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Wavelength-Gated Photochemical Synthesis of Phenalene Diimides

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

Abstract:
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.

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Verlagsausgabe §
DOI: 10.5445/IR/1000131171
Veröffentlicht am 08.04.2021
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Technische Chemie und Polymerchemie (ITCP)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2021
Sprache Englisch
Identifikator ISSN: 1433-7851, 0570-0833, 1521-3773
KITopen-ID: 1000131171
Erschienen in Angewandte Chemie - International Edition
Verlag Wiley
Schlagwörter Diels–Alder reaction; ortho-quinodimethane; persistent neutral radicals; phenalene diimide; wavelength-gated synthesis
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