π‐Radical Cascade to a Chiral Saddle‐Shaped Peropyrene

Author:

Bernhardt Annika1,Čavlović Daniel1ORCID,Mayländer Maximilian2ORCID,Blacque Olivier1ORCID,Cruz Carlos M.13ORCID,Richert Sabine2ORCID,Juríček Michal1ORCID

Affiliation:

1. Department of Chemistry University of Zurich Winterthurerstrasse 190 8057 Zurich Switzerland

2. Institute of Physical Chemistry University of Freiburg Albertstraße 21 79104 Freiburg Germany

3. Department of Organic Chemistry University of Granada Avenida de la Fuente Nueva S/N 18071 Granada Spain

Abstract

AbstractReactions 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.

Funder

H2020 European Research Council

Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung

Universität Zürich

Deutsche Forschungsgemeinschaft

Publisher

Wiley

Cited by 3 articles. 订阅此论文施引文献 订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献

1. Chiral Teropyrenes: Synthesis, Structure, and Spectroscopic Studies;Angewandte Chemie International Edition;2024-07-15

2. Chiral Teropyrenes: Synthesis, Structure, and Spectroscopic Studies;Angewandte Chemie;2024-07-15

3. Regioselective On-Surface Synthesis of [3]Triangulene Graphene Nanoribbons;Journal of the American Chemical Society;2024-05-30

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