Citation: Emine Gul Cansu-Ergun. Covering the More Visible Region by Electrochemical Copolymerization of Carbazole and Benzothiadiazole Based Donor-Acceptor Type Monomers[J]. Chinese Journal of Polymer Science, ;2019, 37(1): 28-35. doi: 10.1007/s10118-019-2181-8 shu

Covering the More Visible Region by Electrochemical Copolymerization of Carbazole and Benzothiadiazole Based Donor-Acceptor Type Monomers

Emine Gul Cansu-Ergun ^,

Department of Electrical and Electronics Engineering, Baskent University, TR-06810 Ankara, Turkey

Corresponding author: Emine Gul Cansu-Ergun, egulcansu@baskent.edu.tr
Received Date: 22 June 2018
Revised Date: 10 August 2018
Accepted Date: 13 August 2018
Available Online: 5 September 2018

An electrochromic copolymer film of 2-(3,3-dihexyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepin-6-yl)-7-(3,3-dihexyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepin-8-yl)-9H-carbazole ( M1 ) and 4,7-bis(thiophen-2-yl)benzo[c][1,2,5]thiadiazole ( M2 ) was prepared via electrochemical technique. The copolymerization was performed with one to one monomer feed ratio. Electrochemical and optical properties of the resulting copolymer film ( P3 ) and the homopolymer films of M1 and M2 ( P1 and P2 ) were investigated by using cyclic voltammetry and UV-Vis spectrometry techniques, and the corresponding results were compared. Incorporation of M1 and M2 into copolymer matrix was clearly observed on the resulting cyclic voltammograms and UV-Vis spectra. P3 covered the visible regions coming from both P1 and P2 , and exhibited a neutral state darker color than those of homopolymers. P3 film was found to have a multichromic behavior, appearing as brown in its neutral state while changing its color upon oxidation to dark-gray (at about 0.3 V), to blue (at about 0.6 V) and finally to grayish cyan (beyond 0.9 V), with a corresponding optical band gap of 1.65 eV.
- Electrochemical polymerization,
- Copolymer,
- Electrochromic polymers
1. [1]
  Pennisi, A.; Simone, F.; Barletta, G.; Di Marco, G.; Lanza, L. Preliminary test of a large electrochromic window. Electrochim. Acta 1999, 44, 3237-3243. doi: 10.1016/S0013-4686(99)00042-0
2. [2]
  Rauh, R. Electrochromic Windows: an overview. Electrochim. Acta 1999, 44, 3165-3176. doi: 10.1016/S0013-4686(99)00034-1
3. [3]
  Mortimer, R. G. Electrochromic materials. Chem. Soc. Rev. 1997, 26, 147-156. doi: 10.1039/cs9972600147
4. [4]
  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. Multicolored electrochromism in polymers: structures and devices. Chem. Mater. 2004, 16, 4401-4412. doi: 10.1021/cm049669l
5. [5]
  Mortimer, R. J.; Dyer, A. L.; Reynolds, J. R. Electrochromic organic and polymeric materials for display applications. Displays 2006, 27, 2-18. doi: 10.1016/j.displa.2005.03.003
6. [6]
  Bradley, D. D. C. Conjugated polymer electroluminescence. Synt. Met. 1993, 54, 401-415. doi: 10.1016/0379-6779(93)91086-H
7. [7]
  Kelly, F. M.; Meunier, L.; Cochrane, C.; Koncar, V. Polyaniline: application as solid state electrochromic in a flexible textile display. Displays 2013, 34, 1-7. doi: 10.1016/j.displa.2012.10.001
8. [8]
  Lee, K.; Povlich, L. K.; Kim, J. Recent advances in fluorescent and colorimetric conjugated polymer-based biosensors. Analyst 2010, 135, 2179-2189. doi: 10.1039/c0an00239a
9. [9]
