Wavelength-Gated Photochemical Synthesis of Phenalene Diimides.

Autor: Feist F; Centre for Materials Science, Queensland University of Technology (QUT), 2 George St., Brisbane, QLD, 4000, Australia.; School of Chemistry and Physics, Queensland University of Technology (QUT), 2 George St., Brisbane, QLD, 4000, Australia.; Max Planck Institute for Polymer Research (MPIP), Ackermannweg 10, 55128, Mainz, Germany.; Macromolecular Architectures, Institute for Chemical Technology and Polymer Chemistry, Karlsruhe Institute of Technology (KIT), Engesserstrasse 18, 76131, Karlsruhe, Germany.; Institute of Nanotechnology, Hermann-von-Helmholtz-Platz 1, 76344, Eggenstein-Leopoldshafen, Germany., Walden SL; Centre for Materials Science, Queensland University of Technology (QUT), 2 George St., Brisbane, QLD, 4000, Australia.; School of Chemistry and Physics, Queensland University of Technology (QUT), 2 George St., Brisbane, QLD, 4000, Australia., Alves J; Centre for Materials Science, Queensland University of Technology (QUT), 2 George St., Brisbane, QLD, 4000, Australia.; School of Chemistry and Physics, Queensland University of Technology (QUT), 2 George St., Brisbane, QLD, 4000, Australia., Kunz SV; Centre for Materials Science, Queensland University of Technology (QUT), 2 George St., Brisbane, QLD, 4000, Australia.; School of Chemistry and Physics, Queensland University of Technology (QUT), 2 George St., Brisbane, QLD, 4000, Australia., Micallef AS; Centre for Materials Science, Queensland University of Technology (QUT), 2 George St., Brisbane, QLD, 4000, Australia., Brock AJ; Centre for Materials Science, Queensland University of Technology (QUT), 2 George St., Brisbane, QLD, 4000, Australia.; School of Chemistry and Physics, Queensland University of Technology (QUT), 2 George St., Brisbane, QLD, 4000, Australia., McMurtrie JC; Centre for Materials Science, Queensland University of Technology (QUT), 2 George St., Brisbane, QLD, 4000, Australia.; School of Chemistry and Physics, Queensland University of Technology (QUT), 2 George St., Brisbane, QLD, 4000, Australia., Weil T; Max Planck Institute for Polymer Research (MPIP), Ackermannweg 10, 55128, Mainz, Germany., Blinco JP; Centre for Materials Science, Queensland University of Technology (QUT), 2 George St., Brisbane, QLD, 4000, Australia.; School of Chemistry and Physics, Queensland University of Technology (QUT), 2 George St., Brisbane, QLD, 4000, Australia., Barner-Kowollik C; Centre for Materials Science, Queensland University of Technology (QUT), 2 George St., Brisbane, QLD, 4000, Australia.; School of Chemistry and Physics, Queensland University of Technology (QUT), 2 George St., Brisbane, QLD, 4000, Australia.; Macromolecular Architectures, Institute for Chemical Technology and Polymer Chemistry, Karlsruhe Institute of Technology (KIT), Engesserstrasse 18, 76131, Karlsruhe, Germany.; Institute of Nanotechnology, Hermann-von-Helmholtz-Platz 1, 76344, Eggenstein-Leopoldshafen, Germany.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2021 Apr 26; Vol. 60 (18), pp. 10402-10408. Date of Electronic Publication: 2021 Mar 18.
DOI: 10.1002/anie.202016632
Abstrakt: Herein, we pioneer a wavelength-gated synthesis route to phenalene diimides. Consecutive Diels-Alder reactions of methylisophthalaldehydes and maleimides afford hexahydro-phenalene-1,6-diol diimides via 5-formyl-hexahydro-benzo[f]isoindoles as the intermediate. Both photoreactions are efficient (82-99 % yield) and exhibit excellent diastereoselectivity (62-98 % d.r.). The wavelength-gated nature of the stepwise reaction enables the modular construction of phenalene diimide scaffolds by choice of substrate and wavelength. Importantly, this synthetic methodology opens a facile avenue to a new class of persistent phenalenyl diimide neutral radicals, constituting a versatile route to spin-active molecules.
(© 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)
Databáze: MEDLINE
Externí odkaz: