Towards rational design of nanoparticle catalysis in ionic liquids

Catalysts

Volumn 3, Issue 2, 2013, Pages 543-562

  Zhang, Bin ^a   Yan, Ning ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

Green catalysis; Ionic liquid; NP catalysis; Stabilizer

Indexed keywords

EID: 84898413708     PISSN: None     EISSN: 20734344     Source Type: Journal    
DOI: 10.3390/catal3020543     Document Type: Article

References (95)

1. Dupont, J.; Fonseca, G.S.; Umpierre, A.P.; Fichtner, P.F.P.; Teixeira, S.R. Transition-Metal Nanoparticles in Imidazolium Ionic Liquids: Recycable Catalysts for Biphasic Hydrogenation Reactions. J. Am. Chem. Soc. 2002, 124, 4228-4229.
2. Lee, J.W.; Shin, J.Y.; Chun, Y.S.; Jang, H.B.; Song, C.E.; Lee, S.-G. Toward Understanding the Origin of Positive Effects of Ionic Liquids on Catalysis: Formation of More Reactive Catalysts and Stabilization of Reactive Intermediates and Transition States in Ionic Liquids. Acc. Chem. Res. 2010, 43, 985-994.
3. Ariga, K.; Vinu, A.; Yamauchi, Y.; Ji, Q.; Hill, J.P. Nanoarchitectonics for Mesoporous Materials. Bull. Chem. Soc. Jpn. 2012, 85, 1-32.
4. Datta, K.K.R.; Reddy, B.V.S.; Ariga, K.; Vinu, A. Gold Nanoparticles Embedded in a Mesoporous Carbon Nitride Stabilizer for Highly Efficient Three-Component Coupling Reaction. Angew. Chem. Int. Ed. 2010, 49, 5961-5965.
5. Yan, N.; Zhao, C.; Luo, C.; Dyson, P.J.; Liu, H.; Kou, Y. One-Step Conversion of Cellobiose to C6-Alcohols Using a Ruthenium Nanocluster Catalyst. J. Am. Chem. Soc. 2006, 128, 8714-8715.
6. Prechtl, M.H.; Scariot, M.; Scholten, J.D.; Machado, G.; Teixeira, S.R.; Dupont, J. Nanoscale Ru(0) particles: Arene hydrogenation catalysts in imidazolium ionic liquids. Inorg. Chem. 2008, 47, 8995-9001.
7. Stratton, S.A.; Luska, K.L.; Moores, A. Rhodium nanoparticles stabilized with phosphine functionalized imidazolium ionic liquids as recyclable arene hydrogenation catalysts. Catal. Today 2012, 183, 96-100.
8. Roucoux, A.; Nowicki, A.; Philippot, K. Rhodium and Ruthenium Nanoparticles in Catalysis; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2008; pp. 349-388.
9. Leger, B.; Denicourt-Nowicki, A.; Olivier-Bourbigou, H.; Roucoux, A. Imidazolium-functionalized bipyridine derivatives: a promising family of ligands for catalytical Rh(0) colloids. Tetrahedron Lett. 2009, 50, 6531-6533.
10. Seddon, K.R.; Stark, A. Selective catalytic oxidation of benzyl alcohol and alkylbenzenes in ionic liquids. Green Chem. 2002, 4, 119-123.
11. Qiu, L.; Liu, B.; Peng, Y.; Yan, F. Fabrication of ionic liquid-functionalized polypyrrole nanotubes decorated with platinum nanoparticles and their electrocatalytic oxidation of methanol. Chem. Commun. 2011, 47, 2934-2936.
12. Balanta, A.; Godard, C.; Claver, C. Pd nanoparticles for C-C coupling reactions. Chem. Soc. Rev. 2011, 40, 4973-4985.
