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

Cyanation of bis(4,5-dicyano-1-methyl-2-imidazolyl)am using cyanogen chlori de 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 mois ture giving 1. Nucleophilic;aromatic substitution(SNAr) reaction of the sod ium salt of I with cyanuric chloride gave N,N,N,N',N ",N "-hexakis(4,5-dicy ano-1-methyl-2-imidazolyl)melamine(5), as a white microcrystalline solid; C ompound 5 is thermally stable up to 300 degrees C in nitrogen and air. Comp ound 5 showed strong emission bands at 476 Mn in acetonitrile and 448 nn in DMF. Therefore, 5 may be used as a fluorescent probe. (C) 1998 Elsevier Sc ience Ltd. All rights reserved.