Solvent-free synthesis of nitrone-containing template as a chemosensor for selective detection of Cu(II) in water

Author(s)

Carneiro, Leonardo M. ^[1] ; Bartoloni, Fernando H. ^[1] ; Angolini, Celio F. F. ^[1] ; Keppler, Artur F. ^[1]

Affiliation

^[1] Univ Fed ABC, Ctr Ciencias Nat & Humanas, Ave Estados 5001, BR-09210580 Santo Andre, SP - Brazil

• Document type: Journal article
• Source: SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY; v. 267, n. 2 FEB 15 2022.
• Web of Science Citations: 0

Abstract

A state-of-the-art method was developed for repurposing nitrone-containing compounds in the chemosensory field, the ability of the designed molecules to chelate metal cations was evaluated, and their unprecedented solubility in water was confirmed. A facile, rapid, and solvent-free method of synthesizing small molecular mass chemosensors was developed by using a modulative alpha-aryl -N-aryl nitrone template. alpha-(Z)-Imidazol-4-ylmethylen-N-phenyl nitrone (Nit1) and alpha-(Z)-2-pyridyl-N-phenyl nitrone (Nit2) were prepared in 15 min, isolated in less than 60 min with ca. 90% yield, and screened against nine metal cations. Nit1 is a small-molecular-mass compound (188 g mol(-1)) that is watersoluble and has specificity for sensing Cu2+ with an association constant of K = 1.53 x 10(10) and a limit of detection (LOD) of 0.06 ppm. These properties make Nit1 a competitive chemosensor for the detection of Cu2+ in aqueous solution. The nitrone-containing template used in this study is a step forward for new and small chemosensory entities. (C) 2021 Elsevier B.V. All rights reserved. (AU)

• FAPESP's process: 12/07717-5 - Nitrones and hydroxylamines with pharmacological properties: synthesis, exploration of antioxidant activity and cellular studies
• Grantee: Artur Franz Keppler
• Support Opportunities: Research Grants - Young Investigators Grants
• FAPESP's process: 12/13807-7 - New tools for the study of electron transfer reactions in PS II model systems
• Grantee: Fernando Heering Bartoloni
• Support Opportunities: Regular Research Grants