Abstract
An efficient synthesis of 1-methyl-2-ethynyl-4,5-dicyanoimidazole via Sonogashira coupling is described. Our optimized method generates 1-methyl-2-ethynyl-4,5-dicyanoimidazole in almost 80% yield from 1-methyl-2-bromo-4,5-dicyanoimidazole. Syntheses of the ethyl, propyl, and p-methoxybenzyl derivatives of 2-ethynyl-4,5-dicyanoimidazole are also reported. The polymerization of 1-methyl-2-ethynyl-4,5-dicyanoimidazole with transition-metal catalysts and triethylamine is described. Variation of catalyst concentration, reaction time, and temperature is also described. A more complete mechanistic picture of acetylene polymerizations, especially those with electron-withdrawing substituents, is presented. Solid samples of 1-methyl-2-ethynyl-4,5-dicyanoimidazole oligomers are EPR-active, and the number of free spins was quantified. Cyclic voltammetry was used to investigate the reduction of 1-methyl-2-ethynyl-4,5-dicyanoimidazole oligomers and other dicyanoimidazole derivatives.
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