Hexyl-derivatized poly(3,4-ethylenedioxyselenophene): Novel highly stable organic electrochromic material with high contrast ratio, high coloration efficiency, and low-switching voltage

Advanced Materials

Volumn 21, Issue 17, 2009, Pages 1707-1711

  Li, Mao ^a   Patra, Asit ^a   Sheynin, Yana ^a   Bendikov, Michael ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

AG/AGCL; ALKYL CHAIN; BAND GAPS; COATED GLASS; COLORATION EFFICIENCIES; CONSTANT POTENTIAL; ELECTROCHROMIC; ELECTROCHROMIC MATERIALS; HIGH CONTRAST RATIO; INDIUM TIN OXIDE; POLYMER BACKBONES; POLYSELENOPHENE; SWITCHING VOLTAGES;

ELECTRIC CONDUCTIVITY MEASUREMENT; ELECTROCHROMISM; ENERGY GAP; OXIDE FILMS; TIN;

INDIUM;

EID: 66149134018     PISSN: 09359648     EISSN: None     Source Type: Journal    
DOI: 10.1002/adma.200802259     Document Type: Article

References (48)

1. a) P. M. S. Monk, R. J. Mortimer, D. R. Rosseinsky, in Electrochromism: Fundamentals and Applications, Wiley-VCH, Weinheim, Germany 1995.
2. b) A. L. Dyer, J. R. Reynolds, in Handbook of Conducting Polymers. Conjugated Polymers: Theory, Synthesis, Properties, and Characterization, 3nd ed. (Eds: T. A. Skotheim, J. R. Reynolds), CRC Press, Boca Raton, FL, USA 2007, Ch. 20.
3. c) R. J. Mortimer, Chem. Soc. Rev. 1997, 26, 147.
4. d) D. R. Rosseinsky, R. J. Mortimer, Adv. Mater. 2001, 13, 783.
5. e) K. Bange, T. Bambke, Adv. Mater. 1990, 2, 10.
6. a) A. A. Argun, A. Cirpan, J. R. Reynolds, Adv. Mater. 2003, 15, 1338.
7. b) S. I. Cho, W. J. Kwon, S. Choi, P. Kim, S. Park, J. Kim, S. J. Son, R. Xiao, S. Kim, S. B. Lee, Adv. Mater. 2005, 17, 171.
8. c) H. Meng, D. Tucker, S. Chaffins, Y. Chen, R. Helgeson, B. Dunn, F. Wudl, Adv. Mater. 2003, 15, 146.
9. d) A. L. Dyer, C. R. G. Grenier, J. R. Reynolds, Adv. Funct. Mater. 2007, 17, 1480.
10. D. M. DeLongchamp, M. Kastantin, P. T. Hammond, Chem.Mater. 2003, 15, 1575.
11. K Krishnamoorthy,, A. V. Ambade, M. Kanungo, A. Q. Contractor, A. J. Kumar, J. Mater. Chem. 2001, 11, 2909.
12. a) G. Sonmez, H. Meng, F. Wudl, Chem. Mater. 2004, 16, 574.
13. b) G. Sonmez, H. Meng, Q. Zhang, F. Wudl, Adv. Funct. Mater. 2003, 13, 726.
14. a) L. Groenendaal, F. Jonas, D. Freitag, H. Pielartzik, J. R. Reynolds, Adv. Mater. 2000, 12, 481.
15. b) L. Groenendaal, G. Zotti, P. H. Aubert, S. M. Waybright, J. R. Reynolds, Adv. Mater. 2003, 15, 855.
16. a) G. Heywang, F. Jonas, Adv. Mater. 1992, 4, 116.
17. b) G. A. Sotzing, J. R. Reynolds, P. J. Steel, Adv. Mater. 1997, 9, 795.
18. c) H. W. Heuer, R. Wehrmann, S. Kirchmeyer, Adv. Funct. Mater. 2002, 12, 89.
19. d) B. Sankaran, J. R. Reynolds, Macromolecules 1997, 30, 2582.
20. e) I. Schwendeman, C. L. Gaupp, J. M. Hancock, L. Groenendaal, J. R. Reynolds, Adv. Funct. Mater. 2003, 13, 541.
21. f) C. Wang, J. L. Schindler, C. R. Kannewurf, M. G. Kanatzidis, Chem. Mater. 1995, 7, 58.
22. g) D. M. Welsh, A. Kumar, E. W. Meijer, J. R. Reynolds, Adv. Mater. 1999, 11, 1379.
