Electrochemistry, morphology, thermoelectric and thermal degradation behaviors of free-standing copolymer films made from 1,12-bis(carbazolyl) dodecane and 3,4-ethylenedioxythiophene

Polymer Journal

Volumn 43, Issue 6, 2011, Pages 531-539

  Yue, Ruirui ^a   Lu, Baoyang ^a   Xu, Jingkun ^a   Chen, Shuai ^a   Liu, Congcong ^a  

^a JIANGXI SCIENCE AND TECHNOLOGY NORMAL UNIVERSITY   (China)

Author keywords

3,4 ethylenedioxythiophene; carbazole; conducting polymers; electrochemical copolymerization; fluorescence; thermoelectric properties

Indexed keywords

3 ,4-ETHYLENEDIOXYTHIOPHENE; BLUE LIGHT; CARBAZOLE; CARBAZOLYL; COPOLYMER FILMS; DODECANE; ELECTRICAL CONDUCTIVITY; ELECTROCHEMICAL COPOLYMERIZATION; ELECTROCHEMICAL STABILITIES; FEED RATIOS; FOUR-ORDER; FREESTANDING FILMS; POLY-3 ,4-ETHYLENEDIOXYTHIOPHENE; POLYMER OPTOELECTRONICS; POTENTIAL APPLICATIONS; REDOX ACTIVITY; TETRABUTYLAMMONIUM TETRAFLUOROBORATE; THERMAL DEGRADATIONS; THERMOELECTRIC MATERIAL; THERMOELECTRIC PROPERTIES;

CONDUCTING POLYMERS; COPOLYMERIZATION; CYCLIC VOLTAMMETRY; DICHLOROMETHANE; ELECTRIC CONDUCTIVITY; ELECTROCHEMICAL PROPERTIES; ELECTROCHEMISTRY; MECHANICAL PROPERTIES; ORGANIC CONDUCTORS; PLASTIC PRODUCTS; POLYCYCLIC AROMATIC HYDROCARBONS; REDOX REACTIONS; THERMOELECTRIC EQUIPMENT; THERMOELECTRICITY;

COPOLYMERS;

EID: 79958083836     PISSN: 00323896     EISSN: 13490540     Source Type: Journal    
DOI: 10.1038/pj.2011.26     Document Type: Article

References (43)

