Synthesis and characterization of benzo[1,2- b:3,4- b′:5,6- b″ ]trithiophene (BTT) oligomers

Journal of Organic Chemistry

Volumn 76, Issue 10, 2011, Pages 4061-4070

  Kashiki, Tomoya ^a   Kohara, Masahiro ^a   Osaka, Itaru ^a   Miyazaki, Eigo ^a   Takimiya, Kazuo ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE CHANNELS; CONJUGATED SYSTEMS; ENERGY LEVEL; EXTENDED SYSTEMS; FILM STATE; FRONTIER ORBITALS; HEXAMERS; HOMO-LUMO ENERGY GAP; HOMO-LUMO GAPS; IMPROVED SOLUBILITY; N-CHANNEL; ORGANIC SEMICONDUCTOR; PLANAR MOLECULAR STRUCTURES; SINGLE CRYSTAL X-RAY ANALYSIS; SPIN-COATED THIN FILMS; TETRAMERS;

AMORPHOUS FILMS; DIHEDRAL ANGLE; FIELD EFFECT TRANSISTORS; MOLECULAR ORIENTATION; MOLECULAR STRUCTURE; ORGANIC POLYMERS; SINGLE CRYSTALS; SOLUBILITY; THIN FILMS;

DIMERS;

2',5',8' TRIS[5,8 DIOCTYLBENZO(1,2 B:3,4 B':5,6 B'')TRITHIOPHEN 2 YL]BENZO[1,2 B:3,4 B':5,6 B'']TRITHIOPHENE; 2,2' BI [5,8 DIOCTYLBENZO(1,2 B:3,4 B':5,6 B'')TRITHIOPHENE]; 2,2' BI [BENZO(1,2 B:3,4 B':5,6 B'')TRITHIOPHENE]; 2,2' BIS[5,8 BIS[5'',8'' DIOCTYLBENZO(1,2 B:3,4 B':5,6 B'')TRITHIOPHEN 2'' YL]]BENZO[1,2 B:3,4 B':5,6 B'']TRITHIOPHENE; 2,5 DIOCTYL 8 IODOBENZO[1,2 B:3,4 B':5,6 B'']TRITHIOPHENE; 2,5 DIOCTYLBENZO[1,2 B:3,4 B':5,6 B'']TRITHIOPHENE; 2,5,8 TRIBROMOBENZO[1,2 B:3,4 B':5,6 B'']TRITHIOPHENE; 2,5,8 TRIS [[5',8' BIS[5'',8'' DIOCTYLBENZO(1,2 B:3,4 B':5,6 B'')TRITHIOPHEN 2'' YL]BENZO(1,2 B:3,4 B':5,6 B'')TRITHIOPHEN 2' YL]]BENZO[1,2 B:3,4 B':5,6 B'']TRITHIOPHENE; 2,5,8 TRIS(TRIMETHYLSTANNYL)BENZO[1,2 B:3,4 B':6 B'']TRITHIOPHENE; 8' BROMO 5,5'',8,8'' TETRAOCTYL 2,2':5',2'' TERBENZO[1,2 B:3,4 B':5,6 B'']TRITHIOPHENE; [5,8 DIOCTYLBENZO(1,2 B:3,4 B':5,6'')TRITHIOPHEN 2 YL]TRIMETHYLSTANNANE; MONOMER; OLIGOMER; PALLADIUM; TETRAMER; THIOPHENE DERIVATIVE; TRIMETHYL[5,5'',8,8'' TETRAOCTYL[2,2':5',2''TERBENZO(1,2 B:3,4 B':5,6 B'')TRITHIOPHEN] 8' YL]STANNANE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; CHEMICAL REACTION; CONJUGATION; CRYSTAL STRUCTURE; CYCLIC POTENTIOMETRY; DERIVATIZATION; ENERGY; FIELD EFFECT TRANSISTOR; FILM; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; SOLUBILITY; SOLUBILIZATION; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS; X RAY ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 79956109431     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2005044     Document Type: Article

References (58)

