Prof. Przemyslaw Data
Professor @ Silesian University of Technology
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Synthesis and characterization of chalcogenophene-based monomers with pyridine acceptor unit
Publications
Year
2016
Type(s)
Journal Article
Author(s)
Pander, P. and Data, P. and Turczyn, R. and Lapkowski, M. and Swist, A. and Soloducho, J. and Monkman, A.P.
Source
Electrochimica Acta, 210: 773—782, 2016
Url
https://www.scopus.com/inward/record.uri?eid=2-s2.0-84974733610&doi=10.1016%2fj.electacta.2016.05.185&partnerID=40&md5=30d1646e56bae7e8a9844b8338823bca
BibTeX
BibTeX
BibTeX
@ARTICLE{Pander2016773, author={Pander, P. and Data, P. and Turczyn, R. and Lapkowski, M. and Swist, A. and Soloducho, J. and Monkman, A.P.}, title={Synthesis and characterization of chalcogenophene-based monomers with pyridine acceptor unit}, journal={Electrochimica Acta}, year={2016}, volume={210}, pages={773-782}, doi={10.1016/j.electacta.2016.05.185}, note={cited By 13}, url={https://www.scopus.com/inward/record.uri?eid=2-s2.0-84974733610&doi=10.1016%2fj.electacta.2016.05.185&partnerID=40&md5=30d1646e56bae7e8a9844b8338823bca}, affiliation={Faculty of Chemistry, Silesian University of Technology, M. Strzody 9, Gliwice, 44-100, Poland; University of Durham, Physics Department, South Road, Durham, DH1 3LE, United Kingdom; Center of Polymer and Carbon Materials, Polish Academy of Sciences, M. Curie-Sklodowskiej 34, Zabrze, 41-819, Poland; Wroclaw University of Technology, Faculty of Chemistry, Wybrzeze Wyspianskiego 27, Wroclaw, 50-370, Poland}, abstract={2,4,6-Trisubstituted pyridine derivatives with different electropolymerizable groups were investigated. It was shown that steric hindrance caused by bichalcogenophene substituents in the 2,6-positions of pyridine enables successful electropolymerization whereas previous studies on 3,5-substituted pyridines shown difficulties caused by the presence of the pyridine nitrogen lone electron pair. Cyclic voltammetry and differential pulse voltammetry techniques were used to determine the electronic properties of the studied compounds and obtained polymers. UV-Vis-NIR and EPR spectroelectrochemistry were used to determinate the behavior of the polymers in the doping-dedoping cycles. The polymers were found to have coloration efficiency up to 245 cm2 C-1 and exhibit sufficient stability for application and highlighting their possible use as electroactive layers in electrochromic devices. © 2016 Elsevier Ltd. All rights reserved.}, author_keywords={EPR; pyridine; selenophene; thiophene; UV-Vis-NIR spectroelectrochemistry}, keywords={Cyclic voltammetry; Electronic properties; Electropolymerization; Infrared devices; Paramagnetic resonance; Polymers; Pyridine; Spectroelectrochemistry; Thiophene; Voltammetry, Coloration efficiencies; Differential pulse voltammetry techniques; Lone electron pair; Pyridine derivatives; Pyridine nitrogen; Selenophene; Synthesis and characterizations; UV-Vis NIR, Synthesis (chemical)}, funding_details={Narodowym Centrum NaukiNarodowym Centrum Nauki, NCN}, funding_text 1={This work was funded by a research grant no. 2011/03/B/ST5/01475 from National Science Centre, Poland .}, references={Winokur, M., Moon, Y.B., Heeger, A.J., Barker, J., Bott, D.C., Shirakawa, H., X-Ray Scattering from Sodium-Doped Polyacetylene: Incommensurate-Commensurate and Order-Disorder Transformations (1987) Phys. Rev. 