Synthesis and characterization of cyclopentadithiophene (CPDT)-naphthalene (NDI) push-pull ABA-type oligomers and copolymers

10.6843/NTHU.2013.00347

李淳漢

conjugated polymer ； n-type material ； C-H direct arylation

清華大學化學工程學系學位論文

2013年

碩士

堀江正樹

英文

This thesis presents the synthesis, characterization, and device performance of a series of cyclopentadithiophene (CPDT)-naphthalene (NDI) donor-acceptor (D-A) ABA-type oligomers and copolymers. These oligomers composed of CPDT-NDI-CPDT unit with various alkyl chains are successfully synthesized via direct arylation using palladium complex catalyst. The corresponding copolymers are synthesized by oxidative polymerization using FeCl3. All of oligomers and copolymers are systematically characterized and analyzed by gel permeation chromatography (GPC), 1H NMR and UV-vis-NIR absorption spectroscopies, cyclic voltammetry (CV), thermogravimetric analysis (TGA), X-ray diffraction (XRD) and differential scanning calorimetry (DSC). GPC measurement shows that these polymers are of relatively high molecular weight, Mn = 21800-76000. These copolymers show deep-red absorption including near-infrared region (up to 1100 nm) due to their quite narrow bandgap. Impressively, the electrochemical property of the resulting copolymers exhibits lowest unoccupied molecular orbital (LUMO) at about - 3.7 eV, which has been considered as the favorable level as n-type materials for use in organic photovoltaic devices (OPVs). These copolymers exhibit only n-type property giving the highest electron mobility of 3.7 x 10-4 cm2 V-1 s-1 in organic field-effect transistor because of its strong intermolecular interaction. On the other hand, the copolymer with highly soluble branched alkyl chain shows the highest power conversion efficiency of 0.25% in organic photovoltaic device. To investigate the versatile reactivity of C-H direct arylation, the copolymers composed of above unit with benzothiadiazole, thiophene, or bithiophene are also II synthesized by direct arylation polymerization. All polymers have higher molecular weight (Mn = 18000-52000) than the alternative polymers of dibromo-NDI and CPDT obtained from similar reaction condition. The optical and electrochemical properties of these polymers are measured by UV-vis-NIR spectra, 1H-NMR, GPC and CVs.

