Unusual doping of donor-acceptor-type conjugated polymers using lewis acids

Journal of the American Chemical Society

Volumn 136, Issue 13, 2014, Pages 5138-5149

  Poverenov, Elena ^a   Zamoshchik, Natalia ^a   Patra, Asit ^a   Ridelman, Yonatan ^a   Bendikov, Michael ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ENERGY GAP;

2 ,1 ,3-BENZOSELENADIAZOLE; 2 ,1 ,3-BENZOTHIADIAZOLE; 3 ,4 ETHYLENEDIOXYTHIOPHENE (EDOT); CONDUCTIVE POLYMER; CONDUCTIVITY CHANGES; COORDINATION MODES; DONOR ACCEPTOR DONORS; LEWIS ACIDS AND BASIS;

DOPING (ADDITIVES);

2 HEXYLBENZOTRIAZOLE; 2,1,3 BENZOSELENADIAZOLE; 2,1,3 BENZOXADIAZOLEBENZO[2,1,5]OXODIAZOLE; 3,4 ETHYLENEDIOXYSELENOPHENE; 3,4 ETHYLENEDIOXYTHIOPHENE; BENZOTRIAZOLE DERIVATIVE; LEWIS ACID; MONOMER; OLIGOMER; POLYMER; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; CHEMICAL BINDING; CONDUCTANCE; CONJUGATION; CRYSTAL STRUCTURE; CRYSTALLIZATION; DENSITY FUNCTIONAL THEORY; ELECTRON TRANSPORT; MOLECULAR STABILITY; OXIDATION REDUCTION REACTION; POLYMERIZATION; STILLE REACTION; SYNTHESIS;

EID: 84897567756     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja501024n     Document Type: Article

References (104)

