Purpald containing poly(2,5-dithienylpyrrole)-based multifunctional conducting polymer: synthesis, characterization, and electrochromic properties

Liang C, Wang H (2017) Indacenodithiophene-based D-A conjugated polymers for application in polymer solar cells. Org Electron Phys, Mater Appl 50:443–457. https://doi.org/10.1016/j.orgel.2017.06.059 Kim NK, Shin ES, Noh YY, Kim DY (2018) A selection rule of solvent for highly aligned diketopyrrolopyrrole-based conjugated polymer film for high performance organic field-effect transistors. Org Electron Phys, Mater Appl 55:6–14. https://doi.org/10.1016/j.orgel.2018.01.006 Han R, Lu S, Wang Y et al (2015) Influence of monomer concentration during polymerization on performance and catalytic mechanism of resultant poly(3,4-ethylenedioxythiophene) counter electrodes for dye-sensitized solar cells. Electrochim Acta 173:796–803. https://doi.org/10.1016/j.electacta.2015.05.130 Qin L, Zhen S, Xu J et al (2014) Poly(thieno[3,4- b ]-1,4-oxathiane): medium effect on electropolymerization and electrochromic performance. Langmuir 30:15581–15589. https://doi.org/10.1021/la503948f Zhang Z, Zheng W, Cheng H et al (2013) Tricolor electrochromism of copolymer based on selenophene and 3,4-ethylenedioxythiophene. Synth Met 162:2428–2432. https://doi.org/10.1016/j.synthmet.2012.11.026 Gicevicius M, Bagdziunas G, Abduloglu Y, Ramanaviciene A, Gumusay O, Ak M, Soganci T, Ramanavicius A (2018) Experimental and theoretical investigations of an electrochromic azobenzene and 3,4-ethylenedioxythiophene-based electrochemically formed polymeric semiconductor. ChemPhysChem 19:2735–2740. https://doi.org/10.1002/cphc.201800478 Ak M, Camurlu P, Yılmaz F et al (2006) Electrochromic properties and electrochromic device application of copolymer ofN-(4-(3-thienyl methylene)-oxycarbonylphenyl)maleimide with thiophene. J Appl Polym Sci 102:4500–4505. https://doi.org/10.1002/app.24834 Guzel M, Ak M (2019) A solution-processable electrochromic polymer designed with Reactive Yellow 160 and 2-hydroxy carbazole. Org Electron 75:105436. https://doi.org/10.1016/j.orgel.2019.105436 Abashev GG, Bushueva AY, Shklyaeva EV (2011) N-substituted 2,5-di(2-thienyl)pyrroles: application, production, properties, and electrochemical polymerization (review). Chem Heterocycl Compd 47:130–154 Beaujuge PM, Reynolds JR (2010) Color control in π-conjugated organic polymers for use in electrochromic devices. Chem Rev 110:268–320. https://doi.org/10.1021/cr900129a Gumusay O, Soganci T, Soyleyici HC et al (2017) Electrochemistry of secondary amine substituted 2,5-di(2-thienyl)pyrrole derivative and its copolymer. J Electrochem Soc 164:421–429. https://doi.org/10.1149/2.0291707jes Guzel M, Soganci T, Karatas E, Ak M (2018) Donor-acceptor type super-structural triazine cored conducting polymer containing carbazole and quinoline for high-contrast electrochromic device. J Electrochem Soc 165:316–323. https://doi.org/10.1149/2.1201805jes Karatas E, Guzel M, Ak M (2017) Asymmetric star-shaped functionalized triazine architecture and its electrochromic device application. J Electrochem Soc 164:H463–H469. https://doi.org/10.1149/2.0731707jes Kurtay G, Soganci T, Ak M, Gullu M (2016) Synthesis and computational bandgap engineering of new 3,4-Alkylenedioxypyrrole (ADOP) derivatives and investigation of their electrochromic properties. J Electrochem Soc 163:H896–H905. https://doi.org/10.1149/2.0131610jes Lee SH, Cho W, Hwang DK et al (2017) Synthesis of poly(3,4-ethylene dioxythiophene)/ammonium vanadate nanofiber composites for counter electrode of dye-sensitized solar cells. Electrochim Acta 245:607–614. https://doi.org/10.1016/j.electacta.2017.05.194 Thomas JP, Rahman MA, Srivastava S, Kang JS, McGillivray D, Abd-Ellah M, Heinig NF, Leung KT (2018) Highly conducting hybrid silver-nanowire-embedded poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate) for