Synthesis and characterization of an electrochromic copolymer based on 9, 10-di (furan-2-yl)anthracene and 3,4-ethylenedioxythiophene

KALÇIK, Ali; BEZGIN CARBAS, BUKET; Kivrak, Arif

doi:10.55730/1300-0527.3419

Synthesis and characterization of an electrochromic copolymer based on 9, 10-di (furan-2-yl)anthracene and 3,4-ethylenedioxythiophene

Ali KALÇIK, (Karamanoğlu Mehmetbey Üniversitesi, Mühendislik Fakültesi, Enerji Sistemleri Mühendisliği Bölümü, Karaman, Türkiye)

Arif KIVRAK, (Eskişehir Osmangazi Üniversitesi, Fen Fakültesi, Kimya Bölümü, Eskişehir, Türkiye)

BUKET BEZGIN CARBAS (Karamanoğlu Mehmetbey Üniversitesi, Mühendislik Fakültesi, Enerji Sistemleri Mühendisliği Bölümü, Karaman, Türkiye)

Turkish Journal of Chemistry

4 0

Yıl: 2022 Cilt: 46 Sayı: 4 Sayfa Aralığı: 1110 - 1119 Metin Dili: İngilizce DOI: 10.55730/1300-0527.3419 İndeks Tarihi: 06-12-2022

Synthesis and characterization of an electrochromic copolymer based on 9, 10-di (furan-2-yl)anthracene and 3,4-ethylenedioxythiophene

Öz:

In this study, a new copolymer, which is a combination of two chemical structure (9,10-di(furan-2-yl)anthracene and 3,4-ethylenedioxythiophene was synthesized via electrochemical synthesis methods in the electrolyte medium of 0.1 M TBAPF6/ ACN solution. PEDOT homopolymer was also electrosynthesized for comparator experiments of the polymer formations in the same medium. The characterizations of polymers were achieved with general optical and electrochemical characterization techniques. The corresponding electrochromic copolymer shows blue and lilac color in its neutral and oxidized states, respectively. The copolymer has an optical band gap of 1.65 eV and 24% optical contrast at 500 nm with a high coloration efficiency (170 $cm^2$ /C) and a fast switching time (1.0 s).

Anahtar Kelime: Conducting polymers electrochemical copolymerization electrochromism electrochromic materials anthracene