13. Fernandez, F.; Cordero, B.; Durand, J.; Muller, G.; Malbosc, F.; Kihn, Y.; Teuma, E.; Gomez, M. Palladium catalyzed Suzuki C-C couplings in an ionic liquid: Nanoparticles responsible for the catalytic activity. Dalton Trans. 2007, 5572-5581.
14. Durand, J.; Teuma, E.; Malbosc, F.; Kihn, Y.; Gómez, M. Palladium nanoparticles immobilized in ionic liquid: An outstanding catalyst for the Suzuki C-C coupling. Catal. Commun. 2008, 9, 273-275.
15. Calò, V.; Nacci, A.; Monopoli, A.; Cotugno, P. Palladium-Nanoparticle-Catalysed Ullmann Reactions in Ionic Liquids with Aldehydes as the Reductants: Scope and Mechanism. Chem. Eur. J. 2009, 15, 1272-1279.
16. Cheng, J.; Tang, L.; Xu, J. An Economical, Green Pathway to Biaryls: Palladium Nanoparticles Catalyzed Ullmann Reaction in Ionic Liquid/Supercritical Carbon Dioxide System. Adv. Synth. Catal. 2010, 352, 3275-3286.
17. Xiao, C.-X.; Cai, Z.-P.; Wang, T.; Kou, Y.; Yan, N. Aqueous-phase Fischer-Tropsch synthesis with a ruthenium nanocluster catalyst. Angew. Chem. Int. Ed. 2008, 47, 746-749.
18. Yinghuai, Z.; Widjaja, E.; Pei Sia, S.L.; Zhan, W.; Carpenter, K.; Maguire, J.A.; Hosmane, N.S.; Hawthorne, M.F. Ruthenium(0) Nanoparticle-Catalyzed Isotope Exchange between 10 B and 11 B Nuclei in Decaborane(14). J. Am. Chem. Soc. 2007, 129, 6507-6512.
19. Geldbach, T.J.; Zhao, D.; Castillo, N.C.; Laurenczy, G.; Weyershausen, B.; Dyson, P.J. Biphasic Hydrosilylation in Ionic Liquids: A Process Set for Industrial Implementation. J. Am. Chem. Soc. 2006, 128, 9773-9780.
20. Yinghuai, Z.; Chenyan, K.; Peng, A.T.; Emi, A.; Monalisa, W.; Kui-Jin Louis, L.; Hosmane, N.S.; Maguire, J.A. Catalytic Phenylborylation Reaction by Iridium(0) Nanoparticles Produced from Hydridoiridium Carborane. Inorg. Chem. 2008, 47, 5756-5761.
21. Lin, Q.; Yang, C.; Jiang, W.; Chen, H.; Li, X. Carbonylation of iodobenzene catalyzed by water-souble palladium-phosphine complexes in ionic liquid. J. Mol. Catal. A 2007, 264, 17-21.
22. Fei, Z.; Geldbach, T.J.; Zhao, D.; Dyson, P.J. From dysfunction to bis-function: On the design and applications of functionalized ionic liquids. Chem. Eur. J. 2006, 12, 2122-2130.
23. Dupont, J.; Scholten, J.D. On the structural and surface properties of transition-metal nanoparticles in ionic liquids. Chem. Soc. Rev. 2010, 39, 1780-1804.
24. Prechtl, M.H.G.; Campbell, P.S.; Scholten, J.D.; Fraser, G.B.; Machado, G.; Santini, C.C.; Dupont, J.; Chauvin, Y. Imidazolium ionic liquids as promoters and stabilizing agents for the preparation of metal(0) nanoparticles by reduction and decomposition of organometallic complexes. Nanoscale 2010, 2, 2601-2606.
25. Prechtl, M.H.G.; Scholten, J.D.; Dupont, J. Carbon-Carbon Cross Coupling Reactions in Ionic Liquids Catalysed by Palladium Metal Nanoparticles. Molecules 2010, 15, 3441-3461.
26. Yan, N.; Xiao, C.; Kou, Y. Transition metal nanoparticle catalysis in green solvents. Coord. Chem. Rev. 2010, 254, 1179-1218.
