Wavelength-Gated Photochemical Synthesis of Phenalene Diimides

Autor: Feist, Florian, Walden, Sarah L., Alves, Jessica, Kunz, Susanna V., Micallef, Aaron S., Brock, Aidan, McMurtrie, John C., Weil, Tanja, Blinco, James P., Barner-Kowollik, Christopher
Jazyk: angličtina
Rok vydání: 2021
Předmět:
Zdroj: Angewandte Chemie-International Edition, 60 (18), 10402-10408
ISSN: 1433-7851
0570-0833
1521-3773
DOI: 10.5445/ir/1000131171
Popis: 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.
Databáze: OpenAIRE
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