Synthesis and anion binding studies of o-phenylenevinylene-bridged tetrapyrrolic macrocycle as an expanded analogue of calix[4]pyrrole

Sudip Kumar Ghosh, Masatoshi Ishida, Jiazhu Li, Won Young Cha, Vincent M. Lynch, Dongho Kim, Jonathan L. Sessler

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

An o-phenylenevinylene-bridged tetrapyrrolic macrocycle (2) was synthesized by means of a Horner-Wadsworth-Emmons reaction between benzylbisphosphonate and SEM-protected diformylpyrrole, followed by deprotection of the SEM groups. This conformationally flexible tetrapyrrole can be considered as an expanded calix[4]pyrrole analogue, which acts as a receptor for the chloride and bromide anions in THF-d 8 , but undergoes deprotonation upon exposure to the fluoride anion. This journal is

Original languageEnglish
Pages (from-to)3753-3756
Number of pages4
JournalChemical Communications
Volume50
Issue number28
DOIs
Publication statusPublished - 2014 Apr 11

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Anions
Negative ions
Tetrapyrroles
Deprotonation
Scanning electron microscopy
Bromides
Fluorides
Chlorides
calix(4)pyrrole

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

Cite this

Ghosh, Sudip Kumar ; Ishida, Masatoshi ; Li, Jiazhu ; Cha, Won Young ; Lynch, Vincent M. ; Kim, Dongho ; Sessler, Jonathan L. / Synthesis and anion binding studies of o-phenylenevinylene-bridged tetrapyrrolic macrocycle as an expanded analogue of calix[4]pyrrole. In: Chemical Communications. 2014 ; Vol. 50, No. 28. pp. 3753-3756.
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Synthesis and anion binding studies of o-phenylenevinylene-bridged tetrapyrrolic macrocycle as an expanded analogue of calix[4]pyrrole. / Ghosh, Sudip Kumar; Ishida, Masatoshi; Li, Jiazhu; Cha, Won Young; Lynch, Vincent M.; Kim, Dongho; Sessler, Jonathan L.

In: Chemical Communications, Vol. 50, No. 28, 11.04.2014, p. 3753-3756.

Research output: Contribution to journalArticle

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