Citation: OUYANG Mi, FU Zhi-Yan, LÜ Xiao-Jing, CHEN Huan-Le, HU Bin, XIA Xu-Feng, ZHANG Cheng. Enhanced Film-Forming and Electrochromic Properties by Incorporating Bithiophene into Triphenylamine[J]. Acta Physico-Chimica Sinica, ;2013, 29(05): 996-1002. doi: 10.3866/PKU.WHXB201302282 shu

Enhanced Film-Forming and Electrochromic Properties by Incorporating Bithiophene into Triphenylamine

1.
State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, International Science & Technology Cooperation Base of Energy Materials and Application, College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014, P. R. China

Received Date: 7 December 2012
Available Online: 28 February 2013
Fund Project: 国家重点基础研究发展计划(973)前期专项项目(2010CB635108, 2011CBA00700) (973)前期专项项目(2010CB635108, 2011CBA00700) 国际科技合作重点项目计划(2012DFA51210) (2012DFA51210)国家自然科学基金(51203138, 51273179)资助 (51203138, 51273179)

An electrochromic (EC) material consisting of triphenylamine (TPA) core and peripheral bithiophene groups was synthesized, and the corresponding polymer was prepared by electrochemical oxidative cross-linking. The electrochemical properties of the 4,4',4?-tris[4-(2-bithienyl)phenyl]amine (TBTPA) monomer, and spectroelectrochemical and electrochromic properties of the poly(4,4',4?-tris [4-(2-bithienyl)phenyl]amine) (PTBTPA) polymer, were also systematically investigated. TBTPA possessing two thiophene groups exhibited better redox reversibility than that of the reported tris[4-(2-thienyl)phenyl] amine (TTPA). During electropolymerization, PTBTBA exhibited excellent film-forming property and strong adhesion to the ITO electrode, satisfying the basic requirements for achieving high EC performance. PTBTPA exhibited three different colors under various potentials (darkorange, olivegreen and dimgray). PTBTPA indicated enhanced EC performances and a higher contrast ratio of 44.7% compared with that of reported poly(tris[4-(2-thienyl)phenyl]amine) (PTTPA). PTBTPA also exhibited a higher optical contrast (ΔT) of 49% and 52% at 720 and 1100 nm, respectively. It showed fast switching responses of 0.93 and 0.91 s at 720 and 1100 nm, respectively, and higher coloration efficiencies of 198 and 285 cm²·C^-1 at 720 and 1100 nm, respectively. Scanning electron microscopy (SEM) revealed that the PTBTPA film surface had accumulated clusters of globules, which were smaller than those of PTTPA. The superior performances of PTBTPA suggested its potential as an efficient EC material.
- Triphenylamine core,
- Electropolymerization,
- Film-forming,
- Electrochromism,
- High optical contrast
1. [1]
  
