4,4-Difluoro-3-(3-phenylisoxazol-5-yl)-8-trifluoromethyl-5-(naphthalen-2-yl)-4-bora-3a,4a-diaza-<i>s</i>-indacene

Abstract

The title compound, 4,4-difluoro-3-(3-phenylisoxazol-5-yl)-8-trifluoromethyl-5-(2-naphthalen-2-yl)-4-bora-3a,4a-diaza-s-indacene (1), was synthesized for the first time in a 62% yield by the P2O5-promoted condensation of 2,2,2-trifluoro-1-[5-(naphthalen-2-yl)-1H-pyrrol-2-yl]-ethan-1-ol (2) with 3-phenyl-5-(1H-pyrrol-2-yl)isoxazole (3) followed by the oxidation of dipyrromethane 4 and the complexation of dipyrromethene thus formed with BF3. The product fluoresces in a long wave region (651–662 nm) with a high quantum yield (0.49–0.61).

Keywords

• fluorophore BODIPY
• 2,2,2-trifluoro-1-(1<i>H</i>-pyrrol-2-yl)ethan-1-ol
• 3-phenyl-5-(1<i>H</i>-pyrrol-2-yl)isoxazole
• condensation