Single-walled carbon nanotubes under the influence of dynamic coordination and supramolecular chemistry

Small

Volumn 1, Issue 4, 2005, Pages 452-461

  Chichak, Kelly S ^a   Star, Alexander ^b   Virginia, M ^c   Altoe P ^b   Stoddart, J Fraser ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b Nanomix Inc   (United States)

^c NONE

Author keywords

Carbon nanotubes; Coordination chemistry; Devices; Self assembly; Separation science

Indexed keywords

FIELD EFFECT TRANSISTORS; LIGHT ABSORPTION; PORPHYRINS; SELF ASSEMBLY; SOLUTIONS; TRANSMISSION ELECTRON MICROSCOPY;

COORDINATION CHEMISTRY; CYCLIC COMPLEXES; DEVICES; SEPARATION SCIENCE;

CARBON NANOTUBES;

CARBON NANOTUBE; NANOTUBE;

ABSORPTION; ADSORPTION; ARTICLE; ATOMIC FORCE MICROSCOPY; CHEMISTRY; CONFORMATION; ELECTROCHEMISTRY; INSTRUMENTATION; METHODOLOGY; NANOTECHNOLOGY; SEMICONDUCTOR; SPECTROPHOTOMETRY; TRANSMISSION ELECTRON MICROSCOPY;

ABSORPTION; ADSORPTION; CHEMISTRY, ANALYTICAL; ELECTROCHEMISTRY; MICROSCOPY, ATOMIC FORCE; MICROSCOPY, ELECTRON, TRANSMISSION; MOLECULAR CONFORMATION; NANOTECHNOLOGY; NANOTUBES; NANOTUBES, CARBON; SPECTROPHOTOMETRY; TRANSISTORS;

EID: 22144442558     PISSN: 16136810     EISSN: 16136829     Source Type: Journal    
DOI: 10.1002/smll.200400070     Document Type: Article

References (98)

