Issue 14, 2019

Multi-point interaction-based recognition of fluoride ions by tert-butyldihomooxacalix[4]arenes bearing phenolic hydroxyls and thiourea

Abstract

A series of p-tert-butyldihomooxacalix[4]arenes bearing phenolic hydroxyls and thiourea moieties were prepared to investigate their anion binding behavior. These compounds showed F binding according to 1H NMR titration experiments. Among them, dihomooxacalix[4]arenes bearing phenyl and benzyl thiourea (2a and 2b) showed multiple interactions with added F, including N–H⋯F, O–H⋯F hydrogen bonds and “through-space” C–H⋯F interactions between F and the attached aromatic segment of thiourea. A conformational change of the dihomooxacalix[4]arene cavity was observed as well and proved by theoretical calculations. The dihomooxacalix[4]arene bearing methyl thiourea (2c) also showed the formation of N–H⋯F, O–H⋯F hydrogen bonds, but less conformational change of the dihomooxacalix[4]arene cavity according to 1H NMR titration results. The bis-dihomooxacalix[4]arene (3) showed clear N–H⋯F hydrogen bond formation upon addition of F as characterized by 1H NMR spectroscopy.

Graphical abstract: Multi-point interaction-based recognition of fluoride ions by tert-butyldihomooxacalix[4]arenes bearing phenolic hydroxyls and thiourea

Supplementary files

Article information

Article type
Paper
Submitted
15 Dec 2018
Accepted
05 Mar 2019
First published
20 Mar 2019

New J. Chem., 2019,43, 5503-5511

Multi-point interaction-based recognition of fluoride ions by tert-butyldihomooxacalix[4]arenes bearing phenolic hydroxyls and thiourea

L. Zhao, X. Yang, H. Chong, Y. Wang and C. Yan, New J. Chem., 2019, 43, 5503 DOI: 10.1039/C8NJ06333H

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