, Volume 56, Issue 1, pp 67–74 | Cite as

Synthesis and characterization of a cobalt(II) tetrakis(3-fluorophenyl) porphyrin with a built-in 4-vinylphenyl surface attachment moiety

  • D. Khusnutdinova
  • M. Flores
  • A. M. Beiler
  • G. F. MooreEmail author


Metalloporphyrins serve important roles in biology and as components in emerging technological assemblies for energy conversion. In this report, we describe the synthesis and characterization of a novel cobalt(II) 5,10,15,20-tetrakis (3-fluorophenyl)porphyrin bearing a 4-vinylphenyl surface attachment group at a beta position on the macrocycle. Electrochemical measurements show the 3-fluorophenyl groups at the meso positions of the porphyrin perturb the reduction potentials of the complex to more positive values as compared to non-fluorinated analogs, thus allowing access to reduced cobalt porphyrin species at significantly less negative applied bias potentials. The complex, cobalt(II) 5,10,15,20-tetrakis(3-fluorophenyl)-2-(4-vinylphenyl)porphyrin, is abbreviated in this article as Gov-1 in honor of Govindjee for his pioneering investigations in the role of fluorine as a promoter of novel protein-substrate interactions and the inspirational role he continues to have in encouraging young investigators in the areas of natural and artificial photosynthesis.

Additional key words

artificial photosynthesis fluorine porphyrins surface chemistry 





electron paramagnetic resonance




Fourier transform infrared


gradient correlation spectroscopy


cobalt(II) 5,10,15,20-tetrakis(3- fluorophenyl)-2-(4-vinylphenyl)porphyrin


abbreviation representing the dimensionless quantity formed by dividing the ratio of the mass of an ion to the unified atomic mass unit, by its charge number


matrix assisted laser desorption/ ionization time-of-flight mass spectrometer




nuclear magnetic resonance


standard calomel reference electrode




4-vinylphenyl boronic acid


chemical shift


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Copyright information

© The Institute of Experimental Botany 2018

Authors and Affiliations

  • D. Khusnutdinova
    • 1
  • M. Flores
    • 1
  • A. M. Beiler
    • 1
  • G. F. Moore
    • 1
    Email author
  1. 1.School of Molecular Sciences and the Biodesign Institute Center for Applied Structural Discovery (CASD)Arizona State UniversityTempeUSA

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