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

✍ Scribed by Dr. Abdullah Aydogan; Ahmet Akar

Publisher
John Wiley and Sons
Year
2012
Tongue
English
Weight
546 KB
Volume
18
Category
Article
ISSN
0947-6539

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✦ Synopsis

Abstract

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 NaN~3~ 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.

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