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Synfacts 2010(9): 1013-1013  
DOI: 10.1055/s-0030-1257926
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Polymer-Bound Molecular Tweezers

Contributor(s): Timothy M. Swager, D. Barney Walker
J. Leblond, H. Gao, A. Petitjean*, J.-C. Leroux*
Université de Montréal and Queen’s University, Kingston, Canada; ETH Zürich, Switzerland
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Publication History

Publication Date:
23 August 2010 (online)

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Significance

A pH-sensitive ‘molecular tweezer’ embedded within a polymer backbone is reported. Polymer 1 contains multiple pendant groups each comprised of a 2,6-bis(2-methoxyphenyl)-pyridine switching unit tethered to two naphthalene groups. Together, the terminal aromatic surfaces act as a molecular binding pocket for specific substrates. On addition of acid, the pyridinium species formed is predisposed to form hydrogen bonds with the sterically accessible phenoxy groups, and the stacked naphthalene arrangement is disrupted resulting in substrate release (2).