Fluorinated porphyrins and corroles: Synthesis, electrochemistry, and applications

Stephen G. Dimagno, Justin C. Biffinger, Haoran Sun

Research output: Chapter in Book/Report/Conference proceedingChapter

11 Scopus citations


Fluorination alters the electronic structure of aromatic systems in a predictable manner, and these effects can be exploited in the design of aromatic, macrocyclic ligand systems for a variety of applications. Equally important is that ring fluorination has an exceptionally modest steric effect. Thus, fluorination permits electronic effects to be severed from structural changes that confound interpretations of other substituent effect studies. Here the preparation, physical properties, and applications of fluorinated and perfluoroalkylated porphyrins and corroles are briefly reviewed. Special attention is given to the preparation of the most useful fluorinated heterocyclic building blocks underlie most of the synthetic approaches to these macrocycles. Among the predictable changes fluorination engenders in the properties of these aromatic, tetrapyrrole ligands, the most commonly exploited in applications are: (1) an increase in oxidative stability, and (2) a decrease in ring nitrogen basicity that is reflected in more Lewis-acidic, electron-deficient chelated metal ions.

Original languageEnglish (US)
Title of host publication5-Membered Heterocycles and Macrocycles
PublisherSpringer International Publishing
Number of pages32
ISBN (Electronic)9783319043463
ISBN (Print)3319043455, 9783319043456
StatePublished - Dec 1 2014


  • Catalysis
  • Corroles
  • Electrochemistry
  • Fluorination
  • Fluoropyrroles
  • Macrocycle synthesis
  • Porphyrins

ASJC Scopus subject areas

  • General Chemistry


Dive into the research topics of 'Fluorinated porphyrins and corroles: Synthesis, electrochemistry, and applications'. Together they form a unique fingerprint.

Cite this