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

Antoine Goujon; Lou Rocard; Thomas Cauchy; Piétrick Hudhomme

doi:10.26434/chemrxiv.11878086.v1

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

21 February 2020, Version 1

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Abstract

AzaBenzannulated PDI (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 is demonstrated, and allows the easy preparation of dimeric AzaBPDI as potential non-fullerene acceptors for organic solar cells.

Keywords

perylenediimide

chromophore

photocyclization

Pictet-Spengler-type cyclization

Supplementary materials

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

Antoine Goujon, Lou Rocard, Thomas Cauchy, Piétrick Hudhomme journal article

The Journal of Organic Chemistry , Volume 85, Issue 11

Online publication date: Apr 30, 2020

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Feb 21, 2020 Version 1

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The content is available under CC BY NC ND 4.0

DOI

10.26434/chemrxiv.11878086.v1

Author’s competing interest statement

The authors declare no competing financial interest

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

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Abstract

Keywords

Supplementary materials

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Author’s competing interest statement

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