Dynamic chirality in donor-acceptor pretzelanes

Y. Liu, S. A. Vignon, X. Zhang, P. A. Bonvallet, S. I. Khan, K. N. Houk, J. F. Stoddart*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

Abstract

A series of donor-acceptor pretzelanes has been synthesized, using self-assembly and template-directed protocols, and the dynamic processes that these pretzelanes undergo have been investigated in solution. These compounds exist as libraries of diastereoisomers as a result of their multiple Stereoelements, which are dynamically interconverted by several different, in some cases competing, processes. Altering the structure of the pretzelanes changes the rates and mechanisms by which these diastereoisomers equilibrate. Additionally, inserting an element of fixed chirality allows the equilibrium to be biased, while maintaining the barrier to the equilibration processes. These results bode well for the future construction of molecular devices based on switchable diastereoisomerism involving metastable states.

Original languageEnglish (US)
Pages (from-to)9334-9344
Number of pages11
JournalJournal of Organic Chemistry
Volume70
Issue number23
DOIs
StatePublished - Nov 11 2005

ASJC Scopus subject areas

  • Organic Chemistry

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