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Efficient Templated Synthesis of Donor–Acceptor Rotaxanes Using Click Chemistry

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The Power of Click Chemistry for Molecular Machines and Surface Patterning

Part of the book series: Springer Theses ((Springer Theses))

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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) (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.

This Chapter is reproduced in part with permission from: Dichtel WR, Miljanić OŠ, Spruell JM, Heath JR, Stoddart JF. J. Am. Chem. Soc.2006, 128, 10388–10390.

Author Contributions: W.R. Dichtel and J.F. Stoddart prepared the original manuscript. W.R. Dichtel, O.Š. Miljanić, and J.M. Spruell conceived of the project. W.R. Dichtel and J.M. Spruell synthesized the compounds reported in the communication (J.M. Spruell synthesized compounds 2 and 5). J.F. Stoddart and J.R. Heath supervised the original research.

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  1. Institute and Materials Research Laboratory, University of California, Santa Barbara, CA, USA

    Jason M. Spruell

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Correspondence to Jason M. Spruell .

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Spruell, J.M. (2011). Efficient Templated Synthesis of Donor–Acceptor Rotaxanes Using Click Chemistry. In: The Power of Click Chemistry for Molecular Machines and Surface Patterning. Springer Theses. Springer, New York, NY. https://doi.org/10.1007/978-1-4419-9647-3_2

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