Observation of a large current on the cyclic voltammetry of acylaminoferrocenes in the solid state: An efficient electron-transfer pathway through continuous NH⋯O=C hydrogen-bond chains and π-conjugation

Bulletin of the Chemical Society of Japan

Volumn 78, Issue 7, 2005, Pages 1270-1278

  Okamura, Taka Aki ^a   Sakauye, Keiko ^a   Doi, Mototsugu ^a   Yamamoto, Hitoshi ^a   Ueyama, Norikazu ^a   Nakamura, Akira ^b  

^a OSAKA UNIVERSITY   (Japan)

^b OM Research   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTAL STRUCTURE; ELECTRON GAS; HYDROGEN BONDS; X RAYS;

ACYLAMINOFERROCENES; HYDROGEN-BOND CHAINS;

CYCLIC VOLTAMMETRY;

ALKYL GROUP; AMINOFERROCENE DERIVATIVE; CARBON; FERROCENE DERIVATIVE; HYDROGEN; NITROGEN; OXYGEN; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; CONJUGATION; CRYSTAL STRUCTURE; CYCLIC POTENTIOMETRY; DISSOCIATION; ELECTRIC POTENTIAL; ELECTROCHEMICAL ANALYSIS; ELECTRON TRANSPORT; HYDROGEN BOND; INFRARED SPECTROSCOPY; OXIDATION REDUCTION REACTION; SOLID STATE; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS; X RAY ANALYSIS;

EID: 23244432819     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.78.1270     Document Type: Article

References (47)

