By reacting tribenzo b,e,g1,4 dioxocin-7,8-dicarbonitrile or 4,11-dimethyl-2,13-di-p-tolyltribenzo b,e,g 1,4 dioxocin-7,8-dicarbonitrile with sodium methylate in methanol followed by treatment with hydrochloric acid, 11H-dibenzo5,6:7,81,4 dioxocin2,3-fisoindole-11,13(12H)-dione and 1,8-dimethyl-3,6-di-p-tolyl-11H-dibenzo5,6:7,81,4 dioxocin2,3-fisoindole-11,13(12H)-dione were obtained, respectively. Their condensation with quinaldine followed by treatment with BFEtO in the presence of triethylamine leads to the formation of 12-difluoroboryl-13-(quinolin-2-methylene)-12,13-dihydro-11H-dibenzo5,6:7,8 1,4 dioxocin2,3-fisoindol-11-one and 12-difluoroboryl-1,8-dimethyl-13-(quinolin-2-methylene)-3,6-di-p-tolyl-12,13-dihydro-11H-dibenzo5,6:7,81,4 dioxocin2,3- fisoindol-11-one, respectively. The structure of the synthesized compounds is confirmed by elemental analysis, massspectrometry, vibrational and NMR spectroscopy. The complexes demonstrate high luminescence quantum yields (up to 0.65) with insignificant Stokes shifts (up to 15 nm). Based on DFT and TD- DFT calculations, bands in the electronic absorption spectra were assigned to specific electronic transitions.
A. A. Nabasov (Wed,) studied this question.