A bioinspired approach for controlling accessibility in calix[4]arene-bound metal cluster catalysts

Nature Chemistry

Volumn 2, Issue 12, 2010, Pages 1062-1068

  De Silva, Namal ^a,c,d   Ha, Jeong Myeong ^a,c,d   Solovyov, Andrew ^a   Nigra, Michael M ^a   Ogino, Isao ^a   Yeh, Sheila W ^b   Durkin, Kathleen A ^a   Katz, Alexander ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b Chevron Richmond Technology Center   (United States)

^c DUPONT COMPANY   (United States)

^d Korea Institute of Science and Technology   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

2 MERCAPTONAPHTHALENE; 2-NAPHTHALENETHIOL; CALIXARENE; ENZYME; GOLD; METAL; METAL NANOPARTICLE; NAPHTHALENE DERIVATIVE; PHOSPHINE DERIVATIVE; THIOL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; SPECTROFLUOROMETRY;

CALIXARENES; CATALYSIS; ENZYMES; GOLD; METAL NANOPARTICLES; METALS; NAPHTHALENES; PHOSPHINES; SPECTROMETRY, FLUORESCENCE; SULFHYDRYL COMPOUNDS;

EID: 78649524352     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.860     Document Type: Article

References (49)

1. Beinert, H. Iron-sulfur proteins: ancient structures, still full of surprises. J. Biol. Inorg. Chem. 5, 2-15 (2000).
2. Robbins, A. H. & Stout, C. D. Structure of activated aconitase: formation of the [4Fe-4S] cluster. Proc. Natl Acad. Sci. USA 86, 3639-3643 (1989).
3. Quintanar, L. et al. Spectroscopic and electronic structure studies of the trinuclear Cu cluster active site of the multicopper oxidase laccase: nature of its coordination unsaturation. J. Am. Chem. Soc. 127, 13832-13845 (2005).
4. Banavar, J. R. & Maritan, A. Physics of proteins. Annu. Rev. Biophys. Biomol. Struct. 36, 261-280 (2007).
5. Xu, Z. et al. Size-dependent catalytic activity of supported metal clusters. Nature 372, 346-348 (1994).
6. Corma, A. & Garcia, H. Supported gold nanoparticles as catalysts for organic reactions. Chem. Soc. Rev. 37, 2096-2126 (2008).
7. Hashmi, A. S. K. & Hutchings, G. J. Gold catalysis. Angew. Chem. Int. Ed. 45, 7896-7936 (2006).
8. Choundhary, T. V. & Goodman, D. W. Oxidation catalysis by supported gold nano-clusters. Top. Catal. 21, 25-34 (2002).
9. Corma, A. et al. Gold nanoparticles in organic capsules: a supramolecular assembly of gold nanoparticles and cucurbituril. Eur. J. Chem. 13, 6359-6364 (2007).
10. Nowicki, A. et al. Supramolecular shuttle and protective agent: a multiple role of methylated cyclodextrins in the chemoselective hydrogenation of benzene derivatives with ruthenium nanoparticles. Chem. Commun. 3, 296-298 (2006).
11. Denicourt-Nowicki, A., Ponchel, A., Monflier, E. & Roucoux, A. Methylated cyclodextrins: an efficient protective agent in water for zerovalent ruthenium nanoparticles and a supramolecular shuttle in alkene and arene hydrogenation reactions. Dalton Trans. 48, 5714-5719 (2007).
12. Denicourt-Nowicki, A., Roucoux, A. & Wyrwalski, F. Carbon-supported ruthenium nanoparticles stabilized by methylated cyclodextrins: a new family of heterogeneous catalysts for the gas-phase hydrogenation of arenes. Eur. J. Chem. 14, 8090-8093 (2008).
13. Gopidas, K. R., Whitesell, J. K. & Fox, M. A. Nanoparticle-cored dendrimers: synthesis and characterization. J. Am. Chem. Soc. 125, 6491-6502 (2003).
14. Crooks, R. M., Zhao, M., Sun, L., Chechik, V. & Yeung, L. K. Dendrimerencapsulated metal nanoparticles: synthesis, characterization and applications to catalysis. Acc. Chem. Res. 34, 181-190 (2001).
15. Toshima, N. Nanoscopic structure and function of polymer-protected metal clusters. Macromol. Symp. 156, 45-52 (2000).
16. Baiker, A. Progress in asymmetric heterogeneous catalysis: design of novel chirally modified platinum metal catalysts. J. Mol. Cat. A 115, 473-493 (1997).
17. Ha, J.-M., Solovyov, A. & Katz, A. Postsynthetic modification of gold nanoparticles with calix[4]arene enantiomers: origin of chiral surface plasmon resonance. Langmuir 25, 153-158 (2009).
18. Ha, J.-M., Solovyov, A. & Katz, A. Synthesis and characterization of accessible metal surfaces in calixarene-bound gold nanoparticles. Langmuir 25, 10548-10553 (2009).
19. Xu, W., Puddephatt, R. J., Manojlovic-Muir, L., Muir, K. W. & Frampton, C. S. J. Calixarenes: structure of an acetonitrile inclusion complex and some transition metal rimmed derivatives. J. Incl. Phenom. 19, 277-290 (1994).
20. Dieleman, C. B., Matt, D. & Harriman, A. Coordination chemistry of calixphosphanes: cooperativity in the assembly of a tetragold calixarene complex. Eur. J. Inorg. Chem. 831-834 (2000), and references therein.
