Facile preparation of organic nanoparticles by interfacial cross-linking of reverse micelles and template synthesis of subnanometer Au-Pt nanoparticles

ACS Nano

Volumn 5, Issue 4, 2011, Pages 2637-2646

  Zhang, Shiyong ^a   Zhao, Yan ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

gold clusters; luminescence; nanoalloy; reverse micelle; template synthesis; thiol ene reaction

Indexed keywords

GOLD CLUSTERS; NANOALLOY; REVERSE MICELLE; TEMPLATE SYNTHESIS; THIOL-ENE REACTION;

CATIONIC SURFACTANTS; DYES; EXTRACTION; GOLD COMPOUNDS; LUMINESCENCE; METALS; MICELLES; NANOPARTICLES; PLATINUM; REDUCING AGENTS; SALTS; SYNTHESIS (CHEMICAL);

GOLD;

EID: 79955384648     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn102666k     Document Type: Article

References (75)

1. Mueller, A.; O'Brien, D. F. Supramolecular Materials via Polymerization of Mesophases of Hydrated Amphiphiles Chem. Rev. 2002, 102, 727-757 (Pubitemid 35381632)
2. Gin, D. L.; Gu, W.; Pindzola, B. A.; Zhou, W. J. Polymerized Lyotropic Liquid Crystal Assemblies for Materials Applications Acc. Chem. Res. 2001, 34, 973-980
3. Eastoe, J.; Summers, M.; Heenan, R. K. Control over Phase Curvature Ssing Mixtures of Polymerizable Surfactants Chem. Mater. 2000, 12, 3533-3537 (Pubitemid 32065714)
4. Yan, F.; Texter, J. Polymerization of and in Mesophases Adv. Colloid Interface Sci. 2006, 128-130, 27-35 (Pubitemid 46215537)
5. Tajima, K.; Aida, T. Controlled Polymerizations with Constrained Geometries Chem. Commun. 2000, 2399-2412 (Pubitemid 32001324)
6. Larrabee, C. E.; Sprague, E. D. Radiation-Induced Polymerization of Sodium 10-Undecenoate in Aqueous Micelle Solutions J. Polym. Sci., Part C: Polym. Lett. 1979, 17, 749-757
7. Paleos, C. M.; Stassinopoulou, C. I.; Malliaris, A. Comparative Studies between Monomeric and Polymeric Sodium 10-Undecenoate Micelles J. Phys. Chem. 1983, 87, 251-254
8. Joynes, D.; Sherrington, D. C. Novel Polymerizable Mono- and Divalent Quaternary Ammonium Cationic Surfactants 1. Synthesis, Structural Characterization and Homopolymerization Polymer 1996, 37, 1453-1462 (Pubitemid 126401938)
9. Dais, P.; Paleos, C. M.; Nika, G.; Malliaris, A. Positional Effects of the Methacrylate Group on Polymerization and Microstructure of Micelle-Forming Quaternary Ammonium-Salts Studied by NMR-Spectroscopy Makromol. Chem. 1993, 194, 445-450
10. Ringsdorf, H.; Schlarb, B.; Venzmer, J. Molecular Architecture and Function of Polymeric Oriented Systems: Models for the Study of Organization, Surface Recognition, and Dynamics of Biomembranes Angew. Chem., Int. Ed. Engl. 1988, 27, 113-158 (Pubitemid 18043271)
11. Fendler, J. H.; Tundo, P. Polymerized Surfactant Aggregates- Characterization and Utilization Acc. Chem. Res. 1984, 17, 3-8
12. Higashi, N.; Adachi, T.; Niwa, M. A Novel 2-Dimensional Photopolymerization at an Oriented Bilayer Surface-Effective Molecular-Weight Control Using Membrane State and Chain Transfer Macromolecules 1990, 23, 1475-1480 (Pubitemid 20659556)
