180° unidirectional bond rotation in a biaryl lactone artificial molecular motor prototype

Bart J. Dahl, Bruce P. Branchaud

Research output: Contribution to journalArticle

28 Scopus citations

Abstract

(Diagram presented) A bifunctional biaryl lactone has been synthesized that should be capable of iterative unidirectional aryl-aryl bond rotation via: (1) a diastereoselective lactone ring opening, (S)-1 to (P,S)-2 or (M,S)-2; (2) a chemoselective lactonization, (P,S)-2 or (M,S)-2 to (S)-3; and (3) a chemoselective hydrolysis, (S)-3 to (S)-1. Preliminary results of a racemic sample have indicated unidirectional 180° rotation with very high directional selectivity per individual artificial molecular motor molecule through the first two steps of this sequence.

Original languageEnglish (US)
Pages (from-to)5841-5844
Number of pages4
JournalOrganic Letters
Volume8
Issue number25
DOIs
StatePublished - Dec 7 2006

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ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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