An Eco-Friendly, Multicomponent Reaction for 2-(5-Amino-4-cyano-1H-1,2,3-triazol-1-yl)-N-aryl Acetamides: A Fine Tunable Push-Pull Chromophore With Photoelectrochemical Properties

Heterocyclic scaffolds with nitrogen atoms play a crucial role in biology and material science. 1,2,3-Triazole containing push-pull chromophores were tethered to aryl acetamides and studied for photoelectrochemical properties. The desired compounds were synthesized via nucleophilic substitution of 2-chloro-N-aryl acetamides with azide followed by a 1,3-dipolar cycloaddition reaction with malononitrile in the presence of a base under eco-friendly, one-pot reaction condition which avoids the isolation of the hazardous intermediate. The reaction condition tolerates a wide range of electron-donating and electron-withdrawing functional groups on the aryl ring with good yields, short reaction time and ease of operation. The oxidation potential and photocurrent measurements indicated that the presence of the electron-withdrawing substituents afforded better results with a lower oxidation potential and higher photocurrent.