Tri-substituted hexahomotrioxacalix[3]arene derivatives bearing imidazole units: synthesis and extraction properties for cations and chromate anions

Ni, Xin-Long, Jin, Cheng-Cheng, Jiang, Xue-Kai, Takimoto, Masashi, Rahman, Shofiur, Zeng, Xi, Hughes, David L., Redshaw, Carl and Yamato, Takehiko (2013) Tri-substituted hexahomotrioxacalix[3]arene derivatives bearing imidazole units: synthesis and extraction properties for cations and chromate anions. Organic & Biomolecular Chemistry, 11 (33). pp. 5435-5442. ISSN 1477-0520

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Abstract

The article describes the synthesis and extraction properties of the new hexahomotrioxacalix[3]arene-based derivatives cone- and partial-cone-2 bearing 1-methyl-1H-imidazole moieties at the lower rim. It has been demonstrated that O-alkylation of the flexible macrocycle 1 with 2-(chloromethyl)-1-methyl-1H-imidazole hydrochloride affords tri-O-alkylated products with a cone or partial-cone conformation. Alkali metal salts such as NaH and Cs2CO3 can play an important role in the conformer distribution via a template effect. The conformation of receptors 2 has been confirmed by X-ray crystallographic analysis. Furthermore, the complexation properties of receptors 2 toward selected alkali/transition metal cations and alkylammonium ions are reported. The new 1-methyl-1H-imidazole-substituted hexahomotrioxacalix[3]arene frameworks are also efficient extractors of HCr2O7−/Cr2O72− anions at low pH.

Item Type:	Article
Faculty \ School:	Faculty of Science > School of Chemistry
Depositing User:	Pure Connector
Date Deposited:	11 Jan 2016 17:00
Last Modified:	31 Oct 2022 17:31
URI:	https://ueaeprints.uea.ac.uk/id/eprint/56211
DOI:	10.1039/c3ob40601f

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