Ferrocene-Bearing Dodecylphthalocyanines: Synthesis, Spectroscopic and Electrochemical Behavior.

Ferrocenylbutoxy-bearing dodecylated phthalocyanines, MPc(CH)(OCHFc) with M = 2H (compound series and ) or Zn (compound series , and ), ≤ 8 and ≤ 4, were synthesized through either metal-free statistical condensation between 3,6-bis(dodecyl)phthalonitrile, , and 4- (), or 3-(4'-ferrocenylbutoxy)phthalonitrile, , or a zinc template statistical condensation between 4,5-bis(dodecyl)phthalonitrile, , and in the presence of anhydrous zinc acetate, or by zinc insertion into metal-free phthalocyanines. Compounds were designed to have eight nonperipheral dodecyl substituents, six nonperipheral dodecyl, either one peripheral or one nonperipheral 4'-ferrocenylbutoxy substituent, four nonperipheral dodecyl and two peripheral 4'-ferrocenylbutoxy substituents, or four peripheral 4'-ferrocenylbutoxy substituents. The compound having six peripheral dodecyl and one peripheral 4'-ferrocenylbutoxy substituents was also synthesized.

Octakis(dodecyl)phthalocyanines: Influence of Peripheral versus Non-Peripheral Substitution on Synthetic Routes, Spectroscopy and Electrochemical Behaviour.

Non-peripherally octakis-substituted phthalocyanines (Pc's), MPc(CH) with M = 2H () or Zn (), as well as peripherally octakis-substituted phthalocyanines (Pc's) with M = Zn (), Mg () and 2H (), were synthesized by cyclotetramerization of 3,6- () or 4,5-bis(dodecyl)phthalonitrile (), template cyclotetramerization of precursor phthalonitriles in the presence of Zn or Mg, metal insertion into metal-free phthalocyanines, and removal of Mg or Zn from the phthalocyaninato coordination cavity. The more effective synthetic route towards Pc was demetalation of . Pc's were more soluble than Pc's.