Abstract
Mono and di-heteroaryl-4,4′-difluoro-8-(aryl)-4-bora-3a,4a-diaza-s-indacene (BODIPy) (1–5) were synthesized using Suzuki–Miyaura couplings. Hetero aryl substitution on 3- or 3,5-positions caused large bathochromic shifts (up to ∼150nm) in absorption (569–652nm) and fluorescence maxima (586–679nm) in comparison to classical BODIPy. Quantum yields were found to be as high as 0.65. Singlet oxygen production activities of these compounds were studied by monitoring the absorbance quenching of 1,3-diphenylisobenzofuran, on exposure to light (>600nm). Cellular uptake of compound 4 was demonstrated using cervical cancer cells and fibroblast cell line and was confirmed by the images obtained using confocal microscope.
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