet-triplet (T-1-T-n) absorption spectra were identified for four dyes 1B, 2B, 4B, and 6B substituted with one, two, four, and six Br atoms, respectively. The triplet quantum yield (Phi(T)) of a usual BODIPY dye is negligible and has rarely been studied. So is the case for the parent compound 0B (8-phenyl boron-dipyrromethene), in which no Br atom is present. The substitution of the first Br atom into the pi ring of BODIPY allowed a dramatic increase of Phi(T) from 0.0 of 0B to 0.39 for 1B. The further addition of Br number increased Phi(T) to 0.46, 030, and 0.66 for 2B, 4B, and 6B, respectively. The triplet lifetimes tau(T) are also fairly long, which is 43, 39, 36, and 26 mu s, for 1B, 2B, 4B and 6B, respectively. The brominated BODIPY dyes are therefore efficient singlet oxygen photosensitizers with the formation quantum yield of 0.39, 0.45, 0.49, and 0.64 for 1B, 2B, 4B, and 6B, respectively. The result indicates their potential application in photodynamic therapy of cancer. The fluorescence properties of the dyes were also measured.