1. x. J. Chem. Soc. Chem. Commun. 16, 578-580 (1977)
2. Heeger, A. J. Semiconducting and metallic polymers: the fourth generation of polymeric materials. J. Phys. Chem. B 105, 8475-8491 (2001). (Pubitemid 35338780)
3. MacDiarmid, A. G. Synthetic metals: a novel role for organic polymers. Synth. Met. 125, 11-22 (2002). (Pubitemid 33142150)
4. Udum, Y. A., Ergun, Y., Sahin, Y., Pekmez, K. & Yildiz, A. Electrochemical synthesis and characterization of a new soluble conducting polymer. J. Mater. Sci. 44, 3148-3155 (2009).
5. Winder, C. & Sariciftci, N. S. Low bandgap polymers for Photon Harvesting in bulk heterojunction solar cells. J. Mater. Chem. 14, 1077-1086 (2004).
6. Kim, Y. G., Thompson, B. C., Ananthakrishnan, N., Padmanaban, G., Ramakrishnan, S. & Reynolds, J. R. Variable band gap conjugated polymers for optoelectronic and redox applications. J. Mater. Res. 20, 3188-3198 (2005). (Pubitemid 43072366)
7. Reddinger, J. L., Sotzing, G. A. & Reynolds, J. R. Muticoloured electrochromic polymers derived from easily oxidized bis[2-(3,4-ethylenedioxy) thienyl]carbazoles. Chem. Commun. 15, 1777-1778 (1996). (Pubitemid 126443671)
8. Pickup, D. F., Yi, H. N. & Iraqi, A. Preparation and properties of alternating 2,7-linked carbazole copolymers with phenylene units with varying number of fluorine substitu-ents. J. Mater. Sci. 44, 3172-3178 (2009).
9. Low, P. J., Paterson, M. A. J., Yufit, D. S., Howart, J. A. K., Cherryman, J. C., Tackley, D. R., Brook, R. & Brown, B. Towards an understanding of structure-property relationships in hole-transport materials: the influence of molecular conformation on oxidation potential in poly(aryl)amines. J. Mater. Chem. 15, 2304-2315 (2005). (Pubitemid 40891944)
10. MacClenaghan, N. D., Passalacqua, R., Loiseau, F., Campagna, S., Verheyde, B., Hameurlaine, A. & Dehaen, W. Ruthenium(II) dendrimers containing carbazole-based chromophores as branches. J. Am. Chem. Soc. 125, 5356-5365 (2003). (Pubitemid 36588344)
11. Trannekar, P., Fulghum, T., Baba, A., Patton, D. & Advincula, R. Quantitative electrochemical and electrochromic behavior of terthiophene and carbazole containing conjugated polymer network film precursors: EC-QCM and EC-SPR. Langmuir 23, 908-917 (2007). (Pubitemid 46226610)
12. Grazulevicius, J. V., Strohriegl, P., Pelichowski, J. & Pelichowski, K. Carbazole-contain-ing polymers: synthesis, properties and applications. Prog. Polym. Sci. 28, 1297-1353 (2003).
13. Grigoras, M. & Antonia, N. C. Synthesis and characterization of some carbazole-based imine polymers. Eur. Polym. J. 41, 1079-1089 (2005). (Pubitemid 40305041)
14. Kimoto, A., Cho, J. S., Higuchi, M. & Yamamoto, K. Synthesis of asymmetrically arranged dendrimers with a carbazole dendron and a phenylazomethine dendron. Macromolecules 37, 5531-5537 (2004).
15. Bloudin, N. & Leclerc, M. Poly(2,7-carbazole)s: structureproperty relationships. Acc. Chem. Res. 41, 1110-1119 (2008).
16. 00-Tris(N-azolyl)- triphenylamines. Tetrahedron Lett. 41, 481-483 (2000). (Pubitemid 30059253)
17. Koyuncu, S., Gultekin, B., Zafer, C., Bilgili, H., Can, M., Demic, S., Kay, I. & Icli, S. Electrochemical and optical properties of biphenyl bridged-dicarbazole oligomer films: electropolymerization and electrochromism. Electrochim. Acta 54, 5694-5702 (2009).
18. Chen, J. P. & Natansohn, A. Synthesis and characterization of novel carbazole-containing soluble polyimides. Macromolecules 32, 3171-3177 (1999).
19. Qu, J., Kawasaki, R., Shiotsuki, M., Sonda, F. & Masuda, T. Synthesis and properties of polyacetylenes carrying N-phenylcarbazole and triphenylamine moieties. Polymer 47, 6551-6559 (2006). (Pubitemid 44279745)
20. Clouted, E., Olivero, C., Ades, D., Castex, M. C. & Siove, A. Synthesis and blue luminescence of a soluble newly designed carbazole main-chain polymer. Polymer 43, 3489-3495 (2002). (Pubitemid 34453519)
21. Cosnier, S., Fologea, D., Szunerits, S. & Marks, R. S. Poly(dicarbazole-N-hydroxysuc-cinimide) film: a new polymer for the reagentless grafting of enzymes and redox mediators. Electrochem. Commun. 2, 827-831 (2000). (Pubitemid 32047903)
22. Marrec, P., Dano, C., Gueguen-Simonet, N. & Simonet, J. The anodic oxidation and polymerization of carbazoles and dicarbazoles N-substituted by polyether chains. Synth. Met. 89, 171-179 (1997). (Pubitemid 127369705)
