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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
Working Paper
This content is an early or alternative research output and has not been peer-reviewed by Cambridge University Press at the time of posting.

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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SI
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Molecular Calculation Report
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Now Published

An Imine Photocyclization as an Alternative to the Pictet–Spengler Reaction for the Synthesis of AzaBenzannulated Perylenediimide Dyes [opens in a new tab]
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

Version History

Feb 21, 2020 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv.11878086.v1
D O I: 10.26434/chemrxiv.11878086.v1 [opens in a new tab]

Author’s competing interest statement

The authors declare no competing financial interest

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