Coupled protonic and electronic conduction in the molecular conductor [2-(2-1H-benzimidazolyl)-1H-benzimidazolium]-TCNQ

Chemistry - A European Journal

Volumn 8, Issue 19, 2002, Pages 4402-4411

  Akutagawa, Tomoyuki ^a,b   Hasegawa, Tatsuo ^a   Nakamura, Takayoshi ^a   Inabe, Tamotsu ^a   Saito, Gunzi ^c  

^a HOKKAIDO UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c KYOTO UNIVERSITY   (Japan)

Author keywords

Charge transfer; Conducting materials; Cooperative effects; Electron transport; Hydrogen bonds; Proton transport; Quinodimethanes

Indexed keywords

CRYSTALS; DIMERS; ELECTRIC CONDUCTIVITY; ELECTRONS; MAGNETIC SUSCEPTIBILITY; PROTONS; SEMICONDUCTOR MATERIALS;

ELECTROCRYSTALLIZATION;

PHASE TRANSITIONS;

2 (2 1H BENZIMIDAZOLYL) 1H BENZIMIDAZOLIUM; 7,7,8,8 TETRACYANO 4 QUINODIMETHANE; ALKANE DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; CHLORIDE ION; UNCLASSIFIED DRUG; WATER;

ARTICLE; CRYSTALLIZATION; ELECTRIC CONDUCTIVITY; ELECTROCHEMISTRY; ELECTRON TRANSPORT; HYDROGEN BOND; PROTON TRANSPORT;

EID: 0037020283     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20021004)8:19<4402::AID-CHEM4402>3.0.CO;2-H     Document Type: Article

References (64)

