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π-Radical Cascade to a Chiral Saddle-Shaped Peropyrene
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 |
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