Surface Confined Metallosupramolecular Architectures: Formation and Scanning Tunneling Microscopy Characterization

Accounts of Chemical Research

Volumn 42, Issue 2, 2009, Pages 249-259

  Li, Shan Shan ^a   Northrop, Brian H ^b   Yuan, Qun Hui ^a   Wan, Li Jun ^a   Stang, Peter J ^b  

^a INSTITUTE OF CHEMISTRY   (China)

^b UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

METAL; NANOMATERIAL;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROCHEMISTRY; METHODOLOGY; NANOTECHNOLOGY; SCANNING TUNNELING MICROSCOPY; SURFACE PROPERTY;

ELECTROCHEMISTRY; METALS; MICROSCOPY, SCANNING TUNNELING; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NANOSTRUCTURES; NANOTECHNOLOGY; SURFACE PROPERTIES;

EID: 61749083748     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar800117j     Document Type: Article

References (60)

1. See, for example: Kay, E. R.; Leigh, D. A.; Zerbetto, F. Synthetic Molecular Motors and Mechanical Machines. Angew. Chem., Int. Ed. 2007, 46, 72-191.
2. (a) Lathan, A. H.; Williams, M. E. Controlling Transport and Chemical Functionality of Magnetic Nanoparticles. Acc. Chem. Res. 2008, 41, 411-420.
3. b) Rosi, N. L.; Giljohann, D. A.; Thaxton, C. S.; Lytton-Jean, A.; Han, M. S.; Mirkin, C. A. Oligonucleotide-Modified Gold Nanoparticles for Intracellular Gene Regulation. Science 2006, 372, 1027-1030.
4. Barlow, S. M.; Raval, R. Complex Organic Molecules at Metal Surfaces: Bonding, Organization and Chirality. Surf. Sci. Rep. 2003, 50, 201-341, and references therein.
5. See, for example: van Delden, R. A.; ter Wiel, M. K. J.; Pollard, M. M.; Vicario, J.; Koumura, N.; Feringa, B. L. Undirectional Molecular Motor on a Gold Surface. Nature 2005, 437, 1337-1340.
6. Gates, B. G.; Xu, Q.; Stewart, M.; Ryan, D.; Wilson, C. G.; Whitesides, G. M. New Approaches to Nanofabrication: Molding, Printing, and Other Techniques. Chem. Rev.2005, 105, 1171-1196.
7. (a) Gomar-Nadal, E.; Puigmarti-Luis, J.; Amabilino, D. B. Assembly of Functional Molecular Nanostructures on Surfaces. Chem. Soc. Rev. 2008, 37, 409-504.
8. b) Guo, L. J. Nanoimprint Lithography: Methods and Material Requirements. Adv. Mater. 2007, 79, 495-513.
9. c) Henzie, J.; Barton, J. E.; Stender, C. L.; Odom, T. W. Large-Area Nanoscale Patterning: Chemistry Meets Fabrication. Acc. Chem. Res. 2006, 39, 249-257.
10. Balzani, G.; Credi, A.; Venturi, M. The Bottom-Up Approach to Molecular-Level Devices and Machines. Chem - Eur. J. 2002, 8, 5525-5532.
11. Lehn, J. M. Toward Complex Matter: Supramolecular Chemistry and Self-Organization. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4763-4768.
12. Whitesides, G. M.; Boncheva, M. Beyond Molecules: Self-Assembly of Mesoscopic and Macroscopic Components. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4769-4774.
13. Lehn, J. M. Supramolecular Chemistry: Concept and Perspectives; VCH: New York, 1995.
14. Howard, J. Mechanics of Motor Proteins and the Cytoskeleton; Sinauer: Sunderland, MA, 2001.
15. Kolb, D. M. Electrochemical Surface Science. Angew. Chem., Int. Ed. 2001, 40, 1162-1181.
16. De Feyter, S.; De Schryver, F. C. Self-Assembly at the Liquid/Solid Interface: STM Reveals. J. Phys. Chem. B 2005, 109, 4290-4302.
17. Gimzewski, J. K.; Joachim, C. Nanoscale Science of Single Molecules using Local Probes. Science 1999, 283, 1683-1688.
18. Barth, J. V.; Costantini, G.; Kern, K. Engineering Atomic and Molecular Nanostructures at Surfaces. Nature 2005, 437, 671-679.
19. (a) Seidel, S. R.; Stang, P. J. High Symmetry Coordination Cages via Self-Assembly. Acc. Chem. Res. 2002, 35, 972-983.
20. b) Leininger, S.; Olenyuk, B.; Stang, P. J. Self-Assembly of Discrete Cyclic Nanostructures Mediated by Transition Metals. Chem. Rev. 2000, 100, 853-907.
