One-dimensional self-assembly of planar π-conjugated molecules: Adaptable building blocks for organic nanodevices

Accounts of Chemical Research

Volumn 41, Issue 12, 2008, Pages 1596-1608

  Zang, Ling ^a,c   Che, Yanke ^a,c   Moore, Jeffrey S ^b  

^a SOUTHERN ILLINOIS UNIVERSITY   (United States)

^b UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^c UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 58149089172     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar800030w     Document Type: Article

References (32)

1. Hu, J.; Odom, T. W.; Lieber, C. M. Chemistry and physics in one dimension: Synthesis and properties of nanowires and nanotubes. Acc. Chem. Res. 1999, 32, 435-445.
2. Xia, Y.; Yang, P.; Sun, Y.; Wu, Y.; Mayers, B.; Gates, B.; Yin, Y.; Kim, F.; Yan, H. One-dimensional nanostructures: Synthesis, characterization, and applications. Adv. Mater. 2003, 15, 353-389.
3. Wu, J.; Pisula, W.; Muellen, K. Graphenes as potential material for electronics. Chem. Rev. 2007, 107, 718-747.
4. Schenning, A. P. H. J.; Meijer, E. W. Supramolecular electronics; nanowires from self-assembled p-conjugated systems. Chem. Commun. 2005, 3245-3258.
5. Nguyen, T.-Q.; Martel, R.; Avouris, P.; Bushey, M. L.; Brus, L.; Nuckolls, C. Molecular interactions in one-dimensional organic nanostructures. J. Am. Chem. Soc. 2004, 126, 5234-5242.
6. Wang, Z.; Medforth, C. J.; Shelnutt, J. A. Porphyrin nanotubes by ionic selfassembly. J. Am. Chem. Soc. 2004, 126, 15954-15955.
7. Shirakawa, M.; Fujita, N.; Shinkai, S. A stable single piece of unimolecularly pi-stacked porphyrin aggregate in a thixotropic low molecular weight gel: A one-dimensional molecular template for polydiacetylene wiring up to several tens of micrometers in length. J. Am. Chem. Soc. 2005, 127, 4164-4165.
8. Hill, J. P.; Jin, W.; Kosaka, A.; Fukushima, T.; Ichihara, H.; Shimomura, T.; Ito, K.; Hashizume, T.; Ishii, N.; Aida, T. Self-assembled hexa-peri-hexabenzocoronene graphitic nanotube. Science 2004, 304, 1481-1483.
9. Kato, T. Self-assembly of phase-segregates liquid crystal structures. Science 2002, 295, 2414-2418.
10. van Hameren, R.; Schoen, P.; van Buul, A. M.; Hoogboom, J.; Lazarenko, S. V.; Gerritsen, J. W.; Engelkamp, H.; Christianen, P. C. M.; Heus, H. A.; Maan, J. C.; Rasing, T.; Speller, S.; Rowan, A. E.; Elemans, J. A. A. W.; Nolte, R. J. M. Macroscopic hierarchical surface patterning of porphyrin trimers via self-assembly and dewetting. Science 2006, 314, 1433-1436.
11. Zhao, Y. S.; Fu, H.; Hu, F.; Peng, A. D.; Yao, J. Multicolor emission from ordered assemblies of organic 1D nanomaterials. Adv. Mater. 2007, 19, 3554-3558.
12. Xu, B. Q.; Xiao, X.; Yang, X.; Zang, L.; Tao, N. J. Large gate modulation in the current of a room temperature single molecule transistor. J. Am. Chem. Soc. 2005, 127, 2386-2387.
13. Li, X.; Xu, B. Q.; Xiao, X.; Yang, X.; Zang, L.; Tao, N. J. Controlling charge transport in single molecules using electrochemical gate. Faraday Discuss. 2006, 131, 111-120.
14. Newman, C. R.; Frisbie, C. D.; da Silva Filho, D. A.; Bredas, J.-L.; Ewbank, P. C.; Mann, K. R. Introduction to organic thin film transistors and design of n-channel organic semiconductors. Chem. Mater. 2004, 16, 4436-4451.
15. Zang, L.; Liu, R.; Holman, M. W.; Nguyen, K. T.; Adams, D. M. A single-molecule probe based on intramolecular electron transfer. J. Am. Chem. Soc. 2002, 124, 10640-10641.