21. Ungaro, R., Pochini, A., Andreetti, G. D. & Domiano, P. Molecular inclusion in functionalized macrocycles: the crystal and molecular-structure of para-tertbutylcalix[4]arene anisole (2-1) complex-a new type of cage compound. J. Chem. Soc. Perkin Trans. II, 197-201 (1985).
22. Bartlett, P. A., Bauer, B. & Singer, S. J. Synthesis of water-soluble undecagold cluster compounds of potential importance in electron microscopies and other studies of biological systems. J. Am. Chem. Soc. 100, 5085-5089 (1978).
23. 7 species. Chem. Commun. 1210-1211 (1970).
24. +. Rec. Trav. Chim. Pays-Bas 99, 137-141 (1980).
25. 3. J. Cryst. Spec. Rec. 13, 355-363 (1983).
26. Safer, D., Lizann, B. & Leigh, J. S. Undecagold clusters for site-specific labeling of biological macromolecules: simplified preparation and model applications. J. Inorg. Biochem. 26, 77-91 (1986).
27. Yang, Y. & Chen, S. Surface manipulation of the electronic energy of subnanometer-sized gold clusters: an electrochemical and spectroscopic investigation. Nano Lett. 3, 75-79 (2003).
28. 11 cluster with sterically demanding phosphine ligands by single crystal X-ray diffraction and XPS spectroscopy. Bull. Chem. Soc. Jpn 76, 1601-1602 (2003).
29. Woehrle, G. H., Warner, M. G. & Hutchison, J. E. Ligand exchange reactions yield subnanometer, thiol-stabilized gold particles with defined optical transitions. J. Phys. Chem. B 106, 9979-9981 (2002).
30. Yanagimoto, Y., Negishi, Y., Fujihara, H. & Tsukuda, T. Chiroptical activity of BINAP-stabilized undecagold clusters. J. Phys. Chem. B 110, 11611-11614 (2006).
31. Hall, K. P. & Mingos, D. M. P. Homonuclear and heteronuclear cluster compounds of gold. Prog. Inorg. Chem. 32, 237-325 (1984), and references therein.
32. Woehrle, G. H. & Hutchison, J. E. Thiol-functionalized undecagold clusters by ligand exchange: synthesis, mechanism and properties. Inorg. Chem. 44, 6149-6158 (2005).
33. 2) clusters. J. Organomet. Chem. 433, 189-201 (1992).
34. Hostetler, M. J. 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 14, 17-30 (1998).
35. 4-based cluster assemblies. Dalton Trans. 39, 2194-2197 (2010).
36. Menard, L. D. et al. Sub-nanometer Au monolayer-protected clusters exhibiting molecule-like electronic behavior: quantitative high-angle annular dark-field scanning transmission electron microscopy and electrochemical characterization of clusters with precise atomic stoichiometry. J. Phys. Chem. B 110, 12874-12883 (2006).
37. Chusuei, C. C., Lai, X., Luo, K. & Goodman, D. W. Modeling heterogeneous catalysts: metal clusters on planar oxide supports. Top. Catal. 14, 71-83 (2001).
38. Mason, M. G. Electronic-structure of supported small metal-clusters. Phys. Rev. B 27, 748-762 (1983).
39. 13 and larger Au monolayer-protected clusters as revealed by X-ray absorption spectroscopy and transmission electron microscopy. J. Phys. Chem. B 110, 14564-14573 (2006).
40. 2-supported gold catalysts. J. Phys. Chem. C 113, 269-280 (2009).
41. Cariati, F. & Naldini, L. Trianionoeptakis (triarylphosphine) undecagold cluster compounds. Inorg. Chim. Acta 5, 172-174 (1971).
42. Vollenbroek, F. A., Bour, J. J., Trooster, J. M. & van der Veldon, J. W. A. Reactions of gold-phosphine cluster compounds. Chem. Commun. 907-909 (1978).
43. Zhang, P. & Sham T. K. X-ray studies of the structure and electronic behavior of alkanethiolate-capped gold nanoparticles: the interplay of size and surface effects. Phys. Rev. Lett. 90, 245502(2003).
44. Corma, A. & Garcia, H. Supported Gold Nanoparticles as Oxidation Catalysts in Nanoparticles and Catalysis 389-426 (Wiley VCH Verlag, 2008).
45. 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 Ångstrom resolution. Science 318, 430-433 (2007).
46. Ha, J.-M., Katz, A., Drapailo, A. B. & Kalchenko, V. I. Mercaptocalixarenecapped gold nanoparticles via postsynthetic modification and direct synthesis: effect of calixarene cavity-metal interactions. J. Phys. Chem. C 113, 1137-1142 (2009).
47. Jaguar, version 7.5, MacroModel, version 9.6, Schrodinger, New York (2008).
48. Zhao, Y. & Truhlar, D. G. Density functionals with broad applicability in chemistry. Acc. Chem. Res. 41, 157-167 (2008).
49. Zhao, Y., Schultz, N. E. & Truhlar, D. G. Exchange-correlation functional with broad accuracy for metallic and nonmetallic compounds, kinetics and noncovalent interactions. J. Chem. Phys. 123, 161103(2005).