Anion-controlled redox process in a cross-linked polyviologen film toward electrochemical anion recognition

Langmuir

Volumn 17, Issue 1, 2001, Pages 155-163

  Kamata, Kaori ^a   Kawai, Tadashi ^a   Iyoda, Tomokazu ^a  

^a TOKYO METROPOLITAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; ANIONIC POLYMERIZATION; BROMINE COMPOUNDS; CHEMICAL VAPOR DEPOSITION; CROSSLINKING; CYCLIC VOLTAMMETRY; ELECTROCHEMISTRY; ELECTROLYTES; ELECTROPOLYMERIZATION; MONOMERS; REDOX REACTIONS; SPECTROPHOTOMETRY;

ANION IMPRINTED ELECTROPOLYMERIZATION; POLYVIOLOGEN;

PLASTIC FILMS;

EID: 0035130093     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la001145m     Document Type: Article

References (70)

1. Tomalia, V. D. A.; Naylor, A. M.; Goddard, W. A., III. Angew. Chem. 1990, 102, 119.
2. (a) Lehn, J. M. Pure Appl. Chem. 1978, 50, 871.
3. (b) Lehn, J. M. Acc. Chem. Res. 1978, 11, 49.
4. (a) Wulff, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1812.
5. (b) Sellergren, B.; Lepisto, M.; Mosbach, K. J. Am. Chem. Soc. 1988, 110, 5850.
6. (a) Dall'Olio, A.; Dascola, Y.; Varacca, V.; Bocchi, V. C. R. Acad. Sci. Ser. C 1968, 267, 433.
7. (b) Diaz, A. F.; Kanazawa, K. K.; Gardini, G. P. J. Chem. Soc., Chem. Commun. 1979, 635.
8. (a) Tourillon, G.; Garnier, F. J. Electronal. Chem. Interfacial Electrochem. 1982, 135, 173.
9. (b) Kaneto, K.; Yosyino, K.; Inuishi, Y. Solid State Commun. 1983, 46, 389.
10. (c) Hotta, S.; Hosaka, T.; Shimotsuma, W. Synth. Met. 1983, 6, 69.
11. (a) Hosoya, K.; Yoshizako, K.; Shiyasu, Y.; Kimata, K.; Araki, T.; Tanaka, N.; Hahinaka, J. J. Chromatogr. A 1996, 728, 139.
12. (b) Kempe, M.; Mosbach, K. J. Chromatogr. A 1995, 694, 3.
13. (a) Schweitz, L.; Andersson, L. I.; Nilsson, S. J. Chromatogr. A 1997, 792, 401.
14. (b) Fischer, L.; Müller, R.; Ekberg, B.; Mosbach, K. J. Am. Chem. Soc. 1991, 113, 9358.
15. (c) Lin, J.-M.; Nakagama, T.; Wu, X.-Z.; Uchiyama, K.; Hobo, T. J. Anal. Chem. 1997, 357, 130.
16. Vlatakis, G.; Andersson, L. I.; Müller, R.; Mosbach, K. Nature 1993, 361, 645.
17. (a) Matsui, J.; Nicholls, I.; Karube, I.; Mosbach, K. J. Org. Chem. 1996, 61, 5414.
18. (b) Karmalkar, R. N.; Kulkarni, M. G.; Mashelkar, R. A. Macromolecules 1996, 29, 1366.
19. Kamata, K.; Suzuki, T.; Kawai, T.; Iyoda,T. J. Electroanal. Chem. 1999, 473, 145.
20. (a) Schwarz, W. E.; Kosower, E. M.; Shain, I. J. Am. Chem. Soc. 1961, 83, 3164.
21. (b) Carelli, I.; Cardinali, M. E. J. Electroanal. Chem. 1981, 124, 147.
22. (c) Webber, A.; Eisner, E. K.; Osteryoung, J.; Hernolin, J. J. Electrochem. Soc. 1982, 129, 2725.
23. (d) Webber, A.; Osteryoung, J. J. Electrochem. Soc. 1982, 129, 2731.
24. (e) Ageishi, K.; Endo, T.; Okawara, M. J. Polym. Sci., Polym. Chem. Ed. 1983, 21, 293.
25. (f) Kitamura, N.; Nambu, Y.; Endo, T. J. Polym. Sci., Polym. Chem. Ed. 1988, 26, 993.
