Self-assembled nanolayers of conjugated silane with π - π interlocking

ACS Nano

Volumn 4, Issue 7, 2010, Pages 3773-3780

  Jiang, Jinyue ^a   Lima, Ocelio V ^a   Pei, Yong ^b   Jiang, Zhang ^c   Chen, Ziguang ^a   Yu, Chichao ^a   Wang, Jin ^c   Zeng, Xiao Cheng ^b   Forsythe, Eric ^d   Tan, Li ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

^b UNIVERSITY OF NEBRASKA LINCOLN   (United States)

^c ARGONNE NATIONAL LABORATORY   (United States)

^d U S ARMY RESEARCH LABORATORY   (United States)

Author keywords

interlocking; conjugation; nanolayer; self assembly; silane

Indexed keywords

AMPHIPHILICS; BUILDING BLOCKES; CONJUGATION; ELECTRONIC MOLECULES; HYDROGEN BONDINGS; LINEAR POLYMER CHAINS; MOLECULAR DESIGN; NANO LAYERS; NONCOVALENT; ORGANIC ELECTRONICS; ORGANIC MOLECULES; ORGANIC TRANSISTOR; PLANAR STRUCTURE; SELF-ASSEMBLED; SURFACE NORMALS;

BONDING; HYDROGEN BONDS; MOLECULAR ELECTRONICS; POLYCONDENSATION; SELF ASSEMBLY;

MOLECULES;

EID: 77955537721     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn100273m     Document Type: Article

References (39)

