Efficient templated synthesis of donor - Acceptor rotaxanes using click chemistry

William R. Dichtel, Ognjen S. Miljanić, Jason M. Spruell, James R. Heath*, J. Fraser Stoddart

*Corresponding author for this work

Research output: Contribution to journalArticle

160 Scopus citations

Abstract

The mild reaction conditions, remarkable functional group compatibility, and complete regioselectivity of the Cu-catalyzed Huisgen 1,3-dipolar cycloaddition ("click chemistry") between organic azides and terminal alkynes have led to a threading-followed-by-stoppering approach to the synthesis of donor-acceptor rotaxanes incorporating cyclobis(paraquat-p-phenylene) (CBPQT4+) as the π-accepting ring component. Rotaxane formation is initiated by reacting azide-functionalized pseudorotaxanes containing π-donating 1,5-dioxynaphthalene (DNP) recognition units with appropriate alkyne-functionalized stoppers. The high yields obtained in this efficient, kinetically controlled post-assembly covalent modification, as well as the excellent convergence of the synthetic protocol, are demonstrated by the preparation of [2]-, [3]-, and [4]rotaxanes containing multiple DNP/CBPQT4+ donor-acceptor recognition motifs.

Original languageEnglish (US)
Pages (from-to)10388-10390
Number of pages3
JournalJournal of the American Chemical Society
Volume128
Issue number32
DOIs
StatePublished - Aug 16 2006

ASJC Scopus subject areas

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

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