Unique inclusion behaviour of 5,11,17,23-tetra-tert-butyl-25,26,27,28- tetraaminothiacalix[4]- Arene towards small organic molecules

Naoya Morohashi, Hiroshi Katagiri, Takanori Shimazaki, Yuichi Kitamoto, Shinya Tanaka, Chizuko Kabuto, Nobuhiko Iki, Tetsutaro Hattori, Sotaro Miyano

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Tetraaminothiacalixarene 3, bearing fouramino groups instead of the hydroxy groups of p-tert-butylthiacalix[4]arene 2, exhibits inclusion properties different fromthose of compound 2 towards small organicmolecules upon crystallisation fromneat solvents or guest solutions. X-ray crystallographic analyses reveal that nitromethane and acetonitrile are included into the cone-shaped cavity of compound 3, as is often seen in inclusion crystals of compound 2, whereas dichloromethane occupies a space between two distal benzene rings of compound 3, adopting a 1,3-alternate conformation. Acetic acid, which forms a dimer, fills a pore surrounded by four host molecules with a pinched cone conformation. Furthermore, guest-free crystals of compound 3 with a 1,3-alternate conformation absorb acetonitrile to give inclusion crystals with the same crystal structure as that obtained by the crystallisation. Thus, compound 3 flexibly changes its conformation according to the structures of guest compounds.

Original languageEnglish
Pages (from-to)812-818
Number of pages7
JournalSupramolecular Chemistry
Volume25
Issue number12
DOIs
Publication statusPublished - 2013 Dec 1

Keywords

  • Amino group
  • Calixarene
  • Crystallisation
  • Inclusion
  • Molecular recognition

ASJC Scopus subject areas

  • Chemistry(all)

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