High Nitrogen Chemistry: Synthesis and Properties of N,N-bis(4,5-dicyano-1-methyl-2-imidazolyl)cyanamide and N,N,N',N',N',N'-Hexakis(4,5-dicyano-1-methyl-2-imidazolyl)melamine

摘要

Cyanation of bis(4,5-dicyano-1-methyl-2-imidazolyl)amine(1) using cyanogen chloride gave N,N-bis(4,5-dicyano-1-methyl-2-imidazolyl)cyanamide(3) as a light yellow solid. Compound 3 is thermally labile and upon heating the N-CN bond is cleaved and the reactive amine intermediate readily reacts with the moisture giving 1. Nucleophilic aromatic substitution(S_NAr) reaction of the sodium salt of 1 with cyanuric chloride gave N,N,N',N',N",N"-hexakis(4,5-dicyano-1-methyl-2-imidazolyl)melamine(5), as a white microcrystalline solid. Compound 5 is thermally stable up to 300 deg C in nitrogen and air. Compound 5 showed strong emission bands at 476 nm is acetonitrile and 448 nm is DMF. Therefore, 5 may be used as a fluorescent probe.