27. Luska, K.L.; Moores, A. Functionalized Ionic Liquids for the Synthesis of Metal Nanoparticles and their Application in Catalysis. ChemCatChem 2012, 4, 1534-1546.
28. Scholten, J.D.; Leal, B.C.; Dupont, J. Transition Metal Nanoparticle Catalysis in Ionic Liquids. ACS Catal. 2012, 2, 184-200.
29. Neouze, M.-A. About the interactions between nanoparticles and imidazolium moieties: emergence of original hybrid materials. J. Mater. Sci. 2010, 20, 9593-9607.
30. Vollmer, C.; Janiak, C. Naked metal nanoparticles from metal carbonyls in ionic liquids: Easy synthesis and stabilization. Coord. Chem. Rev. 2011, 255, 2039-2057.
31. Katsyuba, S.A.; Zvereva, E.E.; Yan, N.; Yuan, X.; Kou, Y.; Dyson, P.J. Rationalization of Solvation and Stabilization of Palladium Nanoparticles in Imidazolium-Based Ionic Liquids by DFT and Vibrational Spectroscopy. ChemPhysChem 2012, 13, 1781-1790.
32. Zhao, D.; Fei, Z.; Geldbach, T.J.; Scopelliti, R.; Dyson, P.J. Nitrile-Functionalized Pyridinium Ionic Liquids: Synthesis, Characterization, and Their Application in Carbon-Carbon Coupling Reactions. J. Am. Chem. Soc. 2004, 126, 15876-15882.
33. Schrekker, H.S.; Gelesky, M.A.; Stracke, M.P.; Schrekker, C.M.L.; Machado, G.; Teixeira, S.R.; Rubim, J.C.; Dupont, J. Disclosure of the imidazolium cation coordination and stabilization mode in ionic liquid stabilized gold(0) nanoparticles. J. Colloid Interface Sci. 2007, 316, 189-195.
34. Yang, X.; Fei, Z.; Geldbach, T.J.; Phillips, A.D.; Hartinger, C.G.; Li, Y.; Dyson, P.J. Suzuki Coupling Reactions in Ether-Functionalized Ionic Liquids: The Importance of Weakly Interacting Cations. Organometallics 2008, 27, 3971-3977.
35. Zhang, H.; Cui, H. Synthesis and Characterization of Functionalized Ionic Liquid-Stabilized Metal (Gold and Platinum) Nanoparticles and Metal Nanoparticle/Carbon Nanotube Hybrids. Langmuir 2009, 25, 2604-2612.
36. Fei, Z.; Zhao, D.; Pieraccini, D.; Ang, W.H.; Geldbach, T.J.; Scopelliti, R.; Chiappe, C.; Dyson, P.J. Development of Nitrile-Functionalized Ionic Liquids for C-C Coupling Reactions: Implication of Carbene and Nanoparticle Catalysts. Organometallics 2007, 26, 1588-1598.
37. Venkatesan, R.; Prechtl, M.H.G.; Scholten, J.D.; Pezzi, R.P.; Machado, G.; Dupont, J. Palladium nanoparticle catalysts in ionic liquids: Synthesis, characterisation and selective partial hydrogenation of alkynes to Z-alkenes. J. Mater. Sci. 2011, 21, 3030-3036.
38. Tatumi, R.; Fujihara, H. Remarkably stable gold nanoparticles functionalized with a zwitterionic liquid based on imidazolium sulfonate in a high concentration of aqueous electrolyte and ionic liquid. Chem. Commun. 2005, 83-85.
39. Yang, X.; Yan, N.; Fei, Z.; Crespo-Quesada, R.M.; Laurenczy, G.; Kiwi-Minsker, L.; Kou, Y.; Li, Y.; Dyson, P.J. Biphasic Hydrogenation over PVP Stabilized Rh Nanoparticles in Hydroxyl Functionalized Ionic Liquids. Inorg. Chem. 2008, 47, 7444-7446.
