A high-yield, one-step synthesis of o-phenylene ethynylene cyclic trimer via precipitation-driven alkyne metathesis

Wei Zhang, Scott M. Brombosz, Jose L. Mendoza, Jeffrey S. Moore

Research output: Contribution to journalArticle

Abstract

A shape-persistent, conjugated o-phenylene ethynylene cyclic trimer was prepared in one step from tetrasubstituted benzene monomer 4 in 86% isolated yield through precipitation-driven alkyne metathesis. The template-free, selective generation of the molecular triangle 5 is a thermodynamically favored process and under equilibrium control. A novel tetrameric macrocycle 7 was generated via scrambling metathesis between tricycle 5 and hexacycle 6 using this dynamic covalent chemistry.

Original languageEnglish (US)
Pages (from-to)10198-10201
Number of pages4
JournalJournal of Organic Chemistry
Volume70
Issue number24
DOIs
StatePublished - Nov 25 2005

ASJC Scopus subject areas

  • Organic Chemistry

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