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

被引:62
作者
Bishop, Lee M. [1 ]
Yeager, Joseph C. [1 ]
Chen, Xin [1 ]
Wheeler, Jamie N. [1 ]
Torelli, Marco D. [1 ]
Benson, Michelle C. [1 ]
Burke, Steven D. [1 ]
Pedersen, Joel A.
Hamers, Robert J. [1 ]
机构
[1] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA
基金
美国国家科学基金会;
关键词
SENSITIZED SOLAR-CELLS; ZINC-OXIDE; MAGNETITE NANOPARTICLES; AQUEOUS SUSPENSIONS; TIO2; NANOPARTICLES; ZNO ELECTRODES; SPECTROSCOPY; ADSORPTION; CYCLOADDITION; DECOMPOSITION;
D O I
10.1021/la204145t
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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, multidentate carboxylate binding to metal oxide nanoparticles, while also enabling subsequent multistep 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.
引用
收藏
页码:1322 / 1329
页数:8
相关论文
共 49 条
[1]   Suggested modifications to a distillation-free solvent purification system [J].
Alaimo, PJ ;
Peters, DW ;
Arnold, J ;
Bergman, RG .
JOURNAL OF CHEMICAL EDUCATION, 2001, 78 (01) :64-64
[2]   THERMAL-DECOMPOSITION OF CITRIC-ACID [J].
BARBOOTI, MM ;
ALSAMMERRAI, DA .
THERMOCHIMICA ACTA, 1986, 98 :119-126
[3]   Efficient hybrid solar cells from zinc oxide nanoparticles and a conjugated polymer [J].
Beek, WJE ;
Wienk, MM ;
Janssen, RAJ .
ADVANCED MATERIALS, 2004, 16 (12) :1009-+
[4]   Versatile PEG-derivatized phosphine oxide ligands for water-dispersible metal oxide nanocrystals [J].
Bin Na, Hyon ;
Lee, In Su ;
Seo, Heonjin ;
Park, Yong Il ;
Lee, Jung Hee ;
Kim, Sang-Wook ;
Hyeon, Taeghwan .
CHEMICAL COMMUNICATIONS, 2007, (48) :5167-5169
[5]   Highly Stable Molecular Layers on Nanocrystalline Anatase TiO2 through Photochemical Grafting [J].
Franking, Ryan A. ;
Landis, Elizabeth C. ;
Hamers, Robert J. .
LANGMUIR, 2009, 25 (18) :10676-10684
[6]   CONTROLLED NUCLEATION FOR REGULATION OF PARTICLE-SIZE IN MONODISPERSE GOLD SUSPENSIONS [J].
FRENS, G .
NATURE-PHYSICAL SCIENCE, 1973, 241 (105) :20-22
[7]   Linkers for anchoring sensitizers to semiconductor nanoparticles [J].
Galoppini, E .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (13-14) :1283-1297
[8]   Self-assembly and bonding of alkanephosphonic acids on the native oxide surface of titanium [J].
Gawalt, ES ;
Avaltroni, MJ ;
Koch, N ;
Schwartz, J .
LANGMUIR, 2001, 17 (19) :5736-5738
[9]   Monolayer vs. multilayer self-assembled alkylphosphonate films: X-ray photoelectron spectroscopy studies [J].
Gouzman, I ;
Dubey, M ;
Carolus, MD ;
Schwartz, J ;
Bernasek, SL .
SURFACE SCIENCE, 2006, 600 (04) :773-781
[10]   Dye-sensitized solar cells [J].
Grätzel, M .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY C-PHOTOCHEMISTRY REVIEWS, 2003, 4 (02) :145-153