Chiral benzimidazole derived bis‐phenyl triazoles as chiroptical sensors for iodide and chiral amines

Abstract

AbstractA series of chiral 2‐hydroxy ethyl/benzyl benzimidazole based aryl triazole tweezers have been prepared using click chemistry in high yields. Chiral pool strategy has been used to obtain the benzimidazole‐based tweezers in very high enantiomerically enriched form. The aryl triazole tweezers, S‐(−)‐5a and S‐(+)‐8a displayed a high degree of selectivity for iodide anion over other anions, including other halides. The aryl triazole tweezers, S‐(−)‐5a and S‐(+)‐8a display significant enantio‐discrimination for chiral amines. The chiral recognition studies were carried out using UV and circular dichroism (CD) spectroscopy. NMR analysis has been used for establishing the sites for ligation of the iodide anion.