Preparation of new phenacene derivatives

Phenacenes are known as stable compounds with resistance to oxygen and light, which makes these planar π-conjugated compounds suitable for utilization as functional materials in numerous applications. The introduction of nitrogen atoms into the phenacene skeleton leads to the formation of a dipole moment which is reflected in modified physicochemical properties when compared to their carbo analogs. Recently, a novel methodology for the synthesis of aza[n]phenacenes (n = 4 – 6) was successfully developed utilizing photocyclodehydrochlorination reaction of starting 2-chloro-N-aryl-1-naphthamides. Also, a novel N,N-didodecyl-3,10-diazapicenium salts with bromide and hexafluorophosphate counterions were synthesized as an exfoliant, a stabilizer, and a p-dopant for liquid phase exfoliated graphene.

 

  • 3,10-Diazapicene as p-Doping of Graphene. Chem. Sci. 8, 3494-3499, 2017. DOI
  • Azaphenacenes by Oxidative Photocyclization of Aromatic Schiff Bases. Int. J. Mol. Sci. 21, 5868, 2020. DOI
  • Aza[n]phenacenes (n = 4-6) via Photocyclodehydrochlorination. J. Org. Chem. 86(19), 13252–13264, 2021. DOI
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