Metal phthalocyanine tetrasulfonic acids, metal phthalocyanine octacarboxylic acids, metal octakis(hexyloxymethyl)phthalocyanines, and metal anthraquinocyanines have been synthesized. Then, zinc bis(1,4-didecylbenzo)-bis(3,4-pyrido)porphyrazines, the cyclotetramerization products of a 1:1 mixture of 3,6-didecylphthalonitrile and 3,4-dicyanopyridine, were synthesized. Futher, subphthalocyanine and its derivatives, with substituents such as thiobutyl and thiophenyl moieties were synthesized. Electrochemical measurements were performed on the abovementioned phthalocyanine derivatives and analogues in order to examine their electron transfer abilities and electrochemical reaction mechanisms in an organic solvent. Moreover, 1,4,8,11,15,18,22,25-octakis(thio-phenylmethyl)phthalocyanes were synthesized. The Q-bands of the latter compounds appeared in the near-infrared region. Furthermore, non-colored transparent films in the visible region can be produced.
ABSTRACT:The cyclotetramerisation products from the 1, 8-diazabicyclo[5,4,0]undec-7-ene catalysed reaction of a 1:1 mol mixture of 3,6-didecylphthalonitrile and 3,4-dicynopyridine in the presence of zinc chloride have been isolated by chromatography. The fractions comprise zinc octadecylphthalocyanine and compounds in which one, two, three and four pyridinoid rings replace the didecylbenzenoid moiety. The zinc bis(1,4-didecylbenzo)bis(3,4-pyrido)porphyrazine fraction was separated further into four sub-fractions and the components have been characterised by 400 MHz proton nuclear magnetic resonance spectroscopy, visible region spectroscopy, fluorescence spectroscopy and by cyclic voltammetry.
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