Tri- and Pentacalix[4]pyrroles: Synthesis, Characterization and Their Use in the Extraction of Halide Salts


Aydoğan A. , AKAR A.

CHEMISTRY-A EUROPEAN JOURNAL, cilt.18, ss.1999-2005, 2012 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 18 Konu: 7
  • Basım Tarihi: 2012
  • Doi Numarası: 10.1002/chem.201101605
  • Dergi Adı: CHEMISTRY-A EUROPEAN JOURNAL
  • Sayfa Sayıları: ss.1999-2005

Özet

Calixpyrrole-based oligomeric compounds were synthesized by click chemistry from the corresponding alkyne- and azide-functionalized calix[4]pyrroles. Calix[4]pyrrole 3, possessing an alkyne functional group, was prepared through a mixed condensation of pyrrole with acetone and but-3-ynyl 4-oxopentanoate. Another alkyne-group-containing calix[4]pyrrole 5 was obtained by treatment of 4'-hydroxyphenyl-functionalized calixpyrrole 4 with propargyl bromide. Tetrakis(azidopentyl)-functionalized calix[4]pyrrole 7 was synthesized by reacting NaN3 with tetrabromopentyltetraethylcalix[4]pyrrole 6, which was prepared through a condensation reaction of pyrrole and 7-bromohept-2-one. Oligomeric calixpyrrole compounds were found to be capable of extracting tetrabutylammonium chloride and fluoride salts from aqueous media. Extraction abilities of the oligomeric compounds were monitored by NMR and UV/Vis spectroscopy and thermogravimetric analysis.