1. S. lijima, T. Ichihashi, Nature 1993, 363, 603-605.
2. a) M. S. Dresselhaus, G. Dresselhaus, P. C. Eklund, Science of Fullerenes and Carbon Nanotubes, Academic Press, New York, 1996;
3. b) M. S. Dresselhaus, G. Dresselhaus, P. Avouris, Carbon Nanotube Synthesis, Structure, Properties, and Applications, Springer, Berlin, 2001.
4. a) P. M. Ajayan, Chem. Rev. 1999, 99, 1787-1799;
5. b) P. M. Ajayan, O. Z. Zhou, Top. Appl. Phys. 2001, 80, 391-425;
6. c) Hirsch, Angew. Chem. 2002, 114, 1933-1939;
7. Angew. Chem. Int. Ed. 2002, 41, 1853-1859;
8. d) H. Dai, Acc. Chem. Res. 2002, 35, 1035-1044
9. e) S. Niyogi, M. A. Hamon, H. Hu, J. Zhao, P. Bhowmik, R. Sen, M. E. Itkis, R. C. Haddon, Ace. Chem. Res. 2002, 35, 1105-1113;
10. f) S. Banerjee, M. G. C. Kahn, S.S. Wong, Chem. Eur. J. 2003, 9, 1898-1908;
11. g) C. A. Dyke, J. M. Tour, Chem. Eur. J. 2004, 10, 812-817.
12. a) S. J. Tans, M. H. Devoret, H. Dai, A. Thess, R. E. Smalley, L. J. Geerligs, C. Dekker, Nature 1997, 386, 474-477;
13. b) S. J. Tars, A. R. M. Verschnesen, C. Dekker, Nature 1998, 393, 49-52;
14. c) S. J. Tans, C. Dekker, Nature 2000, 404, 834-835;
15. d) S. G. Louie, Top. Appl. Phys. 2001, 80, 113-145;
16. e) B. I. Yakobscn, P. Avouris, Top. Appl. Phys. 2001, 80, 287-327;
17. f) M. Ouyar g, J.-L Huang, C.M. Lieber, Acc. Chem. Res. 2002, 35, 1018-1025.
18. a) D. Chattopadhyay, I. Galeska, F. Papadimitrakopoulos, J. Aπ. Chem. Soc. 2003, 125, 3370-3375;
19. b) R. Krupke, F. Hennrich, H. van Löhneysen, M. M. Kappes, Science 2003, 301, 344-347;
20. c) Z. Chen, X. Du, M.-H. Du, C. D. Rancken, H.-P. Cheng, A. G. Rinzler, Nano Lett. 2003, 3, 1245-1249;
21. d) D. A. Heller, R. M. Mayrhofer, S. Baik, Y.V. Grinkova, M. L. Usrey, M.S. Strano, J. Am. Chem. Soc. 2004, 126, 14567-14573;
22. e) S. Baik, M. Usrey, L. Rotkina, M. Strano, J. Phys. Chem. B 2004, 108, 15560-15564.
23. J. Liu, A. G. Rinzler, H. Dai, J. H. Hafner, R. K. Bradley, P. J. Boul, A. Lu, T. Iverson, K. Shelimov, C. B. Huffman, F. Rodriguez-Macias, Y.-S. Shon, T. R. Lee, D. T. Colbert, R. E. Smalley, Science 1998, 280, 1253-1256.
24. a) J. Chen, M. A. Hamon, H. Hu, Y. Chen, A. M. Rao, P. C. Eklund, R. C. Haddon, Science 1998, 282, 95-98;
25. b) M. A. Hamon, J. Chen, H. Hu, Y. Chen, M. E. Itkis, A. M. Rao, P. C. Ecklund, R. C. Haddon, Adv. Mater. 1999, 11, 834-840;
26. c) P. J. Boul, J. Liu, E.T. Mickelson, C.B. Huffman, L. M. Ericson, I.W. Chiang, K. A. Smith, D.T. Colbert, R. H. Hauge, J. L. Margrave, R. E. Smalley, Chem. Phys. Lett. 1999, 310, 367-372;
27. d) J. E. Riggs, Z. Guo, D. L Carroll, Y.-P. Sun, J. Am. Chem. Soc. 2000, 122, 5879-5880;
28. e) J. L. Bahr, J. M. Tour, Chem. Mater. 2001, 13, 3823-3824;
29. f) Y.-P. Sun, K. Fu, Y. Lin, W. Huang, Acc. Chem. Res. 2002. 35, 1096-1104;
30. g) C. Dyke, J. M. Tour, J. Am. Chem. Soc. 2003. 125, 1156-1157;
31. h) M. Holzinger, J. Abraham, P. Whelan, R. Graupner, L. Ley, F. Hennrich, M. Kappes, A. Hirsch, J. Am. Chem. Soc. 2003, 125, 8566-8580;
32. D. Tasis, N. Tagmatarchis, V. Georgakilas, M. Prato, Chem. Eur. J. 2003, 9, 4000-4008;
33. j) Y. Zhang, J. Li, Y. Shen, M. Wang, J. Li, J. Phys. Chem. B 2004, 108, 15 343 -15 346;
34. k) C. A. Dyke, J. M. Tour, Chem. Eur. J. 2004, 10, 812-817;
