Articles producció científica> Química Física i Inorgànica

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

  • Identification data

    Identifier: imarina:5128847
    Authors:
    Martinez-Rodriguez, LuisBandeira, Nuno A. G.Bo, CarlesKleij, Arjan W.
    Abstract:
    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 ¿ 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.
  • Others:

    Author, as appears in the article.: Martinez-Rodriguez, Luis; Bandeira, Nuno A. G.; Bo, Carles; Kleij, Arjan W.;
    Department: Química Física i Inorgànica
    URV's Author/s: Bo Jané, Carles
    Keywords: Supramolecular chirality Salens Multiwavelength spectroscopic data Induction Identity Host-guest systems Equilibrium-constants Encapsulation Enantiomeric excess Complexes Circular-dichroism Chirogenesis Chirality transfer Calixarenes Amino-alcohols host-guest systems encapsulation chirality transfer calixarenes
    Abstract: 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 ¿ 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.
    Thematic Areas: Química Organic chemistry Medicina i Materiais Interdisciplinar General medicine General chemistry Farmacia Engenharias iii Engenharias ii Ciências biológicas iii Ciências biológicas ii Ciências biológicas i Ciências agrárias i Chemistry, multidisciplinary Chemistry (miscellaneous) Chemistry (all) Chemistry Catalysis Biotecnología Biodiversidade Astronomia / física
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    Author's mail: carles.bo@urv.cat
    Author identifier: 0000-0001-9581-2922
    Record's date: 2024-09-07
    Papper version: info:eu-repo/semantics/acceptedVersion
    Link to the original source: https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.201500333
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Papper original source: Chemistry-A European Journal. 21 (19): 7144-7150
    APA: Martinez-Rodriguez, Luis; Bandeira, Nuno A. G.; Bo, Carles; Kleij, Arjan W.; (2015). Highly efficient chirality transfer from diamines encapsulated within a self-assembled calixarene-salen host. Chemistry-A European Journal, 21(19), 7144-7150. DOI: 10.1002/chem.201500333
    Article's DOI: 10.1002/chem.201500333
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2015
    Publication Type: Journal Publications
  • Keywords:

    Catalysis,Chemistry,Chemistry (Miscellaneous),Chemistry, Multidisciplinary,Organic Chemistry
    Supramolecular chirality
    Salens
    Multiwavelength spectroscopic data
    Induction
    Identity
    Host-guest systems
    Equilibrium-constants
    Encapsulation
    Enantiomeric excess
    Complexes
    Circular-dichroism
    Chirogenesis
    Chirality transfer
    Calixarenes
    Amino-alcohols
    host-guest systems
    encapsulation
    chirality transfer
    calixarenes
    Química
    Organic chemistry
    Medicina i
    Materiais
    Interdisciplinar
    General medicine
    General chemistry
    Farmacia
    Engenharias iii
    Engenharias ii
    Ciências biológicas iii
    Ciências biológicas ii
    Ciências biológicas i
    Ciências agrárias i
    Chemistry, multidisciplinary
    Chemistry (miscellaneous)
    Chemistry (all)
    Chemistry
    Catalysis
    Biotecnología
    Biodiversidade
    Astronomia / física
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