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An exocyclic π-system extension of the phenanthriporphyrin framework: towards azaaceneporphyrinoids

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Abstract

A facile method for the exocyclic π-extension of the carbaporphyrinoid embedding phenanthrene moiety – phenanthriporphyrin – has been described. The reaction between 5,6-dioxophenanthriporphyrin and a series of aliphatic and aromatic amines provided a family of carbaporphyrinoids incorporating azaacene components. The 1H NMR spectroscopic, electrochemical, and optical properties of azaaceneporphyrinoids strongly depend on the structure of the incorporated moiety. The π-system extension of the attached azaacene subunit reduces the macrocyclic antiaromatic character.

Graphical abstract: An exocyclic π-system extension of the phenanthriporphyrin framework: towards azaaceneporphyrinoids

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Article information


Submitted
09 Apr 2020
Accepted
29 Apr 2020
First published
30 Apr 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

An exocyclic π-system extension of the phenanthriporphyrin framework: towards azaaceneporphyrinoids

B. Szyszko, D. Dróżdż, A. Sarwa, S. G. Mucha, A. Białońska, M. J. Białek, K. Matczyszyn and L. Latos-Grażyński, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00436G

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