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Synfacts 2006(3): 0217-0217  
DOI: 10.1055/s-2006-931937
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Covalent Template Approach to Macrocycle Synthesis

Contributor(s): Timothy M. Swager, Anne J. McNeil
A. Ziegler, W. Mamdouh, A. Ver Heyen, M. Surin, H. Uji-I, M. M. S. Abdel-Mottaleb, F. C. De Schryver, S. De Feyter*, R. Lazzaroni*, S. Höger*
Max Planck Institute for Polymer Research, Universität Karlsruhe, Germany; Katholieke Universiteit Leuven and Université de Mons-Hainaut, Belguim
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Publication Date:
21 February 2006 (online)

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Significance

Shape-persistent macrocycles are an emerging class of functional materials due to their spontaneous self-assembly in solution and on surfaces. The columnar self-assembly is of current interest in electro-optical applications. In this contribution, Höger et al. apply their covalent template approach (J. Org. Chem. 1997, 62, 4556-4557) to generate the desired macrocycle in 81% yield - a substantial improvement from the 29% isolated yield obtained for an analogous molecule via intermolecular cyclization.