Selective oxidative synthesis of meso-beta fused porphyrin dimers

Bradley J. Brennan, Jaro Arero, Paul A. Liddell, Thomas A Moore, Ana L Moore, John Devens Gust

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

An efficient route to meso-β doubly connected fused porphyrin dimers was developed. Synthesis of the dimers incorporated two successive C-C bond-forming steps selectively coupling unsubstituted meso-and β-positions. Using Cu(BF4)2 as an oxidant in nitromethane solvent, the radical coupling of Cu(II)-porphyrins occurred in high yield and without side-products, allowing chromatography-free purification. Efficient demetalation of the product yielded free-base derivatives and the possibility to incorporate other metals into the macrocycles. The absorption and electrochemical properties vary with the inserted metal, showing broad UV-visible-NIR absorption and multiple one-electron oxidations/reductions in a relatively narrow electrochemical window.

Original languageEnglish
Pages (from-to)247-251
Number of pages5
JournalJournal of Porphyrins and Phthalocyanines
Volume17
Issue number4
DOIs
Publication statusPublished - Apr 2013

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Porphyrins
Dimers
Metals
Chromatography
Electrochemical properties
Oxidants
Purification
Derivatives
Electrons
Oxidation-Reduction
nitromethane

Keywords

  • copper
  • dimer
  • porphyrin
  • radical coupling
  • synthesis

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Selective oxidative synthesis of meso-beta fused porphyrin dimers. / Brennan, Bradley J.; Arero, Jaro; Liddell, Paul A.; Moore, Thomas A; Moore, Ana L; Gust, John Devens.

In: Journal of Porphyrins and Phthalocyanines, Vol. 17, No. 4, 04.2013, p. 247-251.

Research output: Contribution to journalArticle

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