13. Fukuda, H.; Diem, T.; Stefely, J.; Kezdy, F. J.; Regen, S. L. Polymer-Encased Vesicles Derived from Dioctadecyldimethylammonium Methacrylate J. Am. Chem. Soc. 1986, 108, 2321-2327
14. Sisson, T. M.; Srisiri, W.; O'Brien, D. F. Novel Polymer Architectures via the Selective Polymerization of Lyotropic Liquid Crystals of Heterobifunctional Amphiphiles J. Am. Chem. Soc. 1998, 120, 2322-2329 (Pubitemid 28149779)
15. Srisiri, W.; Sisson, T. M.; OBrien, D. F.; McGrath, K. M.; Han, Y. Q.; Gruner, S. M. Polymerization of the Inverted Hexagonal phase J. Am. Chem. Soc. 1997, 119, 4866-4873 (Pubitemid 27272471)
16. Deng, H.; Gin, D. L.; Smith, R. C. Polymerizable Lyotropic Liquid Crystals Containing Transition-Metal and Lanthanide Ions: Architectural Control and Introduction of New Properties into Nanostructured Polymers J. Am. Chem. Soc. 1998, 120, 3522-3523
17. Reppy, M. A.; Gray, D. H.; Pindzola, B. A.; Smithers, J. L.; Gin, D. L. A New Family of Polymerizable Lyotropic Liquid Crystals: Control of Feature Size in Cross-Linked Inverted Hexagonal Assemblies via Monomer Structure J. Am. Chem. Soc. 2001, 123, 363-371 (Pubitemid 32105124)
18. Smith, R. C.; Fischer, W. M.; Gin, D. L. Ordered Poly(p -phenylenevinylene) Matrix Nanocomposites via Lyotropic Liquid-Crystalline Monomers J. Am. Chem. Soc. 1997, 119, 4092-4093 (Pubitemid 27224435)
19. Kerr, R. L.; Miller, S. A.; Shoemaker, R. K.; Elliott, B. J.; Gin, D. L. New Type of Li Ion Conductor with 3D Interconnected Nanopores via Polymerization of a Liquid Organic Electrolyte-Filled Lyotropic Liquid-Crystal Assembly J. Am. Chem. Soc. 2009, 131, 15972-15973
20. Lee, Y. S.; Yang, J. Z.; Sisson, T. M.; Frankel, D. A.; Gleeson, J. T.; Aksay, E.; Keller, S. L.; Gruner, S. M.; Obrien, D. F. Polymerization of Nonlamellar Lipid Assemblies J. Am. Chem. Soc. 1995, 117, 5573-5578
21. Yang, D.; O'Brien, D. F.; Marder, S. R. Polymerized Bicontinuous Cubic Nanoparticles (Cubosomes) from a Reactive Monoacylglycerol J. Am. Chem. Soc. 2002, 124, 13388-13389 (Pubitemid 35285908)
22. Yang, D.; Armitage, B.; Marder, S. R. Cubic Liquid-Crystalline Nanoparticles Angew. Chem., Int. Ed. 2004, 43, 4402-4409 (Pubitemid 39268845)
23. Gray, D. H.; Hu, S. L.; Juang, E.; Gin, D. L. Highly Ordered Polymer-Inorganic Nanocomposites via Monomer Self-Assembly: In Situ Condensation Approach Adv. Mater. 1997, 9, 731-736 (Pubitemid 127534334)
24. Zhou, M. J.; Kidd, T. J.; Noble, R. D.; Gin, D. L. Supported Lyotropic Liquid-Crystal Polymer Membranes: Promising Materials for Molecular-Size- Selective Aqueous Nanofiltration Adv. Mater. 2005, 17, 1850-1853 (Pubitemid 41120185)
25. Gin, D. L.; Lu, X. Y.; Nemade, P. R.; Pecinovsky, C. S.; Xu, Y. J.; Zhou, M. J. Recent Advances in the Design of Polymerizable Lyotropic Liquid-Crystal Assemblies for Heterogeneous Catalysis and Selective Separations Adv. Funct. Mater. 2006, 16, 865-878
26. Fendler, J. H. Membrane Mimetic Chemistry: Characterizations and Applications of Micelles, Microemulsions, Monolayers, Bilayers, Vesicles, Host-Guest Systems, and Polyions; Wiley: New York, 1982.
27. Pileni, M. P. Structure and Reactivity in Reverse Micelles; Elsevier: Amsterdam, 1989.
