Stereospecific Winding of Polycyclic Aromatic Hydrocarbons into Trinacria Propellers

Dario Mosca, Antoine Stopin, Johan Wouters, Nicola Demitri, Davide Bonifazi

Résultats de recherche: Contribution à un journal/une revueArticle

Résumé

The stereospecific trimerization of enantiomerically pure binaphthols with hexakis(bromomethyl)benzene gives access in one step to enantiomerically pure molecular propellers, in which three binaphthyl rings are held together with dioxecine rings. X-ray diffraction analysis revealed that three out the six naphthyl moieties are folded in a (EF)3 -type arrangement held by three intramolecular C-H⋅⋅⋅π interactions. This slips outward the three remaining naphthyl rings in a blade-like fashion, just like in three-folded propeller components. This peculiar conformation shows striking similarity to the mythological Sicilian symbol of Trinacria, from which the name "trinacria propeller" derives. The propeller conformation is also preserved in chlorinated solutions, as displayed by the presence of a peak at 4.7 ppm typical of an aromatic proton resonance engaged in a C-H⋅⋅⋅π interaction. The denaturation of the propeller-like conformation is obtained at high temperature, corresponding to activation energy for the ring inversion of ca. 18.2 kcal mol-1 . Notably, halide-functionalized molecular propellers exposing I-atoms at the leading and trailing edges could be prepared stereo- and regiospecifically by choosing the relevant iodo-bearing BINOL derivative.

langue originaleAnglais
Pages (de - à)15348-15354
Nombre de pages7
journalChemistry - A European Journal
Volume23
Numéro de publication61
Les DOIs
Etat de la publicationPublié - 2 nov. 2017
Modification externeOui

Empreinte digitale Examiner les sujets de recherche de « Stereospecific Winding of Polycyclic Aromatic Hydrocarbons into Trinacria Propellers ». Ensemble, ils forment une empreinte digitale unique.

  • Équipement

  • Ensembles de données

    CCDC 1037158: Experimental Crystal Structure Determination

    BONIFAZI, D. (Contributeur), Demitri, N. (Contributeur), Mosca, D. (Contributeur), Stopin, A. (Contributeur) & WOUTERS, J. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2017

    Ensemble de données

    CCDC 1037157: Experimental Crystal Structure Determination

    BONIFAZI, D. (Contributeur), Demitri, N. (Contributeur), Mosca, D. (Contributeur), Stopin, A. (Contributeur) & WOUTERS, J. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2017

    Ensemble de données

    CCDC 1548318: Experimental Crystal Structure Determination

    BONIFAZI, D. (Contributeur), Demitri, N. (Contributeur), Mosca, D. (Contributeur), Stopin, A. (Contributeur) & WOUTERS, J. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2017

    Ensemble de données

    Contient cette citation