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Stereospecific winding of polycyclic aromatic hydrocarbons into Trinacria propellers

Mosca, Dario, Stopin, Antoine, Demitri, Nicola, Wouters, Johan and Bonifazi, Davide 2017. Stereospecific winding of polycyclic aromatic hydrocarbons into Trinacria propellers. Chemistry: A European Journal 23 (61) , pp. 15348-15354. 10.1002/chem.201702032

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Abstract

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 through 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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: Wiley
ISSN: 0947-6539
Date of First Compliant Deposit: 6 June 2017
Date of Acceptance: 19 May 2017
Last Modified: 20 Jul 2018 19:08
URI: http://orca.cf.ac.uk/id/eprint/101189

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