22π-Electrons [] pentaphyrin as a new photosensitizing agent for water disinfection: experimental and theoretical characterization

  • Marta E. AlbertoEmail author
  • Clara Comuzzi
  • Merlyn Thandu
  • Carlo Adamo
  • Nino Russo
Regular Article
Part of the following topical collections:
  1. Health & Energy from the Sun: a Computational Perspective


In view of their promising photosensitizing features, expanded porphyrins are gaining wide attention for their potential use both in photodynamic therapy of cancer and as likely photoactivated agent for water disinfection. Herein, we report a joint experimental and theoretical investigation on the 20-(4′-carboxyphenyl)-2,13-dimethyl-3,12-diethyl-[22] pentaphyrin complex 4. The synthesis, NMR, UV–Vis and mass characterization of the new compound together with a detailed theoretical investigation of the photophysical properties, are presented. In particular, type I and type II photoreactions have been explored by means of DFT and its TDDFT formulation characterizing the electronic absorption spectra, providing singlet–triplet energy gap, vertical ionization potential and electron affinity. Results show that title compound is able to generate the cytotoxic singlet oxygen species supporting the application of the proposed molecule as a photoactivated agent for water disinfection.





M.E.A. would like to thank the Research Executive Agency (REA) and European Commission for the MSCA Individual Fellowship grant (call: H2020-MSCA-IF-2014, Project ID: 652999). This work was granted access to the HPC resources of MesoPSL financed by the Region Ile de France and the project Equip@Meso (reference ANR-10-EQPX-29-01) of the programme Investissements d’Avenir supervised by the Agence Nationale pour la Recherche. Università della Calabria, Università di Udine and ENSCP are gratefully acknowledged.

Supplementary material

214_2015_1794_MOESM1_ESM.doc (1.3 mb)
ESI–MS of PCCox, computed main bond lengths (Å) and main dihedral angles (degrees) for PCCox, main vertical singlet electronic energies for several conformations of PCCox obtained with different XC functionals in methanol, computed UV–Vis spectra, NMR computations (DOC 1346 kb)


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Copyright information

© Springer-Verlag Berlin Heidelberg 2016

Authors and Affiliations

  • Marta E. Alberto
    • 1
    Email author
  • Clara Comuzzi
    • 2
  • Merlyn Thandu
    • 2
  • Carlo Adamo
    • 1
  • Nino Russo
    • 3
  1. 1.Institut de Recherche de Chimie Paris, IRCP CNRS UMR-8247, École Nationale Superieure de Chimie de ParisChimie ParisTechParisFrance
  2. 2.Department of Chemistry, Physic and EnvironmentUniversity of UdineUdineItaly
  3. 3.Dipartimento di Chimica e Tecnologie ChimicheUniversità della CalabriaRendeItaly

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