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Switching and Extension of a [c2]Daisy-Chain Dimer Polymer

Clark, Paul G. and Day, Michael W. and Grubbs, Robert H. (2009) Switching and Extension of a [c2]Daisy-Chain Dimer Polymer. Journal of the American Chemical Society, 131 (38). pp. 13631-13633. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20091013-093448965

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Abstract

We report the synthesis of a [c2]daisy-chain dimer via ruthenium-catalyzed ring-closing olefin metathesis. Confirmation of the interlocked nature of the structure was achieved through single-crystal X-ray diffraction analysis. The dimer could be readily switched from the bound to the unbound conformation by treatment with 3.0 equiv of KOH and subsequently reprotonated by treatment with 3.0 equiv of HPF_6. Azide functionalization of the dimer enabled incorporation in linear step-growth polymer chains using the alkyne-azide “click” reaction. Gel permeation chromatography coupled with multiangle laser light scattering analysis showed the polymers contained 22 dimers and had a radius of gyration of 14.8 nm. Acylation of the amines of the dimers sterically forced elongation of the interlocked units, and MALLS analysis of the polymer showed a 48% increase in the R_g (21.4 nm).


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja905924uDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja905924uPublisherArticle
ORCID:
AuthorORCID
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 2009 American Chemical Society. Received July 16, 2009; Publication Date (Web): September 3, 2009. We thank Dr. Erin Guidry and Prof. J. Fraser Stoddart for useful discussions. The ruthenium metathesis catalyst was received as a generous gift from Materia, Inc. We thank Lawrence M. Henling for X-ray crystallographic data. The work was supported by the Office of Naval Research through its MURI program and the NSF (NSF CHE-0809418).
Funders:
Funding AgencyGrant Number
Office of Naval Research (ONR)UNSPECIFIED
NSFCHE-0809418
Issue or Number:38
Record Number:CaltechAUTHORS:20091013-093448965
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20091013-093448965
Official Citation:Switching and Extension of a [c2]Daisy-Chain Dimer Polymer Paul G. Clark, Michael W. Day, Robert H. Grubbs Journal of the American Chemical Society 2009 131 (38), 13631-13633
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:16301
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:21 Oct 2009 21:02
Last Modified:08 Dec 2016 22:17

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