Photolithographically-patterned electroactive films and electrochemically modulated diffraction gratings

Langmuir

Volumn 16, Issue 2, 2000, Pages 795-810

  Schanze, Kirk S ^a   Bergstedt, Troy S ^a   Hauser, Brain T ^a   Cavalaheiro, Carla S P ^a,b  

^a University of Florida ^*  (United States)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC POLYMERS; CONDUCTIVE PLASTICS; DIFFRACTION GRATINGS; ELECTROCHROMISM; OSMIUM; PHOTOLITHOGRAPHY; PLASTIC FILMS; RUTHENIUM;

ELECTROACTIVE FILMS; ELECTROCHROMIC GRATINGS;

ELECTROCHEMICAL ELECTRODES;

EID: 0033640165     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la990836j     Document Type: Article

References (118)

1. Abruña, H. D., Skotheim, T. A., Ed.; Marcel Dekker: New York, 1988; Vol. 1, p 97.
2. Abruña, H. D. Coord. Chem. Rev. 1988, 86, 135-189.
3. Murray, R. W. Molecular Design of Electrode Surfaces; Wiley and Sons: New York, 1992.
4. Grundmeier, G.; Reinartz, C.; Rohwerder, M.; Stratmann, M. Electrochim. Acta 1998, 43, 165-174.
5. Offord, D. A.; Sachs, S. B.; Ennis, M. S.; Eberspacher, T. A.; Griffin, J. H.; Chidsey, C. E. D.; Collman, J. P. J. Am. Chem. Soc. 1998, 120, 4478-4487.
6. Hutchison, J. E.; Postlethwaite, T. A.; Chen, C. H.; Hathcock, K. W.; Ingram, R. S.; Ou, W.; Linton, R. W.; Murray, R. W.; Tyvoll, D. A.; Chng, L. L.; Collman, J. P. Langmuir 1997, 13, 2143-2148.
7. Leasure, R. M.; Ou, W.; Moss, J. A.; Linton, R. W.; Meyer, T. J. Chem. Mater. 1996, 8, 264-273.
8. O'Toole, T. R.; Meyer, T. J.; Sullivan, B. P. Chem. Mater. 1989, 1, 574-576.
9. Younathan, J. N.; Wood, K. S.; Meyer, T. J. Inorg. Chem. 1992, 37, 3280-3285.
10. Collombdunandsauthier, M. N.; Deronzier, A.; Ziessel, R. Inorg. Chem. 1994, 33, 2961-2967.
11. Chardon-Noblat, S.; Deronzier, A.; Ziessel, R.; Zsoldos, D. J. Electroanal. Chem. 1998, 444, 253-260.
12. Caix, C.; ChardonNoblat, S.; Deronzier, A.; Ziessel, R. J. Electroanal. Chem. 1996, 403, 189-202.
13. Hagfeldt, A.; Gratzel, M. Chem. Rev. 1995, 95, 49-68.
14. Thompson, D. W.; Kelly, C. A.; Farzad, F.; Meyer, G. J. Langmuir 1999, 15, 650-653.
15. Kelly, C. A.; Farzad, F.; Thompson, D. W.; Meyer, G. J. Langmuir 1999, 15, 731-737.
16. Moss, J. A.; Stipkala, J. M.; Yang, J. C.; Bignozzi, C. A.; Meyer, G. J.; Meyer, T. J.; Wen, X. G.; Linton, R. W. Chem. Mater. 1998, 10, 1748-1750.
17. Ricco, A. J.; Crooks, R. M. Acc. Chem. Res. 1998, 31, 200-200.
18. Reddinger, J. L.; Reynolds, J. R. Macromolecules 1997, 30, 673-675.
19. Kumar, A.; Reynolds, J. R. Macromolecules 1996, 29, 7629-7630.
20. Skotheim, T. A.; Elsenbaumer, R. L.; Reynolds, J. R. Handbook of Conducting Polymers, 2nd ed.; Marcel Dekker: New York, 1998.
21. Okano, M.; Itoh, K.; Fujishima, A.; Honda, K. Chem. Lett. 1986, 469-472.
22. Okano, M.; Itoh, K.; Fujishima, A.; Honda, K. J. Electrochem. Soc. 1987, 134, 837-841.
23. Okano, M.; Kikuchi, E.; Itoh. K.; Fujishima, A. J. Electrochem. Soc. 1988, 135, 1641-1645.
24. Yoneyama, H.; Kawai, K.; Kuwabata, S. J. Electrochem. Soc. 1988, 135, 1699-1702.
25. Zhang, H. T.; Bebel, J. C.; Hupp, J. T. J. Electroanal. Chem. 1989, 261, 423-429.
26. Wuu, Y. M.; Fan, F. R. F.; Bard, A. J. J. Electrochem. Soc. 1989, 736, 885-886.
27. Gould, S.; Otoole, T. R.; Meyer, T. J. J. Am. Chem. Soc. 1990, 112, 9490-9496.
28. Gould, S.; Gray, K. H.; Linton, R. W.; Meyer, T. J. Inorg. Chem. 1992, 31, 5521-5525.
29. Leasure, R. M.; Moss, J. A.; Meyer, T. J. Inorg. Chem. 1994, 33, 1247-1248.
30. Gould, S.; Leasure, R. M.; Meyer, T. J. Chem. Br. 1995, 31, 891-893.
31. Angelopoulos, M.; Shaw, J. M.; Lee, K. L.; Huang, W. S.; Lecorre, M. A.; Tissier, M. J. Vac. Sci. Technol., B 1991, 9, 3428-3431.
32. Yang, R.; Naoi, K.; Evans, D. F.; Smyrl, W. H.; Hendrickson, W. A. Langmuir 1991, 7, 556-558.
33. Vandyke, L. S.; Brumlik, C. J.; Martin, C. R.; Yu, Z. G.; Collins, G. J. Synth. Met. 1992, 52, 299-304.
34. Cai, S. X.; Kanskar, M.; Nabity, J. C.; Keana, J. F. W.; Wybourne, M. N. J. Vac. Sci. Technol., B 1992, 10, 2589-2592.
35. Huang, W. S. Polymer 1994, 35, 4057-4064.
36. Lowe, J.; Holdcroft, S. Macromolecules 1995, 28, 4608-4616.
37. Lowe, J.; Holdcroft, S. Synth. Met. 1997, 85, 1427-1430.
38. Yu, J. F.; Abley, M.; Yang, C.; Holdcroft, S. J. Chem. Soc., Chem. Commun. 1998, 1503-1504.
39. Wu, Y.; Pfennig, B. W.; Bocarsly, A. B.; Vicenzi, E. P. Inorg. Chem. 1995, 34, 4262-4267.
40. Bocarsly, A. B.; Chang, C. C.; Wu, Y.; Vicenzi, E. P. J. Chem. Educ. 1997, 74, 663-667.
41. Renak, M. L.; Bazan, G. C.; Roitman, D. Adv. Mater. 1997, 9, 392-395.
42. Gigli, G.; Rinaldi, R.; Turco, C.; Visconti, P.; Cingolani, R. App. Phys. Lett. 1998, 73, 3926-3928.
43. Lidzey, D. G.; Bradley, D. D. C.; Martin, S. J.; Pate, M. A. IEEE J. Quantum Electron. 1998, 4, 113-118.
44. Wong, T. K. S.; Gao, S.; Hu, X.; Liu, H.; Chan, Y. C.; Lam, Y. L. Mater. Sci. Eng., B 1998, 55, 71-78.
45. Pede, D.; Serra, G.; De Rossi, D. Mater. Sci. Eng., C 1998, 5, 289-291.
46. Kobayashi, N.; Teshima, K.; Hirohashi, R. J. Mater. Chem. 1998, 8, 497-506.
47. Persson, S. H. M.; Dyreklev, P.; Inganas, O. Adv. Mater. 1996, 8, 405-408.
48. Huang, Z. Y.; Wang, P. C.; MacDiarmid, A. G.; Xia, Y. N.; Whitesides, G. Langmuir 1997, 13, 6480-6484.
49. Chang, S.-C.; Bharathan, J.; Yang, Y.; Helgeson, R.; Wudl, F.; Ramey, M.; Reynolds, J. R. Appl. Phys. Lett. 1998, 73, 2561-2563.
50. Smela, E. J. Micromech. Microeng. 1999, 9, 1-18.
51. By arbitrary we mean that the electroactive materials can be patterned in the plane of the electrode surface into any microstructure defined by the user, regardless of the shape of the electrode. Note that Wrighton and co-workers pioneered the use of microelectrode arrays to produce (nonarbitrary) patterns of electroactive materials (ref 52).
52. Natan, M. J.; Wrighton, M. S. Prog. Inorg. Chem. 1989, 37, 391-494.
53. Hauser, B. T.; Bergstedt, T. S.; Schanze, K. S. J. Chem. Soc., Chem. Commun. 1995, 19, 1945-1946.
54. Bergstedt, T. S.; Hauser, B. T.; Schanze, K. S. J. Am. Chem. Soc. 1994, 116, 8380-8381.
55. Schanze, K. S.; Bergstedt, T. S.; Hauser, B. T. Adv. Mater. 1996, 8, 531.
56. Joannopoulos, J. D. Photonic Crystals: Molding the Flow of Light; Princeton University Press: Princeton, NJ, 1995.
