Dynamic combinatorial libraries based on hydrogen-bonde molecular boxes

J.M.C.A. Kerckhoffs, Miguel Mateos timoneda, David Reinhoudt, Mercedes Crego Calama

    Research output: Contribution to journalArticleAcademicpeer-review

    22 Citations (Scopus)

    Abstract

    This article describes two different types of dynamic combinatorial libraries of host and guest molecules. The first part of this article describes the encapsulation of alizarin trimer 2 a3 by dynamic mixtures of up to twenty different self-assembled molecular receptors together with the amplification and selection of the best binder. Receptors (1 a-d)3(DEB)6 are formed by the self-assembly of six diethyl barbiturate (DEB) and calix[4]arene dimelamine derivatives 1 a-d by using hydrogen bonds. The largest amplification factor (2.8) for a host assembly (1 a3 (DEB)6) was observed after the addition of 2 a to four-component library 1 an1 b(3-n)(DEB)6 (n=0-3). Addition of 2 a to twenty-component library 1 an1 bm1 co1 d(3-(n+m+o))(DEB)6 (n, m, o=0-3; (n+m+o)3) also showed amplification of receptor 1 a3(DEB)6. The second part of this article describes the complexation of libraries of different alizarin-like guest molecules (2 a-d) and the self-assembled receptor 1 a3(DEB)6. This receptor is able to template the formation of the best-fitting guest trimer.
    Original languageUndefined
    Pages (from-to)2377-2385
    Number of pages9
    JournalChemistry: a European journal
    Volume13
    Issue number8
    DOIs
    Publication statusPublished - 2007

    Keywords

    • Binding selectivity
    • Hydrogen bonds
    • Self-Assembly
    • combinatorial chemistry
    • molecular capsules
    • METIS-241413
    • IR-72332

    Cite this

    Kerckhoffs, J.M.C.A. ; Mateos timoneda, Miguel ; Reinhoudt, David ; Crego Calama, Mercedes. / Dynamic combinatorial libraries based on hydrogen-bonde molecular boxes. In: Chemistry: a European journal. 2007 ; Vol. 13, No. 8. pp. 2377-2385.
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    abstract = "This article describes two different types of dynamic combinatorial libraries of host and guest molecules. The first part of this article describes the encapsulation of alizarin trimer 2 a3 by dynamic mixtures of up to twenty different self-assembled molecular receptors together with the amplification and selection of the best binder. Receptors (1 a-d)3(DEB)6 are formed by the self-assembly of six diethyl barbiturate (DEB) and calix[4]arene dimelamine derivatives 1 a-d by using hydrogen bonds. The largest amplification factor (2.8) for a host assembly (1 a3 (DEB)6) was observed after the addition of 2 a to four-component library 1 an1 b(3-n)(DEB)6 (n=0-3). Addition of 2 a to twenty-component library 1 an1 bm1 co1 d(3-(n+m+o))(DEB)6 (n, m, o=0-3; (n+m+o)3) also showed amplification of receptor 1 a3(DEB)6. The second part of this article describes the complexation of libraries of different alizarin-like guest molecules (2 a-d) and the self-assembled receptor 1 a3(DEB)6. This receptor is able to template the formation of the best-fitting guest trimer.",
    keywords = "Binding selectivity, Hydrogen bonds, Self-Assembly, combinatorial chemistry, molecular capsules, METIS-241413, IR-72332",
    author = "J.M.C.A. Kerckhoffs and {Mateos timoneda}, Miguel and David Reinhoudt and {Crego Calama}, Mercedes",
    year = "2007",
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    Dynamic combinatorial libraries based on hydrogen-bonde molecular boxes. / Kerckhoffs, J.M.C.A.; Mateos timoneda, Miguel; Reinhoudt, David; Crego Calama, Mercedes.

    In: Chemistry: a European journal, Vol. 13, No. 8, 2007, p. 2377-2385.

    Research output: Contribution to journalArticleAcademicpeer-review

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    T1 - Dynamic combinatorial libraries based on hydrogen-bonde molecular boxes

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    AU - Mateos timoneda, Miguel

    AU - Reinhoudt, David

    AU - Crego Calama, Mercedes

    PY - 2007

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    AB - This article describes two different types of dynamic combinatorial libraries of host and guest molecules. The first part of this article describes the encapsulation of alizarin trimer 2 a3 by dynamic mixtures of up to twenty different self-assembled molecular receptors together with the amplification and selection of the best binder. Receptors (1 a-d)3(DEB)6 are formed by the self-assembly of six diethyl barbiturate (DEB) and calix[4]arene dimelamine derivatives 1 a-d by using hydrogen bonds. The largest amplification factor (2.8) for a host assembly (1 a3 (DEB)6) was observed after the addition of 2 a to four-component library 1 an1 b(3-n)(DEB)6 (n=0-3). Addition of 2 a to twenty-component library 1 an1 bm1 co1 d(3-(n+m+o))(DEB)6 (n, m, o=0-3; (n+m+o)3) also showed amplification of receptor 1 a3(DEB)6. The second part of this article describes the complexation of libraries of different alizarin-like guest molecules (2 a-d) and the self-assembled receptor 1 a3(DEB)6. This receptor is able to template the formation of the best-fitting guest trimer.

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    KW - molecular capsules

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