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Publicly Available Published by De Gruyter March 20, 2012

Functional oligothiophenes toward molecular wires in single-molecular electronics

  • Yutaka Ie , Masaru Endou , Aihong Han , Ryo Yamada , Hirokazu Tada and Yoshio Aso

The synthesis of 3-hexylthiophene-based oligothiophenes with a length of approximately 10 nm bearing anchor units at both terminal positions has been accomplished. In addition, we have designed and synthesized completely encapsulated oligothiophenes to investigate single-molecule conductance. Their properties are evaluated by UV–vis absorption spectra and cyclic voltammetry (CV) measurements. The conductance of a single-molecule junction for thiol-introduced oligothiophenes was measured by 10-nm-scale nanogap gold electrodes or modified scanning tunneling microscope (STM) techniques.


Conference

International Symposium on Novel Aromatic Compounds (ISNA-14), International Symposium on Novel Aromatic Compounds, ISNA, Novel Aromatic Compounds, 14th, Eugene, USA, 2011-07-24–2011-07-29


References

1 10.1016/0009-2614(74)85031-1, A. Aviram, M. Ratner. Chem. Phys. Lett.29, 277 (1974).Search in Google Scholar

2a 10.1038/nnano.2006.130, N. J. Tao. Nat. Nanotech.1, 173 (2006).Search in Google Scholar PubMed

2b J. C. Cuevas, E. Scheer (Eds.). Molecular Electronics: An Introduction to Theory and Experiment: World Scientific, Singapore (2010).10.1142/7434Search in Google Scholar

3 10.1126/science.1087481, B. Xu, N. J. Tao. Science301, 1221 (2003).Search in Google Scholar PubMed

4a 10.1126/science.261.5117.73, J. K. Whitesell, H. K. Chang. Science261, 73 (1993).Search in Google Scholar PubMed

4b 10.1039/b906286f, Y. Ie, T. Hirose, A. Yao, T. Yamada, N. Takagi, M. Kawai, Y. Aso. Phys. Chem. Chem. Phys.11, 4949 (2009).Search in Google Scholar PubMed

4c 10.1021/ja109577f, Y. Ie, T. Hirose, H. Nakamura, M. Kiguchi, N. Takagi, M. Kawai, Y. Aso. J. Am. Chem. Soc.133, 3014 (2011).Search in Google Scholar PubMed

5a 10.1021/jp807479g, K. Matsuda, H. Yamaguchi, T. Sakano, M. Ikeda, N. Tanifuji, M. Irie. J. Phys. Chem. C112, 17005 (2008).Search in Google Scholar

5b 10.1021/jp9043573, F. L. E. Jakobsson, P. Marsal, S. Braun, M. Fahlman, M. Berggren, J. Cornil, X. Crispin. J. Phys. Chem. C113, 18396 (2009) and refs. cited therein.Search in Google Scholar

6a 10.1021/cr950257t, J. Roncali. Chem. Rev.97, 173 (1997).Search in Google Scholar PubMed

6b 10.1002/adma.200600277, J. Gierschner, J. Cornil, H.-J. Egelhaaf. Adv. Mater.19, 173 (2007).Search in Google Scholar

7a D. Fichou (Ed.). Handbook of Oligo-and Polythiophenes, Wiley-VCH, Weinheim (1999).10.1002/9783527611713Search in Google Scholar

7b 10.1246/bcsj.74.1789, T. Otsubo, Y. Aso, K. Takimiya. Bull. Chem. Soc. Jpn.74, 1789 (2001).Search in Google Scholar

7c 10.1021/cr8004229, A. Mishra, C.-Q. Ma, P. Bäuerle. Chem. Rev.109, 1141 (2009).Search in Google Scholar PubMed

7d I. F. Perepichka, D. F. Perepichka (Eds.). Handbook of Thiophene-based Materials, Wiley-VCH, Weinheim (2009).10.1002/9780470745533Search in Google Scholar

7e 10.1021/cm102402t, L. Luo, S. H. Choi, C. D. Frisbie. Chem. Mater.23, 631 (2011).Search in Google Scholar

