Supramolecular self-assembly of π-conjugated hydrocarbons via 2D cooperative CH/π interaction

ACS Nano

Volumn 6, Issue 1, 2012, Pages 566-572

  Li, Qing ^a   Han, Chengbo ^b   Horton, Scott R ^a   Fuentes Cabrera, Miguel ^a   Sumpter, Bobby G ^a   Lu, Wenchang ^a,b   Bernholc, Jerry ^a,b   Maksymovych, Petro ^a   Pan, Minghu ^a  

^a OAK RIDGE NATIONAL LABORATORY   (United States)

^b NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

hydrogen bonding; magic cluster; phenylacetylene; self assembly; STM; supramolecule

Indexed keywords

AB INITIO CALCULATIONS; BENZENE MOLECULES; CHEMICAL FUNCTIONALIZATION; DRIVING FORCES; GRAPHOEPITAXY; HYDROCARBON MOLECULES; INTERMOLECULAR REPULSIONS; MAGIC CLUSTERS; MOLECULE SURFACE; NANOSCALE ARCHITECTURES; PHENYLACETYLENES; RATIONAL DESIGN; SHAPE AND SIZE; STM; SUPRAMOLECULAR CLUSTERS; SUPRAMOLECULAR SELF-ASSEMBLIES; SUPRAMOLECULAR STRUCTURE; SUPRAMOLECULES;

ACETYLENE; BENZENE; CALCULATIONS; HYDROGEN; HYDROGEN BONDS; MOLECULES; ORGANIC POLYMERS; SELF ASSEMBLY; STEREOCHEMISTRY;

SUPRAMOLECULAR CHEMISTRY;

CARBON; HYDROGEN; NANOMATERIAL;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; HYDROGEN BOND; MACROMOLECULE; PARTICLE SIZE; SURFACE PROPERTY; ULTRASTRUCTURE;

CARBON; COMPUTER SIMULATION; HYDROGEN; HYDROGEN BONDING; MACROMOLECULAR SUBSTANCES; MODELS, CHEMICAL; MODELS, MOLECULAR; NANOSTRUCTURES; PARTICLE SIZE; SURFACE PROPERTIES;

EID: 84856201040     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn203952e     Document Type: Article

References (30)