21. c) Stang, P. J.; Olenyuk, B. Self-Assembly, Symmetry and Molecular Architecture: Coordination as the Motif in the Rational Design of Supramolecular Metallacyclic Polygons and Polyhedra. Acc. Chem. Res. 1997, 30, 502-518.
22. d) Northrop, B. H.; Yang, H.-B.; Stang, P. J. Coordination-Driven Self-Assembly of Functionalized Supramolecular Metallacycles. Chem. Commun 2008, 5896-5908.
23. (a) Caulder, D. L.; Raymond, K. N. Supermolecules by Design. Acc. Chem. Res. 1999, 32, 975-982.
24. b) Johnson, D. W.; Raymond, K. N. The Role of Guest Molecules in the Self-Assembly of Metal-Ligand Clusters. Supramol. Chem. 2001, 13, 639-659.
25. c) Xu, J.-D.; Raymond, K. N. Structurally Characterized Quadruple-Stranded Bisbidentate Helicates. Angew. Chem., Int. Ed. 2006, 45, 6480-6485.
26. Fujita, M.; Tominaga, M.; Hori, A.; Therrien, B. Coordination Assemblies from a Pd(11)-Cornered Square Complex. Acc. Chem. Res. 2005, 38, 369-378.
27. (a) Holliday, B. J.; Mirkin, C. A. Strategies for the Construction of Supramolecular Compounds through Coordination Chemistry. Angew. Chem., Int. Ed. 2001, 40, 2022-2043.
28. b) Oliveri, C. G.; Gianneschi, N. C.; Nguyen, S. T.; Mirkin, C. A.; Stern, C. L.; Wawrzak, Z.; Pink, M. Supramolecular Allosteric Cofacial Porphyrin Complexes. J. Am. Chem. Soc. 2006, 128, 16286-16296.
29. Lehn, J. M. From Supramolecular Chemistry Towards Constitutional Dynamic Chemistry and Adaptive Chemistry. Chem. Soc. Rev. 2007, 36, 151-160.
30. Lee, S. J.; Hupp, J. T. Porphyrin-Containing Molecular Squares: Design and Applications. Coord. Chem. Rev. 2006, 250, 1710-1723.
31. See, for example: Thanasekaran, P.; Wu, J.-Y.; Manimaran, B.; Rajendran, T.; Chang, I.-J.; Rajagopal, S.; Lee, G.-H.; Peng, S.-M.; Lu, K.-L. Aggregate of Alkoxyl-Bridged Re(1)-Rectangles as a Probe for Photolulminescence Quenching. J. Phys. Chem. A 2007, 111, 10953-10960.
32. Resendiz, M. J. E.; Noveron, J. C.; Disteldorf, H.; Fischer, S.; Stang, P. J. A Self-Assembled Supramolecular Optical Sensor for Ni(11), Cd(11), and Cr(111). Org. Lett. 2004, 6, 651-653.
33. Ziegler, M.; Davis, A. V.; Johnson, D. W.; Raymond, K. N. Supramolecular Chirality: A Reporter of Structural Memory. Angew. Chem., Int. Ed. 2003, 42, 665-668.
34. (a) Williams, M. E.; Benkstein, K. D.; Abel, C.; Dinolfo, P. H.; Hupp, J. T. Shape-Selective Transport through Rectangle-Based Molecular Materials: Thin-Film Scanning Electrochemical Microscopy Studies. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5171-5177.
35. Wan, L. J. Fabricating and Controlling Molecular Self-Organization at Solid Surfaces: Studies by Scanning Tunneling Microscopy. Acc. Chem. Res. 2006, 39, 334-342.
36. Chiang, S. Scanning Tunneling Microscopy Imaging of Small Adsorbed Molecules on Metal Surfaces in an Ultrahigh Vacuum Environment. Chem. Rev. 1997, 97, 1083-1096.
37. Itaya, K. In Situ Scanning Tunneling Microscopy in Electrolyte Solutions. Prog. Surf. Sci. 1998, 58, 121-247.
38. Wan, L. J.; Noda, H.; Wang, C.; Bai, C. L.; Osawa, M. Controlled Orientation of Individual Molecules by Electrode Potentials. ChemPhysChem 2001, 2, 617-619.
39. Wang, D.; Wan, L. J. Electrochemical Scanning Tunneling Microscopy: Adlayer Structure and Reaction at Solid/Liquid Interface. J. Phys. Chem. C 2007, 111, 16109-16130.
40. Semenov, A.; Spatz, J. P.; Moller, M.; Lehn, J. M.; Sell, B.; Schubert, D.; Weidl, C. H.; Schubert, U. S. Controlled Arrangement of Supramolecular Metal Coordination Arrays on Surfaces. Angew. Chem., Int. Ed. 1999, 38, 2547-2550.
41. Ziener, U.; Lehn, J. M.; Mourran, A.; Moller, M. Supramolecular Assemblies of a Bisfterpyridine) Ligand and of its [2 x 2] Grid-Type Zn-ll and Co-ll Complexes on Highly Ordered Pyrolytic Graphite. Chem - Eur. J. 2002, 8, 951-957.
