Peripherally metalated secoporphyrazines

A new generation of photoactive pigments

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

Research output: Contribution to journalArticle

39 Citations (Scopus)

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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Singlet Oxygen
Quantum yield
pigments
Absorption spectroscopy
Pigments
Condensation
absorption spectroscopy
condensation
Ligands
ligands
oxygen
profiles
palladium chloride

ASJC Scopus subject areas

  • Inorganic Chemistry

Cite this

Sakellariou, E. G., Montalban, A. G., Meunier, H. G., Rumbles, G., Phillips, D., Ostler, R. B., ... 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

Peripherally metalated secoporphyrazines : A new generation of photoactive pigments. / Sakellariou, Efstathia G.; Montalban, Antonio Garrido; Meunier, Hubert G.; Rumbles, Gary; Phillips, David; Ostler, Richard B.; Suhling, Klaus; Barrett, Anthony G M; Hoffman, Brian M.

In: Inorganic Chemistry, Vol. 41, No. 8, 22.04.2002, p. 2182-2187.

Research output: Contribution to journalArticle

Sakellariou, EG, Montalban, AG, Meunier, HG, Rumbles, G, Phillips, D, Ostler, RB, Suhling, K, Barrett, AGM & Hoffman, BM 2002, 'Peripherally metalated secoporphyrazines: A new generation of photoactive pigments', Inorganic Chemistry, vol. 41, no. 8, pp. 2182-2187. https://doi.org/10.1021/ic0111583
Sakellariou EG, Montalban AG, Meunier HG, Rumbles G, Phillips D, Ostler RB et al. Peripherally metalated secoporphyrazines: A new generation of photoactive pigments. Inorganic Chemistry. 2002 Apr 22;41(8):2182-2187. https://doi.org/10.1021/ic0111583
Sakellariou, Efstathia G. ; Montalban, Antonio Garrido ; Meunier, Hubert G. ; Rumbles, Gary ; Phillips, David ; Ostler, Richard B. ; Suhling, Klaus ; Barrett, Anthony G M ; Hoffman, Brian M. / Peripherally metalated secoporphyrazines : A new generation of photoactive pigments. In: Inorganic Chemistry. 2002 ; Vol. 41, No. 8. pp. 2182-2187.
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