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Novel peripherally functionalized seco-porphyrazines: synthesis, characterization and spectroscopic evaluation |
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| Authors: | Efstathia G SakellariouAntonio Garrido Montalban Scott L BeallDavid Henderson Hubert G MeunierDavid Phillips Klaus SuhlingAnthony GM Barrett Brian M Hoffman |
| Institution: | a Department of Chemistry, Imperial College, South Kensington, London SW7 2AZ, UK b Department of Chemistry, Assumption College, Worcester, MA 01609, USA c Department of Chemistry, Northwestern University, Evanston, IL 60208, USA |
| Abstract: | Co-macrocyclizations of 2,3-dipropylmaleonitrile and 2,3-di-(4-(methoxycarbonyl)phenyl)maleonitrile, respectively, with N,N′-dibenzyl-N,N′-di-(11-tetrahydropyranyloxy-3,6,9-trioxo-undecyl))maleonitrile and N,N,N′,N′-tetramethylmaleonitrile were used to prepare derivatives of the 4,5-diamino-porphyrazine systems including the zinc(II) complexes. Subsequent oxidation of the macrocycles with potassium permanganate gave the corresponding seco-porphyrazines. These were shown to be efficient sensitizers for the production of singlet oxygen (ΦΔ=0.15-0.57) by the determination of their photophysical properties. |
| Keywords: | porphyrazine Linstead macrocyclization sensitization singlet oxygen |
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