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Chem., 36, pp. 2042-2047; Mahmood, K., Liu, Z.-P., Li, C., Lu, Z., Fang, T., Liu, X., Zhou, J., Bo, Z., Novel isoindigo-based conjugated polymers for solar cells and field effect transistors (2013) Polym. Chem., 4, p. 3563; Data, P., Zassowski, P., Lapkowski, M., Domagala, W., Krompiec, S., Flak, T., Penkala, M., Danikiewicz, W., Electrochemical and spectroelectrochemical comparison of alternated monomers and their copolymers based on carbazole and thiophene derivatives (2014) Electrochim. Acta, 122, pp. 118-129; Tarkuc, S., Unver, E.K., Udumb, Y.A., Toppare, L., Multi-colored electrochromic polymer with enhanced optical contrast (2010) Eur. Polym. J., 46, pp. 2199-2205; Kawabata, K., Goto, H., Dynamically Controllable Emission of Polymer Nanofibers: Electrofluorescence Chromism and Polarized Emission of Polycarbazole Derivatives (2012) Chem. Eur. J., 18, pp. 15065-15072; Therezio, E.M., Franchello, F., Dias, I.F.L., Laureto, E., Foschini, M., Bottecchia, O.L., De Santana, H., Marletta, A., Emission ellipsometry as a tool for optimizing the electrosynthesis of conjugated polymers thin films (2013) Thin Solid Films, 527, pp. 255-260; Lapkowski, M., Data, P., Nowakowska-Oleksy, A., Soloducho, J., Roszak, S., Electrochemical characterization of alternate conducting carbazole-bisthiophene units (2012) Mater. Chem. Phys., 131, pp. 757-763; Pron, A., Rannou, P., Processible conjugated polymers: From organic semi-conductors to organic metals and superconductors (2002) Prog. Polym. Sci., 27, pp. 135-190; Santos, J., Cook, J.H., Al-Attar, H.A., Monkman, A.P., Bryce, M.R., Fluorene co-polymers with high efficiency deep blue electroluminescence (2015) J. Mater. Chem. C, 3, pp. 2479-2483; Cook, J.H., Santos, J., Al-Attar, H.A., Bryce, M.R., Monkman, A.P., High brightness deep blue/violet fluorescent polymer light-emitting diodes (PLEDs) (2015) J. Mater. Chem. C, 3, pp. 9664-9669; Yang, W., Zhao, J., Cui, C., Kong, Y., Li, P., Characterization and Electrochemical Synthesize from Selenophene-Substituted Poly(Triphenylamine) as Anodically Materials for Electrochromic Devices (2012) Int. J. Electrochem. Sci., 7, pp. 7960-7975; Su, C., Yang, F., Ji, L., Xu, L., Zhang, C., Polytriphenylamine derivative with high free radical density as the novel organic cathode for lithium ion batteries (2014) J. Mater. Chem. A, 2, p. 20083; Barbarella, G., Melucci, M., Sotgiu, G., The versatile thiophene: An overview of recent research on thiophene-based materials (2005) Adv. Mater., 17, pp. 1581-1593; Fichou, D., Structural order in conjugated oligothiophenes and its implications on opto-electronic devices (2000) J. Mater. Chem., 10, pp. 571-588; Patra, A., Wijsboom, Y.H., Zade, S.S., Li, M., Sheynin, Y., Leitus, G., Bendikov, M., Poly(3,4-ethylenedioxyselenophene) (2008) J. Am. Chem. Soc., 130 (21), pp. 6734-6736; Data, P., Motyka, R., Lapkowski, M., Suwinski, J., Monkman, A.P., Spectroelectrochemical Analysis of Charge Carriers as a Way of Improving Poly(p-phenylene)-Based Electrochromic Windows (2015) J. Phys. Chem. C, 119 (34), pp. 20188-20200; Data, P., Lapkowski, M., Motyka, R., Suwinski, J., Influence of heteroaryl group on electrochemical and spectroscopic properties of conjugated polymers (2012) Electrochim. Acta, 83, p. 271; Zykwinska, A., Domagala, W., Lapkowski, M., ESR spectroelectrochemistry of poly(3,4-ethylenedioxythiophene) (PEDOT) (2003) Electrochem. Commun., 