Noncovalent bicomponent self-assemblies on a silicon surface

ACS Nano

Volumn 6, Issue 8, 2012, Pages 6905-6911

  Baris, Bulent ^a   Jeannoutot, Judicaël ^a   Luzet, Vincent ^a   Palmino, Frank ^a   Rochefort, Alain ^b   Chérioux, Frédéric ^a  

^a UNIVERSITÉ DE FRANCHE COMTÉ   (France)

^b ÉCOLE POLYTECHNIQUE DE MONTRÉAL   (Canada)

Author keywords

bicomponent network; scanning probe microscopy; semiconductors; supramolecular self assembly; surface chemistry

Indexed keywords

MULTICOMPONENTS; NETWORKS ON SURFACES; NONCOVALENT; OPEN NETWORK; PERIODIC ARRAYS; SILICON SURFACES; SITE-SPECIFICITY; SUBSTRATE INTERACTION; SUPRAMOLECULAR FRAMEWORK; SUPRAMOLECULAR NETWORKS; SUPRAMOLECULAR SELF-ASSEMBLIES;

FUNCTIONAL MATERIALS; MOLECULES; PRECIOUS METALS; SCANNING PROBE MICROSCOPY; SEMICONDUCTOR MATERIALS; SUPRAMOLECULAR CHEMISTRY; SURFACE CHEMISTRY;

TWO DIMENSIONAL;

BIOPOLYMER; NANOMATERIAL; SILICON;

ADSORPTION; ARTICLE; CHEMISTRY; CONFORMATION; CRYSTALLIZATION; MACROMOLECULE; MATERIALS TESTING; METHODOLOGY; PARTICLE SIZE; SURFACE PROPERTY; ULTRASTRUCTURE;

ADSORPTION; BIOPOLYMERS; CRYSTALLIZATION; MACROMOLECULAR SUBSTANCES; MATERIALS TESTING; MOLECULAR CONFORMATION; NANOSTRUCTURES; PARTICLE SIZE; SILICON; SURFACE PROPERTIES;

EID: 84865612722     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn301827e     Document Type: Article

References (41)

