Complexation properties of preorganized receptor molecules for large, neutral guests

Irene Higler, Willem Verboom, Feike de Jong, Frank C.J.M. van Veggel, David N. Reinhoudt

Research output: Contribution to journalArticleAcademicpeer-review

28 Citations (Scopus)
49 Downloads (Pure)

Abstract

Receptor molecules with a preorganized cavity were synthesized by combining two resorcin[4]arene and one calix[4]-arene building block. Based on predictions from a computational study which matches hosts and guests, several steroids, sugar derivatives, and alkaloids were selected for complexation studies. Experimentally the complexation of such guests by these receptor molecules was proven by 1H-NMR spectroscopy (association constants of 1.0-6.0 × 102 M-1 in CDCl3). One of these receptors with four hydroxyl groups forms a dimeric capsule (Kdimer = 11 M-1 in CDCl3). Evidence for this dimerization comes from 1H-NMR, FAB MS spectroscopy, and molecular mechanics and dynamics calculations.
Original languageEnglish
Pages (from-to)1577-1586
JournalLiebigs Annalen
Volume1997
Issue number7
DOIs
Publication statusPublished - 1997

Keywords

  • Resorcin[4]arenes
  • Host-guest chemistry
  • Dimerization
  • Calix[4]arenes

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