Articles producció científica> Química Física i Inorgànica

Highly efficient chirality transfer from diamines encapsulated within a self-assembled calixarene-salen host

  • Dades identificatives

    Identificador: PC:1191
    Autors:
    Carles BoLuis Martínez-RodríguezNuno A. G. BandeiraArjan W. Kleij
    Resum:
    A calix[4]arene host equipped with two bis-[Zn(salphen)] complexes self-assembles into a capsular complex in the presence of a chiral diamine guest with an unexpected 2:1 ratio between the host and the guest. Effective chirality transfer from the diamine to the calix-salen hybrid host is observed by circular dichroism (CD) spectroscopy, and a high stability constant K2,1 of 1.59×1011 M-2 for the assembled host-guest ensemble has been determined with a substantial cooperativity factor α of 6.4. Density functional calculations are used to investigate the origin of the stability of the host-guest system and the experimental CD spectrum compared with those calculated for both possible diastereoisomers showing that the M,M isomer is the one that is preferentially formed. The current system holds promise for the chirality determination of diamines, as evidenced by the investigated substrate scope and the linear relationship between the ee of the diamine and the amplitude of the observed Cotton effects. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
  • Altres:

    Autor segons l'article: Carles Bo Luis Martínez-Rodríguez Nuno A. G. Bandeira Arjan W. Kleij
    Departament: Química Física i Inorgànica
    Autor/s de la URV: BO JANÉ, CARLES Luis Martínez-Rodríguez Nuno A. G. Bandeira Arjan W. Kleij
    Paraules clau: Calixarenes chirality transfer encapsulation
    Resum: A calix[4]arene host equipped with two bis-[Zn(salphen)] complexes self-assembles into a capsular complex in the presence of a chiral diamine guest with an unexpected 2:1 ratio between the host and the guest. Effective chirality transfer from the diamine to the calix-salen hybrid host is observed by circular dichroism (CD) spectroscopy, and a high stability constant K2,1 of 1.59×1011 M-2 for the assembled host-guest ensemble has been determined with a substantial cooperativity factor α of 6.4. Density functional calculations are used to investigate the origin of the stability of the host-guest system and the experimental CD spectrum compared with those calculated for both possible diastereoisomers showing that the M,M isomer is the one that is preferentially formed. The current system holds promise for the chirality determination of diamines, as evidenced by the investigated substrate scope and the linear relationship between the ee of the diamine and the amplitude of the observed Cotton effects. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
    Àrees temàtiques: Química Química Chemistry
    ISSN: 0947-6539
    Identificador de l'autor: 0000-0001-9581-2922 n/a 0000-0002-5754-7328 0000-0002-7402-4764
    Data d'alta del registre: 2015-08-04
    Pàgina final: 7150
    Volum de revista: 21
    Versió de l'article dipositat: info:eu-repo/semantics/acceptedVersion
    Enllaç font original: http://onlinelibrary.wiley.com/doi/10.1002/chem.201500333/full
    URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
    DOI de l'article: 10.1002/chem.201500333
    Entitat: Universitat Rovira i Virgili
    Any de publicació de la revista: 2015
    Pàgina inicial: 7144
    Tipus de publicació: Article Artículo Article
  • Paraules clau:

    Quiralitat
    Calixarens
    Calixarenes
    chirality transfer
    encapsulation
    Química
    Química
    Chemistry
    0947-6539
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