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- Publisher Website: 10.1021/ja063127i
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Article: Efficient templated synthesis of donor - Acceptor rotaxanes using click chemistry
Title | Efficient templated synthesis of donor - Acceptor rotaxanes using click chemistry |
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Authors | |
Issue Date | 2006 |
Citation | Journal of the American Chemical Society, 2006, v. 128, n. 32, p. 10388-10390 How to Cite? |
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) (CBPQT4+) 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/CBPQT4+ donor-acceptor recognition motifs. Copyright © 2006 American Chemical Society. |
Persistent Identifier | http://hdl.handle.net/10722/332684 |
ISSN | 2023 Impact Factor: 14.4 2023 SCImago Journal Rankings: 5.489 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Dichtel, William R. | - |
dc.contributor.author | Miljanić, Ognjen S. | - |
dc.contributor.author | Spruell, Jason M. | - |
dc.contributor.author | Heath, James R. | - |
dc.contributor.author | Stoddart, J. Fraser | - |
dc.date.accessioned | 2023-10-06T05:13:29Z | - |
dc.date.available | 2023-10-06T05:13:29Z | - |
dc.date.issued | 2006 | - |
dc.identifier.citation | Journal of the American Chemical Society, 2006, v. 128, n. 32, p. 10388-10390 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | http://hdl.handle.net/10722/332684 | - |
dc.description.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) (CBPQT4+) 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/CBPQT4+ donor-acceptor recognition motifs. Copyright © 2006 American Chemical Society. | - |
dc.language | eng | - |
dc.relation.ispartof | Journal of the American Chemical Society | - |
dc.title | Efficient templated synthesis of donor - Acceptor rotaxanes using click chemistry | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1021/ja063127i | - |
dc.identifier.scopus | eid_2-s2.0-33747624198 | - |
dc.identifier.volume | 128 | - |
dc.identifier.issue | 32 | - |
dc.identifier.spage | 10388 | - |
dc.identifier.epage | 10390 | - |
dc.identifier.isi | WOS:000239618700021 | - |