8 10.1021/ja034333i, T. Izumi, S. Kobashi, K. Takimiya, Y. Aso, T. Otsubo. J. Am. Chem. Soc.125, 5286 (2003).Search in Google Scholar PubMed

9a 10.1021/nl050860j, B. Q. Xu, X. L. Li, X. Y. Xiao, H. Sakaguchi, N. J. Tao. Nano. Lett.5, 1491 (2005).Search in Google Scholar PubMed

9b 10.1021/ja062066l, S. Yasuda, S. Yoshida, J. Sasaki, Y. Okutsu, T. Nakamura, A. Taninaka, O. Takeuchi, H. Shigekawa. J. Am. Chem. Soc.128, 7746 (2006).Search in Google Scholar PubMed

10 10.1021/nl0732023, R. Yamada, H. Kumazawa, T. Nobutoshi, S. Tanaka, H. Tada. Nano. Lett.8, 1237 (2008).Search in Google Scholar PubMed

11 10.1143/APEX.2.025002, R. Yamada, H. Kumazawa, S. Tanaka, H. Tada. Appl. Phys. Exp.2, 025002-1 (2009).Search in Google Scholar

12a 10.1021/jo962335y, D. L. Pearson, J. M. Tour. J. Org. Chem.62, 1376 (1997).Search in Google Scholar

12b 10.1021/jo962336q, L. Jones II, J. S. Schumm, J. M. Tour. J. Org. Chem.62, 1388 (1997).Search in Google Scholar

12c 10.1021/jo026907s, C. Xue, F.-T. Luo. J. Org. Chem.68, 4417 (2003).Search in Google Scholar PubMed

12d 10.1021/jo051711o, C. Wang, A. S. Batsanov, M. R. Bryce. J. Org. Chem.71, 108 (2006).Search in Google Scholar PubMed

12e 10.1021/ol052252g, I. W. Tam, J. Yan, R. Breslow. Org. Lett.8, 183 (2006).Search in Google Scholar PubMed

13a 10.1088/0953-8984/20/37/374116, N. Prokopuk, K.-A. Son. J. Phys. Condens. Matter20, 374116 (2008).Search in Google Scholar PubMed

13b 10.1002/adma.201004291, H. Song, M. A. Reed, T. Lee. Adv. Mater.23, 1583 (2011) and refs. cited therein.Search in Google Scholar PubMed

14a 10.1246/bcsj.74.979, N. Sumi, H. Nakanishi, S. Ueno, K. Takimiya, Y. Aso, T. Otsubo. Bull. Chem. Soc. Jpn.74, 979 (2001).Search in Google Scholar

14b 10.1021/ol016511n, J. Ikemoto, K. Takimiya, Y. Aso, T. Otsubo, M. Fujitsuka. O. Ito. Org. Lett.4, 309 (2002).Search in Google Scholar PubMed

14c 10.1021/jp049122u, T. Nakamura, M. Fujitsuka, Y. Araki, O. Ito, J. Ikemoto, K. Takimiya, Y. Aso, T. Otsubo. J. Phys. Chem. B108, 10700 (2004).Search in Google Scholar

15 Thiophene 3-mers and 6-mers with thiol groups at both terminal positions have been reported, see.Search in Google Scholar

15a 10.1021/jp013028l, J. Casado, H. E. Katz, V. Hernández, J. T. L. Navarrete. J. Phys. Chem. B106, 2488 (2002).Search in Google Scholar

15b 10.1016/S0040-4020(02)00098-4, G. Sotgiu, M. Zambianchi, G. Barbarella, C. Botta. Tetrahedron58, 2245 (2002).Search in Google Scholar

15c 10.1021/la0341052, B. de Boer, H. Meng, D. F. Perepichka, J. Zheng, M. M. Frank, Y. J. Chabal, Z. Bao. Langmuir19, 4272 (2003).Search in Google Scholar

16 10.1021/jo062204p, M. Endou, Y. Ie, T. Kaneda, Y. Aso. J. Org. Chem.72, 2659 (2007).Search in Google Scholar