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık

1. Azak H, Yildiz HB, Bezgin Carbas B. Synthesis and characterization of a new poly(dithieno (3,2-b:2′, 3′-d) pyrrole) derivative conjugated polymer: Its electrochromic and biosensing applications. Polymer 2018; 134: 44-52. doi: 10.1016/j.polymer.2017.11.044
2. Cevik E, Bezgin Carbas B, Senel M, Yildiz HB. Construction of conducting polymer/cytochrome C/thylakoid membrane based photo- bioelectrochemical fuel cells generating high photocurrent via photosynthesis. Biosensors and Bioelectronics 2018; 113: 25-31. doi: 10.1016/j.bios.2018.04.055
3. Guler M, Turkoglu V, Kivrak A. Electrochemical detection of malathion pesticide using acetylcholinesterase biosensor based on glassy carbon electrode modified with conducting polymer film. Environmental Science and Pollution Research 2016; 23: 12343-12351. doi: 10.1007/ s11356-016-6385-y
4. Guler M, Turkoglu V, Kivrak A. A novel glucose oxidase biosensor based on poly([2,2′;5′,2′′]-terthiophene-3′-carbaldehyde) modified electrode. International Journal of Biological Macromolecules 2015; 79: 262-268. doi: 10.1016/j.ijbiomac.2015.04.042
5. Bezgin Carbas B, Gulen M, Tolu MC, Sonmezoglu S. Hydrogen sulphate-based ionic liquid-assisted electro-polymerization of PEDOT catalyst material for high-efficiency photoelectrochemical solar cells. Scientific Reports 2017; 7: 11672. doi: 10.1038/s41598-017-11916-4
6. Bezgin Carbas B, Asil D, Friend RH, Önal AM. A new blue light emitting and electrochromic polyfluorene derivative for display applications. Organic Electronics 2014; 15: 500-508. doi: 10.1016/j.orgel.2013.12.003
7. Bingol BE, Tekin B, Bezgin Carbas B. An investigation on electrochromic properties of new copolymers based on dithienylpyrrole and propylenedioxythiophene. Journal of Electroanalytical Chemistry 2017; 806 : 107-115. doi: 10.1016/j.jelechem.2017.10.050
8. Bezgin Carbas B. Novel electrochromic copolymers based on 3-3′-dibromo-2-2′-bithiophene and 3,4 ethylene dioxythiophene. Polymer 2017; 113: 180-186. doi: 10.1016/j.polymer.2017.02.053
9. Bezgin Carbas B, Kivrak A, Kavak E. Electrosynthesis of a new indole based donor-acceptor-donor type polymer and investigation of its electrochromic properties. Materials Chemistry and Physics 2017; 188: 68-74. doi: 10.1016/j.matchemphys.2016.12.040
10. Kivrak A, Yildiz HB, Gokyer S, Bezgin Carbas B. Electrochemical polymerization of a new alkoxy-bridged dithieno (3,2-B:2’,3’-D) pyrrole derivative. Turkish Journal of Chemistry 2018; 42 : 439-447. doi: 10.3906/kim-1709-33
11. Bezgin Carbas B, Tekin B. Poly(3,4-ethylenedioxythiophene) electrode grown in the presence of ionic liquid and its symmetrical electrochemical supercapacitor application. Polymer Bulletin 2018; 75: 1547-1562. doi: 10.1007/s00289-017-2111-2
12. Cannavale A, Cossari P, Eperon GE, Colella S, Fiorito F, et al. Forthcoming perspectives of photoelectrochromic devices: A critical review. Energy & Environmental Science 2016; 9: 2682-2719. doi: 10.1039/C6EE01514J
13. Lin X, Lu Q, Yang C, Wang Y, Zhang W, et al. Multifunctional donor–acceptor conjugated polymers containing isoindigo and benzothiadiazole moieties for electrochromic, photoelectric sensor, 2,4,6- trinitrophenol detection and resistance memory device. Journal of Material Science 2021; 56: 12001–12017. doi: 10.1007/s10853-021-05952-9
14. Huang Q, Chen J, Yan S, Shao X, Dong Y, et al. New Donor–Acceptor–Donor conjugated polymer with twisted donor–acceptor configuration for high-capacitance electrochromic supercapacitor application. ACS Sustainable Chemistry & Engineering 2021; 9 (41): 13807–13817. doi: 10.1021/acssuschemeng.1c04498
15. Algi MP, Öztaş Z, Tirkes S, Cihaner A, Algi F. A new electrochromic copolymer based on dithienylpyrrole and EDOT. Organic Electronics 2013; 14: 1094-1102. doi: 10.1016/j.orgel.2013.01.036
16. Kadac K, Nowaczyk A, Nowaczyk J. Synthesis and characterization of new copolymer of pyrrole and 3,4-ethylenedioxythiophene synthesized by electrochemical route. Synthetic Metals 2015; 206: 145-153. doi: 10.1016/j.synthmet.2015.05.021
17. Xue Y, Xue Z, Zhang W, Zhang W, Chen S, Lin K, Xu J. Enhanced electrochromic performances of Polythieno[3,2-b]thiophene with multicolor conversion via embedding EDOT segment. Polymer 2018; 159: 150-156. doi: 10.1016/j.polymer.2018.11.018
18. Yigitsoy B, Varis S, Tanyeli C, Akhmedov IM, Toppare L. Electrochromic properties of a novel low band gap conductive copolymer. Electrochimica Acta 2007; 52: 6561-6568. doi: 10.1016/j.electacta.2007.04.083
19. Baumgarten M, Muller U, Bohnen A, Mullen K. Oligo(9,10-anthrylenes), Organic Compounds with Stable High-Spin States. Angewandte Chemie International Edition 1992; 31: 448-451. doi: 10.1002/anie.199204481
20. Hodge P, Power GA, Rabjohns MA. Synthesis of poly(anthracene-2,6-diyl) and a copolymer containing alternately anthracene-2,6-diyl and p-phenylene units. Chemical Communications 1997; 1: 73-74. doi: 10.1039/a607405g
21. Haldar R, Prasad K, Samanta PK, Pati S, Maji TK. Luminescent Metal–Organic Complexes of Pyrene or Anthracene Chromophores: Energy Transfer Assisted Amplified Exciplex Emission and Al3+ Sensing. Crystal Growth & Design 2016; 16: 82-91. doi: 10.1021/acs.cgd.5b01448
22. Shin SA, Kim J-H, Park JB, Hwang D-H. Semiconducting Polymers Consisting of Anthracene and Benzotriazole Units for Organic Solar Cells. Journal of Nanoscience and Nanotechnology 2015; 15: 1515-1519.doi: 10.1166/jnn.2015.9325
23. Ayachi S, Alimi K, Bouachrine M, Hamidi M, Mevellec JY, et al. Spectroscopic investigations of copolymers incorporating various thiophene and phenylene monomers. Synthetic Metals 2006; 156: 318-326. doi: 10.1016/j.synthmet.2005.12.010
24. Tao Y, Zhang K, Zhang C, Cheng H, Jiao C, et al. Electrochemical synthesis of copolymers based on 2-(anthracen-9-yl)thiophene: A facile and efficient route to a series of multicolor electrochromic polymers. Materials Science in Semiconductor Processing 2016 ; 56: 66-75. doi: 10.1016/j.mssp.2016.07.019
25. Tao Y-J, Zhang Z-Y, Xu X-Q, Zhou Y-J, Cheng H-F, et al. Facile and economical synthesis of high-contrast multielectrochromic copolymers based on anthracene and 3,4-ethylenedioxythiophene via electrocopolymerization in boron trifluoride diethyl etherate. Electrochimica Acta 2012; 77: 157-162. doi: 10.1016/j.electacta.2012.05.087
26. Tutuncu E, Ozkut MI. Synthesis of an Anthracene-Based Monomer and Its Electrocopolymerization with 3,4-Ethylenedioxythiophene. Journal of the Electrochemical Society 2019; 166: G10-G15. doi: 10.1149/2.1121902jes
27. Yildirim A, Tarkuc S, Ak M, Toppare L. Syntheses of electroactive layers based on functionalized anthracene for electrochromic applications. Electrochimica Acta 2008; 53 : 4875-4882. doi: 10.1016/j.electacta.2008.02.026
28. Wang F, Wilson MS, Rauh RD, et al. Electrochromic linear and star branched poly(3,4-ethylenedioxythiophenedidodecyloxybenzene) polymers. Macromolecules. 2000; 33: 2083-2091.
29. Ho J-H, Chen Y-H, Chou L-T, Lai P-W, Chen P-S. The improvement of π-conjugation by the lateral benzene of anthracene and naphthalene. Tetrahedron Letters 2014 ; 55: 5727-5731. doi: 10.1016/j.tetlet.2014.08.097
30. Kotha S, Ghosh AK, Synthesis of 9,10-Diarylanthracene Derivatives via bis Suzuki-Miyaura Cross-coupling Reaction. Synlet 2002; 3: 451- 452. doi: 10.1055/s-2002-20463
31. Kotha S, Ghosh AK, Deodhar KD, Synthesis of Symmetrical and Unsymmetrical 9,10-Diarylanthracene Derivatives via Bis-Suzuki-Miyaura Cross-Coupling Reaction. Synthesis 2004; 4: 549-557. doi: 10.1055/s-2004-815981
32. Kivrak A, Er ÖF, Kivrak H, Topal Y, Kuş M et al. Synthesis and solar-cell applications of novel furanyl-substituted anthracene derivatives. Optical Materials 2017; 73: 206-212. doi: 10.1016/j.optmat.2017.08.014
33. Akbayrak M, Cansu-Ergun EG, Önal AM. Synthesis and electrooptical properties of a new copolymer based on EDOT and carbazole. Designed Monomers and Polymers, 2016; 19(7): 679-687. doi: 10.1080/15685551.2016.1209627.
34. Ming S, Zhen S, Liu X, Lin K, Liu H et al. Chalcogenodiazolo[3,4-c]pyridine based donor-acceptor-donor polymers for green and near infrared electrochromics. Polymer Chemistry 2015; 6: 8248-8258. doi: 10.1039/C5PY01321F
35. Soganci T, Soyleyici S, Soyleyici HC, Ak M. High contrast electrochromic polymer and copolymer materials based on amide-substituted poly(dithienyl pyrrole). Journal of the Electrochemical Society 2017; 164 (2): H11-H20. doi: 0013-4651/2017/164(2)/H11/10/$33.00