1. 2. H. Sirringhaus, Adv. Mater. 2005, 17, 2411.
   連結：
2. 3. A. Facchetti, Mater. Today. 2007, 10, 28.
   連結：
3. 6. C. Reese, W. J. Chung, M.-m. Ling, M. Roberts, Z. Bao, Appl. Phys. Lett. 2006, 89, 202108.
   連結：
4. 8. H. Sirringhaus, P. J. Brown, R. H. Friend, M. M. Nielsen, K. Bechgaard, B. M. W. Langeveld-Voss, A. J. H. Spiering, R. A. J. Janssen, E. W. Meijer, P. Herwig, D. M. de Leeuw, Nature 1999, 401, 685.
   連結：
5. 17. A. Babel, S. A. Jenekhe, J. Am. Chem. Soc. 2003, 125, 13656.
   連結：
6. 20. T. B. Singh, T. Meghdadi, S. Gunes, N. Marjanovic, G. Horowitz, P. Lang, S. Bauer, N. S. Sariciftci, Adv. Mater. 2005, 17, 2315
   連結：
7. 23. G. Horowitz, Adv. Mater. 1998, 10, 365.
   連結：
8. 26. C. J. Brabec, N. S. Sariciftci, J. C. Hummelen, Adv. Funct. Mater. 2001, 11, 15.
   連結：
9. 27. B. C. Thompson, J. M. J. Fréchet, Angew. Chem. Int. Ed. 2008, 47, 58.
   連結：
10. 31. F. C. Krebs, Sol. Energy Mater. Sol. Cells 2009, 93, 394.
    連結：
11. 32. C. W. Tang, Appl. Phys. Lett. 1986, 48, 183.
    連結：
12. 41. G. Li, R. Zhu, Y. Yang, Nat. Photonics 2012, 6, 153.
    連結：
13. 42. A. Facchetti, Chem. Mater. 2011, 23, 733–758
    連結：
14. 43. Sista, S. et al. Adv. Mater. 2010, 22, 380.
    連結：
15. 45. Y. J. Cheng, S. H. Yang, C. S. Hsu, Chem. Rev. 2009, 109, 5868
    連結：
16. 48. G. Brocks, A. Tol, J. Phys. Chem., 1996, 100, 1838.
    連結：
17. 49. T.J. Prosa, M.J. Winokur, J. Moulton, P. Smith, A.J. Heeger, Macromolecules. 1992, 25, 4364.
    連結：
18. 50. N. Miyaura, Cross-Coupling Reactions: A Practical Guide, Springer, New York, 2002.
    連結：
19. 51. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457
    連結：
20. 53. R. Martin, S. L. Buchwald, Acc. Chem. Res. 2008, 41, 1461
    連結：
21. 54. J. K. Stille, Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
    連結：
22. 55. D. Milstein, J. K. Stille, J. Am. Chem. Soc. 1978, 100, 3636.
    連結：
23. 56. Z. Bao, W. K. Chan, L. Yu, J. Am. Chem. Soc. 1995, 117, 12426.
    連結：
24. 57. P. Espinet, A. M. Echavarren, Angew. Chem. Int. Ed. 2004, 43, 4704 – 4734
    連結：
25. 58. D. J. Schipper, Keith Fagnou, Chem. Mater. 2011, 23, 1594–1600
    連結：
26. 59. L. Ackermann, R. Vicente, A. R. Kapdi, Angew. Chem. Int. Ed. 2009, 48, 9792
    連結：
27. 60. M. Lafrance, K. Fagnou, J. Am. Chem. Soc. 2006, 128, 16496
    連結：
28. 61. G. C. Welch, G. C. Bazan, J. Am. Chem. Soc. 2011, 133, 4632–4644
    連結：
29. 65. A. Facchetti, Chem. Mater. 2011, 23, 733
    連結：
30. 68. Y. Liang, L. Yu, Acc. Chem. Res. 2010, 43, 1227.
    連結：
31. 70. H. Zhou, L. Yang, W. You, Macromolecules 2012, 45, 607−632
    連結：
32. 72. P. Coppo, M. L. Turner, J. Mater. Chem. 2005, 15, 1123
    連結：
33. 73. U. Asawapirom, U. Scherf, Macromol. Rapid. Commun. 2001, 22, 746.
    連結：
34. 80. X. Guo, M. D. Watson, Org. Lett. 2008, 10, 5333.
    連結：
35. 82. L. L. Miller, K. R. Mann, Acc. Chem. Res. 1996, 29, 417.
    連結：
36. 87. M. B. Kim, D. W. Dixon, J. Phys. Org. Chem. 2008, 21 731
    連結：
37. 91. K. Yamazaki , J. Kuwabara , T. Kanbara, Macromol. Rapid Commun. 2013, D, 69−73
    連結：
38. 93. P. Berrouard, A. Najari, A. Pron, D. Gendron, P. Morin, J. Pouliot, J. Veilleux, M. Leclerc, Angew. Chem., Int. Ed. 2012, 51, 2068.
    連結：
39. 94. A. Facchetti, L. Vaccaro and A. Marrocchi, Angew. Chem., Int. Ed., 2012, 51, 3520–3523.
    連結：
40. 96. S. W. Chang, H. Waters, J. Kettle, Z. R. Kuo, C. H. Li, C. Y. Yu, M. Horie, Macromol. Rapid Commun., 2012, 33, 1927−1932.
    連結：
