Fluorinated porphyrins and corroles: Synthesis, electrochemistry, and applications

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

Research output: Chapter in Book/Report/Conference proceedingChapter

4 Citations (Scopus)

Abstract

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 publicationFluorine in Heterocyclic Chemistry
Subtitle of host publicationVolume 1: 5-Membered Heterocycles and Macrocycles
PublisherSpringer International Publishing
Pages589-620
Number of pages32
ISBN (Electronic)9783319043463
ISBN (Print)9783319043456
DOIs
StatePublished - Jan 1 2014

Fingerprint

Fluorination
Porphyrins
Electrochemistry
Tetrapyrroles
Ligands
Alkalinity
Electronic structure
Metal ions
Nitrogen
Physical properties
corrole
Electrons

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

DiMagno, S. G., Biffinger, J. C., & Sun, H. (2014). Fluorinated porphyrins and corroles: Synthesis, electrochemistry, and applications. In Fluorine in Heterocyclic Chemistry: Volume 1: 5-Membered Heterocycles and Macrocycles (pp. 589-620). Springer International Publishing. https://doi.org/10.1007/978-3-319-04346-3_14

Fluorinated porphyrins and corroles : Synthesis, electrochemistry, and applications. / DiMagno, Stephen G.; Biffinger, Justin C.; Sun, Haoran.

Fluorine in Heterocyclic Chemistry: Volume 1: 5-Membered Heterocycles and Macrocycles. Springer International Publishing, 2014. p. 589-620.

Research output: Chapter in Book/Report/Conference proceedingChapter

DiMagno, SG, Biffinger, JC & Sun, H 2014, Fluorinated porphyrins and corroles: Synthesis, electrochemistry, and applications. in Fluorine in Heterocyclic Chemistry: Volume 1: 5-Membered Heterocycles and Macrocycles. Springer International Publishing, pp. 589-620. https://doi.org/10.1007/978-3-319-04346-3_14
DiMagno SG, Biffinger JC, Sun H. Fluorinated porphyrins and corroles: Synthesis, electrochemistry, and applications. In Fluorine in Heterocyclic Chemistry: Volume 1: 5-Membered Heterocycles and Macrocycles. Springer International Publishing. 2014. p. 589-620 https://doi.org/10.1007/978-3-319-04346-3_14
DiMagno, Stephen G. ; Biffinger, Justin C. ; Sun, Haoran. / Fluorinated porphyrins and corroles : Synthesis, electrochemistry, and applications. Fluorine in Heterocyclic Chemistry: Volume 1: 5-Membered Heterocycles and Macrocycles. Springer International Publishing, 2014. pp. 589-620
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