28. Pileni, M. P. Nanosized Particles Made in Colloidal Assemblies Langmuir 1997, 13, 3266-3276 (Pubitemid 127604425)
29. Pileni, M. P. The Role of Soft Colloidal Templates in Controlling the Size and Shape of Inorganic Nanocrystals Nat. Mater. 2003, 2, 145-150
30. Voortmans, G.; De Schryver, F. C. Polymerization in and of Inverse Micelles. In Structure and Reactivity in Reverse Micelles; Pileni, M. P., Ed.; Elsevier: Amsterdam, 1989.
31. Voortmans, G.; Verbeeck, A.; Jackers, C.; Deschryver, F. C. Polymerization of N, N -Didodecyl- N -methyl- N -(2-(methacryloyloxy)ethyl) ammonium Chloride, an Inverse Micelle Forming Detergent Macromolecules 1988, 21, 1977-1980 (Pubitemid 18649141)
32. Jung, H. M.; Price, K. E.; McQuade, D. T. Synthesis and Characterization of Cross-Linked Reverse Micelles J. Am. Chem. Soc. 2003, 125, 5351-5355 (Pubitemid 36582744)
33. Price, K. E.; McQuade, D. T. A Cross-Linked Reverse Micelle-Encapsulated Palladium Catalyst Chem. Commun. 2005, 1714-1716 (Pubitemid 40524132)
34. Dondoni, A. The Emergence of Thiol-Ene Coupling as a Click Process for Materials and Bioorganic Chemistry Angew. Chem., Int. Ed. 2008, 47, 8995-8997
35. Hoyle, C. E.; Lee, T. Y.; Roper, T. Thiol-Enes: Chemistry of the Past with Promise for the Future J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 5301-5338
36. Iha, R. K.; Wooley, K. L.; Nystrom, A. M.; Burke, D. J.; Kade, M. J.; Hawker, C. J. Applications of Orthogonal "Click" Chemistries in the Synthesis of Functional Soft Materials Chem. Rev. 2009, 109, 5620-5686
37. Zheng, J.; Nicovich, P. R.; Dickson, R. M. Highly Fluorescent Noble-Metal Quantum Dots Annu. Rev. Phys. Chem. 2007, 58, 409-431 (Pubitemid 46877596)
38. 8 Nanodots J. Am. Chem. Soc. 2003, 125, 7780-7781 (Pubitemid 36782137)
39. Negishi, Y.; Takasugi, Y.; Sato, S.; Yao, H.; Kimura, K.; Tsukuda, T. Magic-Numbered Au(n) Clusters Protected by Glutathione Monolayers (n = 18, 21, 25, 28, 32, 39): Isolation and Spectroscopic Characterization J. Am. Chem. Soc. 2004, 126, 6518-6519 (Pubitemid 38697329)
40. Tran, M. L.; Zvyagin, A. V.; Plakhotnik, T. Synthesis and Spectroscopic Observation of Dendrimer-Encapsulated Gold Nanoclusters Chem. Commun. 2006, 2400-2401 (Pubitemid 43846390)
41. Duan, H.; Nie, S. Etching Colloidal Gold Nanocrystals with Hyperbranched and Multivalent Polymers: A New Route to Fluorescent and Water-Soluble Atomic Clusters J. Am. Chem. Soc. 2007, 129, 2412-2413 (Pubitemid 46364028)
42. Xie, J.; Zheng, Y.; Ying, J. Y. Protein-Directed Synthesis of Highly Fluorescent Gold Nanoclusters J. Am. Chem. Soc. 2009, 131, 888-889
43. Zheng, J.; Dickson, R. M. Individual Water-Soluble Dendrimer-Encapsulated Silver Nanodot Fluorescence J. Am. Chem. Soc. 2002, 124, 13982-13983 (Pubitemid 35386836)
44. Zhang, J. G.; Xu, S. Q.; Kumacheva, E. Photogeneration of Fluorescent Silver Nanoclusters in Polymer Microgels Adv. Mater. 2005, 17, 2336-2340 (Pubitemid 41454636)
45. Shen, Z.; Duan, H. W.; Frey, H. Water-Soluble Fluorescent Ag Nanoclusters Obtained from Multiarm star Poly(acrylic acid) as "Molecular Hydrogel" Templates Adv. Mater. 2007, 19, 349-352 (Pubitemid 46925422)
