Novel BODIPY derivatives with one 3-ethynylthiophene unit at the 2 position and an iodine at the 6 position or two 3-ethynyl units at the 2, 6 positions or the 4,4' positions were synthesized. The derivative with 4, 4' substitution emits in the green (?max 524 nm), while the 2,6 substituted derivative emits in the red (?max 595  nm). Placing a styryl group at the 3 position of the 2,6 substituted derivative through Knovengeal condensation resulted in a far red emissive BODIPY derivative (?max 635 nm). All the 3-ethynylthiophene containing compounds were taken up and accumulated in human osteosarcoma cells.  In addition, they showed phototoxicity indicating possible singlet oxygen generation. Photooxidation of 1,5-dihydroxynapthelene to juglone in the presence of 3-ethynylthiophene substituted BODIPY derivatives confirmed the singlet  oxygen generation.

Synthesis of green, red, and far red emitting 3-ethynylthiophene substituted BODIPY dyes

245th National Meeting (2013)

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