1. Handbook of Conducting Polymers, 3 rd ed.; Skotheim, T. A., Reynolds, J. R., Eds.; CRC Press: Boca Raton, FL, 2007.
2. Handbook of Organic Conductive Molecules and Polymers; Nalwa, H. S., Ed.; J. Wiley & Sons: New York, 1997.
3. MacDiarmid, A. G. Angew. Chem., Int. Ed. 2001, 40, 2581-2590
4. Facchetti, A. Mater. Today 2007, 10, 28-37
5. Organic Field-Effect Transistors; Bao, Z.; Locklin, J., Eds.; CRC Press: New York, 2007.
6. Handbook of Thiophene-Based Materials; Perepichka, I. F.; Perepichka, D. F., Eds.; Wiley-VCH: Chichester, U.K., 2009.
7. Perepichka, I. F.; Perepichka, D. F.; Meng, H.; Wudl, F. Adv. Mater. 2005, 17, 2281-2305
8. Marsella, M. J.; Reid, R. J.; Estassi, S.; Wang, L. S. J. Am. Chem. Soc. 2002, 124, 12507-12510
9. Jager, E. W. H.; Smela, E.; Inganäs, O. Science 2000, 290, 1540-1546
10. McQuade, D. T.; Pullen, A. E.; Swager, T. M. Chem. Rev. 2000, 100, 2537-2574
11. Yu, G.; Gao, J.; Hummelen, J. C.; Wudl, F.; Heeger, A. J. Science 1995, 270, 1789-1791
12. Sariciftci, N. S.; Smilowitz, L.; Heeger, A. J.; Wudl, F. Science 1992, 258, 1474-1476
13. Liang, Y.; Feng, D.; Wu, Y.; Tsai, S.-T.; Li, G.; Ray, C.; Yu, L. J. Am. Chem. Soc. 2009, 131, 7792-7799
14. Park, S. H.; Roy, A.; Beaupre, S.; Cho, S.; Coates, N.; Moon, J. S.; Moses, D.; Leclerc, M.; Lee, K.; Heeger, A. J. Nat. Photonics 2009, 3, 297-303
15. Barnes, W. L.; Samuel, I. D. W. Science 1999, 285, 211-212
16. Bhadra, S.; Khastgir, D.; Singha, N. K.; Lee, J. H. Prog. Polym. Sci. 2009, 34, 783-810
17. Varela-Alvarez, A.; Sordo, J. A.; Scuseria, G. E. J. Am. Chem. Soc. 2005, 127, 11318-11327
18. Chaudhuri, D.; Kumar, A.; Rudra, I.; Sarma, D. D. Adv. Mater. 2001, 13, 1548-1551
19. Bienkowski, K.; Kulszewicz-Bajer, I.; Genoud, F.; Oddou, J. L.; Pron, A. Synth. Met. 2003, 135-136
20. Kulszewicz-Bajer, I.; Pron, A.; Abramowicz, J.; Jeandey, C.; Oddou, J.-L.; Sobczak, J. W. Chem. Mater. 1999, 11, 552-556
21. Genoud, F.; Kulszewicz-Bajer, I.; Dufour, B.; Rannou, P.; Pron, A. Synth. Met. 2001, 119, 415-416
22. Wang, H.; Helgeson, R.; Ma, B.; Wudl, F. J. Org. Chem. 2000, 65, 5862-5867
23. Irvin, D. J.; DuBois, C. J., Jr.; Reynolds, J. R. Chem.Comm. 1999, 2121-2122
24. Berets, D. J.; Smith, D. S. Trans. Faraday Soc. 1968, 64, 823-8
25. Kaul, S. N.; Fernandez, J. E Macromolecules 1987, 20, 2320-2
26. Can, M.; Oezaslan, H.; Isildak, O.; Pekmez, N. O.; Yildiz, A. Polymer 2004, 45, 7011-7016
27. Alkan, S.; Cutler, C. A.; Reynolds, J. R. Adv. Funct. Mater. 2003, 13, 331-336
28. Baik, W.; Luan, W.; Zhao, Ren H.; Koo, S.; Kim, K.-S. Synth. Met. 2009, 159, 1244-1246
29. Chen, W.; Xue, G. Prog. Polym. Sci. 2005, 30, 783-811
30. Focante, F.; Mercandelli, P.; Sironi, A.; Resconi, L. Coord. Chem. Rev. 2006, 250, 170
31. Monk, P. M. S; Mortimer, R. J.; Rosseinsky, D. R. In Electrochromism and Electrochromic Devices; Cambridge University Press: New York, 2007; Chapter 4.
32. Guzman, A. R.; Harpham, M. R.; Suzer, O.; Haley, M. M.; Goodson, T. G. J. Am. Chem. Soc. 2010, 132, 7840-7841
33. Heeney, M.; Zhang, W.; Crouch, D. J.; Chabinyc, M. L.; Gordeyev, S.; Hamilton, R.; Higgins, S. J.; McCulloch, I.; Skabara, P. J.; Sparrowe, D.; Tierney, S. Chem. Commun. 2007, 5061-5063
34. Sonmez, G.; Meng, H.; Wudl Chem. Mater. 2003, 15, 4923-4929
35. Lee, B.; Yavuz, M. S.; Sotzing, G. A. Macromolecules 2006, 39, 3118-3124
36. Lee, B.; Seshadri, V.; Palko, H.; Sotzing, G. A. Adv. Mater. 2005, 17, 1792-1795
37. Mozer, A. J.; Sariciftci, N. S. In Handbook of Conducting Polymers: Processing and Applications, 3 rd ed.; Skotheim, T. A.; Reynolds, J. R., Eds.; CRC Press: Boca Raton, FL, 2007; Chapter 10, pp 10.1-10.37.
38. Facchetti, A. Chem. Mater. 2011, 23, 733-758
