Molecular Interactions in One-Dimensional Organic Nanostructures

Journal of the American Chemical Society

Volumn 126, Issue 16, 2004, Pages 5234-5242

  Nguyen, Thuc Quyen ^a   Martel, Richard ^b,c   Avouris, Phaedon ^b   Bushey, Mark L ^a   Brus, Louis ^a   Nuckolls, Colin ^a  

^a Columbia University ^*  (United States)

^b IBM T J WATSON RESEARCH CENTER   (United States)

^c UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMIC FORCE MICROSCOPY; FLUORESCENCE; HYDROGEN BONDS; MOLECULAR DYNAMICS; ORGANIC COMPOUNDS; SCANNING ELECTRON MICROSCOPY;

INTERMOLECULAR INTERACTIONS; MOLECULAR NANOSTRUCTURES;

NANOSTRUCTURED MATERIALS;

AROMATIC COMPOUND; ORGANIC COMPOUND; SOLVENT;

ARTICLE; ATOMIC FORCE MICROSCOPY; CHEMICAL STRUCTURE; FLUORESCENCE; HYDROGEN BOND; MEASUREMENT; MOLECULAR INTERACTION; MOLECULAR SIZE; MOLECULE; SCANNING ELECTRON MICROSCOPY; STEADY STATE; STRUCTURE ANALYSIS; SURFACE PROPERTY; TIME;

EID: 1942521166     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja031600b     Document Type: Article

References (51)

