Design of organic semiconductors: Tuning the electronic properties of π-conjugated oligothiophenes with the 3,4-ethylenedioxythiophene (EDOT) building block

Chemistry - A European Journal

Volumn 11, Issue 12, 2005, Pages 3742-3752

  Turbiez, Mathieu ^a   Fr̀re, Pierre ^a   Allain, Magali ^b   Videlot, Christine ^c   Ackermann, Jörg ^d   Roncali, Jean ^a  

^a UNIVERSITÉ D'ANGERS   (France)

^b UNIVERSITÉ D'ANGERS   (France)

^c AIX MARSEILLE UNIVERSITÉ   (France)

^d AIX MARSEILLE UNIVERSITY   (France)

Author keywords

3,4 ethylenedioxythiophene; Oligothiophenes; Pi interactions; Semiconductors; Structure property relationships

Indexed keywords

ABSORPTION SPECTROSCOPY; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; CYCLIC VOLTAMMETRY; ELECTROCHEMISTRY; ELECTRONIC PROPERTIES; FIELD EFFECT TRANSISTORS; HOLE MOBILITY; OLIGOMERS; OXIDATION; SEMICONDUCTOR MATERIALS; SYNTHESIS (CHEMICAL); ULTRAVIOLET SPECTROSCOPY;

3,4-ETHYLENEDIOXYTHIOPHENE; OLIGOTHIOPHENES; PI INTERACTIONS; STRUCTURE PROPERTY RELATIONSHIPS;

SEMICONDUCTING ORGANIC COMPOUNDS;

FUSED HETEROCYCLIC RINGS; ORGANIC COMPOUND; POLY(3,4 ETHYLENE DIOXYTHIOPHENE); POLY(3,4-ETHYLENE DIOXYTHIOPHENE); POLYMER; THIOPHENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTRIC CONDUCTIVITY; EQUIPMENT DESIGN; SEMICONDUCTOR; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BICYCLO COMPOUNDS, HETEROCYCLIC; CRYSTALLOGRAPHY, X-RAY; ELECTRIC CONDUCTIVITY; EQUIPMENT DESIGN; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANIC CHEMICALS; POLYMERS; SEMICONDUCTORS; THIOPHENES;

EID: 20444496981     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200401058     Document Type: Article

References (43)