40. Yan, N.; Yang, X.; Fei, Z.; Li, Y.; Kou, Y.; Dyson, P.J. Solvent-enhanced coupling of sterically hindered reagents and aryl chlorides using functionalized ionic liquids. Organometallics 2009, 28, 937-939.
41. Mathews, C.J.; Smith, P.J.; Welton, T. Palladium catalysed Suzuki cross-coupling reactions in ambient temperature ionic liquids. Chem. Commun. 2000, 1249-1250.
42. Rajagopal, R.; Jarikote, D.V.; Srinivasan, K.V. Ultrasound promoted Suzuki cross-coupling reactions in ionic liquid at ambient conditions. Chem. Commun. 2002, 616-617.
43. Wang, R.; Twamley, B.; Shreeve, J.N.M. A Highly Efficient, Recyclable Catalyst for C-C Coupling Reactions in Ionic Liquids: Pyrazolyl-Functionalized N-Heterocyclic Carbene Complex of Palladium(II). J. Org. Chem. 2005, 71, 426-429.
44. Daguenet, C.; Dyson, P.J. Inhibition of Catalytic Activity in Ionic Liquids: Implications for Catalyst Design and the Effect of Cosolvents. Organometallics 2004, 23, 6080-6083.
45. Yuan, X.; Yan, N.; Katsyuba, S.A.; Zvereva, E.E.; Kou, Y.; Dyson, P.J. A remarkable anion effect on palladium nanoparticle formation and stabilization in hydroxyl-functionalized ionic liquids. Phys. Chem. Chem. Phys. 2012, 14, 6026-6033.
46. Song, H.; Yan, N.; Fei, Z.; Kilpin, K.J.; Scopelliti, R.; Li, X.; Dyson, P.J. Evaluation of ionic liquid soluble imidazolium tetrachloropalladate pre-catalysts in Suzuki coupling reactions. Catal. Today 2012, 183, 172-177.
47. Chiappe, C.; Pieraccini, D.; Zhao, D.; Fei, Z.; Dyson, P.J. Remarkable Anion and Cation Effects on Stille Reactions in Functionalised Ionic Liquids. Adv. Synth. Catal. 2006, 348, 68-74.
48. Khare, V.; Li, Z.; Mantion, A.; Ayi, A.A.; Sonkaria, S.; Voelkl, A.; Thunemann, A.F.; Taubert, A. Strong anion effects on gold nanoparticle formation in ionic liquids. J. Mater. Sci. 2010, 20, 1332-1339.
49. Williams, D.B.; Stoll, M.E.; Scott, B.L.; Costa, D.A.; Oldham, J.W.J. Coordination chemistry of the bis(trifluoromethylsulfonyl)imide anion: molecular interactions in room temperature ionic liquids. Chem. Commun. 2005, 1438-1440.
50. Yuan, Y.; Yan, N.; Dyson, P.J. Advances in the Rational Design of Rhodium Nanoparticle Catalysts: Control via Manipulation of the Nanoparticle Core and Stabilizer. ACS Catal. 2012, 2, 1057-1069.
51. Zhao, C.; Wang, H.-Z.; Yan, N.; Xiao, C.-X.; Mu, X.-D.; Dyson, P.J.; Kou, Y. Ionic-liquid-like copolymer stabilized nanocatalysts in ionic liquids: II. Rhodium-catalyzed hydrogenation of arenes. J. Catal. 2007, 250, 33-40.
52. Yuan, X.; Yan, N.; Xiao, C.; Li, C.; Fei, Z.; Cai, Z.; Kou, Y.; Dyson, P.J. Highly selective hydrogenation of aromatic chloronitro compounds to aromatic chloroamines with ionic-liquid-like copolymer stabilized platinum nanocatalysts in ionic liquids. Green Chem. 2010, 12, 228-233.
