Abstract
Novel helicenoid based 1,2,3-triazole tweezer 4 was synthesized using a multistep synthetic protocol with high yields from 2,7-Dihydroxynaphtlene 3 as a precursor. This helicenoid-based bis-1,2,3-triazole tweezer 4 selectively causes non-covalent interaction with iodide anion. The UV-vis absorption exhibited enhancement while fluorescence spectra exhibited significant quenching. 1H NMR titration showed shift of 1,2,3-triazole C-H signal with an increase in iodide concentration. Association constant of 3.818 × 104 M−1 was recorded for the host interaction with iodide ions. This value of association constant for iodide sensing using 1,2,3-triazole is the best reported so far for hosts with 1,2,3-triazole moiety and suggests that the helicenoid geometry is responsible for this remarkable behavior.
GRAPHICAL ABSTRACT
Supporting information
Procedure for synthesis of compounds 6, 7, 8, and 4 is provided in the supporting information. Full experimental detail, IR, 1H NMR, and 13C NMR, and HRMS spectra can be found via the “Supplementary Content” section of this article’s webpage
Acknowledgments
SBK acknowledges to CSIR-UGC for JRF and SRF funding and Center for Nano Science and Nano Technology, University of Mumbai for UV-vis and Fluorescence study.