Synthesis of self-threading bithiophenes and their structure-property relationships regarding cyclic side-chains with atomic precision

Chemistry - An Asian Journal

Volumn 7, Issue 1, 2012, Pages 75-84

  Ouchi, Yuki ^a,b   Sugiyasu, Kazunori ^a   Ogi, Soichiro ^a   Sato, Akira ^a   Takeuchi, Masayuki ^a,b  

^a NATIONAL INSTITUTE FOR MATERIALS SCIENCE   (Japan)

^b UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

molecular wires; oligomers; side chains; structure property relationships; thiophenes

Indexed keywords

ATOMIC PRECISION; BITHIOPHENES; DIFFERENT SIZES; H NMR SPECTROSCOPY; INSULATED MOLECULAR WIRE; MOLECULAR WIRES; PHOTOPHYSICAL PROPERTIES; POLY-THIOPHENE; SIDE-CHAINS; STRUCTURE-PROPERTY RELATIONSHIPS; THREE-DIMENSIONAL ARCHITECTURE; UV ABSORPTION;

CRYSTAL DEFECTS; DIHEDRAL ANGLE; ELECTRONIC PROPERTIES; FLUORESCENCE SPECTROSCOPY; MONOMERS; NANOWIRES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLIGOMERS; THIOPHENE; WIRE;

STRUCTURAL PROPERTIES;

THIOPHENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

CYCLIZATION; MODELS, MOLECULAR; MOLECULAR STRUCTURE; THIOPHENES;

EID: 84255169500     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201100524     Document Type: Article

References (122)

