Shape-persistent macrocycles: Structures and synthetic approaches from arylene and ethynylene building blocks

Wei Zhang, Jeffrey S. Moore

Research output: Contribution to journalReview article

Abstract

Shape-persistent arylene ethynylene macrocycles have attracted much attention in supramolecular chemistry and materials science because of their unique structures and novel properties. In this Review we describe recent examples of macrocycle synthesis by cross-coupling (Sonogashira: aryl acetylene macrocycle or Glaser: aryl diacetylene macrocycle) and dynamic covalent chemistry. The primary disadvantage of the coupling methods is the kinetically determined product distribution, since a significant portion of oligomers grow beyond the length of the cyclic targets ("overshooting"). Better results have been obtained recently by a dynamic covalent approach involving reversible metathesis reactions that afford macrocycles in one step. Mechanistic studies demonstrate that macrocycle formation is thermodynamically controlled by this route. Remaining synthetic challenges include the efficient preparation of site-specifically functionalized structures and larger, more complex two- and three-dimensional molecules.

Original languageEnglish (US)
Pages (from-to)4416-4439
Number of pages24
JournalAngewandte Chemie - International Edition
Volume45
Issue number27
DOIs
StatePublished - Jul 3 2006

Keywords

  • Cross-coupling
  • Cyclooligomerization
  • Dynamic covalent chemistry
  • Metathesis
  • Shape-persistent macrocycles

ASJC Scopus subject areas

  • Chemistry(all)

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