17 10.1246/cl.2007.224, N. Hatanaka, M. Endo, S. Okumura, Y. Ie, R. Yamada, Y. Aso, K. Tanaka, H. Tada. Chem. Lett.36, 224 (2007).Search in Google Scholar

18a 10.1021/ja050783u, T. Sakai, T. Satou, T. Kaikawa, K. Takimiya, T. Otsubo, Y. Aso. J. Am. Chem. Soc.127, 8082 (2005).Search in Google Scholar

18b 10.1021/ja063312w, K. M. Knoblock, C. J. Silvestri, D. M. Collard. J. Am. Chem. Soc.128, 13680 (2006).Search in Google Scholar

18c 10.1021/ja065995l, D. Yamazaki, T. Nishinaga, N. Tanino, K. Komatsu. J. Am. Chem. Soc.128, 14470 (2006).Search in Google Scholar

19a 10.1002/1521-4095(20020418)14:8<553::AID-ADMA553>3.0.CO;2-F, D. J. Cardin. Adv. Mater.14, 553 (2002).Search in Google Scholar

19b 10.1002/anie.200353519, W.-S. Li, D.-L. Jiang, T. Aida. Angew. Chem., Int. Ed.43, 2943 (2004).Search in Google Scholar

19c 10.1039/b705458k, G. Wenz, B.-H. Han, A. Müller. Chem. Rev.106, 782 (2006).Search in Google Scholar

19d 10.1002/anie.200601780, M. J. Frampton, H. L. Anderson. Angew. Chem., Int. Ed.46, 1028 (2007).Search in Google Scholar

19c 10.1039/b705458k, A. Harada, Y. Takashima, H. Yamaguchi. Chem. Soc. Rev.38, 875 (2009).Search in Google Scholar

20 10.1016/S0379-6779(00)00673-1, S. Tanaka, Y. Yamashita. Synth. Met.119, 67 (2001).Search in Google Scholar

21a 10.1021/jo034754i, A. Wakamiya, D. Yamazaki, T. Nishinaga, T. Kitagawa, K. Komatsu. J. Org. Chem.68, 8305 (2003).Search in Google Scholar PubMed

21b 10.1021/ja039434v, T. Nishinaga, A. Wakamiya, D. Yamazaki, K. Komatsu. J. Am. Chem. Soc.126, 3163 (2004).Search in Google Scholar PubMed

22a 10.1021/ja034894+, D. Lee, T. M. Swager. J. Am. Chem. Soc.125, 6870 (2003).Search in Google Scholar PubMed

22b 10.1021/cm050803r, D. Lee, T. M. Swager. Chem. Mater.17, 4622 (2005).Search in Google Scholar

23 10.1021/ja107444m, K. Sugiyasu, Y. Honsho, R. M. Harrison, A. Sato, T. Yasuda, S. Seki, M. Takeuchi. J. Am. Chem. Soc.132, 14754 (2010).Search in Google Scholar PubMed

24 10.1039/b901354g, Y. Ie, A. Han, T. Otsubo, Y. Aso. Chem. Commun. 3020 (2009).Search in Google Scholar PubMed

25 10.1021/cm9706558, G. Bidan, A. De Nicola, V. Enée, S. Guillerez. Chem. Mater.10, 1052 (1998).Search in Google Scholar

26 10.1021/ar9600446, L. L. Miller, K. R. Mann. Acc. Chem. Res.29, 417 (1996).Search in Google Scholar

27 10.1002/anie.201104700, Y. Ie, M. Endou, S. K. Lee, R. Yamada, H. Tada, Y. Aso. Angew. Chem., Int. Ed.50, 11980 (2011).Search in Google Scholar PubMed

28 10.1021/ja031855p, K. Masui, H. Ikegami, A. Mori. J. Am. Chem. Soc.126, 5074 (2004).Search in Google Scholar PubMed

29 G. Peng, M. Strange, K. S. Thygesen, M. Mavrikakis. J. Phys. Chem. C113, 20697 (2009).10.1021/jp9084603Search in Google Scholar

Online erschienen: 2012-3-20
Erschienen im Druck: 2012-3-20

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