57. Yoshino, K.; Kawagishi, Y.; Tatsuhara, S.; Kajii, H.; Lee, S.; Fujii, A.; Ozaki, M.; Zakhidov, A. A.; Vardeny, Z. V.; Ishikawa, M. Microelectron. Eng. 1999, 47, 49-53.
58. Caspar, J. V.; Meyer, T. J. Inorg. Chem. 1983, 22, 2444-2453.
59. Yang, R.; Evans, D. F.; Hendrickson, W. A. Langmuir 1995, 11, 211-213.
60. The Honda group reported the use of the photo voltage effect to selectively carry out electropolymerization in an illuminated region of an electrode surface prior to Hupp's report.
61. Abruña, H. D.; Desisevich, P.; Umaña, M.; Meyer, T. J.; Murray, R. W. J. Am. Chem. Soc. 1981, 103, 1-5.
62. Unless otherwise noted, all potentials are reported relative to an Ag/AgCl reference electrode.
63. Murray, R. W. Introduction to the Chemistry of Molecularly Designed Surfaces; Murray, R. W., Ed.; John Wiley and Sons: New York, 1992; Vol. 22, pp 1-48.
64. A diffraction pattern produced when a He-Ne laser beam impinges onto a poly-VBV/PETA grating is shown on the cover of this issue of Langmuir.
65. Lewis, T. J.; White, H. S.; Wrighton, M. S. J. Am. Chem. Soc. 1984, 106, 6947-6955.
66. Dalton, D. F.; Murray, R. W. J. Phys. Chem. 1991, 95, 6383-6389.
67. Hatozaki, O.; Ohsaka, T.; Oyama, N. J. Phys. Chem. 1992, 96, 10492-10497.
68. Ostrom, G. S.; Buttry, D. A. J. Phys. Chem. 1995, 99, 15236-15240.
69. Terrill, R. H.; Hutchison, J. E.; Murray, R. W. J. Phys. Chem. B 1997, 101, 1535-1542.
70. Bookbinder, D. C.; Wrighton, M. S. J. Electrochem. Soc. 1983, 130, 1080-1087.
71. Dominey, R. N.; Lewis, T. J.; Wrighton, M. S. J. Phys. Chem. 1983, 87, 5345-5354.
72. Smith, D. K.; Lane, G. A.; Wrighton, M. S. J. Am. Chem. Soc. 1988, 92, 2616-2628.
73. Johansen, O.; Loder, J. W.; Mau, A. W.-H.; Rabani, J.; Sasse, W. H. F. Langmuir 1992, 8, 2577-2581.
74. Schlenoff, J. B.; Laurent, D.; Ly, H.; Stepp, J. Adv. Mater. 1998, 10, 347-349.
75. Since the fully oxidized poly-VBV/PETA film is transparent for λ > 350 nm, the difference spectra shown in Figure 5 closely correspond to the true absorption of the film in two reduced states.
76. Kosower, E. M.; Cotter, J. C. J. Am. Chem. Soc. 1964, 86, 5524-5527.
77. Imabayashi, S.; Kitamura, N.; Tazuke, S.; Tokuda, K. J. Electroanal. Chem. 1988, 243, 143-160.
78. Tang, X.; Schneider, T. W.; Walker, J. W.; Buttry, D. A. Langmuir 1996, 12, 5921-5933.
79. Odian, G. Principles of Polymerization, 3rd ed.; Wiley-Interscience: New York, 1991.
80. Calvert, J. M.; Schmehl, R. H.; Sullivan, B. P.; Facci, J. S.; Meyer, T. J.; Murray, R. W. Inorg. Chem. 1983, 22, 2151-2162.
81. Pickup, P. G.; Murray, R. W. J. Am. Chem. Soc. 1983, 105, 4510-4514.
82. Miller, R. D.; Hofer, D.; Fickes, G. N.; Willson, C. G.; Marinero, E.; Trefonas, P., III; West, R. Polym. Eng. Sci. 1986, 26, 1129-1134.
83. Miller, R. D.; Michl, J. Chem. Rev. 1989, 89, 1359-1410.
84. Tachibana, Y.; Sakurai, Y.; Yokoyama, M. Chem. Lett. 1994, 1119-1122.
85. 2). Thus, we attribute the improved adhesion of the polymer lines in the grating pattern to the larger area under a line.
86. Attempts to prepare thicker films by cycling for a longer period of time invariably lead to a decrease in the spatial resolution.
