Monatshefte für Chemie - Chemical Monthly

, Volume 150, Issue 1, pp 67–75 | Cite as

Synthetic access to new porphyrinoids from 2-nitro-5,10,15,20-tetraphenylporphyrin and an arylacetonitrile

  • Ouafa Amiri
  • Nuno M. M. MouraEmail author
  • Maria A. F. Faustino
  • José A. S. Cavaleiro
  • El Mostapha Rakib
  • Maria G. P. M. S. Neves
Original Paper


In this work, the reactivity of 2-nitro-5,10,15,20-tetraphenylporphyrin with 2-(4-nitrophenyl)acetonitrile in the presence of KOH as base was studied. Under these conditions, three new compounds were isolated: a β-di-substituted derivative, as the major compound, accompanied by two minor products, a π-extended and a β-isoxazoline-fused derivative, all in acceptable yields. A preliminary study was also performed in the presence of K2CO3. It allowed the isolation of a cyclopropyl-annulated chlorin in very good yield. All the obtained products were photochemically and photophysically characterized, some of them showing promising properties to be used as photosensitizers in photodynamic processes.

Graphical abstract


Tetrapyrroles Porphyrins Nucleophilic substitutions Photosensitizer Singlet oxygen 



Thanks are due to FCT/MEC for the financial support to the QOPNA research Unit (FCT UID/QUI/00062/2013), through national funds and when applicable co-financed by the FEDER, within the PT2020 Partnership Agreement and “Compete” 2020, and also to the Portuguese NMR Network. N. M. M. Moura thanks to FCT for his postdoctoral Grant (SFRH/BPD/84216/2012). The authors also thank the Transnational cooperation program, FCT-CNRST (Morocco), for financial assistance.

Supplementary material

706_2018_2283_MOESM1_ESM.docx (138.1 mb)
Supplementary material 1 (DOCX 141450 kb)


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Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Laboratoire de Chimie Organique et Analytique, Faculté des Sciences et TechniquesUniversité Sultan Moulay SlimaneBeni-MellalMorocco
  2. 2.QOPNA and Department of ChemistryUniversity of AveiroAveiroPortugal

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