1. M. J. Frampton, H. L. Anderson, Angew. Chem. 2007, 119, 1046
2. Angew. Chem. Int. Ed. 2007, 46, 1028
3. D. J. Cardin, Adv. Mater. 2002, 14, 553
4. S. Brovelli, F. Cacialli, Small 2010, 6, 2796
5. M. Numata, J. Inclusion Phenom. Macrocyclic Chem. 2010, 68, 25
6. A. Harada, A. Hashidzume, H. Yamaguchi, Y. Takashima, Chem. Rev. 2009, 109, 5974
7. D. Lee, T. M. Swager, Synlett 2004, 149.
8. S. Anderson, H. L. Anderson, Angew. Chem. 1996, 108, 2075
9. Angew. Chem. Int. Ed. Engl. 1996, 35, 1956
10. J. E. H. Buston, F. Marken, H. L. Anderson, Chem. Commun. 2001, 1046
11. P. N. Taylor, M. J. O'Connell, L. A. McNeill, M. J. Hall, R. T. Aplin, H. L. Anderson, Angew. Chem. 2000, 112, 3598
12. Angew. Chem. Int. Ed. 2000, 39, 3456
13. K. Yoshida, T. Shimomura, K. Ito, R. Hayakawa, Langmuir 1999, 15, 910
14. H. Okumura, Y. Kawaguchi, A. Harada, Macromol. Rapid Commun. 2002, 23, 781
15. J. Stahl, J. C. Bohling, E. B. Bauer, T. B. Peters, W. Mohr, J. M. Martin-Alvarez, F. Hempel, J. A. Gladysz, Angew. Chem. 2002, 114, 1951
16. Angew. Chem. Int. Ed. 2002, 41, 1871
17. A. D. Schlüter, J. P. Rabe, Angew. Chem. 2000, 112, 860
18. Angew. Chem. Int. Ed. 2000, 39, 864
19. T. Kaneko, T. Horie, M. Asano, T. Aoki, E. Oikawa, Macromolecules 1997, 30, 3118
20. R. Tang, Y. Chuai, C. Cheng, F. Xi, D. Zou, J. Polym. Sci. Part A 2005, 43, 3126
21. W.-S. Li, D.-L. Jiang, T. Aida, Angew. Chem. 2004, 116, 3003
22. Angew. Chem. Int. Ed. 2004, 43, 2943
23. J.-S. Yang, T. M. Swager, J. Am. Chem. Soc. 1998, 120, 11864
24. R. Fiesel, J. Huber, U. Scherf, Angew. Chem. 1996, 108, 2233
25. Angew. Chem. Int. Ed. Engl. 1996, 35, 2111
26. J. Terao, S. Tsuda, Y. Tanaka, K. Okoshi, T. Fujihara, Y. Tsuji, N. Kambe, J. Am. Chem. Soc. 2009, 131, 16004
27. J. Terao, Y. Tanaka, S. Tsuda, N. Kambe, M. Taniguchi, T. Kawai, A. Saeki, S. Seki, J. Am. Chem. Soc. 2009, 131, 18046
28. Y. Liu, J. Shi, Y. Chen, C.-F. Ke, Angew. Chem. 2008, 120, 7403
29. Angew. Chem. Int. Ed. 2008, 47, 7293.
30. S. Tanaka, Y. Yamashita, Synth. Met. 1999, 101, 532
31. S. Tanaka, Y. Yamashita, Synth. Met. 2001, 119, 67
32. Y. Ie, A. Han, T. Otsubo, Y. Aso, Chem. Commun. 2009, 3020
33. T. Otani, M. Hachiya, D. Hashizume, T. Matsuo, K. Tamao, Chem. Asian J. 2011, 6, 350
34. A. Wakamiya, D. Yamazaki, T. Nishinaga, T. Kitagawa, K. Komatsu, J. Org. Chem. 2003, 68, 8305
35. T. Nishinaga, A. Wakamiya, D. Yamazaki, K. Komatsu, J. Am. Chem. Soc. 2004, 126, 3163
36. P. R. L. Malenfant, J. M. J. Fréchet, Macromolecules 2000, 33, 3634
37. T. Otsubo, S. Ueno, K. Takimiya, Y. Aso, Chem. Lett. 2004, 33, 1154
38. T. Ikeda, M. Higuchi, D. G. Kurth, J. Am. Chem. Soc. 2009, 131, 9158
39. M. van den Boogaard, G. Bonnet, P. vant Hof, Y. Wang, C. Brochon, P. van Hutten, A. Lapp, G. Hadziioannou, Chem. Mater. 2004, 16, 4383
40. K. Sakamoto, Y. Takashima, H. Yamaguchi, A. Harada, J. Org. Chem. 2007, 72, 459
41. C. Lagrost, K. I. C. Ching, J.-C. Lacroix, S. Aeiyach, M. Jouini, P.-C. Lacaze, J. Tanguy, J. Mater. Chem. 1999, 9, 2351
42. Y. Takashima, Y. Oizumi, K. Sakamoto, M. Miyauchi, S. Kamitori, A. Harada, Macromolecules 2004, 37, 3962
43. C. Li, M. Numata, A.-H. Bae, K. Sakurai, S. Shinkai, J. Am. Chem. Soc. 2005, 127, 4548
44. S. S. Zhu, P. J. Caroll, T. M. Swager, J. Am. Chem. Soc. 1996, 118, 8713
45. J. Buey, T. M. Swager, Angew. Chem. 2000, 112, 622
