dc.contributor.author | Bernhardt, Annika | |
dc.contributor.author | Čavlović, Daniel | |
dc.contributor.author | Mayländer, Maximilian | |
dc.contributor.author | Blacque, Olivier | |
dc.contributor.author | Moreno Cruz, Carlos | |
dc.contributor.author | Richert, Sabine | |
dc.contributor.author | Juríček, Michal | |
dc.date.accessioned | 2024-06-05T08:06:30Z | |
dc.date.available | 2024-06-05T08:06:30Z | |
dc.date.issued | 2024-03-22 | |
dc.identifier.citation | Angew. Chem. Int. Ed. 2024, 63, e202318254 doi.org/10.1002/anie.202318254 | es_ES |
dc.identifier.uri | https://hdl.handle.net/10481/92345 | |
dc.description | Author Keywords: phenalenyl · biradicals · peropyrene · negative
curvature · circularly polarized luminescence | es_ES |
dc.description.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 eightmembered
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. | es_ES |
dc.description.sponsorship | H2020 European Research Council. Grant Number: ERC StG 716139 / INSPIRAL | es_ES |
dc.description.sponsorship | Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung. Grant Numbers: CRSK-2_190365, PP00P2_170534, PP00P2_198900, TMCG-2_213829 / CASCADER | es_ES |
dc.description.sponsorship | Universität Zürich. Grant Number: FK-21-131 | es_ES |
dc.description.sponsorship | Deutsche Forschungsgemeinschaft. Grant Number: 417643975 | es_ES |
dc.description.sponsorship | Open Access funding provided by Universität Zürich. | es_ES |
dc.language.iso | eng | es_ES |
dc.publisher | Wiley | es_ES |
dc.rights | Attribution-NonCommercial-NoDerivatives 4.0 Internacional | * |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/4.0/ | * |
dc.subject | Circularly polarized luminescence | es_ES |
dc.subject | Chirality | es_ES |
dc.title | π-Radical Cascade to a Chiral Saddle-Shaped Peropyrene | es_ES |
dc.title.alternative | Pi Radical Cascade to a Chiral Saddle Shaped Peropyrene | es_ES |
dc.type | journal article | es_ES |
dc.rights.accessRights | open access | es_ES |
dc.identifier.doi | 10.1002/anie.202318254 | |
dc.type.hasVersion | VoR | es_ES |