NIR halogenated thieno[3, 2-b]thiophene fused BODIPYs with photodynamic therapy properties in HeLa cells

Commonly, an efficient photosensitizer usually requires a number of excellent properties, such as a larger molar absorption coefficient in the tissue transparency window, a high intersystem spin-crossing (ISC) probability induced by heavy atom and low dark toxicity as well as high photostability. In this study, NIR tetra-bromo thieno[3,2-b]thiophene-fused BODIPYs derivatives 3 was prepared, and fully characterized. Their photophysical properties have been well investigated including absorption, fluorescence profiles and photostability. The novel BODIPYs 2-3 possess long wavelength absorptions of maximum up to 720 nm with large molar absorption coefficients due to extend the effect of π-conjugation system via fusion the thieno[3,2-b]thiophene group. Especially, BODIPY 3 containing heavy atoms (four bromine atoms) exhibits photocytotoxicity upon irradiation with light NIR laser based on the results of MTT assays and flow analyses in living HeLa cells, in the meanwhile, it features lower cytotoxic in the dark. The current research work will contribute to the development of functional dyes and new organic NIR photosensitizer agents.