Peripherally metalated secoporphyrazines: A new generation of photoactive pigments

Efstathia G. Sakellariou, Antonio Garrido Montalban, Hubert G. Meunier, Garry Rumbles, David Phillips, Richard B. Ostler, Klaus Suhling, Anthony G.M. Barrett, Brian M. Hoffman

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Abstract

Base-catalyzed cross condensation of dipropylmaleonitrile 1 with bis(dimethylamino)maleonitrile 2 in an equimolar ratio afforded the porphyrazines 3a, 4a, 5a, 6a and 7a. Subsequent demetalation of 5a with TFA followed by remetalation with Zn(OAc)2 gave ligand 5c in good yield. Compound 5c was, in turn, selectively oxidized and further peripherally functionalized using Pt(PhCN)2Cl2 and PdCl2 to yield the novel seco solitaire porphyrazines 1Oa and 10b. The photophysical profiles of the seco solitaire porphyrazines 10a and 10b were evaluated by means of absorption, emission, and transient absorption spectroscopy. The new pigments 10a and 10b were found to be photochemically more stable than the solitaire complexes 3d and 3e and mediated the generation of singlet oxygen with quantum yields of 0.59 and 0.45, respectively.

Original languageEnglish
Pages (from-to)2182-2187
Number of pages6
JournalInorganic Chemistry
Volume41
Issue number8
DOIs
Publication statusPublished - Apr 22 2002

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ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Inorganic Chemistry

Cite this

Sakellariou, E. G., Montalban, A. G., Meunier, H. G., Rumbles, G., Phillips, D., Ostler, R. B., Suhling, K., Barrett, A. G. M., & Hoffman, B. M. (2002). Peripherally metalated secoporphyrazines: A new generation of photoactive pigments. Inorganic Chemistry, 41(8), 2182-2187. https://doi.org/10.1021/ic0111583