Near infrared electrochromic naphthalene-based polyimides containing triarylamine: Synthesis and electrochemical properties

Electrochimica Acta

Volumn 112, Issue , 2013, Pages 59-67

  Cai, Jiwei ^a   Ma, Lina ^a   Niu, Haijun ^a   Zhao, Ping ^b   Lian, Yongfu ^a   Wang, Wen ^c  

^a HEILONGJIANG UNIVERSITY   (China)

^b EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^c HARBIN INSTITUTE OF TECHNOLOGY   (China)

Author keywords

Electrochemistry; Electrochromism; Polyimides; Triphenylamine

Indexed keywords

COLORATION EFFICIENCIES; DIMETHYL SULFOXIDE (DMSO); ELECTRO-CHROMIC APPLICATIONS; ELECTROCHROMIC BEHAVIOR; FOURIER TRANSFORM INFRARED; POLYMERIZATION PROCESS; QUANTUM CHEMICAL CALCULATIONS; TRIPHENYL AMINES;

CYCLIC VOLTAMMETRY; DIMETHYL SULFOXIDE; ELECTROCHEMISTRY; INFRARED DEVICES; MOLECULAR ORBITALS; NAPHTHALENE; ORGANIC SOLVENTS; POLYIMIDES;

ELECTROCHROMISM;

EID: 84884491352     PISSN: 00134686     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.electacta.2013.08.160     Document Type: Article

References (36)

