Synthesis and study of a calixpyrrole-texaphyrin chimera. A new oligopyrrolic chloride anion receptor

Jonathan L. Sessler, Won Seob Cho, Stephen P. Dudek, Lindsay Hicks, Vincent M. Lynch, Michael T. Huggins

Research output: Contribution to journalArticlepeer-review

65 Scopus citations

Abstract

Reported here is the synthesis and characterization of a new class of macrocycle that represents a hybrid between texaphyrin and calixpyrrole. These polypyrrolic macrocycles were prepared in one step by the acid-catalyzed condensation between diformyl dipyrromethanes and o-phenylenediamines in high yields. The X-ray crystal structure of one of these new "chimeras" was solved. It reveals that the diprotonated Schiff-base macrocycle has a V-shape in which one chloride anion is bound. Isothermal titration calorimetry (ITC) studies served to confirm the ability of the hybrid macrocycles to bind chloride anion in acetonitrile solution. These compounds may be useful as easy-to-make anion receptors.

Original languageEnglish
Pages (from-to)97-104
Number of pages8
JournalJournal of Porphyrins and Phthalocyanines
Volume7
Issue number2
DOIs
StatePublished - 2003
Externally publishedYes

Scopus Subject Areas

  • General Chemistry

Keywords

  • Anion binding
  • Calix[4]pyrrole
  • Dipyrromethane
  • Macrocycles
  • Schiff-base
  • Texaphyrin

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