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

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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-d8, but undergoes deprotonation upon exposure to the fluoride anion.

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

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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

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