Synthesis of p-tert-butylthiacalix[4]arene and its inclusion property

Nobuhiko Iki; Chizuko Kabuto; Takanori Fukushima; Hitoshi Kumagai; Haruhiko Takeya; Setsuko Miyanari; Tsutomu Miyashi; Sotaro Miyano

doi:10.1016/S0040-4020(00)00030-2

Synthesis of p-tert-butylthiacalix[4]arene and its inclusion property

Nobuhiko Iki, Chizuko Kabuto, Takanori Fukushima, Hitoshi Kumagai, Haruhiko Takeya, Setsuko Miyanari, Tsutomu Miyashi, Sotaro Miyano

ENV - Frontier Science for Advanced Environment

Research output: Contribution to journal › Article › peer-review

122 Citations (Scopus)

Abstract

A practical method for the synthesis of p-tert-butylthiacalix[4]arene (TC4A), in which the methylene bridges of p-tert-butylcalix[4]arene (C4A) are replaced by epithio groups, is presented by heating a mixture of p-tert- butylphenol, elemental sulfur S₈, and NaOH as a base catalyst in tetraethylene glycol dimethyl ether. The inclusion behavior of TC4A for a wide range of solvent molecules is examined by recrystallization, showing preference for the guests depending upon the size and/or the substituent of the guests. The X-ray structure of a 1:2 host-guest complex of TC4A with 1,2- dichloroethane reveals that one guest molecule is included in the cavity of TC4A, while the other is included in the crystal lattice to form a clathrate- type complex. It is shown that the inclusion in the cavity is attained by a cooperative deformation of both the host and the guest. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	1437-1443
Number of pages	7
Journal	Tetrahedron
Volume	56
Issue number	11
DOIs	https://doi.org/10.1016/S0040-4020(00)00030-2
Publication status	Published - 2000 Mar 10

Keywords

Calixarenes
Inclusion complex
Sulfurization
Thiacalixarenes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(00)00030-2

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title = "Synthesis of p-tert-butylthiacalix[4]arene and its inclusion property",

abstract = "A practical method for the synthesis of p-tert-butylthiacalix[4]arene (TC4A), in which the methylene bridges of p-tert-butylcalix[4]arene (C4A) are replaced by epithio groups, is presented by heating a mixture of p-tert- butylphenol, elemental sulfur S8, and NaOH as a base catalyst in tetraethylene glycol dimethyl ether. The inclusion behavior of TC4A for a wide range of solvent molecules is examined by recrystallization, showing preference for the guests depending upon the size and/or the substituent of the guests. The X-ray structure of a 1:2 host-guest complex of TC4A with 1,2- dichloroethane reveals that one guest molecule is included in the cavity of TC4A, while the other is included in the crystal lattice to form a clathrate- type complex. It is shown that the inclusion in the cavity is attained by a cooperative deformation of both the host and the guest. (C) 2000 Elsevier Science Ltd.",

keywords = "Calixarenes, Inclusion complex, Sulfurization, Thiacalixarenes",

author = "Nobuhiko Iki and Chizuko Kabuto and Takanori Fukushima and Hitoshi Kumagai and Haruhiko Takeya and Setsuko Miyanari and Tsutomu Miyashi and Sotaro Miyano",

note = "Funding Information: This work was supported by a Grant-in-Aid for Scientific Research (No. 10208202) from the Ministry of Education, Science, Sports and Culture, Japan, and by the Proposal-Based New Industry Creative Type Technology R&D Promotion Program from the New Energy and Industrial Technology Development Organization (NEDO) of Japan.",

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AU - Iki, Nobuhiko

AU - Kabuto, Chizuko

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AU - Kumagai, Hitoshi

AU - Takeya, Haruhiko

AU - Miyanari, Setsuko

AU - Miyashi, Tsutomu

AU - Miyano, Sotaro

N1 - Funding Information: This work was supported by a Grant-in-Aid for Scientific Research (No. 10208202) from the Ministry of Education, Science, Sports and Culture, Japan, and by the Proposal-Based New Industry Creative Type Technology R&D Promotion Program from the New Energy and Industrial Technology Development Organization (NEDO) of Japan.

PY - 2000/3/10

Y1 - 2000/3/10

N2 - A practical method for the synthesis of p-tert-butylthiacalix[4]arene (TC4A), in which the methylene bridges of p-tert-butylcalix[4]arene (C4A) are replaced by epithio groups, is presented by heating a mixture of p-tert- butylphenol, elemental sulfur S8, and NaOH as a base catalyst in tetraethylene glycol dimethyl ether. The inclusion behavior of TC4A for a wide range of solvent molecules is examined by recrystallization, showing preference for the guests depending upon the size and/or the substituent of the guests. The X-ray structure of a 1:2 host-guest complex of TC4A with 1,2- dichloroethane reveals that one guest molecule is included in the cavity of TC4A, while the other is included in the crystal lattice to form a clathrate- type complex. It is shown that the inclusion in the cavity is attained by a cooperative deformation of both the host and the guest. (C) 2000 Elsevier Science Ltd.

AB - A practical method for the synthesis of p-tert-butylthiacalix[4]arene (TC4A), in which the methylene bridges of p-tert-butylcalix[4]arene (C4A) are replaced by epithio groups, is presented by heating a mixture of p-tert- butylphenol, elemental sulfur S8, and NaOH as a base catalyst in tetraethylene glycol dimethyl ether. The inclusion behavior of TC4A for a wide range of solvent molecules is examined by recrystallization, showing preference for the guests depending upon the size and/or the substituent of the guests. The X-ray structure of a 1:2 host-guest complex of TC4A with 1,2- dichloroethane reveals that one guest molecule is included in the cavity of TC4A, while the other is included in the crystal lattice to form a clathrate- type complex. It is shown that the inclusion in the cavity is attained by a cooperative deformation of both the host and the guest. (C) 2000 Elsevier Science Ltd.

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KW - Inclusion complex

KW - Sulfurization

KW - Thiacalixarenes

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Synthesis of p-tert-butylthiacalix[4]arene and its inclusion property

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Keywords

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