16. Wurthner, F. Perylene bisimide dyes as versatile building blocks for functional supramolecular architectures. Chem. Commun. 2004, 1564-79.
17. Zhao, D.; Moore, J. S. Shape-persistent arylene ethynylene macrocycles: Syntheses and supramolecular chemistry. Chem. Commun. 2003, 807-818.
18. Moore, J. S. Shape-persistent molecular architectures of nanoscale dimension. Acc. Chem. Res. 1997, 30, 402-413.
19. Langhals, H. Cyclic carboxylic imide structures as structure elements of high stability. novel developments in perylene dye chemistry. Heterocycles 1995, 40, 477-500.
20. Balakrishnan, K.; Datar, A.; Naddo, T.; Huang, J.; Oitker, R.; Yen, M.; Zhao, J.; Zang, L. Effect of side-chain substituents on self-assembly of perylene diimide molecules: Morphology control. J. Am. Chem. Soc. 2006, 128, 7390-7398.
21. Zhang, W.; Moore, J. S. Shape-persistent macrocycles: Structures and synthetic approaches from arylene and ethynylene building blocks (a review). Angew. Chem., Int. Ed. 2006, 45, 4416-4439.
22. Balakrishnan, K.; Datar, A.; Zhang, W.; Yang, X.; Naddo, T.; Huang, J.; Zuo, J.; Yen, M.; Moore, J. S.; Zang, L. Nanofibril self-assembly of an arylene ethynylene macrocycle. J. Am. Chem. Soc. 2006, 128, 6576-6577.
23. Balakrishnan, K.; Datar, A.; Oitker, R.; Chen, H.; Zuo, J.; Zang, L. Nanobelt selfassembly from an organic n-type semiconductor: Propoxyethyl-PTCDI. J. Am. Chem. Soc. 2005, 127, 10496-10497.
24. Datar, A.; Oitker, R.; Zang, L. Surface-assisted one-dimensional self-assembly of a perylene based semiconductor molecule. Chem. Commun. 2006, 1649-1651.
25. Datar, A.; Balakrishnan, K.; Yang, X. M.; Zuo, X.; Huang, J. L.; Yen, M.; Zhao, J.; Tiede, D. M.; Zang, L. Linearly polarized emission of an organic semiconductor nanobelt. J. Phys. Chem. B 2006, 110, 12327-12332.
26. Che, Y.; Datar, A. X. Y.; Naddo, T.; Zhao, J.; Zang, L. Enhancing one-dimensional charge transport through cofacial π-electronic delocalization: Conductivity improvement for organic nanobelts. J. Am. Chem. Soc. 2007, 129, 6354-6355.
27. Che, Y.; Datar, A.; Balakrishnan, K.; Zang, L. Ultralong nanobelts self-assembled from an asymmetric perylene tetracarboxylic diimide. J. Am. Chem. Soc. 2007, 129, 7234-7235.
28. Che, Y.; Yang, X.; Loser, S.; Zang, L. Expedient Vapor Sensing of Organic Amines Using Fluorescent Nanofibers Fabricated from an n-Type Organic Semiconductor. Nano Lett. 2008, in press.
29. Naddo, T.; Che, Y.; Zhang, W.; Balakrishnan, K. X. Y.; Yen, M.; Zhao, J.; Moore, J. S.; Zang, L. Sensitive Detection of Explosives with a Fluorescent Nanofibril Film. J. Am. Chem. Soc. 2007, 129, 6978-6979.
30. Briseno, A. L.; Mannsfeld, S. C. B.; Lu, X.; Xiong, Y.; Jenekhe, S. A.; Bao, Z.; Xia, Y. Fabrication of Field-Effect Transistors from Hexathiapentacene Single-Crystal Nanowires. Nano Lett. 2007, 7, 668-675.
31. Ahrens, M. J.; Sinks, L. E.; Rybtchinski, B.; Liu, W.; Jones, B. A.; Giaimo, J. M.; Gusev, A. V.; Goshe, A. J.; Tiede, D. M.; Wasielewski, M. R. Self-Assembly of Supramolecular Light-Harvesting Arrays from Covalent Multi-Chromophore Perylene-3,4:9,10-bis(dicarboximide) Building Blocks. J. Am. Chem. Soc. 2004, 126, 8284-8294.
32. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision C.02, Gaussian, Inc.: Wallingford CT, 2004.