87. Denisevich, P.; Abruña, H. D.; Leidner, C. R.; Meyer, T. J.; Murray, R. W. Inorg. Chem. 1982, 21, 2153-2161.
88. Pei, Q.; Zuccarello, G.; Ahlskog, M.; Iganäs, O. Polymer 1994, 35, 1347-1351.
89. Sankaran, B.; Reynolds, J. R. Macromolecules 1997, 30, 2582-2588.
90. Sotzing, G. A.; Reynolds, J. R.; Steel, P. J. Adv. Mater. 1997, 9, 795-797.
91. Irvin, J. A.; Reynolds, J. R. Polymer 1998, 39, 2339-2347.
92. The monomers MDOT-Acr and MDOT-Dec were prepared by acylation of the alcohol-substituted thiophene monomer using acryloyl chloride and decanolyl chloride. The alcohol-substituted thiophene monomer was prepared by a modified literature procedure (refs 93 and 94).
93. Blohm, M. L.; Pickett, J. E.; VanDort, P. C. Substituted 3,4-Polymethylenedioxythiophenes, and Polymers and Electroresponsive Devices made Therefrom. U.S. Patent 5,111,327, 1993.
94. Stephan, O.; Schottland, P.; Le Gall, P.-Y.; Chevrot, C.; Mariet, C.; Carrier, M. J. Electroanal. Chem. 1998, 443, 217-226.
95. 3CN solution of MDOT-Acr (c = 5 mM and 10 potential cycles from -1.0 to -1.8 V).
96. 0.
97. Several other groups have reported the fabrication of gratings that can be switched by an electronic or electrochemical stimulus (refs 98-101).
98. Zhang, J.; Carlen, C. R.; Palmer, S.; Sponsler, M. B. J. Am. Chem. Soc. 1994, 116, 7055-7063.
99. Lindquist, R. G.; Kulick, J. H.; Nordin, G. P.; Jarem, J. M.; Kowel, S. T.; Friends, M. Opt. Lett. 1994, 19, 670-672.
100. Whitney, D. H.; Ingwall, R. T. SPIE Vol. 1213 Photopolymer Device Physics, Chemistry, and Applications 1990, 1213, 18-26.
101. Sainov, S.; Mazakova, M.; Pantcheva, M.; Tontchev, D. Mol. Cryst. Liq. Cryst. 1987, 152, 609-615.
102. Tomlinson, W. J.; Chandross, E. A. Adv. Photochem. 1980, 12, 201-281.
103. Collier, R. J.; Burckhardt, C. B. Optical Holography, Academic Press: New York, 1971.
104. The absorptivity k is a unitless number and is related to the optical density (OD) of a film by the expression k = (2.3λ OD)/(4πT), where T is the film thickness.
105. Fayer, M. D. Annu. Rev. Phys. Chem. 1982, 33, 63-87.
106. Nelson, K. A.; Casalegno, R.; Miller, R. J. D.; Fayer, M. D. J. Chem. Phys. 1982, 77, 1144-1152.
107. Monk, P. M. S.; Mortimer, R. J.; Rosseinsky, D. R. Electrochromism: Fundamentals and Applications; VCH: Weinheim, 1995.
108. Redondo, A.; Ticianelli, E. A.; Gottesfeld, S. Synth. Met. 1989, 29, E265-E270.
109. Gottesfeld, S. Electroanal. Chem. 1989, 15, 143-265.
110. Redondo, A.; Ticianelli, E. A.; Gottesfeld, S. Mol. Cryst. Liq. Cryst. 1988, 160, 185-203.
111. These parameters correspond to a poly-VBV/PETA grating immersed in DMF solvent.
112. •+ redox state.
113. Wooten, F. Optical Properties of Solids; Academic Press: New York, 1972.
114. Olbright, G. R.; Peyghambarian, N. App. Phys. Lett. 1986, 48, 1184-1186.
115. -1 at a concentration of 1.0 M.
116. Sapp, S. A.; Sotzing, G. A.; Reddinger, J. L.; Reynolds, J. R. Adv. Mater. 1996, 8, 808-810.
117. Maness, K. M.; Masui, H.; Wightman, R. M.; Murray, R. W. J. Am. Chem. Soc. 1997, 119, 3987-3993.
118. Long, J. W.; Kim, K.; Murray, R. W. J. Am. Chem. Soc. 1997, 119, 11510-11515.