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

Xin-Long Ni; Cheng-Cheng Jin; Xue-Kai Jiang; Masashi Takimoto; Shofiur Rahman; Xi Zeng; David L. Hughes; Carl Redshaw; Takehiko Yamato

doi:10.1039/c3ob40601f

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

Xin-Long Ni, Cheng-Cheng Jin, Xue-Kai Jiang, Masashi Takimoto, Shofiur Rahman, Xi Zeng, David L. Hughes, Carl Redshaw, Takehiko Yamato

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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.

Original language	English
Pages (from-to)	5435-5442
Number of pages	9
Journal	Organic & Biomolecular Chemistry
Volume	11
Issue number	33
DOIs	https://doi.org/10.1039/c3ob40601f
Publication status	Published - 1 Jan 2013

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10.1039/c3ob40601f

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@article{e7a511957b204da181242f9efd864b25,

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

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.",

author = "Xin-Long Ni and Cheng-Cheng Jin and Xue-Kai Jiang and Masashi Takimoto and Shofiur Rahman and Xi Zeng and Hughes, {David L.} and Carl Redshaw and Takehiko Yamato",

year = "2013",

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doi = "10.1039/c3ob40601f",

language = "English",

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journal = "Organic & Biomolecular Chemistry",

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T1 - Tri-substituted hexahomotrioxacalix[3]arene derivatives bearing imidazole units: synthesis and extraction properties for cations and chromate anions

AU - Ni, Xin-Long

AU - Jin, Cheng-Cheng

AU - Jiang, Xue-Kai

AU - Takimoto, Masashi

AU - Rahman, Shofiur

AU - Zeng, Xi

AU - Hughes, David L.

AU - Redshaw, Carl

AU - Yamato, Takehiko

PY - 2013/1/1

Y1 - 2013/1/1

N2 - 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.

AB - 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.

U2 - 10.1039/c3ob40601f

DO - 10.1039/c3ob40601f

M3 - Article

SN - 1477-0520

VL - 11

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EP - 5442

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 33

ER -