1. Organic Electronics, Manufacturing and Applications; Klauk, H., Ed.; Wiley-VCH: Weinheim, 2006.
2. Electronic Materials: The Oligomer Approache; Müllen, K., Wegner, G., Ed.; Wiley-VCH: Weinheim, 1998.
3. See also a special issue on π-functional materials: Bredas, J.-L.; Marder, S. R.; Reichmanis, E. Chem. Mater. 2011, 23, 309-922
4. Gundlach, D. J.; Lin, Y. Y.; Jackson, T. N.; Nelson, S. F.; Schlom, D. G. IEEE Electron Device Lett. 1997, 18, 87-89
5. Anthony, J. E. Chem. Rev. 2006, 106, 5028-5048
6. Anthony, J. E. Angew. Chem., Int. Ed. 2008, 47, 452-483
7. McCullough, R. D.; Lowe, R. D. J. Chem. Soc., Chem. Commun. 1992, 70-72
8. Chen, T.; Rieke, R. D. J. Am. Chem. Soc. 1992, 114, 10087-10088
9. Roncali, J. Chem. Rev. 1992, 92, 711-738
10. McCullough, R. D. Adv. Mater. 1998, 10, 93-116
11. Bao, Z.; Dodabalapur, A.; Lovinger, A. J. Appl. Phys. Lett. 1996, 69, 4108-4110
12. Sirringhaus, H.; Brown, P. J.; Friend, R. H.; Nielsen, M. M.; Bechgaard, K.; Langeveld-Voss, B. M. W.; Spiering, A. J. H.; Janssen, R. A. J.; Meijer, E. W.; Herwig, P.; De Leeuw, D. M. Nature 1999, 401, 685-688
13. Perepichka, I. F.; Perepichka, D. F.; Meng, H.; Wudl, F. Adv. Mater. 2005, 17, 2281-2305
14. Jeffries-El, M.; McCullough, R. D. In Handbook of Conducting Polymers, 3 rd ed.; Skotheim, T. A.; Reynolds, J. R., Eds; CRC Press: Boca Raton, FL, 2007; Vol. 1, Chapter 9.
15. Ewbank, P. C.; Laird, D.; McCullough, R. D. In Organic Photovoltaics; Brabec, C.; Dyakonov, V.; Scherf, U., Eds; Wiley-VCH: Weinheim, 2008, Chapter 1.
16. Fichou, D.; Zieglar, C. Handbook of Oligo- and Polythiophenes; Fichou, D., Ed.; Wiley-VCH: Weinheim, 1999.
17. Mckeown, N. B. Phthalocyanine Materials: Synthesis, Structure and Function; Cambridge University Press: Cambridge, MA, 1998.
18. Tang, C. W. Appl. Phys. Lett. 1986, 48, 183-185
19. VanSlyke, S. A.; Chen, C. H.; Tang, C. W. Appl. Phys. Lett. 1996, 69, 2160-2162
20. Bao, Z.; Lovinger, A. J.; Dodavalapur, A. Appl. Phys. Lett. 1996, 69, 3066-3068
21. Bao, Z.; Lovinger, A. J.; Brown, J. J. Am. Chem. Soc. 1998, 120, 207-208
22. Xue, J. G.; Uchida, S.; Rand, B. P.; Forrest, S. R. Appl. Phys. Lett. 2004, 85, 5757-5759
23. Simpson, C. D.; Wu, J.; Watson, M. D.; Müllen, K. J. Mater. Chem. 2004, 14, 494-504
24. Wu, J.; Pisula, W.; Müllen, K. Chem. Rev. 2007, 107, 718-747
25. Feng, X.; Marcon, V.; Pisula, W.; Hansen, M. R.; Kirkpatrick, J.; Grozema, F.; Andrienko, D.; Kremer, K.; Müllen, K. Nat. Mater. 2009, 8, 421-426
26. -1 have been reported: Payne, M. M.; Parkin, S. R.; Anthony, J. E.; Kuo, C. C.; Jackson, T. N. J. Am. Chem. Soc. 2005, 127, 4986-4987
27. Takimiya, K.; Ebata, H.; Sakamoto, K.; Izawa, T.; Otsubo, T.; Kunugi, Y. J. Am. Chem. Soc. 2006, 128, 12604-12605
28. Yamamoto, T.; Takimiya, K. J. Am. Chem. Soc. 2007, 129, 2224-2225
29. Ebata, H.; Izawa, T.; Miyazaki, E.; Takimiya, K.; Ikeda, M.; Kuwabara, H.; Yui, T. J. Am. Chem. Soc. 2007, 129, 15732-15733
30. Gao, P.; Beckmann, D.; Tsao, H. N.; Feng, X.; Enkelmann, V.; Baumgarten, M.; Pisula, W.; Müllen, K. Adv. Mater. 2009, 21, 213-216