1. Bartels, L. Tailoring Molecular Layers at Metal Surfaces Nat. Chem. 2010, 2, 87-95
2. Heer, W. A. The Physics of Simple Metal Clusters: Experimental Aspects and Simple Models Rev. Mod. Phys. 1993, 65, 611-676
3. Yokoyama, T.; Yokoyama, S.; Kamikado, T.; Okuno, Y.; Mashiko, S. Selective Assembly on a Surface of Supramolecular Aggregates with Controlled Size and Shape Nature 2001, 413, 619-621
4. Bohringer, M.; Morgenstern, K.; Schneider, W. D.; Berndt, R.; Mauri, F.; Vita., A.; Car, R. Two Dimensional Self-Assembly of Supramolecular Clusters and Chains Phys. Rev. Lett. 1999, 83, 324-327
5. Heim, D.; Seufert, K.; Auwarter, W.; Aurisicchio, C.; Fabbro, C.; Bonifazi, D.; Barth, J. V. Suface-Assisted Assembly of Discrete Porphyrin-Based Cyclic Supramolecules Nano Lett. 2010, 10, 122-128
6. Pimentel, G. C.; McClellan, A. L. Hydrogen Bonding Annu. Rev. Phys. Chem. 1971, 22, 347-385
7. Weckesser, J.; Vita, A.; Barth, J. V.; Cai, C.; Kern, K. Mesoscopic Correlation of Supramolecular Chirality in One-Dimensional Hydrogen-Bonded Assemblies Phys. Rev. Lett. 2001, 87, 096101-1-096101-4
8. Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond in Structural Chemistry and Biology. Oxford University Press: Oxford, UK, 1999.
9. Nishio, M. CH/π Hydrogen Bonds in Crystals CrystEngComm 2004, 6, 130-158
10. Kumar, S.; Subramanian, K.; Srinivasan, R.; Rajagopalan, K.; Schreurs, A. M. M.; Kroon, J.; Steiner, T. N -(p -Methoxyphenyl)- N -prop-2-ynyl-urea: A Crystal Structure with the Rare Z'=5, and Statistical Data on Z' Values J. Mol. Struct. 2000, 520, 131-139
11. Torrente, I. F; Franke, K. J.; Henningsen, N.; Schulze, G.; Alemani, M.; Roth, Ch.; Rurali, R.; Lorente, N.; Pascual, J. I. Spontanous Formation of Triptycene Supramolecules on Surfaces J. Phys. Chem. B 2006, 110, 20089-20092
12. Pivetta, M.; Blüm, M. C.; Patthey, F.; Schneider, W. D. Two-Dimensional Tiling by Rubrene Molecules Self-Assembled in Supramolecular Pentagons, Hexagons, and Heptagons on a Au(111) Surface Angew. Chem., Int. Ed. 2008, 47, 1076-1079
13. Sykes, E. C. H.; Mantooth, B. A.; Han, P.; Donhauser, Z. J.; Weiss, P. S. Substrate-Mediated Intermolecular Interactions: A Quantitative Single Molecule Analysis J. Am. Chem. Soc. 2005, 126, 7255-7260
14. Dougherty, D. B.; Jin, W.; Cullen, W. G.; Reutt-Robey, J. E.; Robey, S. W. Variable Temperature Scanning Tunneling Microscopy of Pentacene Monolayer and Bilayer Phases on Ag(111) J. Phys. Chem. C 2008, 112, 20334-20339
15. Han, P.; Mantooth, B. A.; Skyes, E. C. H.; Donhauser, Z. J.; Weiss, P. S. Benzene on Au(111) at 4 K: Monolayer Growth and Tip-Induced Molecular Cascades J. Am. Chem. Soc. 2004, 126, 10787-10793
16. Perdew, J. P.; Burke, K.; Ernzerhof, M. Generalized Gradient Approximation Made Simple Phys. Rev. Lett. 1996, 77, 3865-3868
17. Dion, M.; Rydberg, H.; Schroder, E.; Langreth, D. C.; Lundqvist, B. I. Van der waals Density Functional for General Geometries Phys. Rev. Lett. 2004, 92, 246401-1-246401-4
18. Steiner, T. Cooperative C≡C-H⋯C≡C-H Interaction: Crystal Structure of dl -Prop-2-ynylglycine and Database Study of Terminal Alkynes J. Chem. Soc., Chem. Commun. 1995, 1, 95-96
19. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Intermolecular Interactions From a Natural Bond Orbital, Donor-Acceptor Viewpoint Chem. Rev. 1988, 88, 899-926
20. Cheng, Z. H.; Gao, L.; Deng, Z. T.; Jiang, N.; Liu, Q.; Shi, D. X.; Du, S. X.; Guo, H. M.; Gao, H. J. Adsorption Behavior of Iron Phthalocyanine on Au(111) Surface at Submonolayer Coverage J. Phys. Chem. C 2007, 111, 9240-9244
21. Ruffieux, P.; Palotás, K.; Gröning, O.; Wasserfallen, D.; Müllen, K.; Hofer, W. A.; Gröning, P.; Fasel, R. Site and Orientation-Selective Anchoring of a Prototypical Molecular Building Block J. Am. Chem. Soc. 2007, 129, 5007-5011
22. Chen, W.; Madhavan, V.; Jamneala, T.; Crommie, M. F. Scanning Tunneling Microscopy Observation of an Electronic Superlattice at the Surface of Clean Gold Phys. Rev. Lett. 1998, 80, 1469-1473
23. Haiss, W. Surface Stress of Clean and Adsorbate-Covered Solids Rep. Pro. Phys. 2001, 64, 591-648
24. Grimme, S. Semiempirical GGA-Type Density Functional Constructed with a Long-Range Dispersion Correction J. Comput. Chem. 2006, 27, 1787-1799
25. Dougherty, D. B.; Maksymovych, P.; Lee, J.; Yates, J. T. Local Spectroscopy of Image-Potential-Derived States: From Single Molecules to Monolayers of Benzene on Cu(111) Phys. Rev. Lett. 2006, 97, 236806-1-236806-4
26. Feng, M.; Zhao, J.; Petek, H. Atomlike, Hollow-Core-Bound Molecular Orbitals of C60 Science 2008, 320, 359-362
27. Horcas, I.; Fernandez, R.; Gomez-Rodriguez, J. M.; Colchero, J.; Gomez-Herrero, J.; Baro, A. M. WSXM: A Software for Scanning Probe Microscopy and a Tool for Nanotechnology Rev. Sci. Instrum. 2007, 78, 013705-1-013705-8
28. Giannozzi, P.; Baroni, P.; Bonini, N.; Calandra, M.; Car, R.; Cavazzoni, C.; Ceresoli, D.; Chiarotti, G. L.; Cococcioni, M.; Dabo, I. et al. Quantum Espresso: A Modular and Open-Source Software Project for Quantum Simulations of Materials J. Phys-Condens. Mater. 2009, 21, 395502-1-395502-19
29. Bengtsson, L. Dipole Correction for Surface Supercell Calculations Phys. Rev. B 1999, 59, 12301-12304
30. Kendall, R. A.; Apra, E.; Bernholdt, D. E.; Bylaska, E. J.; Dupuis, M.; Fann, G. I.; Harrison, R. J.; Ju, J. L.; Nichols, J. A.; Nieplocha, J. et al. High Performance Computational Chemistry: An Overview of NWChem a Distributed Parallel Application Comput. Phys. Commun. 2000, 128, 260-283