Synthesis and self-organization of α,ω-substituted oligothiophenes with long, branched alkyl substituents

Chemistry of Materials

Volumn 19, Issue 5, 2007, Pages 1070-1075

  Ellinger, Stefan ^a   Ziener, Ulrich ^a   Thewalt, Ulf ^a   Landfester, Katharina ^a   Möller, Martin ^b  

^a UNIVERSITY OF ULM   (Germany)

^b Deutsches Wollforschungsinstitut   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

MOLECULAR DYNAMICS; POLARIZATION; REACTION KINETICS; SOLUBILITY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); ULTRAVIOLET SPECTROSCOPY;

ELECTRONIC MATERIALS; MULTISTEP SYNTHESIS; OLIGOTHIOPHENE;

OLEFINS;

EID: 33947193043     PISSN: 08974756     EISSN: None     Source Type: Journal    
DOI: 10.1021/cm062589s     Document Type: Article

References (35)

1. Barbarella, G.; Melucci, M.; Sotgiu, G. Adv. Mater. 2005, 17, 1581-1593.
2. Ponomarenko, S.; Kirchmeyer, S. J. Mater. Chem. 2003, 13, 197-202.
3. Garnier, F.; Yassar, A.; Hajlaoui, R.; Horowitz, G.; Deloffre, F.; Serve, B.; Ries, S.; Alnott, P. J. Am. Chem. Soc. 1993, 115, 8716-8721.
4. Katz, H. E.; Laquindanum, J. G.; Lovinger, A. J. Chem. Mater. 1998, 10, 633-638.
5. Katz, H. E.; Lovinger, A. J.; Laquindanum, J. G. Chem. Mater. 1998, 10, 457-459.
6. Hempenius, M. A.; Langeveld-Voss, B. M. W.; Haare, J. A. E. H. v.; Janssen, R. A. J.; Sheiko, S. S.; Spatz, J. P.; Möller, M.; Meijer, E. W. J. Am. Chem. Soc. 1998, 120, 2798-2804.
7. Hajlaoui, R.; Fichou, D.; Horowitz, G.; Nessakh, B.; Constant, M.; Gamier, F. Adv. Mater. 1997, 9, 557-561.
8. Izumi, T.; Kobashi, S.; Takimiya, K.; Aso, Y.; Otsubo, T. J. Am. Chem. Soc. 2003, 125, 5286-5287.
9. Bäuerle, P. The Synthesis of Oligothiophenes. In Handbook of Oligoand Polythiophenes; Fichou, D., Ed.; Wiley-VCH: Weinheim, Germany, 1999; pp 89-181.
10. Garnier, F.; Hajlaoui, R.; Yassar, A.; Srivastava, P. Science 1994, 265, 1684-1686.
11. Sirringhaus, H.; Tessler, N.; Friend, R. H. Science 1998, 280, 1741-1744.
12. Rogers, J. A.; Bao, Z.; Meier, M.; Dodabalapur, A.; Schueller, O. J.; Whitesides, G. M. Synth. Met. 2000, 115, 5-11.
13. Sirringhaus, H.; Kawase, T.; Shimoda, R. H.; Inbesekaran, M.; Wu, W.; Woo, E. P. Science 2000, 290, 4835-4840.
14. Duchenet, V.; Andreu, C. G.; Catel, J. M.; Coustumer, G. Phosphorus, Sulfur Silicon Relat. Eiern. 1996, 118, 117-128.
15. Luo, T.-m. H.; LeGoff, E. J. Chin. Chem. Soc. 1992, 39, 325-332.
16. Lithiation and subsequent stannylation of compound 14 have been successfully performed and will be published in a forthcoming paper.
17. Stille, J. K. Angew. Chem. 1986, 98, 504-519.
18. Espinet, P.; Echavarren, A. M. Angew. Chem. 2004, 116, 4808-4839.
19. Merz, A.; Ellinger, F. Synthesis 1991, 462-464.
20. Bäuerle, P.; Würthner, F.; Götz, G.; Effenberger, F. Synthesis 1993, 1099-1103.
21. Facchetti, A.; Yoon, M.-H.; Stern, C. L.; Hutchison, G. R.; Ratner, M. A.; Marks, T. J. J. Am. Chem. Soc 2004, 126, 13480-13501.
22. Pope, M.; Svenberg, C. E. Electronic Processes in Organic Crystals; Clarendon: Oxford, U.K., 1982.
23. Kilbinger, A. F. M.; Feast, W. J. J. Mater. Chem. 2000, 10, 1777-1784.
24. Feast, W. J.; Goldoni, F.; Kilbinger, A. F. M.; Meijer, E. W.; Petty, M. C.; Schenning, A. P. H. J. Macromol. Symp. 2001, 175, 151-158.
25. Schenning, A. P. H. J.; Kilbinger, A. F. M.; Biscarini, F.; Cavallini, M.; Cooper, H. J.; Derrick, P. J.; Feast, W. J.; Lazzaroni, R.; Leclere, P.; McDonell, L. A.; Meijer, E. W.; Meskers, S. C. J. J. Am. Chem. Soc. 2002, 124, 1269-1275.
26. Ledere, P.; Surin, M.; Viville, P.; Lazzaroni, R.; Kilbinger, A. F. M.; Henze, O.; Feast, W. J.; Cavallini, M.; Biscarini, F.; Schenning, A. P. H. J.; Meijer, E. W. Chem. Mater. 2004, 16, 4452-4466.
27. Xia, C.; Locklin, J.; Youk, J. H.; Fulghum, T.; Advincula, R. C. Langmuir 2002, 18, 955-957.
28. Apperloo, J. J.; Janssen, R. A. J.; Malenfant, P. R. L.; Frechet, J. M. J. J. Am. Chem. Soc. 2001, 123, 6916-6924.
29. Apperloo, J. J.; Janssen, R. A. J.; Malenfant, P. R. L.; Frechet, J. M. J. Macromolecules 2000, 33, 7038-7043.
30. Kilbinger, A. F. M.; Cooper, H. J.; McDonnell, L. A.; Feast, W. J.; Derrick, P. J.; Schenning, A.; Meijer, E. W. Chem. Commun. 2000, 383-384.
31. Azumi, R.; Götz, G.; Bäuerle, P. Synth. Met. 1999, 101, 544-545.
32. Byron, D.; Matharu, A.; Wilson, R.; Wright, G. Mol. Cryst. Liq. Cryst. Sci. Technol., Sect. A 1995, 265, 61-76.
33. Garnier, F.; Hajlaoui, R.; Kassmi, A. E.; Horowitz, G.; Laigre, L.; Porzio, W.; Armanini, M.; Provasoli, F. Chem. Mater. 1998, 10, 3334-3339.
34. Güntner, R.; Farrell, T.; Scherf, U.; Miteva, T.; Yasuda, A.; Nelles, G. J. Mater. Chem. 2004, 14, 2622-2626.
35. Fichou, D. Handbook of Oligo- and Polythiophenes; Wiley-VCH: Weinheim, Germany, 1999.