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2,3-ethylene-bridged Dihomooxacalix[4]arenes: synthesis, X-ray crystal structures and highly selective binding properties with anions

Abstract

Three novel 2,3-ethylene-bridged p-tert-butyldihomooxacalix[4]arenes 3a-3c were selectively synthesized by direct O-alkylation of p-tert-butyldihomooxacalix[4]arene 1 with excess of 1,2-dibromoethane in controlled basic systems. Their corresponding conformational features were clearly elucidated by 1H NMR spectra and single crystal structures. Their binding abilities toward varity of anions (SO42-, SO32-, CO32-, HSO3-, HCO3-, NO3-, CH3COO-, Br-, I- and Cl-) have been assessed ( 3a was taken for example) and compared to those afforded with the unconstrained p-tert-butyldihomooxacalix[4]arene 1 and the analogous 1,3-di-(2-bromoethyl) substituted calix[4]arene derivative 4 by determining of fluorescent titrations. The results showed that 2,3-ethylene-bridged dihomooxacalix[4]arene 3a has the most significant selective and high affinity for I-. In contrast, p-tert-butyldihomooxacalix[4]arene 1 can mainly bind for most anions (SO32-, CO32-, HCO3-, NO3-, and I-), but has the poor selectivity preference. The analogous 4 only exibits the weak binding ability for I-, which suggests that 2,3-ethylene-bridged p-tert-butyl- dihomooxacalix[4]arene 3a would be useful in the design of new selective supramolecular receptors for anions.

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Publication details

The article was received on 15 Mar 2018, accepted on 08 May 2018 and first published on 09 May 2018


Article type: Paper
DOI: 10.1039/C8NJ01284A
Citation: New J. Chem., 2018, Accepted Manuscript
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    2,3-ethylene-bridged Dihomooxacalix[4]arenes: synthesis, X-ray crystal structures and highly selective binding properties with anions

    L. An, J. wang, C. wang, S. S. zhou, J. Sun and C. G. Yan, New J. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C8NJ01284A

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