  Dance, Z. E. X.; Ahrens, M. J.; Vega, A. M.; Ricks, A. B.; McCamant, D. W.; Ratner, M. A.; Wasielewski, M.R. Direct observation of the preference of hole transfer over electron transfer for radical ion pair recombination in donor-bridge-acceptor molecules. J. Am. Chem. Soc. 2008, 130, 830-832. doi: 10.1021/ja077386z
10. [10]
  Sonmez, G.; Sonmez, H. B.; Shen, C. K. F.; Jost, R. W.; Rubin, Y.; Wudl, F. A processable green polymeric electrochromic. Macromolecules 2005, 38, 669-675. doi: 10.1021/ma0484173
11. [11]
  Zhou, H.; Yang, L.; Stuart, A. C.; Price, S. C.; Liu, S.; You, W. Development of fluorinated benzothiadiazole as a structural unit for a polymer solar cell of 7% efficiency. Angew. Chem. 2011, 50, 2885-2998. doi: 10.1002/anie.201100453
12. [12]
  Song, S.; Jin, Y.; Kim, S. H.; Shim, J. Y.; Son, S.; Kim, I.; Lee, K.; Suh, H. Synthesis and characterization of polyfluorenevinylene with cyano group and carbazole unit. J. Polym. Sci. Part A: Pol. Chem. 2009, 47, 6540-6551. doi: 10.1002/pola.v47:23
13. [13]
  Froehlich, J. D.; Young, R.; Nakamura, T.; Ohmori, Y.; Li, S.; Mochizuk, A. Synthesis of multi-functional POSS emitters for OLED applications. Chem. Mater. 2007, 19, 4991-4997. doi: 10.1021/cm070726v
14. [14]
  Usta, H.; Facchetti, A.; Marks, T. J. Air-stable, solution-processable n-channel and ambipolar semiconductors for thin-film transistors based on the indenofluorenebis(dicyanovinylene) core. J. Am. Chem. Soc. 2008, 130, 8580-8581. doi: 10.1021/ja802266u
15. [15]
  Yang, C.; Kim, J. Y.; Cho, S.; Lee, J. K.; Heeger, A. J.; Wudl, F. Functionalized methanofullerenes used as n-type materials in bulk-heterojunction polymer solar cells and in field-effect transistors. J. Am. Chem. Soc. 2008, 130, 6444-6450. doi: 10.1021/ja710621j
16. [16]
  Malitesta, C.; Losito, I.; Zambonin, P. G. Molecularly imprinted electrosynthesized polymers: new materials for biomimetic sensors. Anal. Chem. 1999, 71, 1366-1370. doi: 10.1021/ac980674g
17. [17]
  John, R.; Spencer, M.; Wallace, G. G.; Smyth, M. R. Development of a polypyrrole-based human serum albümin sensor. Anal. Chim. Acta 1991, 249, 381-385. doi: 10.1016/S0003-2670(00)83010-X
18. [18]
  Duan, C.; Huang, F.; Cao, Y. Recent development of push-pull conjugated polymers for bulk-heterojunction photovoltaics: rational design and fine tailoring of molecular structures. J. Mater. Chem. 2012, 22, 10416-10434. doi: 10.1039/c2jm30470h
19. [19]
  Zhou, H.; Yang, L.; You, W. Rational design of high performance conjugated polymers for organic solar cells. Macromolecules 2012, 45, 607-632. doi: 10.1021/ma201648t
20. [20]
  Durmus, A.; Gunbas, G.; Camurlu, P.; Toppare, L. A neutral state green polymer with a superior transmissive light blue oxidized state. Chem. Commun. 2007, 0, 3246-3248. doi: 10.1039/b704936f
21. [21]
  Durmus, A.; Gunbas, G.; Toppare, L. New, highly stable electrochromic polymers from 3,4-ethylenedioxythiophene-bis-substituted quinoxalines toward greeen polymeric materials. Chem. Mater. 2007, 19, 6247-6251. doi: 10.1021/cm702143c
22. [22]
  Mei, J.; Bao, Z. Side chain engineering in solution processable conjugated polymers, Chem. Mater. 2014, 26, 604-615.
23. [23]
  Kularatne, R. S.; Magurudeniya, H. D.; Sista, P.; Biewer, M. C.; Stefan, M. C. Donor-acceptor semiconducting polymers for organic solar cells. J. Polym. Sci. Part A: Pol. Chem. 2013, 51, 743-768. doi: 10.1002/pola.26425
24. [24]
