π‐radical cascade to a chiral saddle‐shaped peropyrene : = [Pi]-radical cascade to a chiral saddle‐shaped peropyrene

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Abstract: Reactions of open-shell molecular graphene fragments are typically thought of as undesired decomposition processes because they lead to the loss of desired features like π-magnetism. Oxidative dimerization of phenalenyl to peropyrene shows, however, that these transformations hold promise as a synthetic tool for making complex structures via formation of multiple bonds and rings in a single step. Here, we explore the feasibility of using this “undesired” reaction of phenalenyl to build up strain and provide access to non-planar polycyclic aromatic hydrocarbons. To this end, we designed and synthesized a biradical system with two phenalenyl units linked via a biphenylene backbone. The design facilitates an intramolecular cascade reaction to a helically twisted saddle-shaped product, where the key transformations—ring-closure and ring-fusion—occur within one reaction. The negative curvature of the final peropyrene product, induced by the formed eight-membered ring, was confirmed by single-crystal X-ray diffraction analysis and the helical twist was validated via resolution of the product's enantiomers that display circularly polarized luminescence and high configurational stability

Weitere Titel
[Pi]-radical cascade to a chiral saddle‐shaped peropyrene
Standort
Deutsche Nationalbibliothek Frankfurt am Main
Umfang
Online-Ressource
Sprache
Englisch
Anmerkungen
Angewandte Chemie. - 136, 14 (2024) , e202318254, ISSN: 1521-3757

Ereignis
Veröffentlichung
(wo)
Freiburg
(wer)
Universität
(wann)
2024
Urheber

DOI
10.1002/ange.202318254
URN
urn:nbn:de:bsz:25-freidok-2580774
Rechteinformation
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
Letzte Aktualisierung
15.08.2025, 07:34 MESZ

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