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Synthesis and Metal Binding Properties of Salicylate‐, Catecholate‐, and Hydroxypyridinonate‐Functionalized Dendrimers
Author(s) -
Cohen Seth M.,
Petoud Stéphane,
Raymond Kenneth N.
Publication year - 2001
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 - 10.1002/1521-3765(20010105)7:1<272::aid-chem272>3.0.co;2-y
Subject(s) - dendrimer , amidoamine , chemistry , poly(amidoamine) , chelation , metal , titration , metal ions in aqueous solution , electrospray ionization , polymer chemistry , denticity , proton nmr , combinatorial chemistry , organic chemistry , ion
The synthesis, characterization, and metal‐binding studies of chelate‐functionalized dendrimers is reported. Salicylate, catecholate, and hydroxypyridinonate bidentate chelators have been coupled to the surface of both poly(propyleneimine) (Astramol) and poly(amidoamine) (Starburst, PAMAM) dendrimers up to the fifth generation (64 endgroups). A general method has been developed for the facile and high quality chromatographic purification of poly(propyleneimine) and poly(amidoamine) dendrimer derivatives. One‐ and two‐dimensional (TOCSY) 1 H NMR experiments and electrospray ionization mass spectrometry (ESI‐MS) have confirmed the exhaustive coupling of these chelators to the primary amine functionalities of the dendrimers. Spectrophotometric titrations were used to investigate the metal binding ability of these macrochelates. Spectral analysis shows that ferric iron binding to these ligands is localized to the chelating endgroups. The ability of these dendritic polymers to bind large numbers of metal ions may lead to applications as metal sequestering agents for waste remediation technologies.