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Electrochemistry as an Attractive and Effective Tool for the Synthesis and Immobilization of Porphyrins on an Electrode Surface
Author(s) -
Hebié Seydou,
Dimé Abdou K. D.,
Devillers Charles H.,
Lucas Dominique
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201404314
Subject(s) - electrochemistry , porphyrin , nickel , electrolysis , inorganic chemistry , electrode , platinum , amine gas treating , chemistry , materials science , trifluoroacetic acid , electrolyte , catalysis , photochemistry , organic chemistry
Magnesium(II) 10‐phenyl‐5,15‐ p ‐ditolylporphyrin is easily and cleanly transformed by electrolysis. A nitro group is first introduced at the free meso position by anodic substitution. Hydrogenation into the amine is then carried out electrocatalytically under ambient conditions with water as a hydrogen supplier. The synthesized porphyrin under the nickel(II) form can be covalently grafted onto a platinum electrode by electrochemical reduction of the diazonium cation, generated in situ by a reaction of the nickel(II) aminoporphyrin with sodium nitrite and trifluoroacetic acid. The electrosynthesized thin film gives an electrochemical response typical of a porphyrin material. Films grown under our conditions have a maximum surface coverage of approximately 5×10 −10 mol cm −2 . The modified electrode exhibits a reproducible electrochemical behavior and a good level of stability over potential cycling and exposition to air.