4.7 Article

Electrosynthesis of novel π-extended benzofuran derivatives of porphyrincatecholes

Journal

JOURNAL OF ELECTROANALYTICAL CHEMISTRY
Volume 655, Issue 2, Pages 120-127

Publisher

ELSEVIER SCIENCE SA
DOI: 10.1016/j.jelechem.2011.02.029

Keywords

Porphyrins; Catechol; Benzofuranes; Electro synthesis; Nanostructure

Funding

  1. Iranian National Science Foundation (INSF)
  2. Shahid Beheshti University

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Two new functionalized pi-extended benzofuran catechol porphyrins and nanostructured Mn-porphyrins have been synthesized by a green one-pot method and structurally characterized by spectroscopic analysis. The electro-oxidation of 5,10,15,20-tetrakis(2,3-dihydroxyphenyl) porphyrins(1a-b) with four catechol units in the presence of 3-hydroxy-1H-phenalene-1-one (3) as bidentate nucleophile has been done and benzofuran rings have formed by the intermolecular and intramolecular Michel addition reactions. Coulometry and voltammetry results allowed us to propose four independent ECEC mechanisms for the electrochemical oxidation pathway. Functionalization of the porphyrins affected their photophysical properties such as the efficiency of the fluorescence that would support the energy transfer between the porphyrin core and the substituted subunits. (C) 2011 Elsevier B.V. All rights reserved.

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