46. Zheng, J.; Ding, Y.; Tian, B. Z.; Wang, Z. L.; Zhuang, X. W. Luminescent and Raman Active Silver Nanoparticles with Polycrystalline Structure J. Am. Chem. Soc. 2008, 130, 10472-10473
47. Maretti, L.; Billone, P. S.; Liu, Y.; Scaiano, J. C. Facile Photochemical Synthesis and Characterization of Highly Fluorescent Silver Nanoparticles J. Am. Chem. Soc. 2009, 131, 13972-13980
48. Lee, H.; Habas, S. E.; Kweskin, S.; Butcher, D.; Somorjai, G. A.; Yang, P. Morphological Control of Catalytically Active Platinum Nanocrystals Angew. Chem., Int. Ed. 2006, 45, 7824-7828 (Pubitemid 44871354)
49. Narayanan, R.; El-Sayed, M. A. Effect of Catalysis on the Stability of Metallic Nanoparticles: Suzuki Reaction Catalyzed by PVP-Palladium Nanoparticles J. Am. Chem. Soc. 2003, 125, 8340-8347 (Pubitemid 36828598)
50. Tian, N.; Zhou, Z. Y.; Sun, S. G.; Ding, Y.; Wang, Z. L. Synthesis of Tetrahexahedral Platinum Nanocrystals with High-Index Facets and High Electro-oxidation Activity Science 2007, 316, 732-735 (Pubitemid 46717678)
51. Wang, C.; Daimon, H.; Lee, Y.; Kim, J.; Sun, S. Synthesis of Monodisperse Pt Nanocubes and Their Enhanced Catalysis for Oxygen Reduction J. Am. Chem. Soc. 2007, 129, 6974-6975 (Pubitemid 46903244)
52. Tsung, C. K.; Kuhn, J. N.; Huang, W.; Aliaga, C.; Hung, L. I.; Somorjai, G. A.; Yang, P. Sub-10 nm Platinum Nanocrystals with Size and Shape Control: Catalytic Study for Ethylene and Pyrrole Hydrogenation J. Am. Chem. Soc. 2009, 131, 5816-5822
53. Killops, K. L.; Campos, L. M.; Hawker, C. J. Robust, Efficient, and Orthogonal Synthesis of Dendrimers via Thiol-Ene "Click" Chemistry J. Am. Chem. Soc. 2008, 130, 5062-5064 (Pubitemid 351537066)
54. Chan, J. W.; Hoyle, C. E.; Lowe, A. B. Sequential Phosphine-Catalyzed, Nucleophilic Thiol-Ene/Radical-Mediated Thiol-Yne Reactions and the Facile Orthogonal Synthesis of Polyfunctional Materials J. Am. Chem. Soc. 2009, 131, 5751-5753
55. Floyd, N.; Vijayakrishnan, B.; Koeppe, A. R.; Davis, B. G. Thiyl Glycosylation of Olefinic Proteins: S-Linked Glycoconjugate Synthesis Angew. Chem., Int. Ed. 2009, 48, 7798-7802
56. Cuccovia, I. M.; Dias, L. G.; Maximiano, F. A.; Chaimovich, H. Analysis of the Bromide Ion Distribution in the Water Pool of Reverse Micelles of Hexadecyltrimethylammonium Bromide in Chloroform/ n -Dodecane and Isooctane/ n -Hexanol by Chemical Trapping Langmuir 2001, 17, 1060-1068 (Pubitemid 32252592)
57. 3 at 25 °C is 1.3855 and 1.4422, and the viscosity is 0.386 and 0.54 cP, respectively.
58. Flory, P. J. Principles of Polymer Chemistry; Cornell University Press: Ithaca, NY, 1953; pp 495 - 503.
59. Israelachvili, J. N. Intermolecular and Surface Forces: with Applications to Colloidal and Biological Systems; Academic Press: London, 1985; pp 249 - 257.
60. Hostetler, M. J.; Wingate, J. E.; Zhong, C. J.; Harris, J. E.; Vachet, R. W.; Clark, M. R.; Londono, J. D.; Green, S. J.; Stokes, J. J.; Wignall, G. D. et al. Alkanethiolate Gold Cluster Molecules with Core Diameters from 1.5 to 5.2 nm: Core and Monolayer Properties as a Function of Core Size Langmuir 1998, 14, 17-30 (Pubitemid 128575442)