APA	KALÇIK A, Kivrak A, BEZGIN CARBAS B (2022). Synthesis and characterization of an electrochromic copolymer based on 9, 10-di (furan-2-yl)anthracene and 3,4-ethylenedioxythiophene. , 1110 - 1119. 10.55730/1300-0527.3419
Chicago	KALÇIK Ali,Kivrak Arif,BEZGIN CARBAS BUKET Synthesis and characterization of an electrochromic copolymer based on 9, 10-di (furan-2-yl)anthracene and 3,4-ethylenedioxythiophene. (2022): 1110 - 1119. 10.55730/1300-0527.3419
MLA	KALÇIK Ali,Kivrak Arif,BEZGIN CARBAS BUKET Synthesis and characterization of an electrochromic copolymer based on 9, 10-di (furan-2-yl)anthracene and 3,4-ethylenedioxythiophene. , 2022, ss.1110 - 1119. 10.55730/1300-0527.3419
AMA	KALÇIK A,Kivrak A,BEZGIN CARBAS B Synthesis and characterization of an electrochromic copolymer based on 9, 10-di (furan-2-yl)anthracene and 3,4-ethylenedioxythiophene. . 2022; 1110 - 1119. 10.55730/1300-0527.3419
Vancouver	KALÇIK A,Kivrak A,BEZGIN CARBAS B Synthesis and characterization of an electrochromic copolymer based on 9, 10-di (furan-2-yl)anthracene and 3,4-ethylenedioxythiophene. . 2022; 1110 - 1119. 10.55730/1300-0527.3419
IEEE	KALÇIK A,Kivrak A,BEZGIN CARBAS B "Synthesis and characterization of an electrochromic copolymer based on 9, 10-di (furan-2-yl)anthracene and 3,4-ethylenedioxythiophene." , ss.1110 - 1119, 2022. 10.55730/1300-0527.3419
ISNAD	KALÇIK, Ali vd. "Synthesis and characterization of an electrochromic copolymer based on 9, 10-di (furan-2-yl)anthracene and 3,4-ethylenedioxythiophene". (2022), 1110-1119. https://doi.org/10.55730/1300-0527.3419

