Electrochemical and optical properties of 5,6-bis(octyloxy)-2,1,3 benzooxadiazole containing low band gap polymers

Synthetic Metals

Volumn 191, Issue , 2014, Pages 19-27

  Göker, Seza ^a   Hizalan, Gonul ^a   Udum, Yasemin Arslan ^b   Toppare, Levent ^a  

^a MIDDLE EAST TECHNICAL UNIVERSITY   (Turkey)

^b GAZI UNIVERSITY   (Turkey)

Author keywords

Benzooxadiazole; Conjugated polymers; Electropolymerization; Stille coupling

Indexed keywords

ELECTRONIC PROPERTIES; ELECTROPOLYMERIZATION; ITO GLASS;

BENZOOXADIAZOLE; COATED GLASS; CONJUGATED SYSTEMS; LOW BANDGAP POLYMERS; STILLE COUPLING; STILLE COUPLING REACTION; THREE ELECTRODE-SYSTEM;

CONJUGATED POLYMERS;

EID: 84896537073     PISSN: 03796779     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.synthmet.2014.02.010     Document Type: Article

References (40)

1. A.L. Dyer, M.R. Craig, J.E. Babiarz, K. Kiyak, and J.R. Reynolds Orange and red to transmissive electrochromic polymers based on electron-rich dioxythiophenes Macromolecules 43 2010 4460
2. S.O. Hacioglu, S. Toksabay, M. Sendur, L. Toppare, and Synthesis Electrochromic properties of triphenylamine containing copolymers: effect of p-bridge on electrochemical properties J. Polym. Sci., Part A: Polym. Chem. 52 2013 537
3. T. Ameri, N. Li, and C.J. Brabec Highly efficient organic tandem solar cells: a follow up review Energy Environ. Sci. 6 2013 2390
4. J.H. Seo, A. Gutacker, Y. Sun, H. Wu, F. Huang, Y. Cao, U. Scherf, A.J. Heeger, and G.C. Bazan Improved high-efficiency organic solar cells via incorporation of a conjugated polyelectrolyte interlayer J. Am. Chem. Soc. 133 2011 8416 8419
5. S.C. Price, A.C. Stuart, and W. You Low band gap polymers based on benzo[1,2-b:4,5-b′]dithiophene: rational design of polymers leads to high photovoltaic performance Macromolecules 43 2010 4609
6. W. Li, R. Qin, Y. Zhou, M. Andersson, F. Li, C. Zhang, B. Li, Z. Liu, Z. Bo, and F. Zhang Tailoring side chains of low band gap polymers for high efficiency polymer solar cells Polymer 51 2010 3031
7. J.H. Burroughes, D.D.C. Bradley, A.R. Brown, R.N. Marks, K. Mackay, R.H. Friend, P.L. Burns, and A.B. Holmes Light-emitting diodes based on conjugated polymers Nature 347 1990 539
8. K.T. Kamtekar, H.L. Vaughan, B.P. Lyons, A.P. Monkman, S.U. Pandya, and M.R. Bryce Synthesis and spectroscopy of poly(9,9-dioctylfluorene-2,7-diyl-co-2, 8-dihexyldibenzothiophene-S,S-dioxide-3,7-diyl)s: solution-processable, deep-blue emitters with a high triplet energy Macromolecules 43 2010 4481
9. A. Cirpan, L. Ding, and F.E. Karasz Optical and electroluminescent properties of polyfluorene copolymers and their blends Polymer 46 2005 811
10. A. Cirpan, L. Ding, and F.E. Karasz Efficient light emitting diodes from polyfluorene copolymer blends Synth. Met. 150 2005 195
11. N. Stutzmann, R.H. Friend, and H. Sirringhaus Self-aligned, vertical-channel, polymer field-effect transistors Science 299 2003 1881
12. R. Mondal, H.A. Becerril, E. Verploegen, D. Kim, J.E. Norton, S. Ko, N. Miyaki, S. Lee, M.F. Toney, J.L. Bredas, M.D. McGehee, and Z. Bao Thiophene-rich fused-aromatic thienopyrazine acceptor for donor-acceptor low band-gap polymers for OTFT and polymer solar cell applications J. Mater. Chem. 20 2010 5823
13. D.T. McQuade, A.E. Pullen, and T.M. Swager Conjugated polymer-based chemical sensors Chem. Rev. 100 2000 2537
14. A.A. Argun, A. Cirpan, and J.R. Reynolds The first truly all-polymer electrochromic devices Adv. Mater. 15 2003 1338
15. A. Bolduc, S. Dufresne, and W.G. Skene EDOT-containing azomethine: an easily prepared electrochromically active material with tuneable colours J. Mater. Chem. 20 2010 4820
16. A. Pennisi, F. Simone, G. Barlette, G.D. Marco, and M. Lanza Preliminary test of a large electrochromic window Electrochim. Acta 44 1999 3237
17. G. Inzelt, M. Pineri, J.W. Schultze, and M.A. Vorotyntsev Electron and proton conducting polymers: recent developments and prospects Electrochim. Acta 45 2000 2403
18. J. Bouffard, and T.M. Swager Fluorescent conjugated polymers that incorporate substituted 2,1,3-benzooxadiazole and 2,1,3-benzothiadiazole units Macromolecules 41 2008 5559