  Hardeman, T.; Koeckelberghs, G. Synthesis of conjugated polymers by combining different coupling reactions. Polym. Chem. 2017, 8, 3999-4004. doi: 10.1039/C7PY00624A
25. [25]
  Xie, R.; Chen, Z.; Zhang, G.; Huang, Y.; Ying, L.; Huang, F.; Cao, Y. Synthesis and characterization of p-conjugated copolymers based on alkyltriazolyl substituted benzodithiophene. New J. Chem. 2016, 40, 4727-4734. doi: 10.1039/C5NJ03174E
26. [26]
  Akbayrak, M.; Cansu-Ergun, E. G.; Onal, A. M. Synthesis and electro-optical properties of a new copolymer based on EDOT and carbazole. Des. Monomers Pol. 2016, 19, 679-687. doi: 10.1080/15685551.2016.1209627
27. [27]
  Nie, G.; Qu, L.; Xu, J.; Zhang, S. Electrosyntheses and characterizations of a new soluble conducting copolymer of 5-cyanoindole and 3,4-ethylenedioxythiophene. Electrochim. Acta 2008, 53, 8351-8358. doi: 10.1016/j.electacta.2008.06.058
28. [28]
  Aydın, A.; Kaya, I. Syntheses and characterization of yellow and green light emitting novel polymers containing carbazole and electroactive moieties. Electrochim. Acta 2012, 65, 105-114.
29. [29]
  Aydın, A.; Kaya, I. Syntheses of novel copolymers containing carbazole and their electrochromic propertiesç J. Electroanal. Chem. 2013, 691, 1-12. doi: 10.1016/j.jelechem.2012.12.012
30. [30]
  Ates, M.; Uludag, N. Carbazole derivative synthesis and their electropolymerization. J. Solid State Electrochem. 2016, 20, 2599-2612. doi: 10.1007/s10008-016-3269-5
31. [31]
  Carbas, B. B. Novel electrochromic copolymers based on 3-3’-dibromo-2-2’bithiophene and 3,4-ethylenedioxythiophene. Polymer 2017, 113, 180-186. doi: 10.1016/j.polymer.2017.02.053
32. [32]
  Zhou, W.; Xu, J.; Wei, Z.; Pu, S. Electrochemical copolymerization of dibenzofuran and 3-methylthiophene in boron trifluoride diethyl etherate. Chinese J. Polym. Sci. 2008, 26, 81-90. doi: 10.1142/S0256767908002698
33. [33]
  Cansu-Ergun, E. G.; Onal, A. M. Carbazole based electrochromic polymers bearing ethylenedioxy and propylenedioxy scaffolds. J. Electroanal. Chem. 2018, 815, 158-165. doi: 10.1016/j.jelechem.2018.03.014
34. [34]
  Cansu-Ergun, E. G.; Akbayrak, M.; Akdag, A.; Onal, A. M. Effect of thiophene units on the properties of donor-acceptor type monomers and polymers bearing thiophene-benzothiadiazole-scaffolds. J. Electrochem. Soc. 2016, 163, 153-158.
35. [35]
  Zhao, H. P.; Tao, X. T.; Wang, F. Z.; Ren, Y.; Sun, X. Q.; Yang, J. X.; Yan, Y. X.; Zou, D. C.; Zhao, X.; Jiang, M. H. Structure and electronic properties of triphenylamine-substituted indolo[3,2-b]carbazole derivatives as hole-transporting materials for organic light-emitting diodes. Chem. Phys. Lett. 2007, 439, 132-137. doi: 10.1016/j.cplett.2007.03.074
36. [36]
  Bakalis, J.; Cook, A. R.; Asaoka, S.; Forster, M.; Scherf, U.; Miller, J. R. Polarons, compressed polarons, and bipolarons in conjugated polymers. J. Phys. Chem. C 2014, 118, 114-125. doi: 10.1021/jp408910a
37. [37]
  Kumar, A.; Welsh, D. M.; Morvant, M. C.; Piroux, F.; Abboud, K. A.; Reynolds, J. R. Conducting poly(3,4-alkylenedioxythiophene) derivatives as fast electrochromics with high contrast ratios. Chem. Mater. 1998, 10, 896-902. doi: 10.1021/cm9706614
38. [38]
  Beaujuge, P. M.; Reynolds, J. R. Color Control in p-conjugated organic polymers for use in electrochromic devices. Chem. Rev. 2010, 110, 268-320. doi: 10.1021/cr900129a
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