1. H. Shin, Y. Kim, T. Bhuvana, J. Lee, X. Yang, C. Park, and E. Kim Color combination of conductive polymers for black electrochromism ACS Appl. Mater. 4 2012 185
2. C.J. Yao, Y.W. Zhong, H.J. Nie, H.D. Abruña, and J.N. Yao Near-IR electrochromism in electropolymerized films of a biscyclometalated ruthenium complex bridged by 1,2,4,5-tetra(2-pyridyl)benzene ligand J. Am. Chem. Soc. 133 2011 20720
3. S. Beaupre, J. Dumas, and M. Leclerc A variable optical attenuator operating in the near-infrared region based on an electrochromic molybdenum complex Chem. Mater. 18 2006 4011
4. A.M. McDonagh, S.R. Bayly, D.J. Riley, M.D. Ward, J.A. McCleverty, M.A. Cowin, C.N. Morgan, R. Varrazza, R.V. Penty, and I.H. White A variable optical attenuator operating in the near-infrared region based on an electrochromic molybdenum complex Chem. Mater. 12 2000 2523
5. S. Xun, G. LeClair, J. Zhang, X. Chen, J.P. Gao, and Z.Y. Wang Tuning the electrical and optical properties of dinuclear ruthenium complexes for near infrared optical sensing Org. Lett. 8 2006 1697
6. G. Sönmez, P. Schottland, K. Zong, and J.R. Reynolds Highly transmissive and conductive poly[(3,4alkylenedioxy)pyrrole2,5diyl] (PXDOP) films prepared by air or transition metal catalyzed chemical oxidation J. Mater. Chem. 11 2001 289
7. C.S. Grange, A.J.H.M. Meijer, and M.D. Ward Trinuclear ruthenium dioxolene complexes based on the bridging ligand hexahydroxytriphenylene: electrochemistry, spectroscopy, and near-infrared electrochromic behaviour associated with a reversible seven-membered redox chain Dalton Trans. 39 2010 200
8. P. Chandrasekhar, G.C. Birur, P. Stevens, S. Rawal, E.A. Pierson, K.L. Miller, P. Chandrasekhar, G.C. Birur, P. Stevens, S. Rawal, E.A. Pierson, and K.L. Miller Far infrared electrochromism in unique conducting polymer systems Synth. Met. 119 2001 293
9. Y. Zheng, J. Cui, J. Zheng, and X. Wan Near-infrared electrochromic and chiroptical switching polymers: synthesis and characterization of helical poly(N-propargylamides) carrying anthraquinone imide moieties in side chains J. Mater. Chem. 20 2010 5915
10. G. Qian, H. Abu, and Z.Y. Wang A precursor strategy for the synthesis of low band-gap polymers: an efficient route to a series of near-infrared electrochromic polymers J. Mater. Chem. 21 2011 7678
11. S.H. Cheng, S.H. Hsiao, T.H. Su, and G.S. Liou Novel electrochromic aromatic poly(amine- amide-imide)s with pendent triphenylamine structures Polymer 46 2005 5939
12. S.H. Hsiao, G.S. Liou, Y.C. Kung, H.Y. Pan, and C.H. Kuo Electroactive aromatic polyamides and polyimides with adamantylphenoxy-substituted triphenylamine units Eur. Polym. J. 45 2009 2234
13. N.V. Sadavarte, C.V. Avadhani, P.V. Naik, and P.P. Wadgaonkar Regularly alternating poly(amideimide)s containing pendent pentadecyl chains: synthesis and characterization Eur. Polym. J. 46 2010 1307
14. H.R. Kricheldorf, and B. Schmidt New polymer syntheses. 68. Kevlar-type polyaramides derived from 2-phenoxy-1,4-diaminobenzene Hans R. Kricheldorf; Bernd Schmidt Macromolecules 25 1992 5471
15. H.R. Kricheldorf, and R. Burger New polymer syntheses. LXXV. 2,5-Biaryloxyterephthalic acids and rigid-rod polyaramides derived from them Hans R. Kricheldorf; Rolf Bürger J. Polym. Sci., Part A: Polym. Chem. 32 1994 355
16. H.M. Wang, and S.H. Hsiao Electrochemically and electrochromically stable polyimides bearing tert-butyl-blocked N,N,N′,N′-tetraphenyl-1,4- phenylenediamine units Polymer 50 2009 1692
17. S.J. Zhang, Y.F. Li, D.X. Yin, X.Y. Shao, and S.Y. Yang Study on synthesis and characterization of novel polyimides derived from 2,6-Bis(3-aminobenzoyl) pyridine Eur. Polym. J. 41 2005 1097
18. Z.X. Hu, Y. Yin, H. Kita, K. Okamoto, Y. Suto, H.G. Wang, H. Kawasato, Zhaoxia Hu, Yan Yin, Hidetoshi Kita, Ken-ichi Okamoto, Yoshiki Suto, Honguan Wang, Hironobu, and Kawasato Synthesis and properties of novel sulfonated polyimides bearing sulfophenyl pendant groups for polymer electrolyte fuel cell application Polymer 48 2007 1962
19. Y. Shao, Y.F. Li, X. Zhao, T. Ma, C.L. Gong, and F.C. Yang Synthesis and characterization of soluble polyimides derived from a novel unsymmetrical diamine monomer: 1,4-(2′,4″-diaminodiphenoxy)benzene Eur. Polym. J. 43 2007 4389
20. H.S. Choi, I.S. Chung, K. Hong, C.E. Park, and S.Y. Kim Soluble polyimides from unsymmetrical diamine containing benzimidazole ring and trifluoromethyl pendent group Polymer 49 2008 2644
21. M. Ghaemy, and R. Alizadeh Synthesis of soluble and thermally stable polyimides from unsymmetrical diamine containing 2,4,5-triaryl imidazole pendent group Eur. Polym. J. 45 2009 1681
22. Y.C. Kung, W.F. Lee, S.H. Hsiao, and G.S. Liou New polyimides incorporated with diphenylpyrenylamine unit as fluorophore and redox-chromophore J. Polym. Sci., Part A: Polym. Chem. 49 2011 2210
23. A. Iwan, and D. Sek Polymers with triphenylamine units: photonic and electroactive materials Prog. Polym. Sci. 36 2011 1277
24. M. Thelakkat Dendrimeric and polymeric triarylamines as photoconductors and hole transport materials for electro-optical applications Macromol. Mater. Eng. 287 2002 442
25. B. Cho, S. Song, Y. Ji, T.W. Kim, and T. Lee Organic resistive memory devices: performance enhancement, integration, and advanced architectures Adv. Funct. Mater. 21 2011 2806
26. S. Köber, M. Salvador, and K. Meerholz Organic photorefractive materials and applications Adv. Mater. 23 2011 4725 4763
27. K. Ghosh, G. Masanta, R. Fröhlich, and I.D. Petsalakis Triphenylamine-based receptors in selective recognition of dicarboxylic acids J. Phys. Chem. B 113 2009 7800
28. T. Bessho, S.M. Zakeeruddin, C.Y. Yeh, W.G. Eric Diau, and M. Grätzel Highly efficient mesoscopic dye-sensitized solar cells based on donor-acceptor-substituted porphyrins Angew. Chem. Int. Ed. 49 2010 6646
29. G.S. Liou, S.H. Hsiao, M. Ishida, M. Kakimoto, and Y. Imai Synthesis and properties of new aromatic poly(amine-imide)s derived from N,N′-bis(4- aminophenyl)-N,N′-diphenyl-1,4-phenylenediamine J. Polym. Sci., Part A: Polym. Chem. 40 2002 3815
30. H.J. Niu, P.H. Luo, M.L. Zhang, L. Zhang, L.N. Hao, J. Luo, X.D. Bai, and W. Wang Multifunctional, photochromic, acidichromic, electrochromic molecular switch: novel aromatic poly(azomethine)s containing triphenylamine group Eur. Polym. J. 45 2009 3058
31. H.J. Niu, H.Q. Kang, J.W. Cai, C. Wang, X.D. Bai, and W. Wang Novel soluble polyazomethines with pendant carbazole and triphenylamine derivatives: preparation, characterization and optical, electrochemical, electrochromic properties Polym. Chem. 2 2011 2804
32. J.W. Cai, H.J. Niu, C. Wang, L.N. Ma, X.D. Bai, and W. Wang Tuning the bandgaps of polyazomethines containing triphenylamine by different linkage sites of dialdhyde monomers Electrochim. Acta 76 2012 229
33. F.C. Tsai, C.C. Chang, C.L. Liu, W.C. Chen, and S.A. Jenekhe New thiophene-linked conjugated poly(azomethine)s: theoretical electronic structure, synthesis and properties Macromolecules 38 2005 1958
34. C.H. Duan, W.Z. Cai, F. Huang, J. Zhang, M. Wang, T.B. Yang, C.M. Zhong, X. Gong, and Y. Cao Novel silafluorene-based conjugated polymers with pendant acceptor groups for high performance solar cells Macromolecules 43 2010 5262
35. M. Robin, and P. Day Mixed valence chemistry - a survey and classification Adv. Inorg. Radiochem. 10 1968 247
36. S.J. Yoo, J.H. Cho, J.W. Lim, S.H. Park, J. Jang, and Y.E. Sung High contrast ratio and fast switching polymeric electrochromic films based on water-dispersible polyaniline-poly(4-styrenesulfonate) nanoparticles Electrochem. Commun. 12 2010 164