Self-assembly and properties of low-dimensional nanomaterials based on π-conjugated organic molecules

Jing Lv; Huibiao Liu; Yuliang Li

doi:10.1351/pac200880030639

Publicly Available Published by De Gruyter January 1, 2009

Self-assembly and properties of low-dimensional nanomaterials based on π-conjugated organic molecules

Jing Lv , Huibiao Liu and Yuliang Li

From the journal Pure and Applied Chemistry

https://doi.org/10.1351/pac200880030639

Abstract

Building supramolecular architectures with well-defined shapes and functions is of great importance in materials science, nanochemistry, and biomimetic chemistry. In recent years, we have devoted much effort to the construction of well-defined supramolecular structures through noncovalent forces such as hydrogen bonding, π-stacking, metal-ligand bonds, and hydrophilic and hydrophobic interactions, with the aid of functional building blocks. The morphologies and their physical properties were studied, and new methods for the construction of one-dimensional nanoscale structures have been developed. In this review, we summarize our recent studies on the design and synthesis of the supramolecular systems, as well as the physical properties of nanoscale structures.

Keywords: low dimension; methods; properties; self-assembly; supramolecular architectures

Conference

International Symposium on Novel Aromatic Compounds (ISNA-12), International Symposium on Novel Aromatic Compounds, ISNA, Novel Aromatic Compounds, 12th, Awaji Island, Japan, 2007-07-22–2007-07-27

References

1. J. M. Lehn. Supramolecular Chemistry, Weinheim, Germany (1995).10.1002/3527607439Search in Google Scholar

2. doi:10.1126/science.277.5330.1225, M. Muthukumar, C. K. Ober, E. L. Thamas. Science 277, 1225 (1997).Search in Google Scholar

3. S. I. Stupp, M. U. Pralle, G. N. Tew, L. Li, M. Sayar, E. R. Zubarev. MRS Bull. 25, 42 (2000).10.1557/mrs2000.28Search in Google Scholar

4. doi:10.1126/science.1069197, D. N. Reinhoudt, M. Crego-Calama. Science 295, 2403 (2002).Search in Google Scholar

5. doi:10.1126/science.1962191, G. M. Whitesides, J. P. Mathias, C. P. Seto. Science 254, 1312 (1991).Search in Google Scholar

6. doi:10.1039/b304972h, J. A. A.W. Elemans, A. E. Rowan, R. J. M. Nolte. J. Mater. Chem. 13, 2661 (2003).Search in Google Scholar

7. doi:10.1021/ar970272f, K. T. Holman, A. M. Pivovar, J. A. Swift, M. D. Ward. Acc. Chem. Res. 34, 107 (2001).Search in Google Scholar

8. doi:10.1002/1521-4095(200103)13:6<371::AID-ADMA371>3.0.CO;2-K, D. J. Norris, Y. A. Vlasov. Adv. Mater. 13, 371 (2001).Search in Google Scholar

9. doi:10.1038/nature04166, J. V. Barth, G. Costantini, K. Kern. Nature 437, 671 (2005).Search in Google Scholar

10. doi:10.1021/jp054153q, M. Fialkowski, K. J. M. Bishop, R. Klajn, S. K. Smoukov, C. J. Campbell, B. A. Grzybowski. J. Phys. Chem. B 110, 2482 (2006).Search in Google Scholar

11. doi:10.1021/ja0111380, P. Samori, A. Fechtenkotter, F. Jackel, T. Bohme, K. Mullen, J. P. Rabe. J. Am. Chem. Soc. 123, 11462 (2001).Search in Google Scholar

12. doi:10.1021/la00024a003, S. Manne, J. P. Cleveland, H. E. Gaub, G. D. Stucky, P. K. Hansma. Langmuir 10, 4409 (1994).Search in Google Scholar

13. doi:10.1021/ar990144m, D. M. Guldi, M. Prato. Acc. Chem. Res. 33, 695 (2000).Search in Google Scholar

14. doi:10.1021/cr980017o, C. A. Reed, R. D. Bolskar. Chem. Rev. 100, 1075 (2000).Search in Google Scholar

