Self-Assembled Pentamers and Hexamers Linked through Quadruple-Hydrogen-Bonded 2-Ureido-4[1H]-Pyrimidinones

Authors

  • Henk M. Keizer Dr.,

    1. Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, PO Box 513, 5600 MB, Eindhoven, The Netherlands, Fax: (+31) 40-245-1036
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    • Both authors contributed equally to this work.

  • Juan J. González Dr.,

    1. Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain, Fax: (+34) 91-497-3966
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    • Both authors contributed equally to this work.

  • Margarita Segura Dr.,

    1. Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain, Fax: (+34) 91-497-3966
    2. Institute of Chemical Research of Catalonia (ICIQ), Avgda. Països Catalans s/n, 43007 Tarragona, Spain, Fax: (+34) 977-920-226
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  • Pilar Prados Prof. Dr.,

    1. Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain, Fax: (+34) 91-497-3966
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  • Rint P. Sijbesma Dr.,

    1. Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, PO Box 513, 5600 MB, Eindhoven, The Netherlands, Fax: (+31) 40-245-1036
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  • E. W. Meijer Prof. Dr.,

    1. Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, PO Box 513, 5600 MB, Eindhoven, The Netherlands, Fax: (+31) 40-245-1036
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  • Javier de Mendoza Prof. Dr.

    1. Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain, Fax: (+34) 91-497-3966
    2. Institute of Chemical Research of Catalonia (ICIQ), Avgda. Països Catalans s/n, 43007 Tarragona, Spain, Fax: (+34) 977-920-226
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Abstract

The preorganization of bifunctional 2-ureido-4-pyrimidinones mediated by either 1,3-substituted adamantane or meta-substituted phenylene ring linkers leads to the preferred formation of stable pentameric (1)5 and hexameric (2)6 assemblies, respectively. Despite the high binding constant of the 2-ureido-4-pyrimidinone dimers and the highly preorganized structure of the monomer, the predominant formation of cycles (1)5 and (2)6 in solution occurs only within a specific concentration range.

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