1. R. Rulkens, A. J. Lough, I. Manners, S. R. Lovelace, C. Grant, and W. E. Geiger, J. Am. Chem. Soc., 118, 12683 (1996).
2. J.-M. Lehn, "Supramolecular Chemistry-Concepts and Perspectives," VCH, Tokyo (1995).
3. J. C. MacDonald and G. M. Whitesides, Chem. Rev., 94, 2383 (1994).
4. G. R. Desiraju, Angew. Chem., Int. Ed. Engl., 34, 2311 (1995).
5. G. R. Desiraju, Acc. Chem. Res., 29, 441 (1996).
6. C. B. Aakeröy and K. R. Seddon, Chem. Soc. Rev., 22, 397 (1993).
7. D. Philp and J. F. Stoddart, Angew. Chem., Int. Ed. Engl., 35, 1154 (1996).
8. A. D. Burrows, C.-W. Chan, M. M. Chowdgry, J. E. McGray, and D. M. P. Mingos, Chem. Soc. Rev., 24, 329 (1995).
9. D. Braga, F. Grepioni, and G. R. Desiraju, J. Organomet. Chem., 548, 33 (1997).
10. T. Okamura, K. Sakauye, N. Ueyama, and A. Nakamura, Inorg. Chem., 37, 6731 (1998).
11. T. Okamura and N. Ueyama, "Metal-Hydrogen Bond Conjugated Systems," ed by A. Nakamura, N. Ueyama, and K. Yamaguchi, Kodansha, Tokyo (2002), pp. 307-330.
12. M. C. Grossel, M. R. Goldspink, J. A. Hriljac, and S. C. Weston, Organometallics, 10, 851 (1991).
13. K. Kavallieratos, S. Hwang, and R. H. Crabtree, Inorg. Chem., 38, 5184 (1999).
14. D. v. Leusen and B. Hessen, Organometallics, 20, 224 (2001).
15. P. D. Beer, F. Szemes, V. Balzani, C. M. Sala, M. G. B. Drew, S. W. Dent, and M. Maestri, J. Am. Chem. Soc., 119, 11864 (1997).
16. P. D. Beer, A. R. Graydon, A. O. M. Johnson, and D. K. Smith, Inorg. Chem., 36, 2112 (1997).
17. J. D. Carr, L. Lambert, D. E. Hibbs, M. B. Hursthouse, K. M. A. Malik, and J. H. R. Tucker, J. Chem. Soc., Chem. Commun., 1997, 1649.
18. K. Heinze and M. Schlenker, Eur. J. Inorg. Chem., 2004, 2974.
19. D. W. Hall and J. H. Richards, J. Org. Chem., 28, 1549 (1963).
20. T. Okamura, S. Takamizawa, N. Ueyama, and A. Nakamura, Inorg. Chem., 37, 18 (1998).
21. N. Ueyama, N. Nishikawa, Y. Yamada, T. Okamura, S. Oka, H. Sakurai, and A. Nakamura, Inorg. Chem., 37, 2415 (1998).
22. N. Ueyama, N. Nishikawa, Y. Yamada, T. Okamura, and A. Nakamura, Inorg. Chim. Acta, 283, 91 (1998).
23. N. Ueyama, Y. Yamada, T. Okamura, S. Kimura, and A. Nakamura, Inorg. Chem., 35, 6473 (1996).
24. N. Ueyama, T. Okamura, and A. Nakamura, J. Am. Chem. Soc., 114, 8129 (1992).
25. N. F. Zakharchuk, B. Meyer, H. Hennig, F. Scholz, A. Jaworksi, and Z. Stojek, J. Electroanal. Chem., 398, 23 (1995).
26. A. Dostal, B. Meyer, F. Scholz, U. Schröder, A. M. Bond, F. Marken, and S. J. Shaw, J. Phys. Chem., 99, 2096 (1995).
27. A. Dostal, U. Schröder, and F. Scholz, Inorg. Chem., 34, 1711 (1995).
28. A. M. Bond, R. Colton, F. Daniels, D. R. Fernando, F. Marken, Y. Nagaosa, R. F. V. Steveninck, and J. N. Walter, J. Am. Chem. Soc., 115, 9556 (1993).
29. A. M. Bond, R. Colton, F. Marken, and J. N. Walter, Organometallics, 13, 5122 (1994).
30. F. Scholz and B. Meyer, Chem. Soc. Rev., 23, 341 (1994).
31. S. Kitagawa, S. Matsuyama, M. Munakata, N. Osawa, and H. Masuda, J. Chem. Soc., Dalton Trans., 1991, 1717.
32. G. M. Scheldrick, "Crystallographic Computing 3," Oxford University Press (1985), pp. 175-189.
33. G. M. Scheldrick, "SHELXL97, Program for the Refinement of Crystal Structures," University of Göttingen, Germany (1997).
34. D. T. Cromer, "International Tables for X-ray Crystallography," T. K. Press, Birmingham, England (1974).
35. G. R. Knox, P. L. Pauson, D. Willison, E. Solčániová , and S. Toma, Organometallics, 9, 301 (1990).
36. L. Leiserowitz and M. Tuval, Acta Crystallogr., B34, 1230 (1978).
37. H. Adalsteinsson, A. H. Maulitz, and T. C. Bruice, J. Am. Chem. Soc., 118, 7689 (1996).
38. R. Taylor and O. Kennard, Acc. Chem. Res., 17, 320 (1984).
39. R. Taylor and O. Kennard, Acta Crystallogr., B39, 133 (1983).
40. I. Schnell, S. P. Brown, H. Y. Low, H. Ishida, and H. W. Spiess, J. Am. Chem. Soc., 120, 11784 (1998).
41. S. Lu, V. V. Strelets, M. F. Ryan, W. J. Pietro, and A. B. P. Lever, Inorg. Chem., 35, 1013 (1996).
42. A. M. Bond and F. Marken, J. Electroanal. Chem., 372, 125 (1994).
43. F. A. Schultz and T. Kuwana, J. Electroanal. Chem., 10, 95 (1965).
44. M. Sisido, S. Hoshino, H. Kusano, M. Kuragaki, M. Makino, H. Sasaki, T. A. Smith, and K. P. Ghiggino, J. Phys. Chem. B, 105, 10407 (2001).
45. F. Polo, S. Antonello, F. Formaggio, C. Toniolo, and F. Maran, J. Am. Chem. Soc., 127, 492 (2005);
46. S. Antonello, F. Formaggio, A. Moretto, C. Toniolo, and F. Maran, J. Am. Chem. Soc., 125, 2874 (2003).
47. K. Yanagisawa, T. Morita, and S. Kimura, J. Am. Chem. Soc., 126, 12780 (2004).