15. doi:10.1021/ja002154k, H. Imahori, H. Norieda, H. Yamada, Y. Nishimura, I. Yamazaki, Y. Sakata, S. Fukuzumi. J. Am. Chem. Soc. 123, 100 (2001).Search in Google Scholar

16. doi:10.1021/ja0372098, N. D. McClenaghan, C. Absalon, D. M. Bassani. J. Am. Chem. Soc. 125, 13004 (2003).Search in Google Scholar

17. W. A. Fisher. Pigment Handbook, Vol. I: Properties and Economics, T. C. Patton (Ed.), p. 667, John Wiley, New York (1973).Search in Google Scholar

18. doi:10.1002/adma.19960080312, G. Hoprowitz, F. Kouki, P. Spearman, D. Fichou, C. Nogues, X. Pan, F. Garnier. Adv. Mater. 8, 242 (1996).Search in Google Scholar

19. doi:10.1039/a705910h, G. R. J. Muller, C. Meiners, V. Enkelmann, Y. Greerts, K. Mullen. J. Mater. Chem. 8, 61 (1998).Search in Google Scholar

20. doi:10.1021/cm9910613, M. Schneider, K. Mullen. Chem. Mater. 12, 352 (2000).Search in Google Scholar

21. doi:10.1021/ma010615w, M. Thelakkat, P. Posch, H. W. Schmidt. Macromolecules 34, 7441 (2001).Search in Google Scholar

22. doi:10.1039/b205478g, R. Dobrawa, F. Wurthner. Chem. Commun. 1878 (2002).Search in Google Scholar

23. doi:10.1021/jo011133l, F. Wurthner, A. Sautter, J. Schilling. J. Org. Chem. 67, 3037 (2002).Search in Google Scholar

24. doi:10.1002/anie.200352458, K. Sugiyasu, N. Fujita, S. Shinkai. Angew. Chem., Int. Ed. 43, 1229 (2004).Search in Google Scholar

25. J. C. Chambron, V. Heitz, J. P. Sauvage. The Porphyrin Handbook, Vol. 6, K. M. Kadish, K. M. Smith, R. Guilard (Eds.) p. 1, Academic Press, New York (2000).Search in Google Scholar

26. doi:10.1021/ja029548r, T. S. Balaban, R. Goddard, M. Linke-Schaetzel, J. M. Lehn. J. Am. Chem. Soc. 125, 4233 (2003).Search in Google Scholar

27. doi:10.1038/35104607, M. Gratzel. Nature 414, 338 (2001).Search in Google Scholar

28. doi:10.1002/anie.200351773, J. Duschl, M. Michl, W. Kunz. Angew. Chem., Int. Ed. 43, 634 (2004).Search in Google Scholar

29. doi:10.1021/cr9601324, S. Lehninger, B. Oleyunk, J. P. Stang, Chem. Rev. 100, 853 (2000).Search in Google Scholar

30. doi:10.1021/jo001564o, C. Mak, N. Bampos, S. L. Darling, M. Montali, L. Prodi, J. K. M. Sanders. J. Org. Chem. 66, 4476 (2001).Search in Google Scholar

31. doi:10.1039/b404267k, A. Klyszez, M. Lauer, M. Kopaczynska, C. Bottcher, F. Gonzaga, J. H. Fuhrhop. Chem. Commun. 2358 (2004).Search in Google Scholar

32. doi:10.1021/ol0165544, S. I. Tamaru, M. Nakamura, M. Takeuchi, S. Shinkai. Org. Lett. 3, 3631 (2001).Search in Google Scholar

33. doi:10.1126/science.1060835, J. M. Ribo, J. Crusats, F. Sagues, J. Claret, R. Rubires. Science 292, 2063 (2001).Search in Google Scholar

34. doi:10.1021/ja961234e, P. H. J. Schenning, F. B. G. Benneker, H. P. M. Geurts, X. Y. Liu, R. J. M. Nolte. J. Am. Chem. Soc. 118, 8549 (1996).Search in Google Scholar