35. I) R. Blake, Y. K. Gun'ko, J. Coleman, M. Cadek, A. Fonseca, J.B. Nagy, W. J. Blau, J. Am. Chem. Soc. 2004, 126, 10226-10227.
36. a) M.J. O'Connell, S. M. Bachilo, C.B. Huffman, V. C. Moore, M. S. Strano, E. H. Haroz, K. L. Rialou, P. J. Boul, W. H. Noon, C. Kittrell, J. Ma, R. H. Hauge, R. B. Weisman, R. E. Smalley, Science 2002. 297, 593-596;
37. b) Y. Kang, T. A. Taton, J. Am. Chem. Soc. 2003. 125, 5650-5651;
38. c) C. Richard, F. Balaroine, P. Schultz, T.W. Ebbesen, C. Mioskowski, Science 2003, 300, 775-778.
39. Polymers that have been used to prepare composites with SWNTs include polymethylmethacrylate. See: a) M. Yudasaka, M. Zhang, C. Jabs, S. lijima, Appl. Phys. A 2001, 71, 449-451;
40. b) C. Stephan, T. P. Nguyen, M. Lamy de la Chapelle, S. Lefrant, C. Journet, P. Bernier, Synth. Met. 2000, 108, 139-149. Polymers have been used in the spinning of fibers. See:
41. c) B. Vigolo, A. Penicaud, C. Coulon, C. Sauder, R. Pailler, C. Journet, P. Bernier, P. Poulin, Science 2000, 290, 1331-1334. For composite materials formed between nanotubes and poly(m-phenyl-enevinylene-co-2, 5-dioctyloxy-p-phenylenevinylene), see:
42. S.A. Curran, P. M. Ajayan, W. J. Blau, D. L. Carroll, J. N. Coleman, A. B. Dalton, A. P. Davey, A. Drury, B. McCarthy, S. Maier, A. Strevens, Adv. Mater. 1998, 10, 1091-1093;
43. e) J. N. Coleman, A.B. Dalton, S. Curran, A. Rubio, A. P. Davey, A. Drury, B. McCarthy, B. Lahr, P. M. Ajayan, S. Roth, R. C. Barklie, W. J. Blau, Adv. Mater. 2000, 12, 213-216. For an example of noncovalent engineering of the surfaces of SWNTs by rigid, functional conjugated polymers, see:
44. J. Chen, H. Liu, W. A. Weiner, M. D. Halls, D. H. Waldeck, G. C. Walker, J. Am. Chem. Soc. 2002, 124, 9034-9035.
45. For the noncovalent side-wall functionalization of SWNTs with poly(m-phenylenevinylene-co-2,5-dioctyloxy-p-phenylenevinylene), and its derivatives see: a) A. Star, J. F. Stoddart, D. Steuerman, M. Diehl, A Boukai, E.W. Wong, X. Yang, S.W. Chung, H. Choi, J. R. Heath, Angew. Chem. 2001, 223, 1771-1775;
46. Angew. Chem. Int. Ed. 2001, 40, 1721-1725;
47. b) D.W. Steuerman, A. Star, R. Narizzano, H. Choi, R. S. Ries, C. Nicolini, J. F. Stoddart, J. R. Heath, J. Phys. Chem. B 2002, 106, 3124-3130;
48. c) A. Star, Y. Liu, K. Grant, L. Ridvan, J. F. Stoddart, D.W. Steuerman, M. R. Diehl, A. Boukai, J. R. Heath, Macromolecules 2003, 36, 553-560. For a related investigation with a hyperbranched polymer, see:
49. A. Star, J. F. Stoddart, Macromolecules 2002, 35, 7516-7520.
50. For an example of reverse water-solubilization of SWNTs with synthetic polymers, see: M.J. O'Connell, P. Boul, L. M. Ericson, C. Huffman, Y. Wang, E. Haroz, C. Kuper, J. M. Tour, K. D. Ausman, R. E. Smalley, Chem. Phys. Lett. 2001, 342, 265-271.
51. a) G. R. Dieckmann, A. B. Dalton, P. A. Johnson, J. Razal, J. Chen, G. M. Giordano, E. Munzo, I. H. Musselman, R. H. Baughman, R. K. Draper, J. Am. Chem. Soc. 2003, 125, 1770-1777;
52. b) S. Wang, E. S. Humphreys, S.-Y. Chung, D. E. Delduco, S. R. Lustig, H. Wang, K. N. Parker, N.W. Rizzo, S. Subramoney, Y.-M. Chiang, A. Jagota, Nat. Mater. 2003, 2, 196-200;
53. c) M. Zheng, A. Jagota, E. D. Semke, B. A. Diner, R. S. McLean, S. R. Lustig, R. E. Richardson, N. G. Tassi, Nat. Mater. 2003, 2, 338-342;
