4,7-isoindoline-1-one and Its Boronflouride Complex. Synthesis and Spectral-Luminescent Properties

4,7-Bis(octyloxy)isoindoline-1,3-dione was obtained by the reaction of 3,6-bis(octyloxy)phthalonitrile with sodium butoxide in butanol, followed by treatment with hydrochloric acid. Its condensation with quinaldine in the presence of zinc oxide led to the formation of (E,Z)-4,7-bis(octyloxy)-3-(quinolin-2-ylmethylene)isoindoline-1-one, which was treated with BF.sub.3Û°Et.sub.2O in the presence of triethylamine in toluene to give a new unsymmetrical analogue of BODIPY, namely (Z)-2-(difluoroboryl)-4,7-bis(octyloxy)-3-(quinolin-2-ylmethylene)isoindoline-1-one. The complex exhibits a Stokes shift of 25 nm and a high relative fluorescence quantum yield (0.68). To confirm the experimental data, DFT and TD-DFT calculations were performed.