4,7-Bis(1,2,3,4,4a,9a-Hexahydro-9H-carbazol-9-yl)-[1,2,5]oxadiazolo[3,4-d]pyridazine

Abstract

New donor-acceptor-donor (D-A-D)-type structures are widely used to design effective organic light-emitting diodes (OLEDs). In this communication, 4,7-bis(1,2,3,4,4a,9a-hexahydro-9H-carbazol-9-yl)-[1,2,5]oxadiazolo[3,4-d]pyridazine was obtained in a 65% yield by the treatment of 4,7-dichloro[1,2,5]oxadiazolo[3,4-d]pyridazine 1-oxide with 2,3,4,4a,9,9a-hexahydro-1H-carbazole. The structure of the newly synthesized compounds was established by means of an elemental analysis, 1H, 13C NMR, IR and UV spectroscopy, and HRMS and LR mass-spectrometry.

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

“…4,7-Bis(1,2,3,4,4a,9a-hexahydro-9H-carbazol-9-yl)-[1,2,5]oxadiazolo [3,4-d]pyridazine 1 was prepared according to the published method [16]. The solvents and reagents were purchased from commercial sources and used as received.…”

“…Their oxygen analogues [1,2,5]oxadiazolo [3,4-d]pyridazines are less known but are considered promising precursors for these applications [12,13] and as energetic materials [14,15]. We have previously synthesized 4,7-bis(1,2,3,4,4a,9a-hexahydro-9H-carbazol-9-yl)- [1,2,5] oxadiazolo [3,4-d]pyridazine 1 [16]. Herein, we report the preparation of 4,7-di(9H-carbazol-9-yl)-[1,2,5]oxadiazolo [3,4-d]pyridazine 2 by dehydrogenation of [1,2,5]oxadiazolo [3,4d]pyridazine 1 and investigation of its luminescent properties.…”

5,6-Dihydro-[1,2,5]oxadiazolo[3,4-d]pyridazine-4,7-dione

“…[1,2,5]Oxadiazolo [3,4-d]pyridazines are much less studied since the methods for their synthesis are limited by the deoxygenation of the corresponding 1,2,5-oxadiazole N-oxides. Meanwhile, these compounds have been studied for photovoltaic applications [5,6]. 4,7-Dihalogen-substituted 2,1,3-benzoxadiazoles are important precursors for the synthesis of organic solar cell (OSC) and organic light-emitting diode (OLED) components [7].…”