26. Kosower, E.; Cotter, J. L. J. Am. Chem. Soc. 1964, 86, 5524.
27. -2 of charge passed in electropolymerization. After drying, the films became shrunk with many cracks and a part of them was peeled off, so that we failed to get a reliable relationship between the film thickness and the amount of the charge passed on electropolymerization with a laser displacement measurement.
28. +.
29. Monk, P. M. S.; Mortiner, R. J.; Rosseinsky, D. R. Electrochromism: Fundamentals and Applications; VCH: Weinheim, 1995; pp 124-142.
30. Saika, T.; Iyoda, T.; Shimidzu, T. Bull. Chem. Soc. Jpn. 1993, 66, 2054.
31. The FT-IR spectrum of the CPV film indicated that only < 7% of the 4-cyanopyridinium moiety of the trifunctional monomer remained. This small amount of the remaining, that is, unreacted, 4-cyanopyridinium moiety is a strong indication of the highly cross-linked structure in the CPV film.
32. (a) Conway, B. E. Ionic Hydration in Chemistry and Biophysics; Elsevier: New York, 1981; pp 59-74.
33. (b) Bianchi, A.; Bowman-James, K.; Garcia-Espania, E. Supramolecular Chemistry ofAnions; John Wiley & Son: New York, 1997; pp 4-9.
34. -), and hydrated ion radii (3.32, 3.30, and 3.31 by Nightingale). Considering the procedures to derive these values, actual ionic radii in the CPV film would be different from them because of much difference in ionic strength and water structure in the film. The crystallographic radii on the Goldschmidt scale were adopted here.
35. (a) Peter, F.; Gross, M.; Hosseini, M. W.; Lehn, J. M. J. Electroanal. Chem. 1983, 144, 279.
36. (b) Xu, W.; Vittal, J. J.; Puddephatt, R. J. J. Am. Chem. Soc. 1993, 115, 6456.
37. (c) Szumes, F.; Hesek, D.; Chen, Z.; Dent, S. W.; Drew, M. G. B.; Gouleden, A. J.; Graydon, A. R.; Grieve, A.; Mortimer, R. J.; Wear, T.; Weightman, J. A.; Beer, P. D. Inorg. Chem. 1996, 35, 5868.
38. 0; that is, a considerable fraction of the formed viologen should be electrochemically inactive even in the identical electrolytic solution to that used in the electropolymerization, completely different from the cases of conventional polymer-modified electrodes. This unusual feature is characterized by the cross-linked structure with the imprinted cavities.
39. Bard, A. J.; Faulkner, L. R. Electrochemical Methods; John Wiley & Sons: New York, 1980; pp 142-146.
40. -2 of charge passed.
41. (a) Oyama, N.; Yamaguchi, S.; Nishiki, Y.; Tokuda, K.; Matsuda, H.; Anson, F. J. Electroanal. Chem. Interfacial Electrochem. 1982, 139, 371.
42. (b) Ohsaka, T.; Okajima, T.; Oyama, N. J. Electroanal. Chem. Interfacial Electrochem. 1986, 215, 191.
43. (c) Buttry, D. A.; Anson, F. C. J. Am. Chem. Soc. 1983, 105, 685.
44. (d) Ruff, I.; Botar, L. J. Chem. Phys. 1985, 83, 1292.
45. (e) Ruff, I.; Botar, L. Chem. Phys. Lett. 1986, 126, 348.
46. (f) Williams, M. E.; Jeffrey, H. M.; Malik, J. W. L. J.; Murray, R. W. J. Am. Chem. Soc. 1997, 119, 1997.