19. A. Balan, G. Günbaş, A. Durmuş, and L. Toppare Donor-acceptor polymer with benzotriazole moiety: enhancing the electrochromic properties of the "donor unit" Chem. Mater. 20 2008 7510
20. D. Aldakov, M.A. Palacios, P. Anzenbacher, and Benzothiadiazoles Dipyrrolyl quinoxalines with extended conjugated chromophores-fluorophores and anion sensors Chem. Mater. 17 2005 5238
21. P. Blanchard, J.M. Raimundo, and J. Roncali New synthetic strategies towards conjugated NLO-phores and fluorophores Synth. Met. 119 2001 527
22. A. Durmus, G.E. Gunbas, L. Toppare, and New Highly stable electrochromic polymers from 3,4-ethylenedioxythiophene-bis-substituted quinoxalines toward green polymeric materials Chem. Mater. 19 2007 6247
23. G.E. Gunbas, A. Durmus, and L. Toppare A unique processable green polymer with a transmissive oxidized state for realization of potential RGB-based electrochromic device applications Adv. Funct. Mater. 18 2008 2026
24. C.A. Thomas, K. Zong, K.A. Abboud, P.J. Steel, and J.R. Reynolds Donor-mediated band gap reduction in a homologous series of conjugated polymers J. Am. Chem. Soc. 126 2004 16440
25. A.C. Ozelcaglayan, M. Sendur, N. Akbasoglu, D.H. Apaydin, A. Cirpan, and L. Toppare Synthesis and electrochemical properties of a new benzimidazole derivative as the acceptor unit in donor-acceptor-donor type polymers Electrochim. Acta 2012 224
26. B. Zaifoglu, M. Sendur, N.A. Unlu, and L. Toppare High optical transparency in all redox states: Synthesis and characterization of benzimidazole and thieno[3,2-b]thiophene containing conjugated polymers Electrochim. Acta 85 2012 78
27. G. Sonmez, C.K.F. Shen, Y. Rubin, F. Wudl, and A. Red Green, and blue (RGB) polymeric electrochromic device (PECD): the dawning of the PECD era Angew. Chem. Int. Ed. 43 2004 1498
28. B.P. Karsten, L. Viani, J. Gierschner, J. Cornil, and R.A.J. Janssen On the origin of small band gaps in alternating thiophene-thienopyrazine oligomers J. Phys. Chem. A 113 2009 10343
29. E. Kozma, F. Munno, D. Kotowski, F. Bertini, S. Luzzati, and M. Catellani Synthesis and characterization of perylene-based donor-acceptor copolymers containing triple bonds Synth. Met. 160 2010 996
30. 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 Chem. Commun. 2009 6768
31. G.A. Cetin, A. Balan, A. Durmus, G. Gunbas, and L. Toppare A new p- and n-dopable selenophene derivative and its electrochromic properties Org. Electron. 10 2009 34
32. M.I. Ozkut, M.P. Algi, Z. Oztas, F. Algi, A.M. Onal, and A. Cihaner Members of CMY color space: cyan and magenta colored polymers based on oxadiazole acceptor unit Macromolecules 45 2012 729
33. P. Ding, C. Zhong, Y. Zou, C. Pan, H. Wu, and Y. Cao 5,6-bis(decyloxy)-2, 1,3-benzooxadiazole-based polymers with different electron donors for bulk-heterojunction solar cells J. Phys. Chem. C 115 2011 16211
34. J.M. Jiang, H.C. Chen, H.K. Lin, C.M. Yu, S.C. Lan, C.M. Liu, and K.H. Wei Conjugated random copolymers of benzodithiophene-benzooxadiazole- diketopyrrolopyrrole with full visible light absorption for bulk heterojunction solar cells Polym. Chem. 4 2013 5321
35. J.M. Jiang, P.A. Yang, T.H. Hsieh, and K.H. Wei Crystalline low-band gap polymers comprising thiophene and 2,1,3-benzooxadiazole units for bulk heterojunction solar cells Macromolecules 44 2011 9155
36. A. Balan, D. Baran, and L. Toppare Benzotriazole containing conjugated polymers for multipurpose organic electronic applications Chem. Comm. 2 2011 1029
37. A. Kumar, D.M. Welsh, M.C. Morvant, F. Piroux, K.A. Abboud, and J.R. Reynolds Conducting poly(3,4-alkylenedioxythiophene) derivatives as fast electrochromics with high contrast ratios Chem. Mater. 10 1998 896
38. J.A. Irvin, and J.R. Reynolds Low-oxidation-potential conducting polymers: alternating substituted para-phenylene and 3,4-ethylenedioxythiophene repeat units Polymer 39 1998 2339
39. G.A. Sotzing, and J.R. Reynolds Electrochromic conducting polymers via electrochemical polymerization of bis(2-(3,4-ethylenedioxy)thienyl) monomers Chem. Mater. 8 1996 882
40. M. Karakus, A. Balan, D. Baran, L. Toppare, and A. Cirpan Electrochemical and optical properties of solution processable benzotriazole and benzothiadiazole containing copolymers Synth. Met. 162 2012 79