Synthesis of nitro- and amino-functionalized π-conjugated oligomers incorporating 3,4-ethylenedioxythiophene (EDOT) units

Tetrahedron

Volumn 69, Issue 2, 2013, Pages 861-866

  Trippé Allard, Gaëlle ^a   Lacroix, Jean Christophe ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

Diazonium precursors; Electrodeposition; Ethylenedioxythiophene; Oligothiophene synthesis; P Conjugated oligomers

Indexed keywords

3,4 ETHYLENEDIOXYTHIOPHENE; OLIGOMER; PALLADIUM; THIOPHENE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; ASYMMETRIC CATALYSIS; CARBON BOND; CATALYSIS; CONJUGATION; CONTROLLED STUDY; ELECTRIC POTENTIAL; ELECTROCHEMISTRY; HYDROGEN BOND; MOLECULAR ELECTRONICS; PHOTOVOLTAIC; PRIORITY JOURNAL; SPECTROSCOPY; SUZUKI REACTION; SYNTHESIS;

EID: 84874592522     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.10.088     Document Type: Article

References (40)

1. (a) Zhu, Z. T.; Rogers, J. A. Organic Thin-film Transistors: Fundamental and Applied Aspects. Handbook of Organic Electronics and Photonics; 2008; Vol. 1, p. 225;
2. (b) Perepichka, I. F.; Perepichka, D. F. Handbook of Thiophene-based Materials; John Wiley: Chichester, UK, 2009.
3. (a) Roquet, S.; Cravino, A.; Leriche, P.; Aleveque, O.; Frere, P.; Roncali, J. J. Am. Chem. Soc. 2006, 128, 3459;
4. (b) Lacroix, J. C.; Chane-Ching, K. I.; Maquère, F.; Maurel, F. J. Am. Chem. Soc. 2006, 128, 7264.
5. (a) Roncali, J. Chem. Rev. 1992, 92, 711;
6. (b) Roncali, J. Chem. Rev. 1997, 97, 173;
7. (c) Amir, E.; Rozen, S. Angew. Chem., Int. Ed. 2005, 44, 7374;
8. (d) Mishra, A.; Ma, C. Q.; Bauerle, P. Chem. Rev. 2009, 108, 1141.
9. (a) Apperloo, J. J.; Groenendaal, L. B.; Verheyen, H.; Jayakannan, M.; Janssen, R. A. J.; Dkhissi, A.; Beljonne, D.; Lazzaroni, R.; Bredas, J. L. Chem.-Eur. J. 2002, 8, 2384;
10. (b) Akoudad, S.; Roncali, J. Chem. Commun. 1998, 2081;
11. (c) Huchet, L.; Akoudad, S.; Levillain, E.; Emge, A.; Bauerle, P.; Roncali, J. J. Phys. Chem. B 1998, 102, 7776;
12. (d) Thomas, C. A.; Zong, K.; Abboud, K. A.; Steel, P. J.; Reynolds, J. R. J. Am. Chem. Soc. 2004, 126, 16440;
13. (e) Nielsen, C. B.; Angerhofer, A.; Abboud, K. A.; Reynolds, J. R. J. Am. Chem. Soc. 2008, 130, 9734.
14. (a) Turbiez, M.; Frère, P.; Allain, M.; Videlot, C.; Ackermann, J.; Roncali, J. Chem.-Eur. J. 2005, 11, 3742;
15. (b) Beaujuge, P. M.; Vasilyeva, S. V.; Liu, D. Y.; Ellinger, S.; McCarley, T. D.; Reynolds, J. R. Chem. Mater. 2012, 24, 255;
16. (c) Dyer, A. L.; Craig, M. R.; Babiarz, J. E.; Kiyak, K.; Reynolds, J. R. Macromolecules 2010, 43, 4460;
17. (d) Turbiez, M.; Frère, P.; Blanchard, P.; Roncali, J. Tetrahedron 2005, 61, 5521.
18. (a) Lacroix, J. C.; Garcia, P.; Audiére, J. P.; Clement, R.; Kahn, O. New J. Chem. 1990, 14, 87;
19. (b) Genies, E. M.; Tsintavis, C. J. Electroanal. Chem. 1985, 195, 109.
20. (a) Belanger, D.; Pinson, J. Chem. Soc. Rev. 2011, 40, 3995;
21. (b) Mahouche-Chergui, S.; Gam-Derouich, S.; Mangeney, C.; Chehimi, M. M. Chem. Soc. Rev. 2011, 40, 4143.
22. (a) Fave, C.; Leroux, Y.; Trippé, G.; Randriamahazaka, H.; Noel, V.; Lacroix, J.-C. J. Am. Chem. Soc. 2007, 129, 1890;
23. (b) Stockhausen, V.; Ghilane, J.; Martin, P.; Trippé-Allard, G.; Randriamahazaka, H.; Lacroix, J. C. J. Am. Chem. Soc. 2009, 131, 14920;
24. (c) Santos, L.; Ghilane, J.; Martin, P.; Lacaze, P. C.; Randriamahazaka, H.; Lacroix, J.-C. J. Am. Chem. Soc. 2010, 132, 1690.
25. (a) Bergren, A. J.; McCreery, R. L.; Stoyanov, S. R.; Gusarov, S.; Kovalenko, A. J. Phys. Chem. C 2010, 114, 15806;
26. (b) Martin, P.; Della Rocca, M. L.; Anthore, A.; Lafarge, P.; Lacroix, J. C. J. Am. Chem. Soc. 2012, 134, 154;
27. (c) Yan, H.; Bergren, A. J.; McCreery, R. L. J. Am. Chem. Soc. 2011, 133, 19168.
28. Bolognesi, A.; DiGianvincenzo, P.; Giovanella, U.; Mendichi, R.; Giacometti Schieronni, A. Eur. Polym. J. 2008, 44, 793.
29. Borghese, A.; Geldhof, G.; Antoine, L. Tetrahedron Lett. 2006, 47, 9249.
30. (a) Amaladass, P.; Clement, J. A.; Mohanakrishnan, A. K. Tetrahedron 2007, 63, 10363;
31. (b) Arasambattu, K.; Mohanakrishnan, P.; Amaladass, P.; Clement, J. A. Tetrahedron Lett. 2007, 48, 539;
32. (c) Liu, C.-Y.; Zhao, H.; Yu, H.-H. Org. Lett. 2011, 13, 4068.
33. Ca', N. D.; Maestri, G.; Catellani, M. Chem.-Eur. J. 2009, 15, 7850.
34. Tan, L. -S.; Nagvekar, D. S.; Sankaran, B. U.S. Patent. 6,130,339 A, 2000.
35. Flamigni, L.; Venture, B.; Baranooff, E.; Collin, J.-P.; Sauvage, J.-P. Eur. J. Inorg. Chem. 2007, 33, 5189.
36. (a) Roncali, J.; Blanchard, P.; Frère, P. J. Mater. Chem. 2005, 15, 1589;
37. (b) Hergué, N.; Leriche, P.; Blanchard, P.; Allain, M.; Gallego-Planas, N. New J. Chem. 2008, 32, 932.
38. Trippé-Allard, G.; Lacroix, J. C. WO Patent. 2,011,144,873, 2011.
39. Sotzing, G. A.; Reynolds, J. R.; Steel, P. I. Adv. Mater. 1991, 9, 795.
40. Gottlieb, H.; Kotlyar, V.; Nudelman, A. J. Org. Chem. 1997, 62, 7512.