Template-Directed In Crystallo Photopolymerization of a Donor–Acceptor Cyclopropane: When Everything Falls into Place! - Chimie Théorique et Modèles (iSm2) Accéder directement au contenu
Article Dans Une Revue Journal of the American Chemical Society Année : 2024

Template-Directed In Crystallo Photopolymerization of a Donor–Acceptor Cyclopropane: When Everything Falls into Place!

Résumé

A single-crystal-to-single-crystal solid-state reaction of vinylogous donor–acceptor cyclopropanes is documented. The enantiospecific synthesis of new products, distinct from those obtained in solution, is achieved for the target compounds. Photopolymerization occurred upon X-ray exposure to the crystals. Notably, in one case, this reactivity exhibits selectivity since an ordered arrangement of polymers and unreacted cocrystallized monomeric conformers has been observed. Structural characterization of the complete transformation monitored through single-crystal X-ray diffraction and supported by molecular dynamics simulations sheds light on the subtle role of crystal packing in the reaction process. Moreover, the X-ray diffraction (XRD)-resolved structure of a donor–acceptor cyclopropane intermediate reveals an elongation in bond length that corroborates the existence of the so-called “push–pull effect
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Dates et versions

hal-04617160 , version 1 (19-06-2024)

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Domaine public

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Michel Giorgi, Kévin Masson, Sara Chentouf, Laurent Commeiras, Paola Nava, et al.. Template-Directed In Crystallo Photopolymerization of a Donor–Acceptor Cyclopropane: When Everything Falls into Place!. Journal of the American Chemical Society, In press, ⟨10.1021/jacs.4c04899⟩. ⟨hal-04617160⟩

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