Supramolecular chirogenesis in zinc porphyrins: Complexation with enantiopure thiourea derivatives, binding studies and chirality transfer mechanism - Université de Montpellier Accéder directement au contenu
Article Dans Une Revue Journal of Porphyrins and Phthalocyanines Année : 2020

Supramolecular chirogenesis in zinc porphyrins: Complexation with enantiopure thiourea derivatives, binding studies and chirality transfer mechanism

Nele Konrad
  • Fonction : Auteur
Darya Meniailava
  • Fonction : Auteur
Irina Osadchuk
Jasper Adamson
Mohammed Hasan
  • Fonction : Auteur
Riina Aav
Victor Borovkov
Dzmitry Kananovich

Résumé

Complexation of three (1R,2R)-2-aminocyclohexyl arylthioureas (aryl = 3,5-bis(trifluoromethyl)phenyl; phenyl; 3,5-dimethylphenyl) as the guests to ZnTPP and ZnOEP hosts has been studied by means of UV-Vis, CD spectroscopies and computational simulation. The complexation proceeds via coordination of the primary amino group to the zinc ion of the metalloporphyrin and induces a moderate circular dichroism signal in the Soret band of the porphyrins. The association constants increase with larger electron-withdrawing properties of the porphyrin host and larger electron-donating ability of the guest, indicating predominantly electrostatic (Lewis acid-base) character of the complexation. Computational study of the (1R,2R)-2-aminocyclohexyl-(3,5-bis(trifluoromethyl)phenyl)thiourea and ZnTPP complex revealed slight asymmetric distortion of the porphyrin plane caused by the chiral guest and additional π-π interactions between the host and guest molecules. Calculated CD spectrum for the same system reproduces the experimentally observed.
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Dates et versions

hal-02617498 , version 1 (29-05-2020)

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Nele Konrad, Darya Meniailava, Irina Osadchuk, Jasper Adamson, Mohammed Hasan, et al.. Supramolecular chirogenesis in zinc porphyrins: Complexation with enantiopure thiourea derivatives, binding studies and chirality transfer mechanism. Journal of Porphyrins and Phthalocyanines, 2020, 24 (05n07), pp.840-849. ⟨10.1142/S108842461950192X⟩. ⟨hal-02617498⟩
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