1. Yan, Q.; Huang, B.; Yu, J.; Zheng, F.; Zang, J.; Wu, J.; Gu, B. L.; Liu, F.; Duan, W. Intrinsic Current-Voltage Characteristics of Graphene Nanoribbon Transistors and Effect of Edge Doping Nano Lett. 2007, 7, 1469-1473
2. Gandhi, D. D.; Lane, M.; Zhou, Y.; Singh, A. P.; Nayak, S.; Tisch, U.; Eizenberg, M.; Ramanath, G. Annealing-Induced Interfacial Toughening Using a Molecular Nanolayer Nature 2007, 447, 299-302
3. Geim, A. K. Graphene: Status and Prospects Science 2009, 324, 1530-1534
4. Smits, E. C. P.; Mathijssen, S. G. J.; van Hal, P. A.; Setayesh, S.; Geuns, T. C. T.; Mutsaers, K. A. H. A.; Cantatore, E.; Wondergem, H. J.; Werzer, O.; Resel, R.; et al. Bottom-Up Organic Integrated Circuits Nature 2008, 455, 956-959
5. Yang, L.; Peng, H; Huang, K; Mague, J. T.; Li, H.; Lu, Y. Hierarchical Assembly of Organic/Inorganic Building Molecules with π - π Interactions Adv. Funct. Mater. 2008, 18, 1526-1535
6. Diegelmann, S. R.; Gorham, J. M.; Tovar, J. D. One-Dimensional Optoelectronic Nanostructures Derived from the Aqueous Self-Assembly of π-Conjugated Oligopeptides J. Am. Chem. Soc. 2008, 130, 13840-13841
7. Calhoun, M. F.; Sanchez, J.; Olaya, D.; Gershenson, M. E.; Podzorov, V. Electronic Functionalization of the Surface of Organic Semiconductors with Self-Assembled Monolayers Nat. Mater. 2008, 7, 84-89
8. Feng, D. Q.; Wisbey, D.; Tai, Y.; Losovyj Ya, B.; Zharnikov, M.; Dowben, P. A. Abnormal Temperature Dependence of Photoemission Intensity Mediated by Thermally Driven Reorientation of a Monomolecular Film J. Phys. Chem. B 2006, 110, 1095-1098
9. Halik, M.; Klauk, H.; Zschieschang, U.; Schmid, G.; Dehm, C.; Schutz, M.; Maisch, S.; Effenberger, F.; Brunnbauer, M.; Stellacci, F. Low-Voltage Organic Transistors with an Amorphous Molecular Gate Dielectric Nature 2004, 431, 963-966 (Pubitemid 39434413)
10. Sayyad, M. H.; Saleem, M.; Karimov, K. S.; Yaseen, M.; Ali, M.; Cheong, K. Y.; Noor, A. F. M. Synthesis of Zn(II) 5,10,15,20-Tetrakis(4′- isopropylphenyl) Porphyrin and Its Use as a Thin Film Sensor Appl. Phys. A: Mater. Sci. Process. 2010, 98, 103-109
11. Nuzzo, R. G.; Allara, D. L. Adsorption of Bifunctional Organic Disulfides on Gold Surfaces J. Am. Chem. Soc. 1983, 105, 4481-4483
12. Xu, S.; Cruchon-Dupeyrat, S. J. N.; Garno, J. C.; Liu, G. Y.; Jennings, G. K.; Yong, T. H.; Laibinis, P. E. In Situ Studies of Thiol Self-Assembly on Gold From Solution Using Atomic Force Microscopy J. Chem. Phys. 1998, 108, 5002-5012
13. Yu, J. J.; Tan, Y. H.; Li, X.; Kuo, P. K.; Liu, G. Y. A Nanoengineering Approach to Regulate the Lateral Heterogeneity of Self-Assembled Monolayers J. Am. Chem. Soc. 2006, 128, 11574-11581
14. Xu, S.; Laibinis, P. E.; Liu, G. Y. Accelerating the Kinetics of Thiol Self-Assembly on Gold - A Spatial Confinement Effect J. Am. Chem. Soc. 1998, 120, 9356-9361
15. Dhirani, A. A.; Zehner, R. W.; Hsung, R. P.; GuyotSionnest, P.; Sita, L. R. Self-Assembly of Conjugated Molecular Rods: A High-Resolution STM Study J. Am. Chem. Soc. 1996, 118, 3319-3320
16. Maya, F.; Flatt, A. K.; Stewart, M. P.; Shen, D. E.; Tour, J. M. Formation and Analysis of Self-Assembled Monolayers from U-Shaped Oligo(phenylene ethynylene)S as Candidates for Molecular Electronics Chem. Mater. 2004, 16, 2987-2997
17. Sabatani, E.; Cohenboulakia, J.; Bruening, M.; Rubinstein, I. Thioaromatic Monolayers On Gold - A New Family of Self-Assembling Monolayers Langmuir 1993, 9, 2974-2981
18. Ulman, A. Self-Assembled Monolayers of 4-Mercaptobiphenyls Acc. Chem. Res. 2001, 34, 855-863
19. Maoz, R.; Matlis, S.; DiMasi, E.; Ocko, B. M.; Sagiv, J. Self-Replicating Amphiphilic Monolayers Nature 1996, 384, 150-153
