A Citric Acid-derived Ligand for Modular Functionalization of Metal Oxide Surfaces via "Click" Chemistry

TitleA Citric Acid-derived Ligand for Modular Functionalization of Metal Oxide Surfaces via "Click" Chemistry
Publication TypeJournal Article
Year of Publication2012
AuthorsBishop, LM, Yeager, JC, Chen, X, Wheeler, JN, Torelli, MD, Benson, MC, Burke, SD, Pedersen, JA, Hamers, RJ
JournalLangmuir
Volume28
Issue2
Pagination1322-1329
Abstract

Citric acid is a widely used surface-modifying ligand for growth and processing of a variety of nanoparticles; however, the inability to easily prepare derivatives of this molecule has restricted the development of versatile chemistries for nanoparticle surface functionalization. Here, we report the design and synthesis of a citric acid derivative bearing an alkyne group and demonstrate that this molecule provides the ability to achieve stable, multi-dentate carboxylate binding to metal oxide nanoparticles, while also enabling subsequent multi-step chemistry via the Cu(I)-catalyzed Azide-Alkyne Cycloaddition (CuAAC) reaction. The broad utility of this strategy for the modular functionalization of metal oxide surfaces was demonstrated by its application in the CuAAC modification of ZnO, Fe2O3, TiO2, and WO3 nanoparticles.

URLhttp://dx.doi.org/10.1021/la204145t
DOI10.1021/la204145t