Abstract
4,7-Bis(octyloxy)isoindoline-1,3-dione was obtained by reacting 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 leads to the formation of ( E , Z )-4,7-bis(octyloxy)-3-(quinolin-2-ylmethylene)isoindolin-1-one, which was treated with BF3۰Et2O in the presence of triethylamine in toluene to give a new unsymmetrical analogue of BODIPY - ( Z )-2-(difluoroboryl)-4,7-bis(octyloxy)-3-(quinolin-2-ylmethylene)isoindolin-1-one. The complex exhibits a Stokes shift of 25 nm and a high relative fluorescence quantum yield (0.68). To support the experimental data, DFT and TD-DFT calculations were performed.
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