54. d) M. Zheng, A. Jagota, M. S. Strano, P. Barone, S. G. Chou, B. A. Diner, M. S. Dresselhaus, R. S. McLean, G. B. Onoa, G. G. Samsonidze, E. D. Semke, M. Usrey, D. J. Wells, Science 2003, 302, 1545-1548;
55. e) M. S. Strano, M. Zheng, A. Jagota, G. B. Onoa, D. A. Heller, P.W. Barone, M. L. Usrey, Nano Lett. 2004, 4, 543-550;
56. f) V. Zorbas, A. Ortiz-Acevedo, A. B. Dalton, M. M. Yoshida, G. R. Dieckmann, R. K. Draper, R. H. Baughman, M. Jose-Yaca man, I. H. Musselman, J. Am. Chem. Soc. 2004, 126, 7222-7227.
57. a) A. Star, D.W. Steuerman, J. R. Heath, J. F. Stoddart, Angew. Chem. 2002, 114, 2618-2622;
58. Angew. Chem. Int. Ed. 2002, 41, 2508-2512;
59. b) O.-K. Kim, J. Je, J.W. Baldwin, S. Kooi, P. E. Pehrsson, L Buckley, J. Am. Chem. Soc. 2003, 125, 4426-4427.
60. R. Bandyopadhyaya, E. Nativ-Roth, O. Regev, R. Yerushalmi-Rozen, Nano Lett. 2002, 2, 25-28.
61. M. Numata, M. Asai, K. Kaneko, T. Hasegawa, N. Fujita, Y. Kitada, K. Sakurai, S. Shinkai, Chem. Lett. 2004, 33, 232-233.
62. 2 nanoparticles. See: J. Zhu, M. Yudasaka, M. Zhang, S. lijima, J. Phys. Chem. B 2004, 108, 11317-11320.
63. S. J. Rowan, S. J. Cantrill, G. R. L Cousins, J. K. M. Sanders, J. F. Stoddart, Angew. Chem. 2002, 224, 938-993;
64. Angew. Chem. Int. Ed. 2002, 41, 898-952.
65. See, for example: a) K. Tashiro, T. Aida, J.Y. Zheng, K. Kinbara, K. Saigo, S. Sakamoto, K. Yamaguchi, J. Am. Chem. Soc. 1999, 222, 9477-9478;
66. b) D. Sun, F. S. Tham, C. A. Reed, L. Chaker, P. D.W. Boyd, J. Am. Chem. Soc. 2002, 124, 6604-6612;
67. c) Y. Shoji, K. Tashiro, T. Aida, J. Am. Chem. Soc. 2004, 126, 6750-6751.
68. In view of the well-known ability (F. Diederich, M. Gómez- López, Chem. Soc. Rev. 1999, 28, 263-277)
69. 60 and other fullerenes in water (for an early publication, see: T. Anderson, K. Nilsson, M. Sundahl, G. Westman, O. Wennerström, J. Chem. Soc. Chem. Commun. 1992, 604-606),
70. we consider the use of higher homologues in the CD sense to solubilze SWNTs as a result the formation of [n]pseudoro-taxanes of the kind, SWNTcCD, particularly since there was already a report in the literature (J. Chen, M. J. Dyer, M.-F. Yu, J. Am. Chem. Soc. 2001, 223, 6201-6202) that both β- and γ-CDs can be employed in a grinding procedure to cut SWNTs (HiPco), while γ-CD will aid the production by sonication of an aqueous dispersion of SWNTs. The authors ruled out the possibility of [n]pseudorotaxane formation between the SWNTs and γ-CD on the basis that the inner cavity dimensions of this CD are far too small to allow it to thread onto even the small diameter SWNTs. More recently, however, it has been shown
71. (H. Dodziuk, A. Ejchart, W. Anczewski, H. Ueda, E. Krinichnaya, G. Dolgonos, W. Kutner, Chem. Commun. 2003, 986-987) that n-CD, which has 12 α1,4-linked D-glucopyranose residues and is therefore large enough to be able to thread onto SWNTs and does so in water, not only solubilizes the NTs but also permits some partial separations according to their diameters.