31. Kang, M. J.; Doi, I.; Mori, H.; Miyazaki, E.; Takimiya, K.; Ikeda, M.; Kuwabara, H. Adv. Mater. 2011, 23, 1222-1225
32. Shinamura, S.; Osaka, I.; Miyazaki, E.; Nakao, A.; Yamagishi, M.; Takeya, J.; Takimiya, K. J. Am. Chem. Soc. 2011, 133, 5224-5035
33. Proetzsch, R.; Bieniek, D.; Korte, F. Tetrahedron Lett. 1972, 13, 543-544
34. Jayasuriya, N.; Kagan, J.; Owens, J. E.; Kornak, E. P.; Perrine, D. M. J. Org. Chem. 1989, 54, 4203-4205
35. Grayson, S. M.; Frechet, J. M. J. Chem. Rev. 2001, 101, 3819-3868
36. Negishi, N.; Ie, Y.; Taniguchi, M.; Kawai, T.; Tada, H.; Kaneda, T.; Aso, Y. Org. Lett. 2007, 9, 829-832
37. Wong, K.-T.; Lin, Y.-H.; Wu, H.-H.; Fungo, F. Org. Lett. 2007, 9, 4531-4534
38. Jiang, Y.; Lu, Y.-X.; Cui, Y.-X.; Zhou, Q.-F.; Ma, Y.; Pei, J. Org. Lett. 2007, 9, 4539-4542
39. Ma, C.-Q.; Fonrodona, M.; Schikora, M. C.; Wienk, M. M.; Janssen, R. A. J.; Bäuerle, P. Adv. Funct. Mater. 2008, 18, 3323-3331
40. Lo, S.-C.; Burn, P. L. Chem. Rev. 2007, 107, 1097-1116
41. Roncali, J.; Leriche, P.; Cravino, A. Adv. Mater. 2007, 19, 2045-2060
42. Kanibolotsky, A. L.; Perepichka, I. F.; Skabara, P. J. Chem. Soc. Rev. 2010, 39, 2695-2728
43. Bettignies, R. d.; Nicolas, Y.; Blanchard, P.; Levillain, E.; Nunzi, J. M.; Roncali, J. Adv. Mater. 2003, 15, 1939-1943
44. Nicolas, Y.; Blanchard, P.; Levillain, E.; Allain, M.; Mercier, N.; Roncali, J. Org. Lett. 2004, 6, 273-276
45. Piot, L.; Silly, F.; Tortech, L.; Nicolas, Y.; Blanchard, P.; Roncali, J.; Fichou, D. J. Am. Chem. Soc. 2009, 131, 12864-12865
46. Taerum, T.; Lukoyanova, O.; Wylie, R. G.; Perepichka, D. F. Org. Lett. 2009, 11, 3230-3233
47. Demenev, A.; Eichhorn, S. H.; Taerum, T.; Perepichka, D. F.; Patwardhan, S.; Grozema, F. C.; Siebbeles, L. D. A.; Klenkler, R. Chem. Mater. 2010, 22, 1420-1428
48. Kashiki, T.; Shinamura, S.; Kohara, M.; Miyazaki, E.; Takimiya, K.; Ikeda, M.; Kuwabara, H. Org. Lett. 2009, 11, 2473-2475
49. Pommerehne, J.; Vestweber, H.; Guss, W.; Mahrt, R. F.; Bässler, H.; Porsch, M.; Daub, J. Adv. Mater. 1995, 7, 551-554
50. Johansson, T.; Mammo, W.; Svensson, M.; Andersson, M. R.; Inganas, O. J. Mater. Chem. 2003, 13, 1316-1323
51. Devadoss, C.; Bharathi, P.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 9635-9644
52. Devadoss, C.; Bharathi, P.; Moore, J. S. Macromolecules 1998, 31, 8091-8099
53. Ramakrishna, G.; Bhaskar, A.; Bäuerle, P.; Goodson, T. J. Phys. Chem. A 2007, 112, 2018-2026
54. Badaeva, E.; Harpham, M. R.; Guda, R.; Süzer, O.; Ma, C.-Q.; Bäuerle, P.; Goodson, T.; Tretiak, S. J. Phys. Chem. B 2010, 114, 15808-15817
55. MO calculations were carried out with the DFT method at the B3LYP/6-31g(d) level using Gaussian 03 program package. Frisch, M. J. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
56. Dimitrakopoulos, C. D.; Malenfant, P. R. L. Adv. Mater. 2002, 14, 99-117
57. Sheldrick, G. M. SHELXL (SHELX97) Programs for the Refinement of Crystal Structures; University of Goettingen: Germany, 1997.
58. Ong, B. S.; Wu, Y.; Liu, P.; Gardner, S. J. Am. Chem. Soc. 2004, 126, 3378-3379