Electrochromic properties of multicolored novel polymer synthesized via combination of benzotriazole and N-functionalized 2,5-di(2-thienyl)-1H-pyrrole units

Electrochimica Acta

Volumn 138, Issue , 2014, Pages 454-463

  Rende, Eda ^a   Kilic, Cihan E ^a   Udum, Yasemin Arslan ^b   Toffoli, Daniele ^a   Toppare, Levent ^a  

^a MIDDLE EAST TECHNICAL UNIVERSITY   (Turkey)

^b GAZI UNIVERSITY   (Turkey)

Author keywords

Conducting Polymer; DFT; Electrochemical Polymerization; Electrochromism; SNS Derivatives

Indexed keywords

AROMATIC COMPOUNDS; CONDUCTING POLYMERS; CYCLIC VOLTAMMETRY; ELECTROCHROMISM; ELECTROPOLYMERIZATION; MONOMERS; NITROGEN COMPOUNDS;

DEVICE APPLICATION; DFT; ELECTROCHROMIC MATERIALS; ELECTROCHROMIC PROPERTIES; SPECTROSCOPIC PROPERTY; UV-VIS-NIR SPECTROSCOPY; VERTICAL ELECTRON AFFINITIES; VERTICAL IONIZATION POTENTIALS;

ELECTROCHROMIC DEVICES;

EID: 84904962163     PISSN: 00134686     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.electacta.2014.06.153     Document Type: Article

References (40)