1. For leading references on discotic liquid crystals, see: (a) Destrade, C.; Foucher, P.; Gasparoux, H.; Nguyen, H. T.; Levelut, A. M.; Malthete, J. Mol. Cryst. Liq. Cryst. 1984, 106, 121-146.
2. (b) Chandrasekbar, S.; Ranganath, G. S. Rep. Prog. in Phys. 1990, 53, 57-84.
3. (c) Chandrasekhar, S.; Prasad, S. K. Contemporary Phys. 1999, 40, 237-245.
4. (d) Chandrasekhar, S. Handbook Liq. Cryst. 1998, 2B, 749-780.
5. (e) Guillon, D. Struct. Bonding (Berlin) 1999, 95, 41-82.
6. In bulk, several columnar π-stacks have shown potential as one-dimensional electronic materials, see: (a) Boden, N.; Movaghar, B. Handbook Liq. Cryst. 1998, 2B, 781-798.
7. (b) Boden, N.; Bushby, R. J.; Clements, J.; Movaghar, B. J. Mater. Chem. 1999, 9, 2081-2086.
8. (c) van de Craats, A. M.; Stutzmann, N.; Bunk, O.; Nielsen, M. M.; Watson, M.; Mullen, K.; Chanzy, H. D.; Sirringhaus, H.; Friend, R. H. Adv. Mater. 2003, 15, 495-499.
9. (d) Schmidt-Mende, L.; Fechtenkotter, A.; Mullen, K.; Moons, E.; Friend, R. H.; MacKenzie, J. D. Science 2001, 293, 1119-1122.
10. (e) Percec, V.; Glodde, M.; Bera, T. K.; Miura, Y.; Shiyanovskaya, I.; Singer, K. D.; Balagurusamy, V. S. K.; Heiney, P. A.; Schnell, I.; Rapp, A.; Spiess, H. W.; Hudson, S. D.; Duan, H. Nature 2002, 419, 384-387.
11. Gearba, R. I.; Lehmann, M.; Levin, J.; Ivanov, D. A.; Koch, M. H. J.; Barbera, J.; Debije, M. G.; Piris, J.; Geerts, Y. H. Adv. Mater. 2003, 15, 1614-1618.
12. (a) Nguyen, T.-Q.; Bushey, M. L.; Brus, L. E.; Nuckolls, C. J. Am. Chem. Soc. 2002, 124, 15051-15054.
13. (b) Tulevski, G. S.; Bushey, M. L.; Kosky, J. L.; Ruter, S. J. T.; Nuckolls, C. Angew. Chem., Int. Ed., in press.
14. van Gorp, J. J.; Vekemans, J. A. J. M.; Meijer, E. W. J. Am. Chem. Soc. 2002, 124, 14759-14769.
15. Johnkheijm, P.; Hoeben, F. J. M.; Kleppinger, R.; van Herrikhuyzen, J.; Schenning, A. P. H. J.; Meijer, E. W. J. Am. Chem. Soc. 2003, ASAP.
16. (a) Bushey, M. L.; Hwang, A.; Stephens, P. W.; Nuckolls, C. J. Am. Chem. Soc. 2001, 123, 8157-8158.
17. (b) Bushey, M. L.; Hwang, A.; Stephens, P. W.; Nuckolls, C. Angew. Chem., Int. Ed. 2002, 41, 2828-2831.
18. (c) Bushey, M. L.; Nguyen, T.-Q.; Nuckolls, C. J. Am. Chem. Soc. 2003, 125, 8264-8269.
19. For hydrogen bonds used to hold aromatic rings cofacially, see: (a) Matsunaga, Y.; Miyajima, N.; Nakayasu, Y.; Sakai, S.; Yonenaga, M. Bull. Chem. Soc. Jpn. 1988, 61, 207-210.
20. (b) Yasuda, Y.; Iishi, E.; Inada, H.; Shirota, Y. Chem. Lett. 1996, 575-576.
21. (c) Palmans, A. R. A.; Vekemans, J. A. J. M.; Fischer, H.; Hikmet, R. A. ; Meijer, E. W. Chem. Eur. J. 1997, 3, 300-307.
22. (d) Lightfoot, M. P.; Mair, F. S.; Pritchard, R. G.; Warren, J. E. Chem. Commun. 1999, 1945-1946.
23. (e) Brunsveld, L.; Zhang, H.; Glasbeek, M.; Vekemans, J. A. J. M.; Meijer, E. W. J. Am. Chem. Soc. 2000, 122, 6175-6182.
24. (f) Ranganathan, D.; Kurur, S.; Gilardi, R.; Karle, I. L. Biopolymers 2000, 54, 289-295.
25. (g) van Gorp, J. J.; Vekemans, J. A. J. M.; Meijer, E. W. Mol. Cryst. Liq. Cryst. 2003, 397, 491-505.
26. (h) Pucci, D.; Veber, M.; Malthete, J. Liq. Cryst. 1996, 21, 153-155.
27. (i) Ungar, G.; Abramic, D.; Percec, V.; Heck, J. A. Liq. Cryst. 1996, 21, 73-86.
28. (j) Malthete, J.; Levelut, A. M.; Liebert, L. Adv. Mater. 1992, 4, 37-41.
29. Rochefort, A.; Martel, R.; Avouris, P. Nano Lett. 2002, 2, 877-880.
30. (a) Martin, R. B. Chem. Rev. 1996, 96, 3043-3064.
31. (b) Wang, W.; Li, L.-S.; Helms, G.; Zhou, H.-H.; Li, A. D. Q. J. Am. Chem. Soc. 2003, 125, 1120-1121.
32. (c) Wang, W.; Han, J. J.; Wang, L.-Q.; Li, L.-S.; Shaw, W. J.; Li, A. D. Q. Nano Lett. 2003, 3, 455-458.
33. (a) Chattopadhyay, A.; Mukherjee, S.; Raghuraman, H. J. Phys. Chem. B 2002, 106, 13002-13009.
34. (b) Chattopadhyay, A.; Mukherjee, S. Langmuir 1999, 15, 2142-2148.
35. (c) Rawat, S. S.; Mukherjee, S.; Chattopadhyay, A. J. Phys. Chem. B 1997, 101, 1922-1929.
36. Similar to what was observed with for conjugated polymers, see: Nguyen, T.-Q.; Martini, I. B.; Liu, J.; Schwartz, B. J. J. Phys. Chem. B 2000, 104, 237-255.
37. Yau, S. T.; Petsev, D. N.; Thomas, B. R.; Vekilov, P. G. J. Mol. Biol. 2000, 303, 667-678.
38. Shirai, K.; Matsuoka, M.; Fukunishi, K. Dyes Pigm. 1999, 42, 95-101.
39. CRC Handbook of Chemistry and Physics, 76th ed; CRC Press: Boca Raton, FL, 1995-1996; pp 6-245 and 6-249.
40. (a) Sheu, E. Y.; Liang, K. S.; Chiang, L. Y. J. Phys. (Paris) 1989, 50, 1279-1295.
41. (b) Braitbart, O.; Sasson, R.; Weinreb, A. Mol. Cryst. Liq. Cryst. 1988, 159, 233-242.
42. (c) Markovitsi, D.; Germain, A.; Millie, P.; Lecuyer, P.; Gallos, L.; Argyrakis, P.; Bengs, H.; Ringsdorf, H. J. Phys. Chem. 1995, 99, 1005-1017.
43. (d) Phillips, K. E. S.; Katz, T. J.; Jockusch, S.; Lovinger, A. J.; Turro, N. J. J. Am. Chem. Soc. 2001, 123, 11899-11907.
44. (e) Nuckolls, C.; Katz, T. J.; Katz, G.; Collings, P. J.; Castellanos, L. J. Am. Chem. Soc. 1999, 121, 79-88.
45. (f) Nuckolls, C.; Katz, T. J. J. Am. Chem. Soc. 1998, 120, 9541-9544.
46. (g) Rohr, U.; Schilichting, P.; Bohm, A.; Gross, M.; Meerholz, K.; Brauchle, C.; Mullen, K. Angew. Chem., Int. Ed. 1998, 37, 1434-1437.
47. (h) Reference 10b,c.
48. Attard, P. Mol. Phys. 1996, 89, 691-709.
49. Galkin, O.; Vekilov, P. G. J. Am. Chem. Soc. 2000, 122, 156-163.
50. Lin, J.; Zhu, J.; Zhou, D. Eur. Polym. J. 1999, 36, 309-314.
51. Petsev, D. N.; Chen, K.; Gliko, O.; Vekilov, P. G. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 792-796.