1. a) C. D. Dimitrakopoulos, P. R. L. Malenfant, Adv. Mater. 2002, 14, 99;
2. b) J.A. Rogers, Z. Bao, A. Dodabalapur, B. Crone, V.R. Raju, H. E. Katz, V. Kuck, K. J. Ammundson, P. Drzaic, Proc. Nail Acad. Sci. USA Proc. Nail. Acad. Eng. 2001, 98, 4817;
3. c) F. Garnier, Acc. Chem. Res. 1999, 32, 209;
4. d) G. Horowitz, Adv. Mater. 1998, 10, 3;
5. e) H. E. Katz, J. Mater. Chem. 1997, 7, 369;
6. f) G. Barbarella, M. Zambianchi, L. Antolini, P. Ostoja, P. Maccagnani, A. Bongini, E. A. Marseglia, E. Tedesco, G. Gigli, R. Cingolani, J. Am. Chem. Soc. 1999, 121, 8920;
7. g) M. Halik, H. Klauk, U. Zschieschang, G. Schmid, S. Ponomarenko, S. Kirchmeyer, W. Weber, Adv. Mater. 2003, 15, 917.
8. a) U. Mitschke, P. Bauerle, J. Mater. Chem. 2000, 10, 1471;
9. b) F. Geiger, M. Stoldt, R. Schweiser, P. Bäuerle, E. Umbach, Adv. Mater. 1993, 5, 922;
10. c) G. Barbarella, L. Favaretto, G. Sotgiu, P. Zambianchi, A. Bongini, C. Arbizzani, M. Mastragostino, M. Anni, G. Gigli, R. Cingolani, J. Am. Chem. Soc. 2000, 122, 11 971;
11. d) G. Barbarella, L. Favaretto, G. Sotgiu, L. Antolini, G. Gigli, R. Cingolani, A. Bongini, Chem. Mater. 2001, 13, 4112.
12. a) C. Videlot, A. El Kassmi, D. Fichou, Solar Energy Materials & Solar Cells 2000, 63, 69;
13. b) R. de Bettignies, Y. Nicolas, P. Blanchard, E. Levillain, J.-M. Nunzi, J. Roncali, Adv. Mater. 2003, 15, 1939.
14. J. Cornil, J. P. Calbert, D. Beljonne, R. Silbey, J-L. Brédas, Adv. Mater. 2000, 12, 978.
15. J. Roncali, Chem. Rev. 1997, 97, 173.
16. B. L. Groenendaal, F. Jonas, D. Freitag, D. Pielartzik, J. R. Reynolds, Adv. Mater. 2000, 12, 481.
17. a) S. Akoudad, J. Roncali, Chem. Commun. 1998, 2081;
18. b) S. Akoudad, J. Roncali, Synth. Met. 1999, 101, 149;
19. c) I. Perepichka, E. Levillain, J. Roncali, J. Mater. Chem. 2004, 14, 1679.
20. a) J. M. Raimundo, P. Blanchard, P. Frère, N. Mercier. I. Ledoux Rak, R. Hierle, J. Roncali, Tetrahedron Lett. 2001, 42, 150;
21. b) J. M. Raimundo, P. Blanchard, N. Gallego Planas, N. Mercier. I. Ledoux Rak, R. Hierle, J. Org. Chem. 2002, 67, 205.
22. a) S. Akoudad, P. Frère, N. Mercier, J. Roncali, J. Org. Chem. 1999, 64, 4267;
23. b) P. Leriche, M. Turbiez, V. Monroche, P. Frère, P. Blanchard, P. J. Skabara, J. Roncali, Tetrahedron Lett. 2003, 44, 649.
24. a) S. Akoudad, J. Roncali, Synth. Met. 1998, 95, 114;
25. b) G. A. Sotzing, J. R. Reynolds, P. J. Steel, Adv. Mater. 1997, 9, 795.
26. G. A. Sotzing, J. R. Reynolds, P. J. Steel. Chem. Mater. 1996, 8, 882.
27. a) R. G. Hicks, M. B. Nodwell, J. Am. Chem. Soc. 2000, 122, 6746;
28. b) J. J. Apperloo, L. Groenendaal, H. Verheyen, M. Jayakannan, R. A. J. Janssen, A. Dkhissi, D. Beljonne, R. Lazzaroni, J. L. Brédas, Chem. Eur. J. 2002, 8, 2384;
29. c) M. Turbiez. P. Frère, J. Roncali, J. Org. Chem. 2003, 68, 5357.
30. a) A.K. Mohanakrishnan, A. Hucke, M. A. Lyon, M. V. Lakshmikantham, M. P. Cava, Tetrahedron 1999, 55, 11745;
31. b) M. Turbiez, P. Frère, P. Blanchard, J. Roncali, Tetrahedron Lett. 2000, 41, 5521.
32. J. Kagan, S. K. Arora, Heterocyles 1983, 20, 1937.
33. H. Meng, D. F. Perepichka, F. Wudl, Angew. Chem. 2003, 115, 682;
34. Angew. Chem. Int. Ed. 2003, 42, 658.
35. F. Gamier, R. Hajlaoui, A. El Kassmi, G. Horowitz, L. Laigre, W. Porzio, M. Armanini, F. Provasoli, Chem. Mater. 1998, 10, 3334.
36. a) S. D. D. V. Rughooputh, S. Hotta, A. J. Heeger, F. Wudl, J. Polym. Sci. 1987, 25, 1071;
37. b) O. Inganäs, W. Salaneck, J. E. Osterholm, J. Laakso, Synth. Met. 1988, 22, 395.
38. Gaussian 98 (Revision A.9), M. J. Frisch, G.W. Trucks, H.B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J.A. Jr. Montgomery, R.E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J.V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle and J. A. Pople Gaussian, Inc., Pittsburgh, PA, 1998.
39. A. Dkhissi, D. Beljonne, R. Lazzaroni, F. Louwet, L. Groenendaal, J. L. Brédas, Int. J. Quantum Chem. 2003, 91, 517.
40. T. Nishinaga, A. Wakamiya, D. Yamazaki, K. Komatsu, J. Am. Chem. Soc. 2004, 126, 3163.
41. F. Garnier, A. Yassar, R. Hajlaoui, G. Horowitz, F. Deloffre, B. Servet, S. Ries, P. Alnot, J. Am. Chem. Soc. 1993, 115, 8716.
42. C. Videlot, J. Ackermann, P. Blanchard, J-M. Raimundo, P. Frère, M. Allain, R. de Bettignies, E. Levillain, J. Roncali, Adv. Mater. 2003, 15, 306.
43. A. Yassar, G. Horowitz, P. Valat, V. Wintgens, M. Hmyene, F. Deloffre, P. Srivastava, P. Lang, F. Garnier, J. Phys. Chem. 1995, 99, 9155.