23. Cosnier, S., Lepellec, A., Marks, R. S., Perie, K. & Lellouche, J. P. A permselective biotinylated polydicarbazole film for the fabrication of amperometric enzyme electrodes. Electrochem. Commun. 5, 973-977 (2003).
24. Diamant, Y., Furmanovich, E., Landau, A., Lellouche, J. P. & Zaban, A. Electrochemical polymerization and characterization of a functional dicarbazole conducting polymer. Electrochim. Acta 48, 507-512 (2003).
25. Wei, Z. H., Wang, Q., Xu, J. K., Nie, Y. L., Du, Y. K. & Xia, H. Y. Facile electro-syntheses of high tensile strength alkyl-bridged dicarbazole polymer films and its fluorescence Spectra. J. Polym. Sci. Part A Polym. Chem. 46, 5232-5241 (2008).
26. Jia, P., Xu, J., Ma, J. & Lu, X. Enhancement of electrochromic contrast by tethering polyaniline onto cyclotriphosphazene. Eur. Polym. J. 45, 772-778 (2009).
27. Ma, L., Li, Y., Yu, X., Yang, Q. & Noh, C. Fabricating red-blue-switching dual polymer electrochromic devices using room temperature ionic liquid. Sol. Energy Mater. Sol. Cells 93, 564-570 (2009).
28. Ak, M., Şahmetlioǧlu, E. & Toppare, L. Synthesis, characterization and optoelectro-chemical properties of poly(1,6-bis(2,5- di(thiophen-2-yl)-1H-pyrrol-1-yl)hexane) and its copolymer with EDOT. J. Electroanal. Chem. 621, 55-61 (2008).
29. Berlin, A., Zotti, G., Zecchin, S., Schiavon, G., Vercelli, B. & Zanelli, A. New low-gap polymers from 3,4-ethylenedioxythiophene-bis-substituted electron-poor thiophenes. The roles of thiophene, donor-acceptor alternation, and copolymerization in intrinsic Conductivity. Chem. Mater. 16, 3667-3676 (2004).
30. Yildiz, E., Camurlu, P., Tanyeli, C., Akhmedov, I. & Toppare, L. 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 (2008). (Pubitemid 350296120)
31. Zhang, C., Hua, C., Wang, G. H., Ouyang, M. & Ma, C. A. A novel multichromic copolymer via electrochemical copolymerization of (S)-1,1¢-binaphthyl-2,2¢-diyl bis(N-(6-hexanoic acid-1-yl) pyrrole) and 3,4-ethylenedioxythiophene. Electrochim. Acta 55, 4103-4111 (2010).
32. Wagner, K., Pringle, J. M., Hall, S. B., Forsyth, M., Macfarlene, D. R. & Officer, D. L. Investigation of the electropolymerisation of EDOT in ionic liquids. Synth. Met. 153, 257-260 (2005). (Pubitemid 41278018)
33. Raimundo, J. M., Blanchard, P., Frere, P., Mercier, N., Ledoux, R. I., Hierle, R. & Roncali, J. Push-pull chromophores based on 2,2¢-bi(3,4-ethylenedioxythiophene) (BEDOT) p-conjugating spacer. Tetrahedron Lett. 42, 1507-1510 (2001). (Pubitemid 32155850)
34. Walczak, R. M., Cowart, J. S., Abboud, K. A. & Reynolds, J. R. Conformational locking for band gap control in 3,4-propylenedioxythiophene based electrochromic polymers. Chem. Commun. 15, 1604-1606 (2006).
35. Li, Y., Ding, J., Day, M., Tao, Y., Lu, J. & Diorio, M. Synthesis and properties of random and alternating fluorene/carbazole copolymers for use in Blue light-emitting devices. Chem. Mater. 16, 2165-2173 (2004).
36. Li, X. G., Huang, M. R., Duan, W. & Yang, Y. L. Novel multifunctional polymers from aromatic diamines by oxidative polymerizations. Chem. Rev. 102, 2925-3030 (2002). (Pubitemid 35381640)
37. Otero, T. F. & Larreta-Azelain, E. D. Electrochemical generation of polythiophene films on platinum electrodes. Polymer 29, 1522-1527 (1988).
38. Morin, J. F., Leclerc, M., Ades, D. & Siove, A. Polycarbazoles: 25 years of progress. Macromo. Rapid Commun. 26, 761-778 (2005). (Pubitemid 40812006)
39. Innis, P. C., Mazurkiewicz, J., Nguyen, T., Wallace, G. G. & Macfarlane, D. Enhanced electrochemical stability of polyaniline in ionic liquids. Curr. Appl. Phys. 4, 389-393 (2004). (Pubitemid 38360854)
40. Li, M. C., Ma, C. A., Liu, B. Y. & Jin, Z. M. A novel electrolyte 1-ethylimidazolium trifluoroacetate used for electropolymerization of aniline. Electrochem. Commun. 7, 209-212 (2005). (Pubitemid 40159047)
41. Kumar, A., Welsh, D. M., Morvant, M. C., Piroux, F., Abboud, K. A. & Reynolds, J. R. Conducting poly(3,4-alkylenedioxythiophene) derivatives as fast electrochromics with high-contrast ratios. Chem. Mater. 10, 896-902 (1998). (Pubitemid 128485556)
42. Hiroshige, Y., Ookawa, M. & Toshima, N. High thermoelectric performance of poly(2,5-dimethoxyphenylenevinylene) and its derivatives. Synth. Met. 156, 1341-1347 (2006). (Pubitemid 46186827)
43. Lévesque, I., Gao, X., Klug, D. D., Tse, J. S., Ratcliffe, C. I. & Leclerc, M. Highly soluble poly(2,7-carbazolenevinylene) for thermoelectrical applications: from theory to experiment. React. Funct. Polym. 65, 23-36 (2005). (Pubitemid 41508938)