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Perfluoroalkylated Calix[4]pyrroles: Fluoride Ion Extraction from an Aqueous Medium
Author(s) -
Maji Sinchan,
Mandal Debaprasad
Publication year - 2017
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201700897
Subject(s) - fluoride , chloride , pyrrole , aqueous solution , chemistry , ion , fluorine , aqueous medium , inorganic chemistry , surface modification , polymer chemistry , organic chemistry
Octaalkenyl calix[4]pyrrole ((CH 2 =CH(CH 2 ) 2 ) 8 C4P) is highly useful for the postfunctionalization of different calix[4]pyrroles with desired functionalities. Functionalization with perfluoroalkyl chains [CF 3 (CF 2 ) n ; R f n ] gave perfluoroalkyl calix[4]pyrroles (R f n (CH 2 ) 4 ) 8 C4P; n =6, 8), having >60 % fluorine content, which created a hydrophobic environment inside the calix[4]pyrrole cavity and recognized fluoride and chloride ions in solution as well as in the solid state. The fluoride ion is extracted efficiently from aqueous CsF and TBAF solutions by using (R f6 (CH 2 ) 4 ) 8 C4P, as droplets. The fluorinated chain generated a hydrophobic environment which broke the hydration shell associated with the anion and separated out fluoride ions as droplets from aqueous medium. Furthermore, the fluoride ions competitively replaced chloride ions from the (R f6 (CH 2 ) 4 ) 8 C4P cavity.