An Imine Photocyclization as an Alternative to the Pictet-Spengler Reaction for the Synthesis of AzaBenzannulated Perylenediimide Dyes

AzaBenzannulated perylenediimide (AzaBPDI) dyes were synthesized in high yields via a new reaction sequence involving an imine condensation followed by visible light-induced photocyclization. The large scope and efficiency of this alternative to the Pictet-Spengler reaction are demonstrated, allowin...

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Bibliographic Details
Published in:Journal of organic chemistry 2020-06, Vol.85 (11), p.7218-7224
Main Authors: Goujon, Antoine, Rocard, Lou, Cauchy, Thomas, Hudhomme, Piétrick
Format: Article
Language:English
Subjects:
Chemical Sciences
Organic chemistry
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Summary:AzaBenzannulated perylenediimide (AzaBPDI) dyes were synthesized in high yields via a new reaction sequence involving an imine condensation followed by visible light-induced photocyclization. The large scope and efficiency of this alternative to the Pictet-Spengler reaction are demonstrated, allowing easy preparation of dimeric AzaBPDI as potential non-fullerene acceptors for organic solar cells.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c00600