53. Zou, M.; Mu, X.; Yan, N.; Kou, Y. Selective hydrogenation of cinnamaldehyde by ionic copolymer-stabilized Pt nanoparticles in ionic liquids. Cuihua Xuebao 2007, 28, 389-391.
54. Yuan, Y.; Yao, S.; Wang, M.; Lou, S.; Yan, N. Recent Progress in Chemoselective Hydrogenation of α,β-Unsaturated Aldehyde to Unsaturated Alcohol Over Nanomaterials. Curr. Org. Chem. 2013, 17, 400-413.
55. Yan, N.; Zhang, J.-G.; Tong, Y.; Yao, S.; Xiao, C.; Li, Z.; Kou, Y. Solubility adjustable nanoparticles stabilized by a novel PVP based family: Synthesis, characterization and catalytic properties. Chem. Commun. 2009, 4423-4425.
56. Yan, N.; Zhang, J.; Yuan, Y.; Chen, G.-T.; Dyson, P.J.; Li, Z.-C.; Kou, Y. Thermoresponsive polymers based on polyvinylpyrrolidone: Applications in nanoparticle catalysis. Chem. Commun. 2010, 46, 1631-1633.
57. Zhang, J.; Yuan, Y.; Kilpin, K.J.; Kou, Y.; Dyson, P.J.; Yan, N. Thermally responsive gold nanocatalysts based on a modified poly-vinylpyrrolidone. J. Mol. Catal. A 2013, 371, 29-35.
58. Chen, G.-T.; Wang, C.-H.; Zhang, J.-G.; Wang, Y.; Zhang, R.; Du, F.-S.; Yan, N.; Kou, Y.; Li, Z.-C. Toward Functionalization of Thermoresponsive Poly(N-vinyl-2-pyrrolidone). Macromolecules 2010, 43, 9972-9981.
59. Yan, N.; Yuan, Y.; Dyson, P.J. Rhodium nanoparticle catalysts stabilized with a polymer that enhances stability without compromising activity. Chem. Commun. 2011, 47, 2529-2531.
60. Roucoux, A.; Schulz, J.; Patin, H. Reduced Transition Metal Colloids: A Novel Family of Reusable Catalysts? Chem. Rev. 2002, 102, 3757-3778.
61. Yuan, Y.; Yan, N.; Dyson, P.J. pH-Sensitive Gold Nanoparticle Catalysts for the Aerobic Oxidation of Alcohols. Inorg. Chem. 2011, 50, 11069-11074.
62. Axet, M.R.; Castillon, S.; Claver, C.; Philippot, K.; Lecante, P.; Chaudret, B. Chiral diphosphite-modified rhodium(0) nanoparticles: Catalyst reservoir for styrene hydroformylation. Eur. J. Inorg. Chem. 2008, 3460-3466.
63. Salas, G.; Santini, C.C.; Philippot, K.; Colliere, V.; Chaudret, B.; Fenet, B.; Fazzini, P.F. Influence of amines on the size control of in situ synthesized ruthenium nanoparticles in imidazolium ionic liquids. Dalton Trans. 2011, 40, 4660-4668.
64. Denicourt-Nowicki, A.; Leger, B.; Roucoux, A. N-Donor ligands based on bipyridine and ionic liquids: an efficient partnership to stabilize rhodium colloids. Focus on oxygen-containing compounds hydrogenation. Phys. Chem. Chem. Phys. 2011, 13, 13510-13517.
65. Dykeman, R.R.; Yan, N.; Scopelliti, R.; Dyson, P.J. Enhanced rate of arene hydrogenation with imidazolium functionalized bipyridine stabilized rhodium nanoparticle catalysts. Inorg. Chem. 2011, 50, 717-719.
66. Snelders, D.J.M.; Yan, N.; Gan, W.; Laurenczy, G.; Dyson, P.J. Tuning the Chemoselectivity of Rh Nanoparticle Catalysts by Site-Selective Poisoning with Phosphine Ligands: The Hydrogenation of Functionalized Aromatic Compounds. ACS Catal. 2012, 2, 201-207.