high-efficiency planar silicon/organic heterojunction solar cells. ACS Nano 12:9495–9503. https://doi.org/10.1021/acsnano.8b04848 Han Y, Dai L (2019) Conducting polymers for flexible supercapacitors. Macromol Chem Phys 220:1800355. https://doi.org/10.1002/macp.201800355 Ghorbani Zamani F, Moulahoum H, Ak M et al (2019) Current trends in the development of conducting polymers-based biosensors. TrAC Trends Anal Chem 118:264–276. https://doi.org/10.1016/j.trac.2019.05.031 Unlu CG, Acet M, Ocakoglu K et al (2018) An effective non-enzymatic biosensor platform based on copper nanoparticles decorated by sputtering on CVD graphene. Sensors Actuators B Chem 273:1501–1507. https://doi.org/10.1016/j.snb.2018.07.064 Olgac R, Soganci T, Baygu Y et al (2017) Zinc(II) phthalocyanine fused in peripheral positions octa-substituted with alkyl linked carbazole: synthesis, electropolymerization and its electro-optic and biosensor applications. Biosens Bioelectron 98:202–209. https://doi.org/10.1016/j.bios.2017.06.028 Tekbaşoğlu TY, Soganci T, Ak M et al (2017) Enhancing biosensor properties of conducting polymers via copolymerization: synthesis of EDOT-substituted bis(2-pyridylimino)isoindolato-palladium complex and electrochemical sensing of glucose by its copolymerized film. Biosens Bioelectron. https://doi.org/10.1016/j.bios.2016.08.020 Ayranci R, Torlak Y, Soganci T, Ak M (2018) Trilacunary Keggin type polyoxometalate-conducting polymer composites for amperometric glucose detection. J Electrochem Soc 165:B638–B643. https://doi.org/10.1149/2.1061813jes Makelane HR, John SV, Waryo TT et al (2016) AC voltammetric transductions and sensor application of a novel dendritic poly(propylene thiophenoimine)-co-poly(3-hexylthiophene) star co-polymer. Sensors Actuators B Chem 227:320–327. https://doi.org/10.1016/j.snb.2015.12.020 Soganci T, Baygu Y, Kabay N, Gök Y, Ak M (2018) Comparative investigation of peripheral and nonperipheral zinc phthalocyanine-based polycarbazoles in terms of optical, electrical, and sensing properties. ACS Appl Mater Interfaces 10:21654–21665. https://doi.org/10.1021/acsami.8b06206 Göktuğ Ö, Soganci T, Ak M, Şener MK (2017) Efficient synthesis of EDOT modified ABBB-type unsymmetrical zinc phthalocyanine: optoelectrochromic and glucose sensing properties of its copolymerized film. New J Chem 41:14080–14087. https://doi.org/10.1039/C7NJ03250A Xu D, Wang H, Li F et al (2019) Conformal conducting polymer shells on V2O5 nanosheet arrays as a high-rate and stable zinc-ion battery cathode. Adv Mater Interfaces 6:1801506. https://doi.org/10.1002/admi.201801506 Anilkumar KM, Jinisha B, Manoj M et al (2018) Layered sulfur/PEDOT:PSS nano composite electrodes for lithium sulfur cell applications. Appl Surf Sci 442:556–564. https://doi.org/10.1016/j.apsusc.2018.02.178 Kim J, Chae S, Yi A et al Syntheses and optical, electrochemical, and photovoltaic properties of polymers with 6-(2-thienyl)-4H-thieno[2,3-b]indole with a variety of electron-deficient units. J Appl Polym Sci:47624. https://doi.org/10.1002/app.47624 Ayranci R, Demirkol D, Ak M, Timur S (2015) Ferrocene-functionalized 4-(2,5-di(thiophen-2-yl)-1H-pyrrol-1-yl)aniline: a novel design in conducting polymer-based electrochemical biosensors. Sensors 15:1389–1403. https://doi.org/10.3390/s150101389 Koyuncu S, Zafer C, Sefer E et al (2009) A new conducting polymer of 2,5-bis(2-thienyl)-1H-(pyrrole) (SNS) containing carbazole subunit: electrochemical, optical and electrochromic properties. Synth Met 159:2013–2021. https://doi.org/10.1016/j.synthmet.2009.07.027 Yavuz A, Bezgin B, Aras L, Önal AM (2010) Synthesis and electropolymerization of the phthaocyanines with 4-(2,5-di-2-thiophen-2-yl-pyrrol-1-yl) substituents. J Electroanal Chem 639:116–122. https://doi.org/10.1016/j.jelechem.2009.11.033 Tuncagil S, Ozdemir C, Demirkol DO, Timur S, Toppare L (2011) Gold nanoparticle modified conducting