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

Research output: Contribution to journalArticlepeer-review

223 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 languageEnglish
Pages (from-to)1437-1443
Number of pages7
JournalTetrahedron
Volume56
Issue number11
DOIs
Publication statusPublished - 2000 Mar 10

Keywords

  • Calixarenes
  • Inclusion complex
  • Sulfurization
  • Thiacalixarenes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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