35. doi:10.1038/nature01915, J. A. Theobald, N. S. Oxtoby, M. A. Phillips, N. R. Champness, P. H. Beton. Nature 424, 1029 (2003).Search in Google Scholar

36. doi:10.1021/ja020098c, T. Moriuchi, T. Tamura, T. Hirao. J. Am. Chem. Soc. 124, 9356 (2002).Search in Google Scholar

37. doi:10.1021/nl025821b, D. L. Keeling, N. S. Oxtoby, C. Wilson, M. J. Humphry, N. R. Champness, P. H. Beton. Nano. Lett. 3, 9 (2003).Search in Google Scholar

38. doi:10.1016/S0040-4020(00)00986-8, E. A. Archer, H. Gong, M. J. Krische. Tetrahedron 57, 1139 (2001).Search in Google Scholar

39. doi:10.1021/ja963572l, A. Credi, V. Balzani, S. J. Langford, J. F. Stoddart. J. Am. Chem. Soc. 119, 2679 (1997).Search in Google Scholar

40. doi:10.1021/ja000190d, F. Pina, M. J. Melo, M. Maestri, P. Passaniti, V. Balzani. J. Am. Chem. Soc. 122, 4496 (2000).Search in Google Scholar

41. doi:10.1039/a908951i, T. Gunnlaugsson, D. A. MacDonail, D. Parker. Chem. Commun. 93 (2000).Search in Google Scholar

42. doi:10.1002/adma.19970090704, H. Imahori, Y. Sakata. Adv. Mater. 9, 537 (1997).Search in Google Scholar

43. S. Fukuzumi, D. M. Guldi. In Electron Transfer in Chemistry, Vol. 2, V. Balzani (Ed.), pp. 270-326, Weinheim, Germany (2001).10.1002/9783527618248.ch19Search in Google Scholar

44. doi:10.1038/46972, C. C. Page, C. C. Moser, X. Chen, P. L. Dutton. Nature 402, 47 (1999).Search in Google Scholar

45. D. Gust, T. A. Moore, A. L. Moore. In Electron Transfer in Chemistry, Vol. 3, V. Balzani (Ed.), pp. 272-336, Weinheim, Germany (2001).10.1002/9783527618248.ch39Search in Google Scholar

46. doi:10.1002/chem.200305037, H. Li, Y. Li, J. Zhai, G. Cui, H. Liu, S. Xiao, Y. Liu, F. Lu, L. Jiang, D. Zhu. Chem.Eur. J. 9, 6031 (2003).Search in Google Scholar

47. doi:10.1021/ma0490045, F. Lu, S. Xiao, Y. Li, H. Liu, H. Li, J. Zhuang, Y. Liu, N. Wang, X. He, X. Li, L. Gan, D. Zhu. Macromolecules 37, 7444 (2004).Search in Google Scholar

48. doi:10.1039/b008005p, J. J. Gonzalez, S. Gonzalez, E. M. Priego, C. Luo, D. M Guldi, J. Mendoza, N. Martin. Chem. Commun. 163 (2001).Search in Google Scholar

49. doi:10.1039/b008006n, M. T. Rispens, L. Sanchez, J. Knol, J. C. Hummelen. Chem. Commun. 161 (2001).Search in Google Scholar

50. doi:10.1021/ol025614i, Z. Shi, Y. Li, H. Gan, M. Li, S. Xiao, H. Li, H. Liu, S. Xiao, D. Zhu. Org. Lett. 4, 1179 (2002).Search in Google Scholar

51. doi:10.1021/ol026386v, S. Xiao, Y. Li, H. Fang, H. Li, H. Liu, Z. Shi, L. Jiang, D. Zhu. Org. Lett. 4, 3063 (2002).Search in Google Scholar

52. doi:10.1021/ja0205784, C. Ego, D. Marsitzky, S. Becker, J. Zhang, A. C. Grimsdale, K. Mullen, J. D. Mackenzie, C. Silva, R. H. Friend. J. Am. Chem. Soc. 125, 437 (2003).Search in Google Scholar

