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Published August 16, 2006 | Supplemental Material
Journal Article Open

Efficient Templated Synthesis of Donor−Acceptor Rotaxanes Using Click Chemistry


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.

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.

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August 19, 2023
October 25, 2023