41. 1. C. K. Chiang, C. R. Fincher, Jr., Y. W. Park, A. J. Heeger, H. Shirakawa, E. J. Louis, S. C. Gau, A. G. MacDiarmid, Physical Review Letters. 1977, 39, 1098
42. 4. X. W. Zhan, A. Facchetti, S. Barlow, T. J. Marks, M. A. Ratner, M. R. Wasielewski, S. R. Marder, Adv. Mater. 2011, 23, 268.
43. 5. D. J. Gundlach, J. A. Nichols, L. Zhou, T. N. Jackson, Appl. Phys. Lett. 2002, 80, 2925.
44. 7. Kelley, T. W.; Muyres, D. V.; Baude, P. F.; Smith, T. P.; Jones, T. D. Mater. Res. Soc. Symp. Proc. 2003, 771, 169
45. 9. S. Wang, M. Kappl, I. Liebewirth, M. Müller, K. Kirchhoff, W. Pisula, K. Müllen, Adv. Mater. 2012, 24, 417.
46. 10. D. M. deLeeuw, M. M. J. Simenon, A. R. Brown, R. E. F. Einerhand, Synth. Met. 1997, 87, 53.
47. 11. Y. Sakamoto, T. Suzuki, M. Kobayashi, Y. Gao,; Y. Fukai, Y. Inoue, F. Sato, S. Tokito, J. Am. Chem. Soc. 2004, 126, 8138.
48. 12. J. G. Laquindanum, H. E. Katz, A. Dodabalapur, A. J. Lovinger, J. Am. Chem. Soc. 1996, 118, 11331.
49. 13. D. Shukla, S. F. Nelson, D. C. Freeman, M. Rajeswaran, W. G. Ahearn, D. M. Meyer, J. T. Carey, Chem. Mater. 2008, 20, 7486
50. 14. R. C. Haddon, A. S. Perel, R. C. Morris, T. T. M. Palstra, A. F. Hebard, R. M. Fleming, Appl. Phys. Lett. 1995, 67, 121.
51. 15. T. D. Anthopoulos, B. Singh, N. Marjanovic, N. S. Sariciftci, A. M. Ramil, H. Sitter, M. Colle, D. M. d. Leeuw, Appl. Phys. Lett. 2006, 89, 213504.
52. 16. T. B. Singh, N. Marjanovic, P. Stadler, M. Auinger, G. J. Matt, S. Gunes, N. S. Sariciftci, R. Schwodiauer, S. Bauer, J. Appl. Phys. 2005, 97, 083714.
53. 18. H. Yan, Z. H. Chen, Y. Zheng, C. Newman, J. R. Quinn, F. Dotz, M. Kastler, A. Facchetti, Nature 2009, 457, 679.
54. 19. B. Crone, A. Dodabalapur, Y. Y. Lin, R. W. Filas, Z. Bao, A. LaDuca, R. Sarpeshkar, H. E. Katz, W. Li, Nature 2000, 403, 521.
55. 21. E. J. Meijer, D. M. de Leeuw, S. Setayesh, E. van Veenendaal, B. H. Huisman, P. W. M. Blom, J. C. Hummelen, U. Scherf, T. M. Klapwijk, Nat. Mater. 2003, 2, 678.
56. 22. Z. Chen, M. J. Lee, R. Shahid Ashraf, Y. Gu, S. Albert-Seifried, M. Meedom Nielsen, B. Schroeder, T. D. Anthopoulos, M. Heeney, I. McCulloch and H. Sirringhaus, Adv. Mater., 2012, 24, 647–652.
57. 24. Z. Bao, J. A. Rogers, H. E. J. Katz, Mater. Chem. 1999, 9, 1895.
58. 25. J. H. Burroughes, D. D. C. Bradley, A. R. Brown, R. N. Marks, K. Mackay, R. H. Friend, P. L. Burns, A. B. Holmes, Nature 1990, 347, 539.
59. 28. C. R. Newman, C. D. Frisbie, D. A. da Silva Filho, J.-L. Bre´das, P. C. Ewbank, K. R. Mann, Chem. Mater. 2004, 16, 4436.
60. 29. Z. Bao, J. Locklin, Organic Field-Effect Transistors, CRC Press: Taylor & Francis Group, 2007
61. 30. J. Cornil, J. L. Bredas, J. Zaumseil, H. Sirringhaus, Adv. Mater. 2007, 19, 1791
62. 33. G. Yu, J. Gao, J. C. Hummelen, F. Wudl, A. J. Heeger, Science. 1995, 270, 1789
63. 34. J. Peet, A. J. Heeger, G. C. Bazan, Acc. Chem. Res., 2009, 42, 1700
64. 35. D. Venkataraman, S. Yurt, B. H. Venkatraman, N. Gavvalapalli, J. Phys. Chem. Lett. 2010, 1, 947–958
65. 36. S. Gunes, H. Neugebauer, N. S. Sariciftci, Chem. Rev. 2007, 107, 1324.
66. 37. L. Huo, L. Ye, Y. Wu, Z. Li, X. Guo, M. Zhang, S. Zhang, J. Hou, Macromolecules 2012, 45, 6923
67. 38. V. D. Mihailetchi, P. W. M. Blom, J. C. Hummelen, M. T. Rispens, J. Appl. Phys. 2003, 94, 6849.
68. 39. M. C. Scharber, D. Mühlbacher, M. Koppe, P. Denk, C. Waldauf, A. J. Heeger, C. J. Brabec, Adv. Mater. 2006, 18, 789.
69. 40. J. Y. Kim, K. Lee, N. E. Coates, D. Moses, T. Q. Nguyen, M. Dante, A. J. Heeger, Science. 317, 222 (2007)
70. 44. U. Salzner, J. B. Lagowski, P.G. Pickup, R.A. Poirier, Synth Met 1998, 96, 177.