53. doi:10.1039/b205478g, R. Dobrawa, F. Wurthner. Chem. Commun. 1878 (2002).Search in Google Scholar

54. doi:10.1002/1521-3765(20021004)8:19<4470::AID-CHEM4470>3.0.CO;2-F, E. Peeters, P. A. V. Hal, S. C. J. Meskers, R. A. J. Janssen, E. W. Meijer. Chem.Eur. J. 8, 4470 (2002).Search in Google Scholar

55. doi:10.1021/ar00028a010, D. Gust, T. A. Moore, A. L. Moore. Acc. Chem. Res. 26, 198 (1993).Search in Google Scholar

56. doi:10.1021/jp0373853, Y. Liu, S. Xiao, H. Li, Y. Li, H. Liu, F. Lu, J. Zhuang, D. Zhu. J. Phys. Chem. B 108, 6256 (2004).Search in Google Scholar

57. doi:10.1021/jp0372688, B. K. Kaletas, R. Dobrawa, A. Sautter, F. Wurthner, M. Zimine, L. De Cola, R. M. Williams. J. Phys. Chem. A 108, 1900 (2004).Search in Google Scholar

58. doi:10.1021/jo0486037, Y. Liu, Y. Li, L. Jiang, H. Gan, H. Liu, Y. Li, J. Zhuang, F. Lu, D. Zhu. J. Org. Chem. 69, 9049 (2004).Search in Google Scholar

59. doi:10.1002/cphc.200400165, Y. Liu, J. Zhuang, H. Liu, Y. Li, F. Lu, H. Gan, T. Jiu, N. Wang, X. He, D. Zhu. ChemPhysChem 5, 1210 (2004).Search in Google Scholar

60. doi:10.1021/ja053352k, H. Gan, H. Liu, Y. Li, Q. Zhao, Y. Li, S. Wang, T. Jiu, N. Wang, X. He, D. Yu, D. Zhu. J. Am. Chem. Soc. 127, 12452 (2005).Search in Google Scholar

61. doi:10.1021/nl035069u, M. Yun, N. V. Myung, R. P. Vasquez, C. Lee, E. Menke, R. M. Penner. Nano. Lett. 4, 419 (2004).Search in Google Scholar

62. doi:10.1021/nl010081c, A. Noy, A. E. Miller, J. E. Klare, B. L. Weeks, B. W. Woods, J. J. DeYoreo. Nano. Lett. 2, 109 (2002).Search in Google Scholar

63. doi:10.1063/1.1566466, I. Kymissis, A. I. Akiwande. Appl. Phys. Lett. 82, 2347 (2003).Search in Google Scholar

64. doi:10.1063/1.112308, M. Nisoli, V. Pruneri, V. Magni, S. De Silvestri, G. Delleoiane, D. Comoretto, C. Cuniberti, J. Le Moigne. Appl. Phys. Lett. 65, 590 (1994).Search in Google Scholar

65. doi:10.1021/ja0438359, H. Liu, Q. Zhao, Y. Li, Y. Liu, F. Lu, J. Zhuang, S. Wang, L. Jiang, D. Zhu, D. Yu, L. Chi. J. Am. Chem. Soc. 127, 1120 (2005).Search in Google Scholar

66. doi:10.1039/b413616k, A. Khan, S. Muller, S. Hecht. Chem. Commun. 584 (2005).Search in Google Scholar

67. doi:10.1021/ma021250y, S. Dubus, V. Marceau, M. Leclerc. Macromolecules 35, 9296 (2002).Search in Google Scholar

68. doi:10.1021/ja0430696, M. Kastler, W. Pisula, D. Wasserfallen, T. Pakula, K. Mullen. J. Am. Chem. Soc. 127, 4286 (2005).Search in Google Scholar

69. doi:10.1126/science.1097789, J. P. Hill, W. Jin, A. Kosaka, T. Fukushima, H. Ichihara, T. Shimomura, K. Ito, T. Hashizume, N. Ishii, T. Aida. Science 304, 1481 (2004).Search in Google Scholar