APA	KALÇIK A, Kivrak A, BEZGIN CARBAS B (2022). Synthesis and characterization of an electrochromic copolymer based on 9, 10-di (furan-2-yl)anthracene and 3,4-ethylenedioxythiophene. Turkish Journal of Chemistry, 46(4), 1110 - 1119. 10.55730/1300-0527.3419
Chicago	KALÇIK Ali,Kivrak Arif,BEZGIN CARBAS BUKET Synthesis and characterization of an electrochromic copolymer based on 9, 10-di (furan-2-yl)anthracene and 3,4-ethylenedioxythiophene. Turkish Journal of Chemistry 46, no.4 (2022): 1110 - 1119. 10.55730/1300-0527.3419
MLA	KALÇIK Ali,Kivrak Arif,BEZGIN CARBAS BUKET Synthesis and characterization of an electrochromic copolymer based on 9, 10-di (furan-2-yl)anthracene and 3,4-ethylenedioxythiophene. Turkish Journal of Chemistry, vol.46, no.4, 2022, ss.1110 - 1119. 10.55730/1300-0527.3419
AMA	KALÇIK A,Kivrak A,BEZGIN CARBAS B Synthesis and characterization of an electrochromic copolymer based on 9, 10-di (furan-2-yl)anthracene and 3,4-ethylenedioxythiophene. Turkish Journal of Chemistry. 2022; 46(4): 1110 - 1119. 10.55730/1300-0527.3419
Vancouver	KALÇIK A,Kivrak A,BEZGIN CARBAS B Synthesis and characterization of an electrochromic copolymer based on 9, 10-di (furan-2-yl)anthracene and 3,4-ethylenedioxythiophene. Turkish Journal of Chemistry. 2022; 46(4): 1110 - 1119. 10.55730/1300-0527.3419
IEEE	KALÇIK A,Kivrak A,BEZGIN CARBAS B "Synthesis and characterization of an electrochromic copolymer based on 9, 10-di (furan-2-yl)anthracene and 3,4-ethylenedioxythiophene." Turkish Journal of Chemistry, 46, ss.1110 - 1119, 2022. 10.55730/1300-0527.3419
ISNAD	KALÇIK, Ali vd. "Synthesis and characterization of an electrochromic copolymer based on 9, 10-di (furan-2-yl)anthracene and 3,4-ethylenedioxythiophene". Turkish Journal of Chemistry 46/4 (2022), 1110-1119. https://doi.org/10.55730/1300-0527.3419