67. Dykeman, R.R.; Yuan, Y.; Yan, N.; Asakura, H.; Teramura, K.; Tanaka, T.; Dyson, P.J. Rational Design of a Molecular Nanocatalyst-Stabilizer that Enhances both Catalytic Activity and Nanoparticle Stability. ChemCatChem 2012, 4, 1907-1910.
68. Liu, X.; Liu, X. Bimetallic Nanoparticles: Kinetic Control Matters. Angew. Chem. Int. Ed. 2012, 51, 3311-3313.
69. Okazaki, K.-I.; Kiyama, T.; Hirahara, K.; Tanaka, N.; Kuwabata, S.; Torimoto, T. Single-step synthesis of gold-silver alloy nanoparticles in ionic liquids by a sputter deposition technique. Chem. Commun. 2008, 691-693.
70. Pearson, A.; O'Mullane, A.P.; Bansal, V.; Bhargava, S.K. Galvanic replacement mediated transformation of Ag nanospheres into dendritic Au-Ag nanostructures in the ionic liquid [BMIM][BF4]. Chem. Commun. 2010, 46, 731-733.
71. Dash, P.; Scott, R.W.J. 1-Methylimidazole stabilization of gold nanoparticles in imidazolium ionic liquids. Chem. Commun. 2009, 812-814.
72. Xiao, F.; Zhao, F.; Mei, D.; Mo, Z.; Zeng, B. Nonenzymatic glucose sensor based on ultrasonic-electrodeposition of bimetallic PtM (M = Ru, Pd and Au) nanoparticles on carbon nanotubes-ionic liquid composite film. Biosens. Bioelectron. 2009, 24, 3481-3486.
73. Arquilliere, P.P.; Santini, C.C.; Haumesser, P.H.; Aouine, M. Synthesis of copper and copper-ruthenium nanoparticles in ionic liquids for the metallization of advanced interconnect structures. ECS Trans. 2011, 35, 11-16.
74. 2-expanded ionic liquids. Catal. Sci. Technol. 2012, 2, 1403-1409.
75. Dash, P.; Dehm, N.A.; Scott, R.W.J. Bimetallic PdAu nanoparticles as hydrogenation catalysts in imidazolium ionic liquids. J. Mol. Catal. A 2008, 286, 114-119.
76. Dash, P.; Miller, S.M.; Scott, R.W.J. Stabilizing nanoparticle catalysts in imidazolium-based ionic liquids: A comparative study. J. Mol. Catal. A 2010, 329, 86-95.
77. Hu, B.; Wu, T.; Ding, K.; Zhou, X.; Jiang, T.; Han, B. Seeding Growth of Pd/Au Bimetallic Nanoparticles on Highly Cross-Linked Polymer Microspheres with Ionic Liquid and Solvent-Free Hydrogenation. J. Phys. Chem. C 2010, 114, 3396-3400.
78. Yuan, X.; Sun, G.; Asakura, H.; Tanaka, T.; Chen, X.; Yuan, Y.; Laurenczy, G.; Kou, Y.; Dyson, P.J.; Yan, N. Development of Palladium Surface-Enriched Heteronuclear Au-Pd Nanoparticle Dehalogenation Catalysts in an Ionic Liquid. Chem. Eur. J. 2013, 19, 1227-1234.
79. Hutchings, G.J. Nanocrystalline gold and gold-palladium alloy oxidation catalysts: A personal reflection on the nature of the active sites. Dalton Trans. 2008, 5523-5536.
80. Yang, X.; Chen, D.; Liao, S.; Song, H.; Li, Y.; Fu, Z.; Su, Y. High-performance Pd-Au bimetallic catalyst with mesoporous silica nanoparticles as support and its catalysis of cinnamaldehyde hydrogenation. J. Catal. 2012, 291, 36-43.
