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Efficient Templated Synthesis of Donor−Acceptor Rotaxanes Using Click Chemistry

Dichtel, William R. and Miljanić, Ognjen Š. and Spruell, Jason M. and Heath, James R. and Stoddart, J. Fraser (2006) Efficient Templated Synthesis of Donor−Acceptor Rotaxanes Using Click Chemistry. Journal of the American Chemical Society, 128 (32). pp. 10388-10390. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20170427-112457768

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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) (CBPQT^(4+)) 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/CBPQT^(4+) donor−acceptor recognition motifs.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja063127iDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja063127iPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja063127iPublisherSupporting Information
ORCID:
AuthorORCID
Heath, James R.0000-0001-5356-4385
Stoddart, J. Fraser0000-0003-3161-3697
Additional Information:© 2006 American Chemical Society. Received May 4, 2006. Publication Date (Web): July 25, 2006. The collaboration was supported by the Microelectronics Advanced Research Corporation (MARCO, J.F.S.) and its Focus Centers on Functional Engineered NanoArchitectonics (FENA) and Materials Structures and Devices, the Moletronics Program of the Defense Advanced Research Projects Agency (DARPA, J.F.S. and J.R.H.), and the Center for Nanoscale Innovation for Defense (CNID, J.F.S.). J.M.S. gratefully acknowledges the NSF for a Graduate Research Fellowship.
Funders:
Funding AgencyGrant Number
Microelectronics Advanced Research Corporation (MARCO)UNSPECIFIED
Defense Advanced Research Projects Agency (DARPA)UNSPECIFIED
Center for Nanoscale Innovation for Defense (CNID)UNSPECIFIED
NSF Graduate Research FellowshipUNSPECIFIED
Issue or Number:32
Record Number:CaltechAUTHORS:20170427-112457768
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170427-112457768
Official Citation:Efficient Templated Synthesis of Donor−Acceptor Rotaxanes Using Click Chemistry William R. Dichtel, Ognjen Š. Miljanić, Jason M. Spruell, James R. Heath, and J. Fraser Stoddart Journal of the American Chemical Society 2006 128 (32), 10388-10390 DOI: 10.1021/ja063127i
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:77007
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:27 Apr 2017 21:57
Last Modified:03 Oct 2019 17:52

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