2,5,8-Trihydrazino-s-heptazine: a precursor for heptazine-based iminophosphoranes
Résumé
The title compound 1 C6N7(NHNH2)3 was obtained from melem C6N7(NH2)3 or melon [C6N7(NH2)NH]n and hydrazine via an autoclave synthesis. Upon treatment with a 10 % HCl solution it is transformed into the trihydrochloride 2, [C6N7(NHNH3)3]Cl3. Compounds 1 and 2 were analysed with 13C NMR, 15N NMR, FTIR- and Raman-spectroscopy. Furthermore, the single crystal X-ray structure of the pentahydrate of 2 is reported (P-1, a = 674.96(3), b = 1214.17(6), c = 1272.15(6) pm, = 66.288(2)°, = 75.153(2)°, = 80.420(2)°, V = 920.30(8) • 106 pm3, Z = 2, T = 90(2) K). The thermal decomposition of 1 and 2 was investigated with TG/DTA. Reaction of 1 with NaNO2/HCl yields triazido-s-heptazine, C6N7(N3)3 3. Tris(trinbutylphosphinimino)-s-heptazine 4 was synthesized from 3 and characterised by means of 13C, 31P, 1H NMR, FTIR and MALDI-TOF spectroscopy. Similar to s-heptazine derivative 3, compounds 1 and 4 are precursors for graphitic carbon nitrides, which have attracted considerable attention recently, and to various potential applications, such as flame retardants and (photo)catalysis.
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