81. Sheldon, R.A. E factors, green chemistry and catalysis: An odyssey. Chem. Commun. 2008, 3352-3365.
82. Pinto, A.C.; Lapis, A.A.M.; da Silva, B.V.; Bastos, R.S.; Dupont, J.; Neto, B.A.D. Pronounced ionic liquid effect in the synthesis of biologically active isatin-3-oxime derivatives under acid catalysis. Tetrahedron Lett. 2008, 49, 5639-5641.
83. Hajipour, A.R.; Rajaei, A.; Ruoho, A.E. A mild and efficient method for preparation of azides from alcohols using acidic ionic liquid [H-NMP]HSO4. Tetrahedron Lett. 2009, 50, 708-711.
84. Harmer, M.A.; Junk, C.P.; Rostovtsev, V.V.; Marshall, W.J.; Grieco, L.M.; Vickery, J.; Miller, R.; Work, S. Catalytic reactions using superacids in new types of ionic liquids. Green Chem. 2009, 11, 517-525.
85. Yan, N.; Yuan, Y.; Dykeman, R.; Kou, Y.; Dyson, P.J. Hydrodeoxygenation of Lignin-Derived Phenols into Alkanes by Using Nanoparticle Catalysts Combined with Bronsted Acidic Ionic Liquids. Angew. Chem. Int. Ed. 2010, 49, 5549-5553.
86. Yan, N.; Zhao, C.; Dyson, P.J.; Wang, C.; Liu, L.-T.; Kou, Y. Selective degradation of wood lignin over noble-metal catalysts in a two-step process. ChemSusChem 2008, 1, 626-629.
87. 2 catalysts. Chem. Commun. 2010, 46, 412-414.
88. Zhao, C.; Kou, Y.; Lemonidou, A.A.; Li, X.; Lercher, J.A. Highly Selective Catalytic Conversion of Phenolic Bio-Oil to Alkanes. Angew. Chem. Int. Ed. 2009, 48, 3987-3990.
89. Thomazeau, C.; Olivier-Bourbigou, H.; Magna, L.; Luts, S.; Gilbert, B. Determination of an Acidic Scale in Room Temperature Ionic Liquids. J. Am. Chem. Soc. 2003, 125, 5264-5265.
90. Asakura, H.; Teramura, K.; Shishido, T.; Tanaka, T.; Yan, N.; Xiao, C.X.; Yao, S.Y.; Kou, Y. In situ time-resolved DXAFS study of Rh nanoparticle formation mechanism in ethylene glycol at elevated temperature. Phys. Chem. Chem. Phys. 2012, 14, 2983-2990.
91. Yao, S.; Yuan, Y.; Xiao, C.; Li, W.; Kou, Y.; Dyson, P.J.; Yan, N.; Asakura, H.; Teramura, K.; Tanaka, T. Insights into the Formation Mechanism of Rhodium Nanocubes. J. Phys. Chem. C 2012, 116, 15076-15086.
92. Yu, Y.; Chen, X.; Yao, Q.; Yu, Y.; Yan, N.; Xie, J. Scalable and Precise Synthesis of Thiolated Au10-12, Au15, Au18, and Au25 Nanoclusters via pH Controlled CO Reduction. Chem. Mater. 2013, 25, 946-952.
93. Toikkanen, O.; Ruiz, V.; Rönnholm, G.; Kalkkinen, N.; Liljeroth, P.; Quinn, B.M. Synthesis and Stability of Monolayer-Protected Au38 Clusters. J. Am. Chem. Soc. 2008, 130, 11049-11055.
94. Qian, H.; Jin, R. Ambient Synthesis of Au144(SR)60 Nanoclusters in Methanol. Chem. Mater. 2011, 23, 2209-2217.
95. Jadzinsky, P.D.; Calero, G.; Ackerson, C.J.; Bushnell, D.A.; Kornberg, R.D. Structure of a Thiol Monolayer-Protected Gold Nanoparticle at 1.1 Å Resolution. Science 2007, 318, 430-433.