70. doi:10.1002/chem.200600605, Y. Li, Y. Li, J. Li, C. Li, X. Liu, M. Yuan, H. Liu, S. Wang. Chem.Eur. J. 12, 8378 (2006).Search in Google Scholar

71. X. Xu, W. Zhou, X. He, C. Li, X. Liu, H. Liu, Y. Li. Supramol. Chem. (2008). In press.Search in Google Scholar

72. doi:10.1021/la026997w, Y. R. Ma, L. M. Qi, J. M. Ma, H. M. Cheng. Langmuir 19, 4040 (2003).Search in Google Scholar

73. doi:10.1039/b104879c, C. E. Fowler, D. Khushalani, S. Mann. Chem. Commun. 2028 (2001).Search in Google Scholar

74. doi:10.1021/ic00008a041, R. Guilard, N. Senglet, Y. H. Liu, D. Sazou, E. Findsen, D. Faure, T. Des Courieres, K. M. Kadish. Inorg. Chem. 30, 1898 (1991).Search in Google Scholar

75. doi:10.1002/1521-3773(20020301)41:5<853::AID-ANIE853>3.0.CO;2-R, S. Tamaru, M. Takeuchi, M. Sano, S. Shinkai. Angew. Chem., Int. Ed. 41, 853 (2002).Search in Google Scholar

76. doi:10.1039/b409228g, R. Charvet, D. L. Jiang, T. Aida. Chem. Commun. 2664 (2004).Search in Google Scholar

77. doi:10.1002/anie.200600554, Y. Li, X. Li, Y. Li, H. Liu, S. Wang, H. Gan, J. Li, N. Wang, X. He, D. Zhu. Angew. Chem., Int. Ed. 45, 3639 (2006).Search in Google Scholar

78. doi:10.1039/b005903j, A. El-Ghayoury, E. Peeters, A. P. H. J. Schenning, E. W. Meijer. Chem. Commun. 1969 (2000).Search in Google Scholar

79. doi:10.1021/cr990126i, J. J. L. M. Cornelissen, A. E. Rowan, R. J. M. Nolte, N. A. J. M. Sommerdijk. Chem. Rev. 101, 4039 (2001).Search in Google Scholar

80. doi:10.1039/b305550g, M. A. Mateos-Timoneda, M. Crego-Calama, D. N. Reinhoudt. Chem. Soc. Rev. 33, 363 (2004).Search in Google Scholar

81. doi:10.1002/anie.200352790, P. Jonkheijm, A. Miura, M. Zdanowska, F. J. M. Hoeben, S. De Feyter, A. P. H. J. Schenning, F.C.De Schryver, E. W. Meijer. Angew. Chem., Int. Ed. 43, 74 (2004).Search in Google Scholar

82. doi:10.1021/ja010426t, M. Enomoto, A. Kishimura, T. Aida. J. Am. Chem. Soc. 123, 5608 (2001).Search in Google Scholar

83. doi:10.1002/(SICI)1521-3773(19980420)37:7<920::AID-ANIE920>3.0.CO;2-O, C. Kaes, M. W. Hosseini, C. E. F. Rickard, B. W. Skelton, A. H. White. Angew. Chem., Int. Ed. 37, 920 (1998).Search in Google Scholar

84. doi:10.1016/j.tetlet.2007.08.114, J. Xiao, Y. Li, Y. Song, L. Jiang, Y. Li, S. Wang, H. Liu, W. Xu, D. Zhu. Tetrahedron Lett. 48, 7599 (2007).Search in Google Scholar

85. doi:10.1021/ja983803j, I. K. Iverson, S. W. Tam-Chang. J. Am. Chem. Soc. 121, 5801 (1999).Search in Google Scholar

86. X. He, W. Zhou, Y. Li, X. Liu, C. Li, H. Liu, D. Zhu. J. Nanosci. Nanotechnol. (2008). In press.Search in Google Scholar

87. doi:10.1021/cr9601324, S. Leininger, B. Olenyuk, P. J. Stang. Chem. Rev. 100, 853 (2000).Search in Google Scholar

