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Decoration of Gold Nanoparticles by a Double‐Armed Calix[4]pyrrole: A Receptor‐Decorated Nanoensemble for Anion Sensing and Extraction
Author(s) -
Sokkalingam Punidha,
Hong SeongJin,
Aydogan Abdullah,
Sessler Jonathan L.,
Lee ChangHee
Publication year - 2013
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.201300472
Subject(s) - pyrrole , monomer , nanoparticle , colloidal gold , chemistry , conjugate , dichloromethane , extraction (chemistry) , transmission electron microscopy , aqueous solution , inorganic chemistry , nuclear chemistry , materials science , organic chemistry , nanotechnology , solvent , polymer , mathematical analysis , mathematics
Gold nanoparticles decorated with a double‐armed, deep‐cavity calix[4]pyrrole were prepared and fully characterized. Transmission electron microscopy imaging revealed that the average diameter of the particles was approximately 4 nm both before and after attachment of the receptor to the surface. The calix[4]pyrrole‐functionalized nanoparticles exhibited highly elevated sensing behavior (approximately 1000 times in dichloromethane) relative to its monomeric congener while maintaining its guest selectivity. The receptor–nanoparticle conjugate (nanoreceptor) showed significant aggregation upon addition of the biphenolate anion, an effect ascribed to anion‐mediated interparticle linking. The receptor–nanoparticle conjugate is also capable of extracting the fluoride anion (as its tetrabutylammonium salt) from an aqueous layer to an organic medium. Control experiments revealed that this extraction is not possible when using the analogous monomeric receptor.