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

Emine Gul Cansu-Ergun

doi:10.1007/s10118-019-2181-8

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

ARTICLE | Updated：2021-02-18

- Covering the More Visible Region by Electrochemical Copolymerization of Carbazole and Benzothiadiazole Based Donor-Acceptor Type Monomers
- Chinese Journal of Polymer Science Vol. 37, Issue 1, Pages: 28-35(2019)
- Affiliations：
  
  Department of Electrical and Electronics Engineering, Baskent University, TR-06810 Ankara, Turkey
- Author bio：
  
  egulcansu@baskent.edu.tr
- Funds：
- DOI：10.1007/s10118-019-2181-8
  CLC：
- Received：22 June 2018，
  
  Revised：2018-8-10，
  
  Accepted：13 August 2018，
  
  Online First：05 September 2018，
  
  Published：2019-01
- Accepted：
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Citation: Cansu-Ergun, E. G. Covering the more visible region by electrochemical copolymerization of carbazole and benzothiadiazole based donor-acceptor type monomers. Chinese J. Polym. Sci. 2019, 37, 28–35

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.
Citation: Cansu-Ergun, E. G. Covering the more visible region by electrochemical copolymerization of carbazole and benzothiadiazole based donor-acceptor type monomers. Chinese J. Polym. Sci. 2019, 37, 28–35 DOI： 10.1007/s10118-019-2181-8.

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.

摘要

Abstract

An electrochromic copolymer film of 2-(3

3-dihexyl-3

4-dihydro-2

-thieno[3

][1

dioxepin-6-yl)-7-(3

3-dihexyl-3

4-dihydro-2

-thieno[3

][1

dioxepin-8-yl)-9

-carbazole (

) and 4

7-bis(thiophen-2-yl)benzo[

][1

thiadiazole (

) 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 (

) and the homopolymer films of

and

(

and

) were investigated by using cyclic voltammetry and UV-Vis spectrometry techniques

and the corresponding results were compared. Incorporation of

and

into copolymer matrix was clearly observed on the resulting cyclic voltammograms and UV-Vis spectra.

covered the visible regions coming from both

and

and exhibited a neutral state darker color than those of homopolymers.

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.

关键词

Keywords

references

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 http://doi.org/10.1016/S0013-4686(99)00042-0 .

Rauh, R . Electrochromic windows: an overview . Electrochim. Acta , 1999 . 44 3165 - 3176 . DOI: 10.1016/S0013-4686(99)00034-1 http://doi.org/10.1016/S0013-4686(99)00034-1 .

Mortimer, R. G . Electrochromic materials . Chem. Soc. Rev. , 1997 . 26 147 - 156 . DOI: 10.1039/cs9972600147 http://doi.org/10.1039/cs9972600147 .

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 http://doi.org/10.1021/cm049669l .

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 http://doi.org/10.1016/j.displa.2005.03.003 .

Bradley, D. D. C . Conjugated polymer electroluminescence . Synt. Met. , 1993 . 54 401 - 415 . DOI: 10.1016/0379-6779(93)91086-H http://doi.org/10.1016/0379-6779(93)91086-H .

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 http://doi.org/10.1016/j.displa.2012.10.001 .

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 http://doi.org/10.1039/c0an00239a .

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 http://doi.org/10.1021/ja077386z .

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 http://doi.org/10.1021/ma0484173 .

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 http://doi.org/10.1002/anie.201100453 .

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: Polym. Chem. , 2009 . 47 6540 - 6551 . DOI: 10.1002/pola.v47:23 http://doi.org/10.1002/pola.v47:23 .

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 http://doi.org/10.1021/cm070726v .

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 http://doi.org/10.1021/ja802266u .

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 http://doi.org/10.1021/ja710621j .

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 http://doi.org/10.1021/ac980674g .

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 http://doi.org/10.1016/S0003-2670(00)83010-X .

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 http://doi.org/10.1039/c2jm30470h .

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 http://doi.org/10.1021/ma201648t .

Durmus, A.; Gunbas, G.; Camurlu, P.; Toppare, L . A neutral state green polymer with a superior transmissive light blue oxidized state . Chem. Commun. , 2007 . ( 31 ): 3246 - 3248 . DOI: 10.1039/b704936f http://doi.org/10.1039/b704936f .

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 http://doi.org/10.1021/cm702143c .

Mei, J.; Bao, Z . Side chain engineering in solution processable conjugated polymers. Chem . Mater. , 2014 . 26 604 - 615 . .

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: Polym. Chem. , 2013 . 51 743 - 768 . DOI: 10.1002/pola.26425 http://doi.org/10.1002/pola.26425 .

Hardeman, T.; Koeckelberghs, G . Synthesis of conjugated polymers by combining different coupling reactions . Polym. Chem. , 2017 . 8 3999 - 4004 . DOI: 10.1039/C7PY00624A http://doi.org/10.1039/C7PY00624A .

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 http://doi.org/10.1039/C5NJ03174E .

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 Polym. , 2016 . 19 679 - 687 . DOI: 10.1080/15685551.2016.1209627 http://doi.org/10.1080/15685551.2016.1209627 .

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 http://doi.org/10.1016/j.electacta.2008.06.058 .

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 . .

Aydın, A.; Kaya, I . Syntheses of novel copolymers containing carbazole and their electrochromic properties. J . Electroanal. Chem. , 2013 . 691 1 - 12 . DOI: 10.1016/j.jelechem.2012.12.012 http://doi.org/10.1016/j.jelechem.2012.12.012 .

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 http://doi.org/10.1007/s10008-016-3269-5 .

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 http://doi.org/10.1016/j.polymer.2017.02.053 .

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 http://doi.org/10.1142/S0256767908002698 .

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 http://doi.org/10.1016/j.jelechem.2018.03.014 .

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 . .

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 http://doi.org/10.1016/j.cplett.2007.03.074 .

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 http://doi.org/10.1021/jp408910a .

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 http://doi.org/10.1021/cm9706614 .

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 http://doi.org/10.1021/cr900129a .

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