20. Tillman, N.; Ulman, A.; Elman, J. F. A Novel Self-Assembled Monolayer Film Containing a Sulfone-Substituted Aromatic Group Langmuir 1990, 6, 1512-1518
21. Ulman, A. Formation and Structure of Self-Assembled Monolayers Chem. Rev. 1996, 96, 1533-1554
22. Zang, L.; Che, Y. K.; Moore, J. S. One-Dimensional Self-Assembly of Planar π-Conjugated Molecules: Adaptable Building Blocks for Organic Nanodevices Acc. Chem. Res. 2008, 41, 1596-1608
23. Cui, H.; Muraoka, T.; Cheetham, A. G.; Stupp, S. I. Self-Assembly of Giant Peptide Nanobelts Nano Lett. 2009, 9, 945-951
24. Zubarev, E. R.; Pralle, M. U.; Sone, E. D.; Stupp, S. I. Self-assembly of Dendron Rodcoil Molecules into Nanoribbons J. Am. Chem. Soc. 2001, 123, 4105-4106
25. Shimojima, A.; Sugahara, Y.; Kuroda, K. Inorganic - Organic Layered Materials Derived via the Hydrolysis and Polycondensation of Trialkoxy(Alkyl)Silanes Bull. Chem. Soc. Jpn. 1997, 70, 2847-2853
26. Huo, Q. S.; Margolese, D. I.; Stucky, G. D. Surfactant Control of Phases in the Synthesis of Mesoporous Silica-Based Materials Chem. Mater. 1996, 8, 1147-1160
27. Parikh, A. N.; Schivley, M. A.; Koo, E.; Seshadri, K.; Aurentz, D.; Mueller, K.; Allara, D. L. N -Alkylsiloxanes: from Single Monolayers to Layered Crystals. The Formation of Crystalline Polymers from The Hydrolysis of N -Octadecyltrichlorosilane J. Am. Chem. Soc. 1997, 119, 3135-3143
28. Jiang, J.; Lima, O. V.; Pei, Y.; Zeng, X. C.; Tan, L.; Forsythe, E. Dipole-Induced, Thermally Stable Lamellar Structure by Polar Aromatic Silane J. Am. Chem. Soc. 2009, 131, 900-901
29. Dautel, O. J.; Robitzer, M.; Lere-Porte, J. P.; Serein-Spirau, F.; Moreau, J. J. E. Self-Organized Ureido Substituted Diacetylenic Organogel. Photopolymerization of One-Dimensional Supramolecular Assemblies To Give Conjugated Nanofibers J. Am. Chem. Soc. 2006, 128, 16213-16223
30. Luo, Y.; Lin, J.; Duan, H.; Zhang, J.; Lin, C. Self-Directed Assembly of Photoactive Perylenediimide-Bridged Silsesquioxane into a Superlong Tubular Structure Chem. Mater. 2005, 17, 2234-2236
31. van der Boom, M. E.; Evmenenko, G.; Yu, C.; Dutta, P.; Marks, T. J. Interrupted-Growth Studies of the Self-Assembly of Intrinsically Acentric Siloxane-Derived Monolayers Langmuir 2003, 19, 10531-10537
32. Onclin, S.; Ravoo, B. J.; Reinhoudt, D. N. Engineering Silicon Oxide Surfaces Using Self-Assembled Monolayers Angew. Chem., Int. Ed. 2005, 44, 6282-6304
33. Schwartz, D. K.; Steinberg, S.; Israelachvili, J.; Zasadzinski, J. A. N. Growth of a Self-Assembled Monolayer by Fractal Aggregation Phys. Rev. Lett. 1992, 69, 3354-3357
34. Kakudo, M.; Kasai, P. N.; Watase, T. Crystal Structure of Silanols and Their Infrared Spectra J. Chem. Phys. 1953, 21, 1894-1895
35. Zheng, H..; Smith, R. K.; Jun, Y.-w.; Kisielowski, C.; Dahmen, U.; Alivisatos, A. P. Observation of Single Colloidal Platinum Nanocrystal Growth Trajectories Science. 2009, 324, 1309-1312
36. Zhou, Q.; Zhang, J.; Ren, Z.; Yan, S.; Xie, P.; Zhang, R. A Stable and High-Efficiency Blue-Light Emitting Terphenyl-Bridged Ladder Polysiloxane Macromol. Rapid Commun. 2008, 29, 1259-1263
37. Karatsu, T.; Arai, T.; Sakuragi, H.; Tokumaru, K.; Wirz, J. Semiempirical Calculation of the Triplet - Triplet Absorption Spectra of 2-Anthrylethylenes Undergoing Photochemical One-Way Isomerization Bull. Chem. Soc. Jpn. 1994, 67, 891-894
38. Aathimanikandan, S. V.; Sandanaraj, B. S.; Arges, C. G.; Bardeen, C. J.; Thayumanavan, S. Effect of Guest Molecule Flexibility in Access to Dendritic Interiors Org. Lett. 2005, 7, 2809-2812
39. 2): A Potent Hydrosilylation Catalyst Org. Lett. 2002, 4, 2117-2119