72. During the period that our research has been in progress, a report has appeared in the literature (J.-M. Nam, M. A. Ratner, X. Liu, C. A. Mirkin, J. Phys. Chem. B 2003, 107, 4705-4710) on the computational simulations of macrocyde-encircled SWNTs. Molecular mechanics calculations on SWNTs, encircled with metalloorganic macrocycles, have demonstrated that the encirclement process is energetically favorable for both zigzag and armchair SWNTs, with the former a more stabilized arrangement than the latter. The bottom line is that the large predicted energetic stabilization in an aqueous environment suggests that encirclement by metalloorganic macrocycles will promote the solubilities of SWNTs and may even facilitate the separation of SWNTs of different sizes and chiralities.
73. See, for example: a) H. Murakami, T. Nomura, N. Nakashima, Chem. Phys. Lett. 2003, 378, 481-485;
74. b) H. Li, B. Zhou, Y. Lin, L. Gu, W. Wang, K. A. S. Fernando, S. Kumar, L. F. Allard, Y.-P. Sun, J. Am. Chem. Soc. 2004, 226, 1014-1015;
75. c) During the time this paper has been in press, a communication has been published describing how zinc porphyrins can become involved in integrating SWNTs into donor-acceptor nanohybrids. See: D.M. Guldi, G. M. A. Rahman, N. Jux, N. Tagmatarchis, M. Prato, Angew. Chem. 2004, 116, 5642-5646;
76. Angew. Chem. Int. Ed. 2004, 43, 5526-5530.
77. a) M. Fujita, J. Yazaki, K. Ogura, J. Am. Chem. Soc. 1990, 112, 5645-5647;
78. b) M. Fujita, Acc. Chem. Res. 1999, 32, 53-61;
79. c) N. Takeda, K. Umemoto, K. Yamaguchi, M. Fujita, Nature 1999, 398, 794-796;
80. d) M. Fujita, K. Umemoto, M. Yoshizawa, N. Fujita, T. Kusukawa, K. Biradha, Chem. Commun. 2001, 509-518;
81. e) K. Kumazawa, K. Biradha, T. Kusukawa, T. Okano, M. Fujita, Angew. Chem. 2003, 115, 4039-4043;
82. Angew. Chem. Int. Ed. 2003, 42, 3909-3913.
83. a) S. J. Tans, R. M. Verschueren, C. Dekker, Nature 1998, 393, 49-52;
84. b) R. Martel, T. Schmidt, H. R. Shea, T. Hertel, P. Avouris, Appl. Phys. Lett. 1998, 73, 2447-2449;
85. c) A. Bachtold, P. Hadley, T. Nakanishi, C. Dekker, Science 2001, 294, 1317-1320;
86. d) M. Shim, A. Javey, N. W. S. Kam, H. Dai, J. Am. Chem. Soc. 2001, 123, 11 512-11 513;
87. e) P. Avouris, Acc. Chem. Res. 2002, 35, 1026-1034.
88. J.-C. P. Gabriel, Mater. Res. Soc. Symp. Proc. 2003, 776, Q12.7.1-Q12.7.7.
89. 2O (1:1) solutions that could be aided and abetted by the SWNTs. For some recent examples Zn(II) porphyrin self-aggregation see: a) A. Tsuda, T. Nakamura, S. Sakamoto, K. Yamauchi, A. Osika, Angew. Chem. 2002, 114, 2941-2945;
90. Angew. Chem. Int. Ed. 2002, 41, 2817-2821;
91. b) L. Carlucci, G. Ciani, D.M. Proserpio, F. Porta, Angew. Chem. 2003, 115, 331-336;
92. Angew. Chem. Int. Ed. 2003, 42, 317-322;
93. W. Kim, A. Javey, O. Vermesh, Q. Wang, Y. Li, H. Dai, Nano Lett. 2003, 3, 193-198.
94. In previous studies, some of us have observed the marked influence that cations can have on the extent of hysteresis in NTFET devices. See: a) K. Bradley, J. Cumings, A. Star, J.-C. P. Gabriel, G. Grüner, Nano Lett. 2003, 3, 639-641;
95. b) A Star, T.-R. Han, V. Joshi, J. R. Stetter, Electroanalysis 2004, 15, 108-112.
96. P. J. Stang, J. Fan, B. Olenyuk, Chem. Commun. 1997, 1453-1454.
97. H. L. Andersen, C. A. Hunter, M. N. Meah, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5780-5789.
98. S. Wimmer, P. Castan, F. Wimmer, N. P. Johnson, J. Chem. Soc. Dalton Trans. 1989, 403-412.