46. Angew. Chem. Int. Ed. 2000, 39, 608
47. T. Ikeda, M. Higuchi, Langmuir 2011, 27, 4184
48. T. Ikeda, M. Higuchi, A. Sato, D. G. Kurth, Org. Lett. 2008, 10, 2215.
49. R. Yamada, H. Kumazawa, T. Noutoshi, S. Tanaka, H. Tada, Nano Lett. 2008, 8, 1237
50. R. Yamada, H. Kumazawa, S. Tanaka, H. Tada, Appl. Phys. Express 2009, 2, 025002
51. M. Taniguchi, Y. Nojima, K. Yokota, J. Terao, K. Sato, N. Kambe, T. Kawai, J. Am. Chem. Soc. 2006, 128, 15062.
52. F. Cacialli, J. S. Wilson, J. J. Michels, C. Daniel, C. Silva, R. H. Friend, N. Severin, P. Samorí, J. P. Rabe, M. J. O'Connell, P. N. Taylor, H. L. Anderson, Nat. Mater. 2002, 1, 160
53. A. Petrozza, S. Brovelli, J. J. Michels, H. L. Anderson, R. H. Friend, C. Silva, F. Cacialli, Adv. Mater. 2008, 20, 3218
54. S. Brovelli, G. Latini, M. J. Frampton, S. O. McDonnell, F. E. Oddy, O. Fenwick, H. L. Anderson, F. Cacialli, Nano Lett. 2008, 8, 4546
55. S. Brovelli, F. Meinardi, G. Winroth, O. Fenwick, G. Sforazzini, M. J. Frampton, L. Zalewski, J. A. Levitt, F. Marinello, P. Schiavuta, K. Suhling, H. L. Anderson, F. Cacialli, Adv. Funct. Mater. 2010, 20, 272
56. S. Brovelli, T. Virgili, M. M. Mroz, G. Sforazzini, A. Paleari, H. L. Anderson, G. Lanzani, F. Cacialli, Adv. Mater. 2010, 22, 3690.
57. K. Sugiyasu, Y. Honsho, R. M. Harrison, A. Sato, T. Yasuda, S. Seki, M. Takeuchi, J. Am. Chem. Soc. 2010, 132, 14754.
58. D. Vonlanthen, J. Rotzler, M. Neuburger, M. Mayor, Eur. J. Org. Chem. 2010, 35, 120
59. J. Rotzler, D. Vonlanthen, A. Barsella, A. Boeglin, A. Fort, M. Mayor, Eur. J. Org. Chem. 2010, 35, 1096
60. D. Vonlanthen, A. Mishchenko, M. Elbing, M. Neuburger, T. Wandlowski, M. Mayor, Angew. Chem. 2009, 121, 9048
61. Angew. Chem. Int. Ed. 2009, 48, 8886
62. A. Mishchenko, D. Vonlanthen, V. Meded, M. Bürkle, C. Li, I. V. Pobelov, A. Bagrets, J. K. Viljas, F. Pauly, F. Evers, M. Mayor, T. Wandlowski, Nano Lett. 2010, 10, 156
63. A. Mishchenko, L. A. Zotti, D. Vonlanthen, M. Bürkle, F. Pauly, J. C. Cuevas, M. Mayor, T. Wandlowski, J. Am. Chem. Soc. 2011, 133, 184
64. J. Rotzler, H. Gsellinger, M. Neuburger, D. Vonlanthen, D. Häussinger, M. Mayor, Org. Biomol. Chem. 2011, 9, 86.
65. S. Woitellier, J. P. Launay, C. Joachim, Chem. Phys. 1989, 131, 481
66. L. Venkataraman, Y. S. Park, A. C. Whalley, C. Nuckolls, M. S. Hybertsen, M. L. Steigerwald, Nano Lett. 2007, 7, 502
67. L. Venkataraman, J. E. Klare, C. Nuckolls, M. S. Hybertsen, M. L. Steigerwald, Nature 2006, 442, 904.
68. S. D. Walker, T. E. Barder, J. R. Martinelli, S. L. Buchwald, Angew. Chem. 2004, 116, 1907
69. Angew. Chem. Int. Ed. 2004, 43, 1871.
70. S. D. Lepore, Y. He, J. Org. Chem. 2003, 68, 8261.
71. B. Mohr, M. Weck, J.-P. Sauvage, R. H. Grubbs, Angew. Chem. 1997, 109, 1365
72. Angew. Chem. Int. Ed. Engl. 1997, 36, 1308
73. D. A. Leigh, P. J. Lusby, S. J. Teat, A. J. Wilson, J. K. Y. Wong, Angew. Chem. 2001, 113, 1586
74. Angew. Chem. Int. Ed. 2001, 40, 1538.
75. J. A. Wisner, P. D. Beer, M. G. B. Drew, M. R. Sambrook, J. Am. Chem. Soc. 2002, 124, 12469
76. X.-Z. Zhu, C.-F. Chen, J. Am. Chem. Soc. 2005, 127, 13158.
77. T. Shima, F. Hampel, J. A. Gladysz, Angew. Chem. 2004, 116, 5653
78. Angew. Chem. Int. Ed. 2004, 43, 5537
79. A. J. Nawara, T. Shima, F. Hampel, J. A. Gladysz, J. Am. Chem. Soc. 2006, 128, 4962