  (1) Argun, A. A.; Aubert, P. H.; Thompson, B. C.; Schwendeman, I.;Gaupp, C. L.; Hwang, J.; Pinto, N. J.; Tanner, D. B.;MacDiarmid, A. G.; Reynolds, J. R. Chem. Mater. 2004, 16,4401. doi: 10.1021/cm049669l
2. [2]
  (2) Verghese, M. M.; Ram, M. K.; Vardhan, H.; Malhotra, B. D.;Ashraf, S. M. Polymer 1997, 38, 1625. doi: 10.1016/S0032-3861(96)00655-6
3. [3]
  (3) Beaupré, S.; Dumas, J.; Leclerc, M. Chem. Mater. 2006, 18,4011. doi: 10.1021/cm060407o
4. [4]
  (4) Quinto, M.; Bard, A. J. J. Electroanal. Chem. 2001, 498, 67.doi: 10.1016/S0022-0728(00)00266-7
5. [5]
  (5) Azens, A.; Granqvist, C. G. J. Solid State Electrochem. 2003, 7,64.
6. [6]
  (6) Heuer, H.W.;Wehrmann, R.; Kirchmeyer, S. Adv. Funct. Mater.2002, 12, 89. doi: 10.1002/(ISSN)1616-3028
7. [7]
  (7) Mortimer, R. J.; Dyer, A. L.; Reynolds, J. R. Displays 2006, 27,2. doi: 10.1016/j.displa.2005.03.003
8. [8]
  (8) Shah, J.; Brown, R. M., Jr. Appl. Microbiol. Biotechnol. 2005,66, 352. doi: 10.1007/s00253-004-1756-6
9. [9]
  (9) Sapp, A. S.; Sotzing, A. G.; Reynolds, J. R. Chem. Mater. 1998,10, 2101. doi: 10.1021/cm9801237
10. [10]
  (10) Chu, Z. Z.;Wang, D.; Zhang, C.; Zou. D. C. Acta Phys. -Chim.Sin. 2012, 28 (8), 2000. [初增泽, 王丹, 张超, 邹德春.物理化学学报, 2012, 28 (8), 2000.] doi: 10.3866/PKU.WHXB201206071
11. [11]
  (11) Pei, J.; Liang, M.; Chen, J.; Tao, Z. L.; Xu,W. Acta Phys. -Chem.Sin. 2008, 24 (11), 1950. [裴娟, 梁茂, 陈军, 陶占良,许炜. 物理化学学报, 2008, 24 (11), 1950.] doi: 10.1016/S1872-1508(08)60077-7
12. [12]
  (12) Hagberg, D. P.; Edvinsson, T.; Marinado, T.; Boschloo, G.;Hagfeldt, A.; Sun, L. C. Chem. Commun. 2006, No. 21, 2245.
13. [13]
  (13) Karthikeyan, C. S.; Peter, K.;Wietasch, H.; Thelakkat, M. Sol.Energy Mater. Sol. Cells 2007, 91, 432. doi: 10.1016/j.solmat.2006.10.006
14. [14]
  (14) Nelson, R. F.; Adams, R. N. J. Am. Chem. Soc. 1968, 90, 3925.doi: 10.1021/ja01017a004
15. [15]
  (15) Lapkowskia, M.; lba, S.; Soloduchoc, J.; Idzikc, K. SyntheticMet. 2009, 159, 2202. doi: 10.1016/j.synthmet.2009.09.005
16. [16]
  (16) Zhang, C.;Wang, G. H.; Ouyang, M. J. Electroanal. Chem.2011, 660, 45. doi: 10.1016/j.jelechem.2011.06.002
17. [17]
  (17) Idzika, K.; Soloducho, J.; Lapkowski, M.; lba, S.;Electrochim. Acta 2008, 53, 5665. doi: 10.1016/j.electacta.2008.03.019
18. [18]
  (18) Chiu, K. Y.; Su, T. X.; Li, J. H.; Lin, T. H.; Liou, G. S.; Cheng,S. H. J. Electroanal. Chem. 2005, 575, 95. doi: 10.1016/j.jelechem.2004.09.005
19. [19]
  (19) Cheng, X. F.; Zhao, J. S.; Cui, C. S.; Fu, Y. Z.; Zhang, X. X.J. Electroanal. Chem. 2012, 677-680, 24.
20. [20]
  (20) Cho, J. S.; Uchida, K.; Yoshioka, N.; Yamamoto, K. Sci.Technol. Adv. Mat. 2004, 5, 697. doi: 10.1016/j.stam.2004.03.006
21. [21]
  (21) Ouyang, M.;Wang, G. H.; Zhang, C. Electrochim. Acta 2011,56, 4645. doi: 10.1016/j.electacta.2011.02.103
22. [22]
  (22) Gu, C.; Liu, H.; Hu, D. H.; Zhang,W. S.; Lv, Y.; Lu, P.; Lu, D.;Ma, Y. G. Macromol. Rapid Commun. 2011, 32, 1014. doi: 10.1002/marc.v32.13
23. [23]
  (23) Sonmez, G.; Schwendeman, I.; Schottland, P.; Zong, K.;Reynolds, J. R. Macromolecules 2003, 36, 639. doi: 10.1021/ma021108x
24. [24]
  (24) Gu, C.; Dong,W. Y.; Yao, L.; Lv, Y.; Zhang, Z. B.; Lu, D.; Ma,Y. G. Adv. Mater. 2012, 24, 2413. doi: 10.1002/adma.201200559
25. [25]
  (25) Sonmez, G. Chem. Commun. 2005, No. 42, 5251.
26. [26]
  (26) Beyazyildirim, S.; Camurlu, P.; Yilmaz, D.; Gullu, M.; Toppare,L. J. Electroanal. Chem. 2006, 587, 235. doi: 10.1016/j.jelechem.2005.11.018
27. [27]
  (27) Akpinar, H.; Balan, A.; Baran, D.; ünver, E. K.; Toppare, L.Polymer 2010, 51, 6123. doi: 10.1016/j.polymer.2010.10.045
28. [28]
  (28) Deepa, M.; Awadhia, A.; Bhandari, S. Phys. Chem. Chem. Phys.2009, 11, 5674.
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