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Tri‐ and Pentacalix[4]pyrroles: Synthesis, Characterization and Their Use in the Extraction of Halide Salts
Author(s) -
Aydogan Abdullah,
Akar Ahmet
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201101605
Subject(s) - pyrrole , alkyne , propargyl bromide , chemistry , thermogravimetric analysis , bromide , extraction (chemistry) , polymer chemistry , propargyl , chloride , halide , click chemistry , organic chemistry , catalysis
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.