NIR-FLUORESCENT ETHYL 4,7-BIS(5-ARYLTHIOPHEN-2-YL)-1,2,5-OXADIAZOLO[3,4-c]PYRIDINE-6-CARBOXYLATE

摘要

Ethyl 4,7-bis(5-bromothiophen-2-yl)-1,2,5-oxadiazolo[3,4-c]pyridine-6-carboxylate 2 reacted with phenyl-, 4-methylphenyl-, 4-methoxyphenyl-, 3,4-dimethoxyphenyl-, 1-naphthyl-, and 2-naphthyl-boronic acid to give the corresponding pi-extended 4,7-bis(5-arylthiophen-2-yl) derivatives 3a-f, which emitted fluorescence at around 700 nm in DMSO solution. The 4-methoxy and 2-naphthyl derivatives (3c and 3f) emitted fluorescence at 729 nm (13717 cm(-1), Phi = 0.02) and 714 nm (14005 cm(-1) and Phi = 0.11), respectively, with a large Stokes shift (184 and 182 nm for 3c; 4631 cm 4791 cm(-1) for 3f).