1. a) B. Albert, D. Bray, A. Johnson, J. Lewis, M. Raff, K. Roberts, P. Walter, Molecular Biology of the Cell, Garland Publishing Inc., New York, 1994;
2. b) L. Stryer, Biochemistry, Freeman, New York. 1995.
3. a) R. E. Blankenship, Anoxygenic Photosynthetic Bacteria. Advances in Photosynthesis Vol. 2, Kluwer, New York, 1996;
4. b) D. R. Ort, Oxygenic Photosynthesis; The Light Reactions; Advances in Photosynthesis Vol. 4, Kluwer, New York, 1996.
5. a) P. J. P. Williams, Nature 1995, 378, 643;
6. b) S. Iwata, C. Ostermeler, B. Ludwig, H. Michel, Nature 1995, 376, 660.
7. Proton Conductors, solids, membranes and gels materials and devices (Ed.: P. Colomban), Cambridge University Press, Cambridge. 1992.
8. F. M. Gray, Polymer Electrolyte, RSC, Cambridge, 1997.
9. a) R. A. Wallace. J. Appl. Phys. 1971, 42, 3121;
10. b) R. C. Slade, A. Hardwick. P. G. Dickens, Solid State Ionics 1983, 9-10, 1093.
11. L. Glasser, Chem. Rev. 1975, 75, 21.
12. A. Kawada, A. R. McGhie, M. M. Labes, J. Chem. Phys. 1969, 52, 3121.
13. a) T. Akutagawa, T. Nakamura, A. E. Underhill, T. Inabe, J. Mater. Chem. 1996, 7, 135;
14. b) T. Akutagawa, T. Nakamura, T. Inabe, A. E. Underhill, Thin Solid Films 1998, 331, 264;
15. c) T. Akutagawa, Y. Nezu, T. Hasegawa, T. Nakamura, K. Sugiura, Y. Sakata, T. Inabe, A. E. Underhill, Chem. Commun. 1998, 2599;
16. d) T. Akutagawa, T. Hasegawa, T. Nakamura, T. Inabe, K. Sugiura, Y. Sakata, A. E. Underhill, Synth. Met. 1999, 102, 1747;
17. e) T. Akutagawa, T. Nakamura, Coord. Chem. Rev. 2000, 198, 297;
18. f) T. Akutagawa, T. Hasegawa, T. Nakamura, S. Takeda, T. Inabe, K. Sugiura, Y. Sakata, A. E. Underhill, Inorg. Chem. 2000, 39, 2645.
19. a) D. O. Cowan, New Aspects of Organic Chemistry (Eds.: Z. Yoshida, T. Shiba, Y. Oshiro), Kodansha, Tokyo, 1989;
20. b) Organic Conductors (Ed.: J.-P. Farges), Marcel Dekker, New York, 1994;
21. Handbook of Organic Conductive Molecules and Polymers Vol. 1 (Ed.: H. S. Nalwa), Wiley, New York, 1997;
22. d) J. M. Williams, J. R. Ferraro, R. J. Thorn, K. D. Carlson, U. Geiser, H. H. Wang, A. M. Kini, M.-H. Whangbo, Organic Superconductors (Ed.: R. N. Grimes), Prentice-Hall, New Jersey, 1992;
23. e) T. Ishiguro, K. Yamaji, G. Saito, Organic Superconductors, 2nd ed., Springer, New York, 1998.
24. T. Nakamura, T. Akutagawa, K. Honda, A. E. Underhill, A. T. Coomber, R. H. Friend, Nature 1998, 394, 159.
25. T. Akutagawa, T. Hasegawa, T. Nakamura, S. Takeda, K. Sugiura, Y. Sakata, T Inabe, A. E. Underhill, Chem. Eur. J. 2001, 7, 4902.
26. T. Akutagawa, G. Saito, Bull. Chem. Soc. Jpn. 1995, 68, 1753.
27. T. Akutagawa, G. Saito, M. Kusunoki, K. Sakaguchi, Bull. Chem. Soc. Jpn. 1996, 69, 2487.
28. a) J. P. Ferraris, D. O. Cowan, V. Walatka, J. H. Perlstein, J. Am. Chem. Soc. 1973, 95, 498;
29. b) L. B. Coleman, M. J. Cohen, D. J. Sandman, F. G. Yamagishi, A. F. Garito, A. J. Heeger, Solid State Commun. 1973, 12, 1125.
30. Recently, the protonic channel structure of the [18]crown-6 array in a CT salt has been reported; however, its protonic conductivity has not been evaluated yet. S. Rashid, S. Turner, P. Day, M. E. Light, M. B. Hursthouse, S. Firth, R. J. H. Clark, Chem. Commun. 2001, 1462.
31. a) T. Akutagawa, G. Saito, H. Yamochi, M. Kusunoki, K. Sakaguchi, Synth. Met. 1995, 69, 591;
32. b) T. Akutagawa, G. Saito, T. Nakamura, K. Sakaguchi, M. Kusunoki, Mol. Cryst. Liq. Cryst. 1996, 276, 257.
33. T. J. Emge, W. A. Bryden. M. Wiygul, D. O. Cowan, T. J. Kistenmacher, J. Chem. Phys. 1982, 77, 3188.
34. G. Kortüm, W. Vogel, K. Andrussow. Dissociation Constants of Organic Acid in Aquaeous Solution. Butterworths, London, 1961.
35. P. M. S. Monk, The Viologens, Wiley, Chichester. 1998.
36. a) A. J. Berlinsky, J. F. Carolan, L. Weiler, Solid State Commun. 1974. 15, 795;
37. b) F. Herman, D. R. Salahub, R. P. Messmer, Phys. Rev. B 1977, 16, 2453.
38. a) P. S. Flandoris, D. Chasseau, Acta. Crystallogr. Sect. B 1977, 33, 2744;
39. b) T. J. Kistenmacher, T. J. Emge, A. N. Bloch, D. O. Cowan, Acta. Crystallogr. Sect B 1982, 38, 1193.
40. Semiconductors and Semimetals, Highly Conducting Quasi-One-Dimensional Organic Crystals (Ed.: E. Conwell), Academic Press. New York, 1988.
41. a) J. B. Torrance, B. A. Scott, B. Welber, F. B. Kaufman, P. E. Seiden, Phys. Rev. B 1979, 19, 730;
42. b) J. B. Torrance, Acc. Chem. Res. 1979, 12, 79.
43. S. Takeda, unpublished results.
44. A. Bondi, J. Phys. Chem. 1964, 68, 441.
45. a) G. A. Jeffrey, W. Saenger, Hydrogen Bonding in Biological Structures, Springer-Verlag, Berlin, 1991;
46. b) S. Scheiner, Hydrogen Bonding, Theoretical Perspective (Ed.: D. G. Truhlar), Oxford University Press, New York, 1997;
47. c) G. A. Jeffrey, An Introduction to Hydrogen Bonding (Ed.: D. G. Truhlar), Oxford University Press, New York, 1997.
48. D. Boinnard, P. Cassoux, V. Petrouleas, J. M. Savariault, J. P. Tuchagues, Inorg. Chem. 1990, 29, 4114.
49. a) R. D. Amos, Chem. Phys. 1986, 104, 145;
50. b) E. L. Woodbridge, T. Tso, P. M. McGrath, W. J. Hehre, K. C. Lee. J. Chem. Phys. 1986, 85, 6991.
51. M. Meneghetti, A. Girlando, C. Pecile, J. Chem. Phys. 1985, 83, 3134
52. J. C. Bonner, M. E. Fisher, Phys. Rev. A 1964, 3, 640.
53. S. Huizinga, J. Kommandeur, G. A. Sawatzky, K. Kopinga, W. J. M. Jonge, Quasi One-Dimensional Conductor II (Eds.: S. Barisic, S. Bjelis, J. R. Cooper, B. Leontic), Springer-Verlag, Berlin. 1979, p. 45.
54. B. Bodegom, B. C. Larson, H. A. Mook, Phys Rev. B 1981, 24, 1520.
55. N. F. Mott, Meta L-Insulator Transitions, Taylor & Francis, 1990.
56. C. Barthet, M. Guglielmi, J. Electro. Chem. 1995, 388, 35.
57. P. Novak, Z. Q. Shan, R. Bjorklund, J. Electro. Chem. 1987, 134, 1341.
58. Z. Gao, B. Chen, M. Zi, J. Chem. Soc. Chem. Commun. 1993, 675.
59. M. S. Hadad, D. H. Hendrickson, Inorg. Chem. 1978, 17, 2622;
60. B. F. Fieselmann, D. N. Hendrickson, G. D. Stucky, Inorg. Chem. 1978, 17, 2078.
61. Crystal Structure: Single crystal structure analysis software. Ver. 1.0, 2000. Rigaku Corporation and Molecular Structure Corporation For Ortep drawings, see: L. J. Farrugia, J. Appl. Crystallogr. 1997, 32, 565.
62. Crystal Structure: Single crystal structure analysis software. Ver. 1.0, 2000. Rigaku Corporation and Molecular Structure Corporation For Ortep drawings, see: L. J. Farrugia, J. Appl. Crystallogr. 1997, 32, 565.
63. a) T. Mori, A. Kobayashi, Y. Sasaki, H. Kobayashi, G. Saito, H. Inokuchi, Bull. Chem. Soc. Jpn. 1984, 57, 627;
64. b) R. H. Summerville, R. J. Hoffmann, J. Am. Chem. Soc. 1976, 98, 7240.