Elsevier

Tetrahedron Letters

Volume 46, Issue 48, 28 November 2005, Pages 8359-8362
Tetrahedron Letters

Net directed 180° aryl–aryl bond rotation in a prototypical achiral biaryl lactone synthetic molecular motor

https://doi.org/10.1016/j.tetlet.2005.09.151Get rights and content

Abstract

Net directed 180° bond rotation was achieved through diastereoselective ring-opening reactions in an achiral biaryl lactone using a chiral nucleophile followed by re-lactonization. The efficiency of the directed bond rotation has been determined by HPLC–MS to be 50% and 20% with two different chiral nucleophiles. These results demonstrate the potential for a prototype of a chemically driven synthetic molecular motor which has the advantages of both simplicity and flexibility in operation and is the first example of the use of a chiral auxiliary to induce transient axial chirality resulting in net directed bond rotation.

Section snippets

Acknowledgements

We are grateful to NSF-CHE-9986926, PRF #35372AC-1, the US Department of Education GAANN P200A010222-03, and the NSF-IGERT DGE-0114419, for financial support.

References and notes (20)

  • V. Balzani et al.

    Molecular Devices and Machines

    (2003)
    V. Balzani et al.

    Angew. Chem.

    (2000)

    Angew. Chem., Int. Ed.

    (2000)
  • M. Schliwa

    Molecular Motors

    (2003)
  • D.S. Goodsell

    Our Molecular Nature

    (1996)
  • C.P. Mandl et al.

    Angew. Chem.

    (2004)

    Angew. Chem., Int. Ed.

    (2004)
  • N. Koumura et al.

    J. Am. Chem. Soc.

    (2002)
    R.V. van Delden et al.

    Org. Biomol. Chem.

    (2004)
    N. Koumura et al.

    Nature

    (1999)
  • D.A. Leigh et al.

    Nature

    (2003)
    J.V. Hernandez et al.

    Science

    (2004)
  • T.R. Kelly et al.

    Nature

    (1999)
    T.R. Kelly et al.

    J. Am. Chem. Soc.

    (2000)
    T.R. Kelly et al.

    Acc. Chem. Res.

    (2001)
  • H. Jian et al.

    J. Org. Chem.

    (2003)
    D.C. Caskey et al.

    Org. Lett.

    (2004)
    X. Zheng et al.

    J. Am. Chem. Soc.

    (2004)
    A. Carella et al.

    New J. Chem.

    (2005)
    M. Yamaki et al.

    J. Am. Chem. Soc.

    (2005)
    M.F. Hawthorne et al.

    Science

    (2004)
    B.J. Dahl et al.

    Tetrahedron Lett.

    (2004)
  • R.A. Van Delden et al.

    Proc. Nat. Acad. Sci. U.S.A.

    (2002)
    Y. Tabe et al.

    Nat. Mater.

    (2003)
There are more references available in the full text version of this article.

Cited by (28)

  • Making the second generation of molecular motors operate unidirectionally in response to electricity

    2022, Materials Today Chemistry
    Citation Excerpt :

    Therefore, the design and synthesis of artificial molecular motors is of great importance and a lot of works have been done [10,11,17–20]. In recent years, artificial molecular motors driven by various means have been studied, including chemical reactions [21–30], electromagnetic field [31–33], thermal energy [34,35], as well as photoactivated processes [36–56]. Undoubtedly, the best energy inputs to make molecular machines work are photons or electrons, which have the advantages of easy control and fast response [57–60].

  • Dynamic NMR and computational study of 5,5-dimethyl-3,4-di-p-tolyl-2- cylopenten-1-one

    2011, Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
    Citation Excerpt :

    Dynamic NMR studies have been extensively used to explore the kinetics and thermodynamics of the stereodynamic processes, occurring due to restricted intramolecular rotation [4]. For example, the rotational barriers are often measured by dynamic NMR methods, because at low temperatures, NMR signals for the different rotamers can be observed, and the rotational barrier (ΔG‡) can be easily measured at signal coalescence [2–7,12,13]. In this paper, we report the dynamic 1H NMR and computational study of hindered rotation of an aryl substituent in a cyclopentenone derivative.

View all citing articles on Scopus
View full text