Issue 14, 2000

Difference in guest-inclusion abilities of anti- and syn-rotamers

Abstract

Guest inclusion abilities of two rotamers, anti- and syn-N,N ′-bis-(2-tert-butylphenyl)naphthalene-1,4,5,8-tetracarboxylic diimides 1 and 2, were investigated. Rotamers 1 and 2 were synthesised from 2-tert-butylaniline and naphthalene-1,4,5,8-tetracarboxylic dianhydride and separated by conventional column chromatography on silica gel. Recrystallisation of 1 from chloroform in the presence of a guest molecule (3 mole equivalents) was performed, and 15 guest molecules were included with a variety of host∶guest ratios, 1∶1 (chloroform, pyridine, 4-picoline, benzene, quinoline, diphenylacetylene, naphthalene, and p-toluidine), 1∶2 (phenol, 3-ethylphenol, 4-methoxyphenol, indole, 5-methylindole, and tetrathiafulvalene), and 1∶4 (benzothiazole). In contrast, 2 showed no inclusion of guest molecules under the same conditions as those applied to 1. In order to investigate the intermolecular interaction in the crystalline state of 1, 2 and 1·(indole)2, X-ray diffraction of single crystals was measured and these structures were compared.

Article information

Article type
Paper
Submitted
20 Mar 2000
Accepted
15 May 2000
First published
22 Jun 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 2217-2221

Difference in guest-inclusion abilities of anti- and syn-rotamers

K. Kishikawa, C. Iwashima, S. Kohmoto, K. Yamaguchi and M. Yamamoto, J. Chem. Soc., Perkin Trans. 1, 2000, 2217 DOI: 10.1039/B002220I

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