Heteroaromatic polyamides from cyanoimidazoles

Abstract

The synthesis of a new class of heteroaromatic polyamides based on cyanoimidazoles are described. The monomer, 2-amino-4-cyanoimidazole-5-carboxylic acid ( 3 ) is prepared from a two-step hydrolysis of 2-amino-4,5-dicyanoimidazole ( 1 ). A model dimer prepared from condensation of 1 with 4-cyanoimidazole-5-carboxylic acid was structurally characterized by single crystal diffraction. The dimer, C 10 H 8 N 8 O 3 , crystallizes with Z = 2 and includes two waters of hydration in the P 1 space group, a = 7.684 (2), b = 7.864 (3), c = 10.918 (5), Α = 100.14 (3), Β = 93.15 (3), Γ = 103.79 (3). The model dimer is totally planar and shows trans geometry across the amide linkage. The monomer was polymerized by phosphorylation reaction conditions leading to a highly colored oligomeric polyamide. The polymer was characterized by IR spectroscopy, viscometry, GPC chromatography, and luminescence studies. The polymer luminesces strongly under 450 nm laser irradiation at low temperatures.