71. 46. McCullough RD, Ewbank PC. Head-to-tail coupled poly(3-alkylthiophene) and its derivatives. In: Skotheim TA, Elsenbaumer RL, Reynolds JR, editors. Handbook of conducting polymers. 2nd ed. New York: Marcel Dekker; 1998. p. 225.
72. 47. E. E. Havinga, W. ten Hoeve, H. Wynberg, Polym Bull. 1992, 29, 119.
73. 52. M. Sato, N. Miyaura, A. Suzuki, Chem. Lett. 1989, 1405
74. 62. G. L. Gibson, T. M. McCormick, D. S. Seferos, J. Am. Chem. Soc. 2012, 134, 539
75. 63. J. Mei, D. H. Kim, A. L. Ayzner, M. F. Toney, Z. Bao, J. Am. Chem. Soc. 2011, 133, 20130
76. 64. S. Günes, H. Neugebauer, N. S. Sariciftci, Chem. Rev. 2007, 107, 1324
77. 66. K. Zhang, B. Tieke, J. C. Forgie, F. Vilela, P. J. Skabara, Macromolecules. 2012, 45, 743
78. 67. C. J. Brabec, N. S. Sariciftci, J. C. Hummelen, Adv. Funct. Mater. 2001, 11, 15
79. 69. A. C. Grimsdale, K. L. Chan, R. E. Martin, P. G. Jokisz, A, B. Holmes, Chem. Rev. 2009, 109, 897–1091
80. 71. P. T. Boudreault, A. Najari, M. Leclerc, Chem. Mater. 2011, 23, 456–469
81. 74. A. Kraak, A. K. Wiersma, P. Jordens, H. Wynberg, Tetrahedron. 1968, 24, 3381.
82. 75. G. Zotti, G. Schiavon, A. Berlin, G. Fontana, G. Pagani, Macromolecules. 1994, 27, 1938
83. 76. S. Wang, M. Kappl, I. Liebewirth, M. Müller, K. Kirchhoff, W. Pisula, K. Müllen, Adv. Mater. 2012, 24, 417.
84. 77. J. Peet, J. Y. Kim, N. E. Coates, W. L. Ma, D. Moses, A. J. Heeger, G. C. Bazan, Nat. Mater., 2007, 6, 497.
85. 78. S. Albrecht, S. Janietz, W. Schindler, J. Frisch, J. Kurpiers, J. Kniepert, S. Inal, P. Pingel, K. Fostiropoulos, N. Koch, D. Neher, J. Am. Chem. Soc., 2012, 134, 14932
86. 79. X. Guo, F. S. Kim, M. J. Seger, S. A. Jenekhe, M. D. Watson, Chem. Mater. 2012, 24, 1434
87. 81. H. Vollmann, H. Becker, M. Corell, H. Streeck, Liebigs Ann. Chem., 1937, 531, 1.
88. 83. H. E. Katz, A. J. Lovinger, J. Johnson, C. Kloc, T. Siegrist, W. Li, Y. Y. Lin, A. Dodabalapur, Nature. 2000, 404, 478–481.
89. 84. H. Yan, Z. Chen, Y. Zheng, C. Newman, J. R. Quinn, F. Dötz, M. Kastler, A. Facchetti, Nature. 2009, 457, 679.
90. 85. E. Ahmed, G. Q. Ren, F. S. Kim, E. C. Hollenbeck, S. A. Jenekhe, Chem. Mater. 2011, 23, 4563
91. 86. M. Horie, J. Kettle, C. Y. Yu, L. A. Majewski, S. W. Chang, J. Kirkpatrick, S. M. Tuladhar, J. Nelson, B. R. Saunders, M. L. Turner, J. Mater. Chem. 2012, 22, 381.
92. 88. M. R. Andersson, D. Selse, M. Berggren, H. Jarvinen, T. Hjertberg, O. Inganas, O. Wennerstrom and J.-E. Osterholm, Macromolecules. 1994, 27, 6503
93. 89. M. Schubert, D. Dolfen, J. Frisch, S. Roland, R. Steyrleuthner, B. Stiller, Z. Chen, U. Scherf, N. Koch, A. Facchetti, D. Neher, Adv. Energy Mater. 2012, 2, 369
94. 90. M. M. Durban, P. D. Kazarinoff, C. K. Luscombe, Macromolecules. 2010, 43, 6348
95. 92. H. Zhao, C. Y. Liu, S. C. Luo, B. Zhu, T. H. Wang, H. F. Hsu, H. h. Yu, Macromolecules 2012, 45, 7783−7790
96. 95. Q. Wang, R. Takita, Y. Kikuzaki and F. Ozawa, J. Am.Chem. Soc., 2010, 132, 11420–11421
97. 97. T. Okazawa, T. Satoh, M. Miura, M. Nomura, J. Am. Chem. Soc., 2002, 124, 5286-5287
98. 98. A. E. Rudenko, C. A. Wiley, S. M. Stone, J. F. Tannaci, B. C.Thompson, J. Polym. Sci. Part A: Polym. Chem. 2012, 50, 3691–3697.
99. 99. Y. Fujinami, J. Kuwabara, W. Lu, H. Hayashi, T. Kanbara, ACS Macro. Lett. 2012, 1, 67–70.
100. 100. K. Okamoto, J. B. Housekeeper, F. E. Michael, and C, K. Luscombe, Polym. Chem., 2013, 4, 3499–3506
101. 101. J. Zhou, S. Xie, E. F. Amond, M. L. Becker, Macromolecules, 2013, 46 (9), 3391–3394