47. app values should be constant in the case of a sufficiently smaller anion than the template anion, because the viologen moieties are densely and rigidly fixed to the cross-linked structure of the CPV film and therefore the electron exchange rate must be independent of the kind of the counteranions. However, the actual feature was opposite.
48. (a) The anion mobility should be depressed in the entangled structure of the polyion complex film. The cross-linked structure mentioned in this paper could much more completely achieve the anion-diffusion-controlled redox process and, therefore, be more effective at distinguishing the anion size.
49. (b) Ohsaka, T.; Nakanishi, M.; Hatozaki, O.; Oyama, N. Electrochim. Acta 1990, 35, 63.
50. (c) Shimomuya, M.; Utsugi, K.; Horikoshi, J.; Okuyama, K.; Hatozaki, O.; Oyama, N. Langmuir 1991, 7, 760.
51. The Goldschmidt's crystallographic radius of fluoride ion is 1.33 Å.
52. (a) Saurbrey, G. Z. Phys. 1959, 155, 206.
53. (b) Buttry, D. A.; Ward, M. D. Chem. Rev. 1992, 92, 1355.
54. (c) Nomura, T. Anal. Chim. Acta 1981, 124, 81.
55. (a) Nomura, T.; Nagamune, T.; West, T. S. Anal. Chim. Acta 1985, 175, 107.
56. (b) Bruckenstein, S.; Shay, M. Electrochim. Acta 1985, 30, 1295.
57. (c) Kanazawa, K. K.; Gordon, J. C., II. Anal. Chem. 1985, 57, 1771.
58. (d) Lin, Z.-X.; Yip, C. M.; Joseph, I. S.; Ward, M. D. Anal. Chem. 1993, 65, 1546.
59. -1/2, as increasing degree of dissociation of the carboxylic groups, when the pH was changed from 5 to 8. This viscosity increase corresponds to 350 Hz of ΔF in the present EQCM measurement, and therefore, one-half or one-third of the ΔF values found in the CPV film would come from the contribution from the viscosity change. Additionally, the contribution of the hydration of the mobile anion in the film should also be included.
60. (a) Sagara T.; Maeda, H.; Yuan, Y.; Nakashima, N. Langmuir 1999, 15, 3823.
61. (b) John, S. A.; Kitamura F.; Tokuda, K.; Ohsaka, T. Langmuir 2000, 16, 876.
62. (a) Peter, F.; Gross, M.; Hosseini, M. W.; Lehn, J. M.; Sessions, R. B. J. Chem. Soc., Chem. Commun. 1981, 1067.
63. (b) Arago, J.; Bencini, A.; Bianchi, A.; Domenech, A.; Garcia-Espana, E. J. Chem. Soc., Dalton Trans. 1991, 319.
64. (c) Kimura, E.; Sakonaka, A.; Yatsunami, T.; Kodama, M. J. Am Chem. Soc. 1981, 103, 3041.
65. (a) Shimidzu, T.; Ohtani, A.; Iyoda, T.; Honda, K. J. Electroanal. Chem. 1987, 224, 123.
66. (b) Iyoda, T.; Ohtani, A.; Shimidzu, T.; Honda, K. Synth. Met., 1987, 18, 725.
67. McCormick, C. L.; Elliott, D. L.; Blackmon, K. P. Macromolecules 1986, 19, 1516.
68. Okamoto, Y.; Kwei, T. K.; Vyprachticky, D. Macromolecules 1998, 31, 9201.
69. Killmann, E.; Bittler, R. J. Polym. Sci., Part C 1972, 39, 247.
70. Itaya, T.; Kawabata, Y.; Ochiai, H.; Ueda, K.; Imamura, A. Bull. Chem. Soc. Jpn. 1994, 67, 2047.