Abstract

Macrocyclic oligomers possessing direction-defining ester linkages were synthesized via metathesis of the nondirectional alkyne functional group. Alkyne metathesis is expected to scramble the relative orientation of adjacent ester groups, potentially leading to a complex mixture of macrocyclic products. We wondered whether a narrow product distribution would be achievable with a proper choice of the building block structure. Here we show that the shape of the building block determines whether the macrocyclic products are directionally uniform or scrambled. Specifically, two isomeric arylene-ethynylene polyesters afforded significantly different product distributions upon being subjected to depolymerization-macrocyclization. These results underscore the importance of learning how the shape and geometry of the building blocks affect the macrocyclization energy landscape.

Original languageEnglish (US)
Pages (from-to)9114-9117
Number of pages4
JournalJournal of the American Chemical Society
Volume134
Issue number22
DOIs
StatePublished - Jun 6 2012

ASJC Scopus subject areas

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

Fingerprint Dive into the research topics of 'Directional cyclooligomers via alkyne metathesis'. Together they form a unique fingerprint.

Cite this