Novel peripherally functionalized seco-porphyrazines:: synthesis, characterization and spectroscopic evaluation

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 (Phi(Delta)=0.15-0.57) by the determination of their photophysical properties. (C) 2003 Published by Elsevier Ltd.