Synthesis, optical, and electrochemical properties of 2,3-diphenyl-10H-indeno[1,2-g]quinoxaline, 15H-dibenzo[a,c]indeno[1,2-i]phenazine, and 15H-indeno[1,2-i]phenanthro[4,5-abc]phenazine derivatives

•2,3-Diphenyl-10H-indeno[1,2-g]quinoxaline derivatives were synthesized.•15H-Dibenzo[a,c]indeno[1,2-i]phenazine derivatives were synthesized.•15H-Indeno[1,2-i]phenanthro[4,5-abc]phenazine derivatives were synthesized.•The UV–visible absorption and fluorescence properties were studied.•The structure–electro-optical behavior characteristics were discussed.

A series of 2,3-diphenyl-10H-indeno[1,2-g]quinoxaline, 15H-dibenzo[a,c]indeno[1,2-i]phenazine, and 15H-indeno[1,2-i]phenanthro[4,5-abc]phenazine derivatives containing different terminal aromatic units such as phenyl, phenylethynyl, naphthyl, anthryl, pyrenyl, or 4-(diphenylamino)phenyl have been synthesized by employing palladium-catalyzed C–C cross-coupling reactions in good yields. All of the target compounds were characterized using 1H NMR, 13C NMR, high resolution MS, optical absorption, and emission spectra. Even though the electronic absorption spectra of the compounds were influenced by the nature of the peripheral arenes, the emission spectra indicated close similarity for the excited states in the 15H-indeno[1,2-i]phenanthro[4,5-abc]phenazine series compounds. Most compounds possess a medium fluorescence-emitting ability with φFL values in the region of 0.40–0.71 and displayed blue, green, yellow, or red emission depending on the nature of the whole molecule. Structure–optical behavior characteristics and further details of the electronic properties from cyclic voltammetry measurements and theoretical calculations were discussed.

Graphical abstractThe molecular structures of the studied chromophores and fluorescence colors in CH2Cl2 solutions (1 × 10−3 M) under UV light 365 nmFigure optionsDownload full-size imageDownload as PowerPoint slide