42. Kurth, D. G.; Severin, N.; Rabe, J. P. Perfectly Straight Nanostructures of Metallosupramolecular Coordination-Polyelectrolyte Amphiphile Complexes on Graphite. Angew. Chem., Int. Ed. 2002, 41, 3681-3683.
43. (a) Safarowsky, C.; Merz, L.; Rang, A.; Broekmann, P.; Hermann, B. A.; Schalley, C. A. Second-Order Templation: Ordered Deposition of Supramolecular Squares on a Chlorine-Covered CuflOO) Surface. Angew. Chem., Int. Ed. 2004, 43, 1291-1294.
44. b) Jeong, K. S.; Kim, S. Y.; Shin, U.-S.; Kogej, M.; Hai, N. T. M.; Broekmann, P.; Jeong, N.; Kirchner, B.; Reiher, M.; Schalley, C. A. Synthesis of Chiral Self-Assembling Rhombs and Their Characterization in Solution, in the Gas Phase, and at the Liquid-Solid Interface. J. Am. Chem. Soc. 2005, 127, 17672-17685.
45. Yuan, Q. H.; Wan, L. J.; Jude, H.; Stang, P. J. Self-Organization of a Self-Assembled Supramolecular Rectangle, Square, and Three-Dimensional Cage on Au(111) Surfaces. J. Am. Chem. Soc. 2005, 127, 16279-16286.
46. Gong, J. R.; Wan, L. J.; Yuan, Q. H.; Bai, C. L.; Jude, H.; Stang, P. J. Mesoscopic Self-Organization of a Self-Assembled Supramolecular Rectangle on Highly Oriented Pyrolytic Graphite and Au(111) Surfaces. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 971-974.
47. Li, S. S.; Yan, H. J.; Wan, L. J.; Yang, H. B.; Northrop, B. H.; Stang, P. J. Control of Supramolecular Rectangle Self-Assembly with a Molecular Template. J. Am. Chem. Soc. 2007, 129, 9268-9269.
48. Yuan, Q.-H.; Yan, C.-J.; Yan, J.-H.; Wan, L.-J.; Northrop, B. H.; Jude, H.; Stang, P. J. An STM Investigation of a Supramolecular Self-Assembled 3-Dimensional Chiral Prism on a Au(111) Surface. J. Am. Chem. Soc. 2008, 130, 8878-8879.
49. Yuan, Q.-H.; Wan, L.-J. Structural Comparison of Self-Organized Adlayers of Ligands and their Metal-Coordinated Complexes on a Au(111) Surface: An STM Study. Chem-Eur. J. 2006, 72, 2808-2814.
50. (a) Chen, X.; Lenhert, S.; Hirtz, M.; Lu, N.; Fuchs, H.; Chi, L. Langmuir-Blodgett Patterning: A Bottom-Up Way to Build Mesostructures over Large Areas. Acc. Chem. Res. 2007, 40, 393-401.
51. Xu, X. M.; Zhong, H. P.; Zhang, H. M.; Mo, Y. R.; Xie, Z. X.; Long, L S.; Zheng, L. S.; Mao, B. W. Ordered Silver Adlayer Formation by Surface-Induced Dissociation of a Coordination Complex Precursor on Au(111) and Au(100) Surfaces. Chem. Phys. Lett. 2004, 386, 254-258.
52. Ruben, M.; Rojo, J.; Romero-Salguero, F. J.; Uppadine, L. H.; Lehn, J. M. Grid-Type Metal Ion Architectures: Functional Metallosupramolecular Arrays. Angew. Chem., Int. Ed. 2004, 43, 3644-3662.
53. Schalley, C. A.; Lutzen, A.; Albrecht, M. Approaching Supramolecular Functionality. Chem-Eur. J. 2004, 10, 1072-1080.
54. See, for example: Braunschweig, A. B.; Northrop, B. H.; Stoddart, J. F. Structural Control at the Organic-Solid Interface. J. Mater. Chem. 2006, 16, 32-44.
55. Kuehl, C. J.; Huang, S. D.; Stang, P. J. Self-Assembly with Postmodification: Kinetically Stabilized Metalla-Supramolecular Rectangles. J. Am. Chem. Soc. 2001, 123, 9634-9641.
56. 4. J. Am. Chem. Soc. 1995, 117, 6273-6283.
57. Lu, J.; Lei, S. B.; Zeng, Q. D.; Kang, S. Z.; Wang, C.; Wan, L J.; Bai, C. L Template-Induced Inclusion Structures with Copper(11) Phthalocyanine and Coronene as Guests in Two-Dimensional Hydrogen-Bonded Host Networks. J. Phys. Chem. B 2004, 108, 5161-5165.
58. Lu, J.; Zeng, Q. D.; Wang, C.; Zheng, Q. Y.; Wan, L. J.; Bai, C. L. Self-Assembled Two-Dimensional Hexagonal Networks. J. Mater. Chem. 2002, 12, 2856-2858.
59. 3h Symmetry. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4932-4936.
60. Caskey, D. C.; Yamamoto, T.; Addicott, C.; Shoemaker, R. K.; Vacek, J.; Horinek, D.; Hawkridge, A. M.; Muddiman, D. C.; Kottas, G.; Michl, J.; Stang, P. J. Coordination-Driven Face-Directed Self-Assembly of Trigonal Prisms. Face-Based Conformational Chirality. J. Am. Chem. Soc. 2008, 130, 7620-7628.