ArticleAngewandte Chemie (International ed. in English)2021
Wavelength-Gated Photochemical Synthesis of Phenalene Diimides.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Toward Chromoselective Transformations in Biological Systems: Perspectives and Challenges.Angewandte Chemie (International ed. in English) · 2026Review
- α-Methoxy Benzaldehyde Based Photopolymers as a Promising Toolbox for Architected Carbon.Macromolecular rapid communications · 2025Article
- 1,2-Acyl transposition through photochemical skeletal rearrangement of 2,3-dihydrobenzofurans.Science (New York, N.Y.) · 2025Article
- Photochemical Action Plots Map Orthogonal Reactivity in Photochemical Release Systems.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Mechanistic Investigation, Wavelength-Dependent Reactivity, and Expanded Reactivity ofJournal of the American Chemical Society · 2024Article
- Microspheres from light-a sustainable materials platform.Nature communications · 2022Article
- Wavelength-Gated Photochemical Synthesis of Phenalene Diimides.Angewandte Chemie (International ed. in English) · 2021Article
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Authors and funding
10 authors.
Funding
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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