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

Abstract 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.

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Publication Details

Journal
ChemistrySelect
Published
2025-03-01
DOI
https://doi.org/10.1002/slct.202405781
Citations
2
Primary Topic
Click Chemistry and Applications
Type
article
Field-Weighted Citation Impact
1.87

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article

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

Sakthivel Kandaiah, Vipin A. Nair, Gopal Lal Khatik, Vamshikrishna Y. Radhakrishna
2 citations
ChemistrySelect
Click Chemistry and Applications
1.87
article

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

Sakthivel Kandaiah, Vipin A. Nair, Gopal Lal Khatik, Vamshikrishna Y. Radhakrishna
article en
2 citations

Abstract

Abstract 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.

ChemistrySelectVol. 10(10)
National Institute of Pharmaceutical Education and Research (IN), Amrita Vishwa Vidyapeetham (IN), REVA University (IN)
Human Resource Development Group
Openalex Percentile: Top 17%
Click Chemistry and Applications
1.87
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