23. h) D. M. Welsh, L. J. Kloeppner, L. Madrigal, M. R. Pinto, B. C. Thompson, K. S. Schanze, K. A. Abboud, D. Powell, J. R. Reynolds, Macromolecules 2002, 35, 6517.
24. i) B. D. Reeves, B. C. Thompson, K. A. Abboud, B. E. Smart, J. R. Reynolds, Adv. Mater. 2002, 14, 717.
25. C. L. Gaupp, D.M. Welsh, J. R. Reynolds, Macromol. Rapid Commun. 2002, 23, 885.
26. G. L. Gaupp, D. M. Welsh, R. D. Rauh, J. R. Reynolds, Chem. Mater. 2002, 14, 3964.
27. A. Kumar, D. M. Welsh, M. C. Morvant, F. Piroux, K. A. Abboud, J. R. Reynolds, Chem. Mater. 1998, 10, 896.
28. -1 at 95% of a full switch was reported by Skabara's group. R. Berridge, S. P. Wright, P. J. Skabara, A. Dyer, T. Steckler, A. A. Argun, J. R. Reynolds, R. W. Harringtond, W. Clegg, J. Mater. Chem. 2007, 17, 225.
29. a) S. A. Sapp, G. A. Sotzing, J. R. Reynolds, Chem. Mater. 1998, 10, 2101.
30. b) G. Sonmez, H. B. Sonmez, K. F. Shen, R. W. Jost, Y. Rubin, F. Wudl, Macromolecules 2005, 38, 669.
31. c) I. Schwendeman, R. Hickman, G. Sonmez, P. Schottland, K. Zong, D. M. Welsh, J. R. Reynolds, Chem. Mater. 2002, 14, 3118.
32. a) Q. Pei, G. Zuccarello, M. Ahlskog, O. Inganäs, Polymer 1994, 35, 1347.
33. b) M. Dietrich, J. Heinze, G. Heywang, F. Jonas, J. Electroanal. Chem. 1994, 369, 87.
34. c) J. C. Gustafsson, B. Liedberg, O. Inganäs, Solid State Ionics 1994, 69, 145.
35. B. D. Reeves, C. R. G. Grenier, A. A. Argun, A. Cirpan, T. D. McCarley, J. R. Reynolds, Macromolecules 2004, 37, 7559.
36. -1 were obtained by spin-coating a solution processable conducting polymer: C. G. Wu, M. I. Lu, S. J. Chang, C. S. Wei, Adv. Funct. Mater. 2007, 17, 1063.
37. M. Catellani, C. Arbizzani, M. Mastragostino, A. Zanelli, Synth. Met. 1995, 69, 373.
38. A. Patra, Y. H. Wijsboom, S. S. Zade, M. Li, Y. Sheynin, G. Leitus, M. Bendikov, J. Am. Chem. Soc. 2008, 130, 6734.
39. The calculated (PBC/B3LYP/6-31G(d)) HOCO and LUCO levels for PEDOS at k=0 are -3.45 eV and -1.79 eV, respectively. For comparison, the HOCO and LUCO levels of PEDOT at k=0 are -3.54 eV and -1.69 eV, respectively (ref. 16).
40. 4 was used as a supporting electrolyte in acetonitrile and the polymer was obtained by cyclic voltammetry.
41. -2 based on the data in Figure 1.
42. c are the transmittance in the bleached and colored states, respectively. For more details, see ref. [1a,e].
43. All CE values reported in this paper were measured at 100% of a full switch, which corresponds to the highest contrast ratio. We note that even higher CE values can be obtained by narrowing the switching potential window; however the contrast ratio will be compromised. See ref. [8] for details.
44. All Calculations were performed using the Gaussian 03 program. Gaussian 03, Revision C.02, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and J. A. Pople, Gaussian, Inc., Wallingford CT, USA 2004. See Supporting Information for details.
45. 6 at k=0 are -3.38 eV and -1.55 eV, respectively.
46. -2 based on the data in Figure 3a and b.
47. -1 was routinely obtained in several experiments.
48. F. Yalcinkaya, E. T. Powner, Med. Eng. Phys. 1997, 19, 299.