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World Scientific Publishing, Journal of Porphyrins and Phthalocyanines, 05n06(16), p. 674-684, 2012

DOI: 10.1142/s1088424612500678

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Electrochemistry of mono- and bis-porphyrins containing a β,β′-fused tetraazaanthracene group

This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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Abstract

Electrochemical and thin-layer spectroelectrochemical properties of mono- and bis-porphyrins containing a β,β′-fused tetraazaanthracene (TA) group were examined in CH2Cl2, PhCN and pyridine containing 0.1 M tetra-n-butylammonium perchlorate as supporting electrolyte. The investigated mono-porphyrins are represented as (PTA)M, where M = 2H, Cu(II) or Zn(II) and PTA = the dianion of 5,10,15,20-tetrakis-(3,5-di-tert-butylphenyl)-6′,7′-dimethyl-1′,4′,5′,8′-tetraazaanthraceno-[2′,3′b]-porphyrin, while the bis-porphyrins are represented by M(P)-TA-(P)M, where M is H2, Cu(II) , Zn(II) , Ni(II) or Pd(II) and P is the dianion of 5,10,15,20-tetrakis-(3,5-di-tert-butylphenyl)porphyrin. The effect of the fused TA group on the redox potentials and UV-visible spectra of the neutral, electroreduced and electrooxidized porphyrins is discussed and the data compared to what is observed for related mono- and bis-quinoxalinoporphyrins of the type (PQ)M and (QPQ)M, where Q is a β,β′-fused quinoxaline group. Each TA-linked bis-porphyrin exhibits a strong interaction between the two equivalent porphyrin macrocycles, the magnitude of which is dependent upon the specific metal ion.