4,7-Di(9<i>H</i>-carbazol-9-yl)-[1,2,5]oxadiazolo[3,4-<i>d</i>]pyridazine

Abstract

Donor–acceptor–donor (D–A–D)-type molecules are considered as a promising class of NIR fluorescence materials. In this communication, 4,7-di(9H-carbazol-9-yl)-[1,2,5]oxadiazolo[3,4-d]pyridazine was obtained by dehydrogenation of 4,7-bis(1,2,3,4,4a,9a-hexahydro-9H-carbazol-9-yl)-[1,2,5]oxadiazolo[3,4-d]pyridazine with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in toluene. The structure of the synthesized compound was established by elemental analysis; high-resolution mass spectrometry; 1H, 13C NMR, IR, and UV spectroscopy; and mass spectrometry. The photophysical properties of the title compound were studied and compared with spectral data of the [1,2,5]thiadiazolo[3,4-d]pyridazine analogue.

Keywords

• donor-acceptor-donor molecules
• [1,2,5]oxadiazolo[3,4-<i>d</i>]pyridazines
• carbazoles
• dehydrogenation
• luminescent properties