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Oxidative insertion of amines into conjugated macrocycles: transformation of antiaromatic norcorrole into aromatic azacorrole.

Sha LiYahan SunXiaofang LiOskar SmagaSebastian KoniarzMiłosz PawlickiPiotr J Chmielewski
Published in: Chemical communications (Cambridge, England) (2023)
A new group of aromatic porphyrinoids was obtained by an oxidative insertion of primary amines into the antiaromatic ring of 5,14-dimesityl-norcorrolatonickel(II) activated by iodosobenzene. The substituted 10-azacorroles thus formed were characterized by spectroscopic and electrochemical methods, and XRD analysis. Protonated forms of azacorroles were shown to remain aromatic despite disconnection of the original π-electron delocalization path.
Keyphrases
  • amino acid
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