A Novel Cyclophane. Host–Guest Complexation and Selective Inclusion of Aromatic Guests from Nonaqueous Solution

Kazuhiko Saigo, Ru Jang Lin, Masataka Kubo, Akira Youda, Masaki Hasegawa

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

A novel cyclophane, 2,2,20.20-tetramethyl-11,29-dinitro-7,15,25,33-tetraoxaheptacyclo-[32.2.2.2.2.2.1.1]hexatetraconta-3,5,9(44),10,12,16,18,21,23,27(39),28,30,34,36,37,40,42,45-octadecaene(l), was synthesized by the reaction of 3,5-bis(bromomethyl)nitrobenzene (2) with bisphenol A (3). Both stepwise 2:2 cyclization of 2 and 3 via U-shaped precursor 4 and direct 2:2 cyclization of 2 and 3 were performed under several reaction conditions. With the coexistence of benzene in the reaction solvent, relatively high yield of 1 was achieved even without operation under high dilution conditions. This can be explained in term of a “template” effect of benzene in the cyclization step. The cyclophane 1 formed a “column-type” cave and included aromatic guests in this cave. This was confirmed by X-ray crystal structure analysis of the complex with benzene. The stoichiometry and the stability of the various inclusion complexes at high temperatures and under reduced pressure were examined. The remarkable discrimination selectivity in the inclusion complex formation from mixtures of guests is reasonably explained by the “packing-size relationship”.

Original languageEnglish
Pages (from-to)1996-2000
Number of pages5
JournalJournal of the American Chemical Society
Volume108
Issue number8
DOIs
Publication statusPublished - 1986 Jan 1

Fingerprint

Cyclization
Benzene
Complexation
Caves
Nitrobenzene
Complex Mixtures
Stoichiometry
Dilution
Crystal structure
X-Rays
Pressure
X rays
Temperature

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

A Novel Cyclophane. Host–Guest Complexation and Selective Inclusion of Aromatic Guests from Nonaqueous Solution. / Saigo, Kazuhiko; Lin, Ru Jang; Kubo, Masataka; Youda, Akira; Hasegawa, Masaki.

In: Journal of the American Chemical Society, Vol. 108, No. 8, 01.01.1986, p. 1996-2000.

Research output: Contribution to journalArticle

Saigo, Kazuhiko ; Lin, Ru Jang ; Kubo, Masataka ; Youda, Akira ; Hasegawa, Masaki. / A Novel Cyclophane. Host–Guest Complexation and Selective Inclusion of Aromatic Guests from Nonaqueous Solution. In: Journal of the American Chemical Society. 1986 ; Vol. 108, No. 8. pp. 1996-2000.
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