39. Mishra, A.; Ma, C. Q.; Bäuerle, P. Chem. Rev. 2009, 109, 1141-1276
40. Cheng, Y. J.; Yang, S. H.; Hsu, C. S. Chem. Rev. 2009, 109, 5868
41. Cai, W. Z.; Gong, X.; Cao, Y. Sol. Energy Mater. Sol. Cells 2010, 94, 114-127
42. Nelson, J. Mater. Today 2011, 14, 462-470
43. Brabec, C. J.; Gowrisanker, S.; Halls, J. J. M.; Laird, D.; Jia, S.; Williams, S. P. Adv. Mater. 2010, 22, 3839-3856
44. Facchetti, A. Mater. Today 2013, 16, 123
45. Chen, H.-Y.; Hou, J.; Zhang, S.; Liang, Y.; Yang, G.; Yang, Y.; Yu, L.; Wu, Y.; Li, G. Nat. Photonics 2009, 3, 649-653 and references therein
46. Sariciftci, N. S.; Smilowitz, L.; Heeger, A. J.; Wudl, F. Science 1992, 258, 1474-1476
47. Liang, Y.; Feng, D.; Wu, Y.; Tsai, S.-T.; Li, G.; Ray, C.; Yu, L. J. Am. Chem. Soc. 2009, 131, 7792-7799
48. Park, S. H.; Roy, A.; Beaupre, S.; Cho, S.; Coates, N.; Moon, J. S.; Moses, D.; Leclerc, M.; Lee, K.; Heeger, A. J. Nat. Photonics 2009, 3, 297-303
49. Huo, L.; Hou, J.; Zhang, S.; Chen, H.-U.; Yang, Y. Angew. Chem., Int. Ed. Engl. 2009, 49, 1500-1503
50. Wang, M.; Hu, X.; Liu, P.; Li, W.; Gong, X.; Huang, F.; Cao, Y. J. Am. Chem. Soc. 2011, 133, 9638-9641
51. Perepichka, D. F.; Perepichka, I. F.; Meng, H.; Wudl, F. In Organic Light-Emitting Materials and Devices; Li, Z.; Meng, H., Eds.; CRC Press: Boca Raton, FL, 2007; Chapter 2, pp 45-293.
52. Groenendaal, L.; Zotti, G.; Aubert, P.-H.; Waybright, S. M.; Reynolds, J. R. Adv. Mater. 2003, 15, 855-879
53. Mortimer, R. J.; Dyer, A. L.; Reynolds, J. R. Displays 2006, 27, 2-18
54. Balan, A.; Baran, D.; Toppare, L. Polym. Chem. 2011, 2, 1029-1043
55. Jiang, H.; Taranekar, P.; Reynolds, J. R.; Schanze, K. S. Angew. Chem., Int. Ed. 2009, 48, 4300-4316
56. Beaujuge, P. M.; Ellinger, S.; Reynolds, J. R. Nat. Mater. 2008, 7, 795-799
57. Xia, Y.; Wang, L.; Deng, X.; Li, D.; Zhu, X.; Cao, Y. Appl. Phys. Lett. 2006, 89, 081106
58. Steckler, T. T.; Abboud, K. A.; Craps, M.; Rinzler, A. G.; Reynolds, J. R. Chem. Commun. 2007, 4904-4906
59. Sonmez, G.; Meng, H.; Wudl, F. Chem. Mater. 2003, 15, 4923-4929
60. Zhu, Y.; Champion, R. D.; Jenekhe, S. A. Macromolecules 2006, 39, 8712-8719
61. Salzner, U. J. Phys. Chem. B 2002, 106, 9214-9220
62. Ajayaghosh, A. Chem. Soc. Rev. 2003, 32, 181-191
63. Hou, J.; Chen, H. Y.; Zhang, S.; Li, G.; Yang, Y. J. Am. Chem. Soc. 2008, 130, 16144
64. Peet, J.; Kim, Y.; Coates, N. E.; Ma, W. L.; Moses, D.; Heeger, A. J.; Bazan, G. C. Nat. Mater. 2007, 6, 497
65. Kim, J. Y.; Lee, K.; Coates, N. E.; Moses, D.; Nguyen, T. Q.; Dante, M.; Heeger, A. J. Science 2007, 317, 222
66. Thomas, C. A.; Zong, K.; Abboud, K. A.; Steel, P. J.; Reynolds, J. R. J. Am. Chem. Soc. 2004, 126, 16440-16450
67. Chevallier, F.; Charlot, M.; Katan, C.; Mongin, F.; Blanchard-Desce, M. Chem. Commun. 2009, 6, 692-694
68. Akoudad, S.; Roncali, J. Synth. Met. 1999, 101, 149
69. Groenendaal, L. B.; Jonas, F.; Freitag, D.; Pielartzik, H.; Reynolds, J. R. Adv. Mater. 2000, 12, 481-494
70. Groenendaal, L. B.; Zotti, G.; Aubert, P.-H.; Waybright, S. M.; Reynolds, J. R. Adv. Mater. 2003, 15, 855-879
71. Zhang, X.; Steckler, T. T.; Dasari, R. R.; Ohira, S.; Potscavage, W. J.; Tiwari, S. P.; Coppee, S.; Ellinger, S.; Barlow, S.; Bredas, J. L.; Kippelen, B.; Reynolds, J. R.; Marder, S. R. J. Mater. Chem. 2010, 20, 123-134
72. Xu, S.; Liu, Y.; Li, J.; Wang, Y.; Cao, S. Polym. Adv. Technol. 2010, 21, 663-668
73. Kim, J.; Park, S. H.; Cho, S.; Jin, Y.; Kim, J.; Kim, I.; Lee, J. S.; Kim, J. H.; Woo, H. Y.; Lee, K.; Suh, H. Polymer 2010, 51, 390-396
74. Sun, X.; Xu, X.; Qiu, W.; Yu, G.; Zhang, H.; Gao, X.; Chen, S.; Song, Y.; Liu, Y. J. Mater. Chem. 2008, 18, 2709-2715
75. Morikita, T.; Yamaguchi, I.; Yamamoto, T. Adv. Mater. 2001, 13, 1862-1864
76. Welch, G. C.; Coffin, R.; