Electropolymerized three-dimensional randomly branched edot-containing copolymers

Langmuir

Volumn 29, Issue 49, 2013, Pages 15463-15473

  Link, Steffen M ^a   Scheuble, Martin ^a   Goll, Miriam ^a   Muks, Erna ^a   Ruff, Adrian ^a   Hoffmann, Anke ^b   Richter, Thomas V ^a   Lopez Navarrete, Juan T ^c   Ruiz Delgado, M Carmen ^c   Ludwigs, Sabine ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

^b UNIVERSITY OF FREIBURG   (Germany)

^c UNIVERSITY OF MÁLAGA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BRANCHING UNITS; CYCLIC VOLTAMMETRIC; ELECTROCHEMICAL COPOLYMERIZATION; ELECTRODEPOSITED FILMS; HOMO-LUMO GAPS; OPTICAL AND ELECTRONIC PROPERTIES; OXIDATIVE COUPLINGS; THIOPHENE MONOMERS;

ELECTRONIC PROPERTIES; ELECTROPOLYMERIZATION; THIOPHENE; THREE DIMENSIONAL;

COPOLYMERS;

EID: 84890323491     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la403050c     Document Type: Article

References (60)

1. Jonas, F., Heywang, G., Schmidtberg, W., Heinze, J., and Dietrich, M. Polythiophenes, Process for Their Preparation and Their Use. Eur. Pat. 0339340, 1989.
2. Kirchmeyer, S.; Reuter, K. Scientific importance, properties and growing applications of poly(3,4-ethylenedioxythiophene) J. Mater. Chem. 2005, 15, 2077-2088
3. Heywang, G.; Jonas, F. Poly(alkylenedioxythiophene)s- new, very stable conducting polymers Adv. Mater. 1992, 4, 116-118
4. Pei, Q.; Zuccarello, G.; Ahlskog, M.; Inganäs, O. Electrochromic and highly stable poly(3,4-ethylenedioxythiophene) switches between opaque blue-black and transparent sky blue Polymer 1994, 35, 1347-1351
5. Yang, S. Y.; Cicoira, F.; Byrne, R.; Benito-Lopez, F.; Diamond, D.; Owens, R.; Malliaras, G. G. Electrochemical transistors with ionic liquids for enzymatic sensing Chem. Commun. 2010, 46, 7972-7974
6. Heuer, H. W.; Wehrmann, R.; Kirchmeyer, S. Electrochromic window based on conducting poly(3,4-ethylenedioxythiophene)- poly(styrene sulfonate) Adv. Funct. Mater. 2002, 12, 89-94
7. Sirringhaus, H. Device physics of solution-processed organic field-effect transistors Adv. Mater. 2005, 17, 2411-2425
8. Ma, W.; Kim, J. Y.; Lee, K.; Heeger, A. J. Effect of the molecular weight of poly(3-hexylthiophene) on the morphology and performance of polymer bulk heterojunction solar cells Macromol. Rapid Commun. 2007, 28, 1776-1780
9. Reyes-Reyes, M.; Kim, K.; Dewald, J.; Lopez-Sandoval, R.; Avadhanula, A.; Curran, S.; Carrol, D. Meso-structure formation for enhanced organic photovoltaic cells Org. Lett. 2005, 7, 5749-5752
10. Crossland, E. J. W.; Rahimi, K.; Reiter, G.; Steiner, U.; Ludwigs, S. Systematic control of nucleation density in poly(3-hexylthiophene) thin films Adv. Funct. Mater. 2011, 21, 518-524
11. Roncali, J.; Leriche, P.; Cravino, A. From one- to three-dimensional organic semiconductors: in search of the organic silicon? Adv. Mater. 2007, 19, 2045-2060
12. Tour, J. M.; Wu, R.; Schumm, J. S. Extended orthogonally fused conducting oligomers for molecular electronic devices J. Am. Chem. Soc. 1991, 113, 7064-7066
13. Roncali, J.; Guy, A.; Lemaire, M.; Garreau, R.; Hoa, H. A. Tetrathienylsilane as a precursor of highly conducting electrogenerated polythiophene J. Electroanal. Chem. 1991, 312, 277-283
14. Roncali, J.; Thobie-Gautier, C.; Brisset, H.; Favart, J.-F.; Guy, A. Electro-oxidation of tetra(terthienyl)silanes: towards 3D electroactive π -conjugated systems J. Electroanal. Chem. 1995, 381, 257-260
15. Cravino, A.; Aléveque, S. R. O.; Leriche, P.; Frére, P.; Roncali, J. Triphenylamine-oligothiophene conjugated systems as organic semiconductors for opto-electronics Chem. Mater. 2006, 18, 2584-2590
16. Bilge, A.; Zen, A.; Foster, M.; Li, H.; Galbrecht, F.; Nehls, B. S.; Farrell, T.; Neher, D.; Scherf, U. Swivel-cruciform oligothiophene dimers J. Mater. Chem. 2006, 16, 3177-3182
17. Sun, X. B.; Liu, Y. Q.; Chen, S. Y.; Qiu, W. F.; Yu, G.; Ma, Y. Q.; Qi, T.; Zhang, H. J.; Xu, X. J.; Zhu, D. B. X-shaped electroactive molecular materials based on oligothiophene architectures: facile synthesis and photophysical and electrochemical properties Adv. Funct. Mater. 2006, 16, 917-925
18. Benicori, T.; Capaccio, M.; De Angelis, F.; Falciola, L.; Muccini, M.; Mussini, P.; Ponti, A.; Toffanin, S.; Traldi, P.; Sannicolo, F. Spider-like oligothiophenes Chem.-Eur. J. 2008, 14, 459-471
19. Xia, C.; Fan, X.; Locklin, J.; Advincula, R. C. A first synthesis of thiophene dendrimers Org. Lett. 2002, 4, 2067-2070
20. Ma, C.-Q.; Mena-Osteritz, E.; Debaerdemaeker, T.; Wienk, M. M.; Janssen, R.; Bäuerle, P. Functionalized 3D oligothiophene dendrons and dendrimers-novel macromolecules for organic electronics Angew. Chem., Int. Ed. 2007, 46, 1679-1683
21. Mangold, H. S.; Richter, T. V.; Link, S.; Würfel, U.; Ludwigs, S. Optoelectronic properties of hyperbranched polythiophenes J. Phys. Chem. B 2012, 116, 154-159
22. Ma, C.-Q.; Fonrodona, M.; Schikora, M. C.; Wienk, M. M.; Janssen, R. A. J.; Bäuerle, P. Solution-processed bulk-heterojunction solar cells based on monodisperse dendritic oligothiophenes Adv. Funct. Mater. 2008, 18, 3323-3331
23. Visy, C.; Lukkari, J.; Kankare, J. Scheme for the anodic and cathodic transformations in polythiophenes Macromolecules 1993, 26, 3295-3298
24. Visy, C.; Lukkari, J.; Kankare, J. Electrochemically polymerized terthiophene derivatives carrying aromatic substituents Macromolecules 1994, 27, 3322-3329
25. Tanaka, S.; Kumei, M. A new polythiophene prepared by the electropolymerization of a branched sexithienyl J. Chem. Soc., Chem. Commun. 1995, 815-816
26. Zotti, G.; Salmaso, R.; Gallazzi, M. C.; Marin, R. A. In situ conductivity of a polythiophene from a branched alkoxy-substituted tetrathiophene. enhancement of conductivity by conjugated cross-linking of polymer chains Chem. Mater. 1997, 9, 791-795
27. Inzelt, G. Chemical and Electrochemical Syntheses of Conducting Polymers. Conducting Polymers-A New Era in Eletrochemistry; Springer: Heidelberg, 2008; Chapter 4.
28. Richter, T. V.; Link, S.; Hanselmann, R.; Ludwigs, S. Design of soluble hyperbranched polythiophenes with tailor-made optoelectronic properties Macromol. Rapid Commun. 2009, 30, 1323-1327
29. Link, S.; Richter, T.; Yurchenko, O.; Heinze, J.; Ludwigs, S. Electrochemical behavior of electropolymerized and chemically synthesized hyperbranched polythiophenes J. Phys. Chem. B 2010, 114, 10703-10708
30. Donat-Bouillud, A.; Lévesque, I.; Tao, Y.; D'Iorio, M.; Béaupre, S.; Blondin, P.; Ranger, M.; Bouchard, J.; Leclerc, M. Light-emitting diodes from fluorene-based π -conjugated polymers Chem. Mater. 2000, 12, 1931-1936
31. Stéphan, O.; Tran-Van, F.; Chevrot, C. New organic materials for light emitting devices based on dihexylfluorene-co-ethylenedioxythiophene copolymers exhibiting improved hole-injecting properties Synth. Met. 2002, 131, 31-40
32. Berlin, A.; Zotti, G.; Zecchin, S.; Schiavon, G.; Cocchi, M.; Virgili, D.; Sabatini, C. 3,4-Ethylenedioxy-substituted bithiophene-alt-thiophene-S,S dioxide regular copolymers. Synthesis and conductive, magnetic and luminescence properties J. Mater. Chem. 2003, 13, 27-33
33. Huang, H.; Pickup, P. G. A donor-acceptor conducting copolymer with a very low band gap and high intrinsic conductivity Chem. Mater. 1998, 10, 2212-2216
34. Nie, G.; Qu, L.; Xu, J.; Zhang, S. Electrosyntheses and characterizations of a new soluble conducting copolymer of 5-cyanoindole and 3,4- ethylenedioxythiophene Electrochim. Acta 2008, 53, 8351-8358
35. Aubert, P.-H.; Knipper, M.; Groenendaal, L.; Lutsen, L.; Manca, J.; Vanderzande, D. Copolymers of 3,4-ethylenedioxythiophene and of pyridine alternated with fluorene or phenylene units: synthesis, optical properties, and devices Macromolecules 2004, 37, 4087-4098
36. Turbiez, M.; Frére, P.; Blanchard, P.; Roncali, J. Mixed π -conjugated oligomers of thiophene and 3,4-ethylenedioxythiophene (EDOT) Tetrahedron Lett. 2000, 41, 5521-5525
37. Turbiez, M.; Frére, P.; Allain, M.; Videlot, C.; Ackermann, J.; Roncali, J. Design of organic semiconductors: tuning the electronic properties of π -conjugated oligothiophenes with the 3,4-ethylenedioxythiophene (EDOT) building block Chem.-Eur. J. 2005, 11, 3742-3752
38. Roncali, J.; Blanchard, P.; Frére, P. 3,4-Ethylenedioxythiophene (EDOT) as a versatile building block for advanced functional p-conjugated systems J. Mater. Chem. 2005, 15, 1589-1610
39. Algia, M. P.; Öztas, Z.; Tirkes, S.; Cihaner, A.; Algi, F. A new electrochromic copolymer based on dithienylpyrrole and EDOT Org. Electron. 2013, 14, 1094-1102
40. Yua, W.; Chen, J.; Fu, Y.; Xu, J.; Nie, G. Electrochromic property of a copolymer based on 5-cyanoindole and 3,4-ethylenedioxythiophene and its application in electrochromic devices J. Electroanal. Chem. 2013, 700, 17-23
41. Piron, F.; Leriche, P.; Mabon, G.; Grosu, I.; Roncali, J. Electropolymerization of three-dimensional π -conjugated system based on 3,4-ethylenedioxythiophene (EDOT) Electrochem. Commun. 2008, 10, 1427-1430
42. Piron, F.; Leriche, P.; Grosu, I.; Roncali, J. Electropolymerizable 3D π -conjugated architectures with ethylenedioxythiophene (EDOT) end-groups as precursors of electroactive conjugated networks J. Mater. Chem. 2010, 20, 10260-10268
43. Richter, T. V.; Braun, C. H.; Link, S.; Scheuble, M.; Crossland, E. J. W.; Stelzl, F.; Würfel, U.; Ludwigs, S. Regioregular polythiophenes with alkylthiophene side chains Macromolecules 2012, 45, 5782-5788
44. Gritzner, G.; KuÌŠta, J. Recommendations on reporting electrode potentials in nonaqueous solvents Pure Appl. Chem. 1984, 56, 461-466
45. Pommerehne, J.; Vestweber, H.; Guss, W.; Mahrt, R.; Bässler, H.; Porsch, M.; Daub, J. Efficient two layer LEDs on a polymer blend basis Adv. Mater. 1995, 7, 551-554
46. Perepichka, I. F.; Levillain, E.; Roncali, J. Effect of substitution of 3,4-ethylenedioxythiophene (EDOT) on the electronic properties of the derived electrogenerated low band gap conjugated polymers J. Mater. Chem. 2004, 14, 1679-1681
47. Yohannes, T.; Carlberg, J. C.; Inganäs, O.; Solomon, T. Electrochemical and spectroscopic characteristics of copolymers electrochemically synthesized from 3-methylthiophene and 3,4- ethylenedioxythiophene Synth. Met. 1997, 88, 15-21
48. Nie, G.; Qu, L.; Xu, J.; Zhang, S. Electrosyntheses and characterizations of a new soluble conducting copolymer of 5-cyanoindole and 3,4- ethylenedioxythiophene Electrochim. Acta 2008, 53, 8351-8358
49. Latonen, R.; Kvarnström, C.; Ivaska, A. Electrochemical synthesis of a copolymer of poly(3-octylthiophene) and poly(paraphenylene) Electrochim. Acta 1999, 44, 1933-1943
50. Ahonen, H. J.; Lukkari, J.; Kankare, J. n- and p-Doped poly(3,4-ethylenedioxythiophene): two electronically conducting states of the polymer Macromolecules 2000, 33, 6787-6793
51. Fu, Y.; Cheng, H.; Elsenbaumer, R. L. Electron-rich thienylene-vinylene low bandgap polymers Chem. Mater. 1997, 9, 1720-1724
52. Gustafsson, J. C.; Liedberg, B.; Inganäs, O. In situ spectroscopic investigations of electrochromism and ion transport in a poly(3,4- ethylenedioxythiophene) electrode in a solid state electrochemical cell Solid State Ionics 1994, 69, 145-152
53. Shiraishi, K.; Kanbara, T.; Yamamoto, T.; Groenendaal, L. Preparation of a soluble and neutral alkyl derivative of poly(3,4-ethylenedioxythiophene) and its optical properties Polymer 2001, 42, 7229-7232
54. Becke, A. D. Density-functional thermochemistry. III. The role of exact exchange J. Chem. Phys. 1993, 98, 5648-5652
55. Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Phys. Rev. B: Condens. Matter 1988, 37, 785-789
56. Hariharan, P. C.; Pople, J. A. Influence of polarization functions on MO hydrogenation energies Theor. Chim. Acta 1973, 28, 213-222
57. Francl, M. M.; Pietro, W. J.; Hehre, W. J.; Binkley, J. S.; Gordon, M. S.; DeFrees, D. J.; Pople, J. A. Self consistent molecular orbital methods. XXIII. A polarizationtype basis set for secondrow elements J. Chem. Phys. 1982, 77, 3654-3665
58. Hehre, W. J.; Ditchfield, R.; Pople, J. A. Self-consistent molecular orbital methods. XII. Further extensions of Gaussian-type basis sets for use in molecular orbital studies of organic molecules J. Chem. Phys. 1972, 56, 2257-2261
59. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision B.1; Gaussian, Inc.: Wallingford, CT, 2009.
60. Flükinger, P.; Lüthi, H. P.; Portmann, S.; Weber, J. Molekel 4.3 2000; Swiss Center for Scientific Computing.