80. L. Wang, F. Hampel, J. A. Gladysz, Angew. Chem. 2006, 118, 4479
81. Angew. Chem. Int. Ed. 2006, 45, 4372.
82. D. H. Camacho, E. V. Salo, J. W. Ziller, Z. Guan, Angew. Chem. 2004, 116, 1857
83. Angew. Chem. Int. Ed. 2004, 43, 1821
84. M. Lautens, G. Hughes, Angew. Chem. 1999, 111, 160
85. Angew. Chem. Int. Ed. 1999, 38, 129
86. R. Wakabayashi, Y. Kubo, K. Kaneko, M. Takeuchi, S. Shinkai, J. Am. Chem. Soc. 2006, 128, 8744
87. A. Ohashi, A. Satake, Y. Kobuke, Bull. Chem. Soc. Jpn. 2004, 77, 365
88. T. Inomata, K. Konishi, Chem. Commun. 2003, 1282.
89. S. Monfette, D. E. Fogg, Chem. Rev. 2009, 109, 3783.
90. S. M. E. Simpkins, B. M. Kariuki, L. R. Cox, J. Organomet. Chem. 2006, 691, 5517.
91. L. de Quadras, E. B. Bauer, J. Stahl, F. Zhuravlev, F. Hampel, J. A. Gladysz, New J. Chem. 2007, 31, 1594
92. L. de Quadras, E. B. Bauer, W. Mohr, J. C. Bohling, T. B. Peters, J. M. Martín-Alvarez, F. Hampel, J. A. Gladysz, J. Am. Chem. Soc. 2007, 129, 8296
93. G. R. Owen, J. Stahl, F. Hampel, J. A. Gladysz, Chem. Eur. J. 2008, 14, 73.
94. R. S. Macomber, A Complete Introduction to Modern NMR Spectroscopy, Wiley, 1998.
95. C. Zhang, S. Li, J. Zhang, K. Zhu, N. Li, F. Huang, Org. Lett. 2007, 9, 5553
96. C.-C. Hsu, N.-C. Chen, C.-C. Lai, Y.-H. Liu, S.-M. Peng, S.-H. Chiu, Angew. Chem. 2008, 120, 7585
97. Angew. Chem. Int. Ed. 2008, 47, 7475.
98. V. Sashuk, J. Ignatowska, K. Grela, J. Org. Chem. 2004, 69, 7748.
99. M. G. Nilson, R. L. Funk, Org. Lett. 2010, 12, 4912.
100. É. Naudin, N. El Mehdi, C. Soucy, L. Breau, D. Bélanger, Chem. Mater. 2001, 13, 634.
101. J. Gierschner, H.-G. Mack, H.-J. Egelhaaf, S. Schweizer, B. Doser, D. Oelkrug, Synth. Met. 2003, 138, 311
102. P. Hermet, J.-L. Bantignies, A. Rahmani, J.-L. Sauvajol, M. R. Johnson, F. Serein, J. Phys. Chem. A 2005, 109, 1684.
103. J. R. Lakowicz, Principles of Fluorescence Spectroscopy, 3rd ed., Springer, 2006.
104. Handbook of Thiophene-based Materials, Vol. 1: Synthesis and Theory (Eds.:, I. F. Perepichka, D. F. Perepichka,), Wiley, 2009.
105. J. Gierschner, J. Cornil, H.-J. Egelhaaf, Adv. Mater. 2007, 19, 173
106. M. Kertesz, C. H. Choi, S. Yang, Chem. Rev. 2005, 105, 3448
107. J. L. Brédas, G. B. Street, Acc. Chem. Res. 1985, 18, 309
108. J. Roncali, Chem. Rev. 1997, 97, 173
109. J. Gierschner, H.-G. Mack, L. Lüer, D. Oelkrug, J. Chem. Phys. 2002, 116, 8596.
110. C. Alemán, L. Julia, J. Phys. Chem. 1996, 100, 14661.
111. B. D. Allen, A. C. Benniston, A. Harriman, I. Llarena, C. A. Sams, J. Phys. Chem. A 2007, 111, 2641.
112. A. Saeki, S. Seki, Y. Koizumi, T. Sunagawa, K. Ushida, S. Tagawa, J. Phys. Chem. B 2005, 109, 10015.
113. A. Salleo, R. J. Kline, D. M. DeLongchamp, M. L. Chabinyc, Adv. Mater. 2010, 22, 3812
114. Y.-K. Lan, C. H. Yang, H.-C. Yang, Polym. Int. 2010, 59, 16
115. F. C. Grozema, P. Th. Van Duijnen, Y. A. Berlin, M. A. Ratner, L. D. A. Siebbeles, J. Phys. Chem. B 2002, 106, 7791
116. M. Hultell, S. Stafström, Phys. Rev. B 2007, 75, 104304.
117. M. Jurícek, P. H. J. Kouwer, A. E. Rowan, Chem. Commun. DOI
118. C. R. Becer, R. Hoogenboom, U. S. Schubert, Angew. Chem. 2009, 121, 4998
119. Angew. Chem. Int. Ed. 2009, 48, 4900
120. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056
121. Angew. Chem. Int. Ed. 2001, 40, 2004.
122. R. S. Becker, J. S. de Melo, A. L. Macanita, F. Elisei, J. Phys. Chem. 1996, 100, 18683.