88. doi:10.1021/ja028861q, J. Hamacek, S. Blanc, M. Elhabiri, E. Leize, A. Van Dorsselaer, C. Piguet, A.-M. Albrecht-Gary. J. Am. Chem. Soc. 125, 1541 (2003).Search in Google Scholar

89. doi:10.1021/jo0624748, Y. Li, H. Zheng, Y. Li, S. Wang, Z. Wu, P. Liu, Z. Gao, H. Liu, D. Zhu. J. Org. Chem. 72, 2878 (2007).Search in Google Scholar

90. O. Mamula, A. Von Zelewsky. Chem. Rev. 242, 87 (2003).10.1016/S0010-8545(03)00062-6Search in Google Scholar

91. doi:10.1021/jp071706j, X. He, Q. Li, Y. Li, N. Wang, Y. Song, X. Liu, M. Yuan, W. Xu, H. Liu, S. Wang, Z. Shuai, D.Zhu. J. Phys. Chem. B 111, 8063 (2007).Search in Google Scholar

92. doi:10.1038/354056a0, S. Iijima. Nature 354, 56 (1991).Search in Google Scholar

93. doi:10.1126/science.273.5274.483, A. Thess, R. Lee, P. Nikolaev, H. Dai, P. Petit, J. Robert, C. Xu, Y. H. Lee, S. G. Kim, A. G. Rinzler, D. T. Colbert, G. E. Scuseria, D. Tomanek, J. E. Fischer, R. E. Smally. Science 273, 4831 (1996).Search in Google Scholar

94. doi:10.1126/science.265.5172.635, S. Amelinckx, D. Bernaerts, X. B. Zhang, G. Vantendeloo, J. Vantlanduyt. Science 265, 35 (1994).Search in Google Scholar

95. doi:10.1021/ja0280527, H. Liu, Y. Li, L. Jiang, H. Luo, S. Xiao, H. Fang, H. Li, D. Zhu, D. Yu, J. Xu, B. Xiang. J. Am. Chem. Soc. 124, 13370 (2002).Search in Google Scholar

96. doi:10.1126/science.287.5457.1471, J. D. Holmes, K. P. Johnston, R. C. Doty, B. A. Korgel. Science 287, 1471 (2000).Search in Google Scholar

97. doi:10.1126/science.1058120, Z. W. Pan, Z. R. Dai, Z. L. Wang. Science 291, 947 (2001).Search in Google Scholar

98. doi:10.1039/b109881k, J. K. Lee, W. K. Koh, W. S. Chae, Y. R. Kim. Chem. Commun. 138 (2002).Search in Google Scholar

99. doi:10.1021/ja036697g, H. Liu, Y. Li, S. Xiao, H. Gan, T. Jiu, H. Li, L. Jiang, D. Zhu, D. Yu, B. Xiang, Y. Chen. J. Am. Chem. Soc. 125, 10794 (2003).Search in Google Scholar

100. H. Liu, Y. Li, S. Xiao, H. Li, L. Jiang, D. Zhu, B. Xiang, Y. Chen, D. Yu. J. Phys. Chem. B 108, 7744 (2004).10.1021/jp049455rSearch in Google Scholar

101. H. Liu, J. Li, C. Lao, C. Huang, Y. Li, Z. Wang, D. Zhu. Nanotechnology 18, 49 (2007).10.1088/0957-4484/18/49/495704Search in Google Scholar PubMed

102. doi:10.1039/c39940000801, M. Brust, M. Walker, D. Bethell, D. J. Schiffrin, R. Whyman. J. Chem. Soc., Chem. Commun. 7, 801 (1994).Search in Google Scholar

103. doi:10.1002/adma.200400010, D. C. Pan, S. C. Jiang, L. J. An, B. Z. Jiang. Adv. Mater. 16, 982 (2004).Search in Google Scholar

Published Online: 2009-01-01

Published in Print: 2008-01-01

Self-assembly and properties of low-dimensional nanomaterials based on π-conjugated organic molecules

Abstract

Conference

References

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