5, pp. 603-608; Patra, A., Bendikov, M., Polyselenophenes (2010) J. Mater. Chem., 20, pp. 422-433; Swist, A., Cabaj, J., Soloducho, J., Data, P., Lapkowski, M., Novel acridone-based branched blocks as highly fluorescent materials (2013) Synth. Met., 180, pp. 1-8; Lapkowski, M., Zak, J., Karon, K., Marciniec, B., Prukala, W., The mixed carbon-nitrogen conjugation in the carbazole based polymer; The electrochemical, UVVis EPR, and IR studies on 1,4-bis[(E)2-(9H-carbazol-9-yl)vinyl]benzene (2011) Electrochim. Acta, 56, pp. 4105-4111; Lapkowski, M., Plewa, S., Stolarczyk, A., Doskocz, J., Soloducho, J., Cabaj, J., Bartoszek, M., Sulkowski, W.W., Electrochemical synthesis of polymers with alternate phenothiazine and bithiophene units (2008) Electrochim. Acta, 53, pp. 2545-2552; Yamamoto, T., Maruyama, T., Zhou, Z., Ito, T., Fukuda, T., Yoneda, Y., Begum, F., Kubotall, K., π-Conjugated Poly(pyridine-2,5-diyl), Poly(2,2′-bipyridine-5,5′-diyl) and Their Alkyl Derivatives. Preparation, Linear Structure, Function as a Ligand to Form Their Transition Metal Complexes, Catalytic Reactions, n-Type Electrically Conducting Properties, and Alignment on Substrates (1994) J. Am. Chem. Soc., 116, pp. 4832-4845; Ung, T., Hejl, A., Grubbs, R.H., Schrodi, Y., Latent Ruthenium Olefin Metathesis Catalysts That Contain an N-Heterocyclic Carbene Ligand (2004) Organometallics, 23 (23), pp. 5399-5401; Krompiec, M., Krompiec, S., Ignasiak, H., Lapkowski, M., Kus, P., Stanek, L., Penczek, R., Gebarowska, K., (2008) Synth. Met., 158, pp. 831-838; Laba, K., Data, P., Zassowski, P., Karon, K., Lapkowski, M., Wagner, P., Officer, D.L., Wallace, G.G., Electrochemically Induced Synthesis of Poly(2,6-carbazole) (2015) Macromol. Rapid Commun., 36, pp. 1749-1755; Data, P., Pander, P., Lapkowski, M., Swist, A., Soloducho, J., Reghu, R.R., Grazulevicius, J.V., Unusual properties of electropolymerized 2,7- and 3,6-carbazole derivatives (2014) Electrochim. Acta, 128, pp. 430-438; Data, P., Kurowska, A., Pluczyk, S., Zassowski, P., Pander, P., Jedrysiak, R., Czwartosz, M., Monkman, A.P., Exciplex Enhancement as a Tool to Increase OLED Device Efficiency (2016) J. Phys. Chem., 120, pp. 2070-2078; Barth, M., Guilerez, S., Bidan, G., Bras, G., Lapkowski, M., Electrochemical investigation of regioregular alkyl substituted oligothiophenes (2000) Electrochim. Acta, 45, pp. 4409-4417; Sonmez, G., Meng, H., Wudl, F., Organic Polymeric Electrochromic Devices: Polychromism with Very High Coloration Efficiency (2004) Chem. Mater., 16, pp. 574-580; Patra, A., Bendikov, M., Chand, S., Poly(3,4-ethylenedioxyselenophene) and Its Derivatives: Novel Organic Electronic Materials (2014) Acc. Chem. Res., 47, pp. 1465-1474; Gerson, F., Huber, W., (2003) Electron Spin Resonance Spectroscopy of Organic Radicals, , Wiley-VCH Verlag GmbH & Co. KGaA Weinheim; Jahnke, A.C., Spulber, M., Neuburger, M., Palivan, C.G., Wenger, O.S., Electronic coupling mediated by furan, thiophene, selenophene and tellurophene in a homologous series of organic mixed valence compounds (2014) Chem. Commun., 50, p. 10883}, correspondence_address1={Data, P.; Faculty of Chemistry, Silesian University of Technology, M. Strzody 9, Poland; email: Przemyslaw.Data@polsl.pl}, publisher={Elsevier Ltd}, issn={00134686}, coden={ELCAA}, language={English}, abbrev_source_title={Electrochim Acta}, document_type={Article}, source={Scopus},