polymer of 4-(2,5-di(thiophen-2-yl)- 1H-pyrrole-1-l) benzenamine for potential use as a biosensing material. Food Chem 127:1317–1322. https://doi.org/10.1016/j.foodchem.2011.01.089 Söyleyici HC, Ak M, Şahin Y et al (2013) New class of 2,5-di(2-thienyl)pyrrole compounds and novel optical properties of its conducting polymer. Mater Chem Phys 142:303–310. https://doi.org/10.1016/j.matchemphys.2013.07.019 Galindo MA, Hannant J, Harrington RW, Clegg W, Horrocks BR, Pike AR, Houlton A (2011) Pyrrolyl-, 2-(2-thienyl)pyrrolyl- and 2,5-bis(2-thienyl)pyrrolyl-nucleosides: synthesis, molecular and electronic structure, and redox behaviour of C5-thymidine derivatives. Org Biomol Chem 9:1555–1564. https://doi.org/10.1039/c0ob00466a Just PE, Chane-Ching KI, Lacaze PC (2002) Synthesis of 2,5-di(2-thienyl)-1H-pyrrole N-linked with conjugated bridges. Tetrahedron 58:3467–3472. https://doi.org/10.1016/S0040-4020(02)00328-9 Yildiz E, Camurlu P, Tanyeli C et al (2008) A soluble conducting polymer of 4-(2,5-di(thiophen-2-yl)-1H-pyrrol-1-yl)benzenamine and its multichromic copolymer with EDOT. J Electroanal Chem 612:247–256. https://doi.org/10.1016/j.jelechem.2007.10.004 El’shina TS, Sosnin EA, Shklyaeva EV, Abashev GG (2013) N-substituted 2,5-Di(2-thienyl)pyrroles. Synthesis and electrochemical properties. Russ J Gen Chem 83:726–730. https://doi.org/10.1134/S1070363213040208 Soganci T (2019) Effects of N-substitution group on electrochemical, electrochromic and optical properties of dithienyl derivative. J Electrochem Soc 166:1112–1118. https://doi.org/10.1149/2.0341902jes Yiğit D, Hacioglu SO, Güllü M, Toppare L (2016) Synthesis and spectroelectrochemical characterization of multi-colored novel poly(3,6-dithienylcarbazole) derivatives containing azobenzene and coumarin chromophore units. Electrochim Acta 196:140–152. https://doi.org/10.1016/j.electacta.2016.02.168 Yiğit D, Udum YA, Güllü M, Toppare L (2014) Electrochemical and optical properties of novel terthienyl based azobenzene, coumarine and fluorescein containing polymers: multicolored electrochromic polymers. J Electroanal Chem 712:215–222. https://doi.org/10.1016/j.jelechem.2013.11.028 Zhou W, Xu J, Du Y, Yang P (2010) Electrochemical polymerization of p-terphenyl in mixed electrolyte of boron trifluoride diethyl etherate and CH2Cl2. J Appl Polym Sci 117:2688–2694. https://doi.org/10.1002/app.30927 Xu Z, Du H, Yin M et al (2018) Benzothiadiazole, hexylthiophen and alkoxy benzene based solution processable copolymer: effect of the electron withdrawing substituents (fluorine atoms) on electrochemical, optical and electrochromic properties. Org Electron 61:1–9. https://doi.org/10.1016/j.orgel.2018.06.048 Reeves BD, Grenier CRG, Argun AA et al (2004) Spray coatable electrochromic dioxythiophene polymers with high coloration efficiencies. Macromolecules 37:7559–7569. https://doi.org/10.1021/ma049222y Soganci T, Kurtay G, Ak M, Güllü M (2014) Preparation of an EDOT-based polymer: optoelectronic properties and electrochromic device application. RSC Adv 5:2630–2639. https://doi.org/10.1039/C4RA13060J Ak M, Gancheva V, Terlemezyan L, Tanyeli C, Toppare L (2008) Synthesis of a dipyrromethane functionalized monomer and optoelectrochromic properties of its polymer. Eur Polym J 44(8):2567–2573 Soganci T, Ak M, Giziroglu E, Soyleyici HC (2016) Smart window application of a new hydrazide type SNS derivative. RSC Adv 6:1744–1749. https://doi.org/10.1039/c5ra24759d Wang G, Fu X, Huang J et al (2010) Synthesis and spectroelectrochemical properties of two new dithienylpyrroles bearing anthraquinone units and their polymer films. Electrochim Acta 55:6933–6940. https://doi.org/10.1016/j.electacta.2010.07.012 Ak M, Soğancı T, Gümüşay O, Çukurluoğlu S (2017) Synthesis of conducting polymer with green chemistry and its electrochromic properties. Pamukkale Univ J Eng Sci 23:753–758. https://doi.org/10.5505/pajes.2016.66674