Synthesis and Luminescence Properties of (Z)-2-(Difluoroboryl)-3-(quinolin-2-ylmethylidene)-2,3-dihydro-1H-benzo[5,6][1,4]dioxino[2,3-f]isoindol-1-one, a New Unsymmetrical BODIPY Analogue
摘要
The reaction of dibenzo[b,e][1,4]dioxine-2,3-dicarbonitrile with sodium butoxide in butyl alcohol, followed by treatment with nitric acid, gave 1H-benzo[5,6][1,4]dioxino[2,3-f]isoindole-1,3(2H)-dione, which was brought into the condensation with quinaldine to obtain (E,Z)-3-(quinolin-2-ylmethylidene)-2,3-dihydro-1H-benzo[5,6][1,4]dioxino[2,3-f]isoindol-1-one. Treatment of the latter with BF3·Et2O in the presence of triethylamine in toluene afforded a new unsymmetrical BODIPY analogue, (Z)-2-(difluoroboryl)-3-(quinolin-2-ylmethylidene)-2,3-dihydro-1H-benzo[5,6][1,4]dioxino[2,3-f]isoindol-1-one. The product showed luminescence in solution with a Stokes shift of 36 nm and a high relative fluorescence quantum yield (φ = 0.72). The obtained experimental data were supported by DFT and TD-DFT calculations.