The synthesis and characterization of ylideneisoindolinones

Briana R. Schrage, Colton A. Farmer, Victor N. Nemykin, Christopher J. Ziegler

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

1,3-Diiminoisoindoline (DII) and the closely related molecule, iminoisoindolinone are important precursors in the synthesis of macrocycles and chelates such as phthalocyanines, and bis(arylimino)isoindolines, as well as chromophores including aza-BODIPY dyes. A series of seven ylideneisoindolinones are presented in this report. The reaction of various organic CH acids and iminoisoindolinone produce compounds that show strong → *transitions in the UV region. The chromophores have been characterized spectroscopically and the X-ray structures show electronic delocalization across the chromophore. Additionally, DFT and time-dependent DFT calculations confirm the lower energy absorbances are primarily HOMO-LUMO transitions.

Original languageEnglish
Pages (from-to)1048-1054
Number of pages7
JournalJournal of Porphyrins and Phthalocyanines
Volume25
Issue number10
DOIs
StatePublished - Oct 1 2021
Externally publishedYes

Keywords

  • DFT calculations
  • X-ray crystallography
  • chromophores
  • iminoisoindolinone
  • organic acids

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