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

Goujon, Antoine; Rocard, Lou; Cauchy, Thomas; Hudhomme, Piétrick

doi:10.26434/chemrxiv.11878086.v1

Cited by 2 publications

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References 8 publications

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“…Recently, our group reported an alternative to the Pictet-Spengler reaction to access azabenzannulated PDIs 47 (Scheme 15) [35]. This original reaction involves the formation of an imine intermediate, its photocyclization by visible light followed by re-aromatization using DDQ.…”

Section: Resultsmentioning

confidence: 99%

“…Interestingly, PDI-pyridyl based iridium and ruthenium complexes were prepared and characterized; in particular, their phosphorescence in the near-infrared region [73,74]. Recently, our group reported an alternative to the Pictet-Spengler reaction to access azabenzannulated PDIs 47 (Scheme 15) [35]. This original reaction involves the formation of an imine intermediate, its photocyclization by visible light followed by re-aromatization using DDQ.…”

Section: Reactivity Of 1-aminopdimentioning

confidence: 99%

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Nitro-Perylenediimide: An Emerging Building Block for the Synthesis of Functional Organic Materials

2020

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Perylenediimide (PDI) is one of the most important classes of dyes and is intensively explored in the field of functional organic materials. The functionalization of this electron-deficient aromatic core is well-known to tune the outstanding optoelectronic properties of PDI derivatives. In this respect, the functionalization has been mostly addressed in bay-positions to halogenated derivatives through nucleophilic substitutions or metal-catalyzed coupling reactions. Being aware of the synthetic difficulties of obtaining the key intermediate 1-bromoPDI, we will present as an alternative in this review the potential of 1-nitroPDI: a powerful building block to access a large variety of PDI-based materials.

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Section: Resultsmentioning

confidence: 99%

Section: Reactivity Of 1-aminopdimentioning

confidence: 99%

Nitro-Perylenediimide: An Emerging Building Block for the Synthesis of Functional Organic Materials

2020

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

et al. 2020

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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.

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

Cited by 2 publications

References 8 publications

Nitro-Perylenediimide: An Emerging Building Block for the Synthesis of Functional Organic Materials

Nitro-Perylenediimide: An Emerging Building Block for the Synthesis of Functional Organic Materials

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

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