Solvophobically driven self-association of a butadiyne-bridged pyridine macrocycle

Motohiro Sonoda, Yui Yamaguchi, Kazukuni Tahara, Keiji Hirose, Tobe Yoshito*

*Corresponding author for this work

Research output: Contribution to journalArticle

13 Scopus citations

Abstract

A butadiyne-bridged square-shaped pyridinophane 2b having ester groups derived from triethylene glycol monomethyl ether was prepared and its self-assembling properties were investigated to assess the repulsive dipole-dipole interaction in less polar solvent and solvophobic driving force in polar solvents. Concentration-dependent 1H NMR spectra showed that whereas 2b did not self-assemble in chloroform-d, it did in polar solvents consisting of chloroform-d and methanol-d4 (4:6 to 6:4) with increasing association constants with the increasing methanol-d4 composition. Comparison of the free energies of association with those of the previously reported benzene macrocycle 1b indicates that solvophobically induced self-association of 2b is more promoted than 1b. The reasons for this difference are discussed from both enthalpy and entropy points of view.

Original languageEnglish
Pages (from-to)11490-11494
Number of pages5
JournalTetrahedron
Volume64
Issue number50
DOIs
StatePublished - 8 Dec 2008

Keywords

  • Butadiynes
  • Macrocycles
  • Self-assembly
  • Shape-persistent molecules
  • Solvophobic effect

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