61. Alvarez, M. M.; Khoury, J. T.; Schaaff, T. G.; Shafigullin, M. N.; Vezmar, I.; Whetten, R. L. Optical Absorption Spectra of Nanocrystal Gold Molecules J. Phys. Chem. B 1997, 101, 3706-3712 (Pubitemid 127581121)
62. Schaaff, T. G.; Shafigullin, M. N.; Khoury, J. T.; Vezmar, I.; Whetten, R. L.; Cullen, W. G.; First, P. N.; GutierrezWing, C.; Ascensio, J.; JoseYacaman, M. J. Isolation of Smaller Nanocrystal Au Molecules: Robust Quantum Effects in Optical Spectra J. Phys. Chem. B 1997, 101, 7885-7891 (Pubitemid 127576548)
63. Jin, R.; Egusa, S.; Scherer, N. F. Thermally-Induced Formation of Atomic Au Clusters and Conversion into Nanocubes J. Am. Chem. Soc. 2004, 126, 9900-9901 (Pubitemid 39079392)
64. Zheng, J.; Zhang, C.; Dickson, R. M. Highly Fluorescent, Water-Soluble, Size-Tunable Gold Quantum Dots Phys. Rev. Lett. 2004, 93, 077402
65. Daniel, M. C.; Astruc, D. Gold nanoparticles: Assembly, Supramolecular Chemistry, Quantum-Size-Related Properties, and Applications toward Biology, Catalysis, and Nanotechnology Chem. Rev. 2004, 104, 293-346
66. Negishi, Y.; Tsukuda, T. One-Pot Preparation of Subnanometer-Sized Gold Clusters via Reduction and Stabilization by meso -2,3-Dimercaptosuccinic Acid J. Am. Chem. Soc. 2003, 125, 4046-4047 (Pubitemid 36512288)
67. Luminescent materials were also obtained, which formed suspensions in water or methanol.
68. Longenberger, L.; Mills, G. Formation of Metal Particles in Aqueous-Solutions by Reactions of Metal-Complexes with Polymers J. Phys. Chem. 1995, 99, 475-478
69. Esumi, K.; Hosoya, T.; Suzuki, A.; Torigoe, K. Spontaneous Formation of Gold Nanoparticles in Aqueous Solution of Sugar-Persubstituted Poly(amidoamine) Dendrimers Langmuir 2000, 16, 2978-2980 (Pubitemid 30576833)
70. Sakai, T.; Alexandridis, P. Mechanism of Gold Metal Ion Reduction, Nanoparticle Growth and Size Control in Aqueous Amphiphilic Block Copolymer Solutions at Ambient Conditions J. Phys. Chem. B 2005, 109, 7766-7777 (Pubitemid 40643995)
71. Sakai, T.; Alexandridis, P. Single-Step Synthesis and Stabilization of Metal Nanoparticles in Aqueous Pluronic Block Copolymer Solutions at Ambient Temperature Langmuir 2004, 20, 8426-8430
72. Boisselier, E.; Diallo, A. K.; Salmon, L.; Ornelas, C.; Ruiz, J.; Astruc, D. Encapsulation and Stabilization of Gold Nanoparticles with "Click" Polyethyleneglycol Dendrimers J. Am. Chem. Soc. 2010, 132, 2729-2742
73. Hoppe, C. E.; Lazzari, M.; Pardinas-Blanco, I.; Lopez-Quintela, M. A. One-Step Synthesis of Gold and Silver Hydrosols Using Poly(N -vinyl-2-pyrrolidone) as a Reducing Agent Langmuir 2006, 22, 7027-7034 (Pubitemid 44231448)
74. Khullar, P.; Mahal, A.; Singh, V.; Banipal, T. S.; Kaur, G.; Bakshi, M. S. How PEO-PPO-PEO Triblock Polymer Micelles Control the Synthesis of Gold Nanoparticles: Temperature and Hydrophobic Effects Langmuir 2010, 26, 11363-11371
75. Brust, M.; Fink, J.; Bethell, D.; Schiffrin, D. J.; Kiely, C. Synthesis and Reactions of Functionalized Gold Nanoparticles J. Chem. Soc., Chem. Commun. 1995, 1655-1656