Synthesis of bis-1, 2, 3-triazole tweezer with BINOL backbone and amide subunits: An efficient sensor for iodide and magnesium ions

Abstract

The synthesis of novel S-BINOL-based 1, 2, 3-triazoles were carried out by using efficient synthetic protocol with high yields from S-BINOL (1) as the backbone and amide subunits. Selective sensing of iodide and magnesium was observed due to nonbonding interaction of the ions with BINOL-based 1, 2, 3-triazoles tweezers (6). Significantly strong association constant, 1.897 × 10⁵ M⁻¹, was observed for interaction of host with iodide ions and 0.974 × 10⁵ M⁻¹ with magnesium ions. The recorded association constant value for iodide sensing and magnesium sensing is among the best reported so far and this is attributed to tweezer arms with helical BINOL backbone, 1,2,3-Triazoles with acidic proton and electron rich nitrogen atoms, a structural feature suitable for binding with cations and anions. The stronger binding is also attributed to involvement of amide units in bringing the two tweezer arms closer and involvement of the amide unit in binding with ions.

Graphical Abstract

Keywords:

• BINOL
• magnesium sensor
• tweezers
• iodide sensor
• 1
• 2
• 3-triazoles

Acknowledgments

RGT acknowledge help received from IIT Kharagpur for HRMS study.