1. A.J. Heeger Nobel Lecture: Semiconducting and metallic polymers: The fourth generation of polymeric materials Reviews of Modern Physics 73 2001 681 700
2. M. Helgesen, R. Søndergaard, and F.C. Krebs Advanced materials and processes for polymer solar cell devices Journal of Materials Chemistry 20 2010 36 60
3. M.L. Keshtov, D.V. Marochkin, V.S. Kochurov, A.R. Khokhlov, E.N. Koukaras, and G.D. Sharma New conjugated alternating benzodithiophene-containing copolymers with different acceptor units: synthesis and photovoltaic application Journal of Materials Chemistry A 2 2014 155 171
4. A. AydIn, and I. Kaya Synthesis and characterization of yellow and green light emitting novel polymers containing carbazole and electroactive moieties Electrochimica Acta 65 2012 104 114
5. P.T. Nguyen, U. Rammelt, W. Plieth, S. Richter, M. Plötner, W.-J. Fischer, N. Kiriy, K. Potje Kamloth, and H.-J. Adler Experiments with organic field effect transistors based on polythiophene and thiophene oligomers Electrochimica Acta 50 7-8 2005 1757 1763 (Pubitemid 40181542)
6. P.M. Beaujuge, S. Ellinger, and J.R. Reynolds The donor-acceptor approach allows a black-to-transmissive switching polymeric electrochrome Nature Materials 7 2008 795 799
7. A. Balan, D. Baran, G. Gunbas, A. Durmus, F. Ozyurt, and L. Toppare One polymer for all: benzotriazole containing donor-acceptor type polymer as a multi-purpose material Chemical Communications 44 2009 6768 6770
8. F. Garnier, G. Tourillon, M. Gazard, and J.C. Dubois Organic conducting polymers derived from substituted thiophenes as electrochromic material J Electroanal. Chem. 148 1983 299 303 (Pubitemid 14470470)
9. P.M. Beaujuge, and J.R. Reynolds Color control in pi-conjugated organic polymers for use in electrochromic devices Chem. Rev. 110 2010 268 320
10. J.H.R. Tucker, and S.R. Collinson Recent developments in the redox-switched binding of organic compounds Chem. Soc. Rev. 31 2002 147 156
11. J.J. Bu, N.D. Lilienthal, J.E. Woods, C.E. Nohrden, K.T. Hoang, D. Truong, and D.K. Smith Electrochemically controlled hydrogen bonding. Nitrobenzenes as simple redox-dependent receptors for arylureas J. Am. Chem. Soc. 127 2005 6423 6429 (Pubitemid 40627764)
12. G. Gunbas, A. Durmus, and L. Toppare Could green be greener? Novel donor-acceptor-type electrochromic polymers: towards excellent neutral green materials with exceptional transmissive oxidized states for completion of RGB color space Advanced Materials 20 4 2008 691 695
13. J. Roncali Electrogenerated functional conjugated polymers as advanced electrode materials Journal of Materials Chemistry 9 1999 1875 1893
14. Y. Coskun, A. Cirpan, and L. Toppare Construction of electrochromic devices using thiophene based conducting polymers Journal of Material Science 42 1 2007 368 372 (Pubitemid 46154477)
15. C.B. Nielsen, A. Angerhofer, K.A. Abboud, and J.R. Reynolds Discrete photopatternable (-conjugated oligomers for electrochromic devices Journal of the American Chemical Society 130 30 2008 9734 9746
16. C.L. Gaupp, K. Zong, P. Schottland, B.C. Thompson, C.A. Thomas, and J.R. Reynolds Poly(3,4-ethylenedioxypyrrole): Organic electrochemistry of a highly stable electrochromic polymer Macromolecules 33 4 2000 1132 1133 (Pubitemid 30589076)
17. A.F. Diaz, and K.K. Kanazawa Electrochemical polymerization of pyrrole, Journal of the Chemical Society Chemical Communications 14 1979 635 636
18. A.F. Diaz, and J.I. Castillo A polymer electrode with variable conductivity: polypyrrole, Journal of the Chemical Society Chemical Communications 14 1980 397 398
19. A.F. Diaz, J.I. Castillo, J.A. Logan, and W.Y.J. Lee Electrochemistry of conducting polypyrrole films Journal of Electroanalytical Chemistry and Interfacial Electrochemistry 129 1-2 1981 115 132
20. G. Sonmez, P. Schottland, K. Zongb, and J.R. Reynolds Highly transmissive and conductive poly[(3,4-alkylenedioxy)pyrrole-2,5-diyl] (PXDOP) films prepared by air or transition metal catalyzed chemical oxidation Journal of Materials Chemistry 11 2001 289 294 (Pubitemid 32193442)
21. D.R. Rosseinsky, and R.J. Mortimer Electrochromic systems and the prospects for devices Advanced Materials 13 11 2001 783 793 (Pubitemid 32543977)
22. U.H. Yildiz, E. Sahin, I.M. Akhmedov, C. Tanyeli, and L. Toppare A new soluble conducting polymer and its electrochromic devices Journal of Polymer Science Part A Polymer Chemistry 44 7 2006 2215 2225
23. S. Varis, M. Ak, I.M. Akhmedov, C. Tanyeli, and L. Toppare A novel multielectrochromic copolymer based on 1-(4-nitrophenyl)-2,5-di(2-thienyl)-1H- pyrrole and EDOT Journal of Electroanalytical Chemistry 603 1 2007 8 14 (Pubitemid 46507501)