1. Joachim, C.; Gimzewski, J.; Aviram, A. Electronics Using Hybrid-Molecular and Mono-Molecular Devices Nature 2000, 408, 541-548
2. Barth, J. V.; Constantini, G.; Kern, K. Engineering Atomic and Molecular Nanostructures at Surfaces Nature 2005, 437, 671-679
3. Bartels, L. Tailoring Molecular Layers at Metal Surfaces Nat. Chem. 2010, 2, 87-95
4. Canas-Ventura, M. E.; Aït-Mansour, K.; Ruffieux, P.; Rieger, R.; Müllen, K.; Brune, H.; Fasel, R. Complex Interplay and Hierarchy of Interactions in Two-Dimensional Supramolecular Assemblies ACS Nano 2011, 5, 457-469
5. Elemans, J. A. A. W.; Lei, S.; De Feyter, S. Molecular and Supramolecular Networks on Surfaces: From Two-Dimensional Crystal Engineering to Reactivity Angew. Chem., Int. Ed. 2009, 48, 7298-7333
6. Shi, Z.; Lin, N. Structural and Chemical Control in Assembly of Multicomponent Metal-Organic Coordination Networks on a Surface J. Am. Chem. Soc. 2010, 132, 10756-10761
7. 60/ Corannulene on Cu(110): A Surface-Supported Bistable Buckybowl-Buckyball Host-Guest System J. Am. Chem. Soc. 2008, 130, 4767-4771
8. Huang, Y. L.; Chen, W.; Wee, A. T. S. Molecular Trapping on Two-Dimensional Binary Supramolecular Networks J. Am. Chem. Soc. 2011, 133, 820-825
9. Calmettes, B.; Nagarajan, S.; Gourdon, A.; Abel, M.; Porte, L.; Coratger, R. Bicomponent Supramolecular Packing in Flexible Phthalocyanine Networks Angew. Chem., Int. Ed. 2008, 47, 6994-6998
10. Yoshimoto, S.; Honda, Y.; Ito, O.; Itaya, K. Supramolecular Pattern of Fullerene on 2D Bimolecular 'Chessboard' Consisting of Bottom-Up Assembly of Porphyrin and Phtalocyanine Molecules J. Am. Chem. Soc. 2008, 130, 1085-1092
11. Blunt, M. O.; Russell, J. C.; Gimenez-Lopez, M. C.; Taleb, N.; Lin, X.; Schröder, M.; Champness, N. R.; Beton, P. H. Guest-Induced Growth of a Surface-Based Supramolecular Bilayer Nat. Chem. 2011, 3, 74-78
12. Moriarty, P. J. Fullerene Adsorption on Semiconductor Surfaces Surf. Sci. Rep. 2010, 65, 175-227
13. Piot, L.; Silly, F.; Tortech, L.; Nicolas, Y.; Blanchard, P.; Roncali, J.; Fichou, D. Long-Range Alignments of Single Fullerenes by Site-Selective Inclusion into a Double-Cavity 2D Open Network J. Am. Chem. Soc. 2009, 131, 12864-12865
14. Theobald, J. A.; Oxtoby, N. S.; Champness, N. R.; Beton, P. H.; Dennis, T. J. S. Growth Induced Reordering of Fullerene Clusters Trapped in a Two-Dimensional Supramolecular Network Langmuir 2005, 21, 2038-2041
15. Theobald, J. A.; Oxtoby, N. S.; Philipps, M. A.; Champness, N. R.; Beton, P. H. Controlling Molecular Deposition and Layer Structure with Supramolecular Surface Assemblies Nature 2003, 424, 1029-1031
16. Macloed, J. M.; Ivasenko, O.; Fu, C.; Taerum, T.; Roseï, F.; Perepichka, D. Supramolecular Ordering in Oligothiophene-Fullerene Monolayers J. Am. Chem. Soc. 2009, 131, 16844-16850
17. Bonifazi, D.; Kiebele, A.; Stohr, M.; Cheng, F.; Jung, T.; Diederich, F.; Spillmann, H. Supramolecular Nanostructuring of Silver Surfaces via Self-Assembly of [60]Fullerene and Porphyrin Modules Adv. Funct. Mater. 2007, 17, 1051-1062
18. 60 on a Cyclothiophene Monolayer Template Adv. Mater. 2006, 18, 447-451
19. Stepanow, S.; Lingenfelder, M.; Dmitriev, A.; Spillmann, H.; Delvigne, E.; Lin, N.; Deng, X.; Cai, C.; Barth, J. V.; Kern, K. Steering Molecular Organization and Host-Guest Interactions Using Two-Dimensional Nanoporous Coordination Systems Nat. Mater. 2004, 3, 229-233
20. Ruben, M.; Payer, D.; Landa, A.; Comisso, A.; Gattinoni, C.; Lin, N.; Collin, J.-P.; Sauvage, J.-P.; De Vita, A.; Kern, K. 2D Supramolecular Assemblies of Benzene-1,3,5-triyl-tribenzoic Acid: Temperature-Induced Phase Transformations and Hierarchical Organization with Macrocyclic Molecules J. Am. Chem. Soc. 2006, 128, 15644-15651
