Mechanochemically Synthesized Amidetriazoles for Effective Optical and Electrochemical Detection of Anions.

Abstract

Despite the fact that amide and 1,2,3-triazole moieties on their own are widely utilized in designing chemoreceptor structures, their direct connection─amidetriazole is rarely studied. In this work, we present a new class of polyaromatic AIE-active amidetriazoles, their mechanochemical synthesis, and their application as dual-mode anion receptors. Mechanochemical synthesis not only enabled high yields but also shortened the reaction time and reduced the use of solvents and harmful chemicals. The optimization of 1,3-dipolar cycloaddition reactions carried out in solution, as well as in sono- and mechanochemical versions, was mainly based on modifying the copper-ion source, where a nonclassical approach (copper metal mesh) enabled the highest yields to be achieved. The compounds obtained were characterized by spectroscopic methods to fully study their properties derived from the AIE effect. The relationship between their structure and receptor properties was outlined. Ultimately, both AIE-active compounds were successfully employed as anion receptors. Optical and potentiometric methods demonstrated a strong correlation between the receptor structure and its detection properties, as well as the selective interaction of one receptor with SO₄^2- anions.