Controlled Core-Modification of a Porphyrin into an Antiaromatic Isophlorin

Santosh P. Panchal, Santosh C. Gadekar, Venkataramanarao G. Anand

Research output: Contribution to journalArticlepeer-review

30 Scopus citations

Abstract

Partial core-modification of a porphyrin can be employed to synthesize the 20π antiaromatic isophlorin. Unlike the tetra-, tri-, and dipyrrole derivatives of a porphyrin, a monopyrrole porphyrin exhibits antiaromatic characteristics. It undergoes a two-electron reversible ring oxidation to yield the 18π aromatic dication.1H NMR analysis provides distinct evidence of the altered electronic characteristics through typical paratropic and diatropic ring current effects for the 4n and the (4n+2) π-electron systems, respectively.

Original languageEnglish
Pages (from-to)7797-7800
Number of pages4
JournalAngewandte Chemie - International Edition
Volume55
Issue number27
DOIs
StatePublished - 27 Jun 2016
Externally publishedYes

Keywords

  • aromaticity
  • conjugation
  • electron transfer
  • macrocycles
  • porphyrinoids

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry

Fingerprint

Dive into the research topics of 'Controlled Core-Modification of a Porphyrin into an Antiaromatic Isophlorin'. Together they form a unique fingerprint.

Cite this