21. Hossain, M. Z.; Kato, H. S.; Kawai, M. Self-Directed Chain Reaction by Small Ketones with the Dangling Bond Site on the Si(100)-(2 × 1)-H Surface: Acetophenone, a Unique Example J. Am. Chem. Soc. 2008, 130, 11518-11523
22. Lopinski, G. P.; Wayner, D. D. M.; Wolkow, R. A. Self-Directed Growth of Molecular Nanostructures on Silicon Nature 2000, 406, 48-51
23. Harikumar, K. R.; Leung, L.; McNab, I. R.; Polanyi, J.-C.; Lin, H. P.; Hofer, W. A. Cooperative Molecular Dynamics in Surface Reactions Nat. Chem. 2009, 1, 712-716
24. Hamers, R.; Coulter, S. K.; Ellison, M. D.; Hovis, J. S.; Padowitz, D. F.; Schwartz, M. P.; Greenlief, C. M.; Russell, J. N. Cycloaddition Chemistry of Organic Molecules with Semiconductor Surfaces Acc. Chem. Res. 2000, 33, 617-624
25. Sloan, P. A.; Palmer, R. E. Two-Electron Dissociation of Single Molecules by Atomic Manipulation at Room Temperature Nature 2005, 434, 367-371
26. Makoudi, Y.; Arab, M.; Palmino, F.; Duverger, E.; Ramseyer, C.; Picaud, F.; Cherioux, F. A Stable Room-Temperature Molecular Assembly of Zwitterionic Organic Dipole Guided by a Si(111)-7 × 7 Template Effect Angew. Chem., Int. Ed. 2007, 46, 9287-9290
27. Lyo, I.-W.; Kaxiras, E.; Avouris, Ph. Adsorption of Boron on Si(111)-Its Effect on Surface Electronic States and Reconstruction Phys. Rev. Lett. 1989, 62, 1261-1264
28. Makoudi, Y.; Palmino, F.; Duverger, E.; Arab, M.; Cherioux, F.; Ramseyer, C.; Therrien, B.; Tschan, M. J.-L.; Süss-Fink, G. Non-destructive Room-Temperature Adsorption of 2,4,6-Tri(2'-thienyl)-1,3,5-triazine on a Si-B Interface: High-Resolution STM Imaging and Molecular Modeling Phys. Rev. Lett. 2008, 100, 076405
29. Makoudi, Y.; Arab, M.; Palmino, F.; Duverger, E.; Cherioux, F. A Complete Supramolecular Self-Assembled Adlayer on a Silicon Surface at Room-Temperature J. Am. Chem. Soc. 2008, 130, 6670-6671
30. Baris, B.; Luzet, V.; Duverger, E.; Sonnet, Ph.; Palmino, F.; Cherioux, F. Robust and Open Tailored Supramolecular Networks Controlled by the Template Effect of a Silicon Surface Angew. Chem., Int. Ed. 2011, 50, 4094-4098
31. Grimme, S. Do Special Noncovalent π-π Stacking Interactions Really Exist? Angew. Chem., Int. Ed. 2008, 47, 3430-3434
32. Rochefort, A.; Wuest, J. D. Interaction of Substituted Aromatic Compounds with Graphene Langmuir 2009, 25, 210-215
33. Gagnon, E.; Rochefort, A.; Métivaud, V.; Wuest, J. D. Hexaphenylbenzenes as Potential Acetylene Sponges Org. Lett. 2010, 12, 380-383
34. Thompson, B. C.; Fréchet, J.-M. J. Polymer-Fullerene Composite Solar Cells Angew. Chem., Int. Ed. 2008, 47, 58-77
35. Lu, J.; Tao, Y.; D'iorio, M.; Li, Y.; Ding, J.; Day, M. Pure Deep Blue Light-Emitting Diodes from Alternating Fluorene/Carbazole Copolymers by Using Suitable Hole-Blocking Materials Macromolecules 2004, 37, 2442-2449
36. Cherioux, F.; Guyard, L.; Audebert, P. Synthesis and Electrochemical Properties of New Star-Shaped Thiophene Oligomers and Their Polymers Chem. Commun. 1998, 2225-2226
37. Cherioux, F.; Guyard, L. Synthesis, Molecular Computations and Electrochemical Properties of Original 1,3,5-Tris(oligothienyl)benzenes Derivatives: A New Generation of 2D or 3D Reticulating Agent Adv. Funct. Mater. 2001, 11, 305-309
38. 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
39. Janta-Polczynski, B. A.; Cerdá, J. I.; éthier-Majcher, G.; Piyakis, K.; Rochefort, A. Parallel STM Imaging of Low Dimensional Nanostructures J. Appl. Phys. 2008, 104, 023702
40. Valieva, M.; Bylaskaa, E. J.; Govinda, N.; Kowalskia, K.; Straatsmaa, T. P.; Van Dama, H. J. J.; Wanga, D.; Nieplochaa, J.; Aprab, E.; Windusc, T. L. et al. NWChem: A Comprehensive and Scalable Open-Source Solution for Large Scale Molecular Simulations Comput. Phys. Commun. 2010, 181, 1477-1489
41. Grimme, S. Accurate Description of van der Waals Complexes by Density Functional Theory Including Empirical Corrections J. Comput. Chem. 2004, 25, 1463-1473