偶联噻吩引入对三苯胺成膜性提高及电致变色性能增强

doi:10.3866/PKU.WHXB201302282

Abstract

Abstract:

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.

Key words: Triphenylamine core, Electropolymerization, Film-forming, Electrochromism, High optical contrast

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 Phys. -Chim. Sin. 2013, 29(05), 996-1002. doi: 10.3866/PKU.WHXB201302282

References

(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) 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) Beaupré, S.; Dumas, J.; Leclerc, M. Chem. Mater. 2006, 18,4011. doi: 10.1021/cm060407o
(4) Quinto, M.; Bard, A. J. J. Electroanal. Chem. 2001, 498, 67.doi: 10.1016/S0022-0728(00)00266-7
(5) Azens, A.; Granqvist, C. G. J. Solid State Electrochem. 2003, 7,64.
(6) Heuer, H.W.;Wehrmann, R.; Kirchmeyer, S. Adv. Funct. Mater.2002, 12, 89. doi: 10.1002/(ISSN)1616-3028
(7) Mortimer, R. J.; Dyer, A. L.; Reynolds, J. R. Displays 2006, 27,2. doi: 10.1016/j.displa.2005.03.003
(8) Shah, J.; Brown, R. M., Jr. Appl. Microbiol. Biotechnol. 2005,66, 352. doi: 10.1007/s00253-004-1756-6
(9) Sapp, A. S.; Sotzing, A. G.; Reynolds, J. R. Chem. Mater. 1998,10, 2101. doi: 10.1021/cm9801237
(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) 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) Hagberg, D. P.; Edvinsson, T.; Marinado, T.; Boschloo, G.;Hagfeldt, A.; Sun, L. C. Chem. Commun. 2006, No. 21, 2245.
(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) Nelson, R. F.; Adams, R. N. J. Am. Chem. Soc. 1968, 90, 3925.doi: 10.1021/ja01017a004
(15) Lapkowskia, M.; Golba, S.; Soloduchoc, J.; Idzikc, K. SyntheticMet. 2009, 159, 2202. doi: 10.1016/j.synthmet.2009.09.005
(16) Zhang, C.;Wang, G. H.; Ouyang, M. J. Electroanal. Chem.2011, 660, 45. doi: 10.1016/j.jelechem.2011.06.002
(17) Idzika, K.; Soloducho, J.; Lapkowski, M.; Golba, S.;Electrochim. Acta 2008, 53, 5665. doi: 10.1016/j.electacta.2008.03.019
(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) Cheng, X. F.; Zhao, J. S.; Cui, C. S.; Fu, Y. Z.; Zhang, X. X.J. Electroanal. Chem. 2012, 677-680, 24.
(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) Ouyang, M.;Wang, G. H.; Zhang, C. Electrochim. Acta 2011,56, 4645. doi: 10.1016/j.electacta.2011.02.103
(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) Sonmez, G.; Schwendeman, I.; Schottland, P.; Zong, K.;Reynolds, J. R. Macromolecules 2003, 36, 639. doi: 10.1021/ma021108x
(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) Sonmez, G. Chem. Commun. 2005, No. 42, 5251.
(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) Akpinar, H.; Balan, A.; Baran, D.; ünver, E. K.; Toppare, L.Polymer 2010, 51, 6123. doi: 10.1016/j.polymer.2010.10.045
(28) Deepa, M.; Awadhia, A.; Bhandari, S. Phys. Chem. Chem. Phys.2009, 11, 5674.

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[12]	Guan Zi-Sheng, Ma Ying, Cao Ya-An, Ji Xue-Hai, Yao Jian-Nian. Characterization of the Photochromic and Electrochromic Titania Gel [J]. Acta Phys. -Chim. Sin., 2000, 16(01): 5-8.
[13]	Guan Zi-Sheng, Yang Yong-An, Ma Ying, Yao Jian-Nian. Raman Study of the Electrochromic V₂O₅ Films [J]. Acta Phys. -Chim. Sin., 1999, 15(03): 279-283.
[14]	Wu Zheng-Hua,Qiu Si-Chou,Huang Han-Yao,He Hua-Hui. Study on the Characteristics and Mechanism of Electrochromism of NiO_xH_y Thin Film [J]. Acta Phys. -Chim. Sin., 1996, 12(07): 615-620.
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Enhanced Film-Forming and Electrochromic Properties by Incorporating Bithiophene into Triphenylamine

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