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; Yamato, Takehiko

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 Cs 2CO3 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 HCr 2O7-/Cr2O72- anions at low pH. © The Royal Society of Chemistry.

Citation

Ni, X. L., Jin, C. C., Jiang, X. K., Takimoto, M., Rahman, S., Zeng, X., Hughes, D. L., Redshaw, C., & Yamato, T. (2013). Tri-substituted hexahomotrioxacalix[3]arene derivatives bearing imidazole units: Synthesis and extraction properties for cations and chromate anions. Organic & biomolecular chemistry, 11(33), 5435-5442. https://doi.org/10.1039/c3ob40601f

• Journal Article Type: Article
• Acceptance Date: Jun 24, 2013
• Online Publication Date: Jun 24, 2013
• Publication Date: 2013
• Deposit Date: Jun 8, 2022
• Journal: Organic and Biomolecular Chemistry
• Print ISSN: 1477-0520
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 11
• Issue: 33
• Pages: 5435-5442
• DOI: https://doi.org/10.1039/c3ob40601f
• Public URL: https://hull-repository.worktribe.com/output/3622131