24. A. Balan, G. Gunbas, A. Durmus, and L. Toppare Donor-acceptor polymer with benzotriazole moiety: enhancing the electrochromic properties of the donor unit Chemistry of Materials 20 24 2008 7510 7513
25. D. Baran, A. Balan, S. Celebi, B.M. Esteban, H. Neugebauer, N.S. Sariciftci, and L. Toppare Processable multipurpose conjugated polymer for electrochromic and photovoltaic applications Chemistry of Materials 22 9 2010 2978 2987
26. G. Cetin, A. Balan, G. Gunbas, A. Durmus, and L. Toppare A new p- and n-dopable selenophene derivative and its electrochromic properties Organic Electronics 10 1 2009 34 41
27. D. Baran, A. Balan, B.M. Esteban, H. Neugebauer, N.S. Sariciftci, and L. Toppare Spectroelectrochemical and photovoltaic characterization of a solution-processable n-and-p type dopable pyrrole-bearing conjugated polymer Macromolecular Chemistry and Physics 211 24 2010 2602 2610
28. N. Akbasoglu, A. Balan, D. Baran, A. Cirpan, and L. Toppare Electrochemical and optical studies of furan and thieno[3,2-b]thiophene end capped benzotriazole derivatives Journal of Polymer Science Part A Polymer Chemistry 48 23 2010 5603 5610
29. M. Icli, M. Pamuk, F. Algi, A.M. Onal, and A. Cihaner Donor - acceptor polymer electrochromes with tunable colors and performance Chemistry of Materials 22 2010 4034 4044
30. F.E. Kanik, E. Rende, S. Timur, and L. Toppare A novel functional conducting polymer: synthesis and application to biomolecule immobilization Journal of Materials Chemistry 22 2012 22517 22525
31. I. Palamà, F. Di Maria, I. Viola, E. Fabiano, G. Gigli, C. Bettini, and G. Barbarella Live-cell-permeant thiophene fluorophores and cell-mediated formation of fluorescent fibrils Journal of the American Chemical Society 133 44 2011 17777 17785
32. Y. Xia, J. Luo, X. Deng, X. Li, D. Li, X. Zhu, W. Yang, and Y. Cao Novel random low-band-gap fluorine based copolymers for deep red/near infrared light emitting diodes and bulk heterojunction photovoltaic cells Macromolecular Chemistry Physics 207 5 2006 511 520
33. S. Tarkuc, E. Sahmetlioglu, C. Tanyeli, I.M. Akhmedov, and L. Toppare A soluble conducting polymer: 1-Phenyl-2,5-di(2-thienyl)-1H-pyrrole and its electrochromic application Electrochimica Acta 51 25 2006 5412 5419 (Pubitemid 44066344)
34. M. Ak, P. Camurlu, F. YIlmaz, L. Cianga, Y. Yagci, and L. Toppare Electrochromic properties and electrochromic device application of copolymer of N-(4-(3-thienyl methylene)-oxycarbonylphenyl)maleimide with thiophene Journal of Applied Polymer Science 102 5 2006 45004505
35. A.D. Becke Density-functional thermochemistry. III. The role of exact exchange The Journal of Chemical Physics 98 7 1993 5648 5652
36. C. Lee, W. Yang, and R.G. Parr Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Physical Review B 37 2 1988 785 789
37. Gaussian 09, Revision D.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G., Scalmani, V., Barone, B., Mennucci, G. A. Petersson, H., Nakatsuji, M., Caricato, X., Li, H. P. Hratchian, A. F. Izmaylov, J., Bloino, G., Zheng, J. L. Sonnenberg, M., Hada, M., Ehara, K., Toyota, R., Fukuda, J., Hasegawa, M., Ishida, T., Nakajima, Y., Honda, O., Kitao, H., Nakai, T., Vreven, J. A. Montgomery, Jr., J. E. Peralta, F., Ogliaro, M., Bearpark, J. J. Heyd, E., Brothers, K. N. Kudin, V. N. Staroverov, R., Kobayashi, J., Normand, K., Raghavachari, A., Rendell, J. C. Burant, S. S. Iyengar, J., Tomasi, M., Cossi, N., Rega, J. M. Millam, M., Klene, J. E. Knox, J. B. Cross, V., Bakken, C., Adamo, J., Jaramillo, R., Gomperts, R. E. Stratmann, O., Yazyev, A. J. Austin, R., Cammi, C., Pomelli, J. W. Ochterski, R. L. Martin, K., Morokuma, V. G. Zakrzewski, G. A. Voth, P., Salvador, J. J. Dannenberg, S., Dapprich, A. D. Daniels, Ö., Farkas, J. B. Foresman, J. V. Ortiz, J., Cioslowski, D. J. Fox, Gaussian, Inc., Wallingford CT, 2009.
38. K.K. Irikura, R.D. Johnson III, and R.N. Kacker Uncertainties in scaling factors for ab initio vibrational frequencies The Journal of Physical Chemistry A 109 2005 8430 8437 (Pubitemid 41396255)
39. M.P. Anderson, and P. Uvdal New scale factors for harmonic vibrational frequencies using the B3LYP density functional method with the triple-zeta basis set 6-311 + G(d,p) J. Phys. Chem. A 109 2005 2937 2941 (Pubitemid 40527290)
40. S.G. Aziz, S.A. Elroby, A. Alyoubi, O.I. Osman, R. Hilal, Experimental and the-oretical assignment of the vibrational spectra of triazoles and benzotriazoles.Identification of IR marker bands and electric response properties, J. Mol. Model20 (2014) 115.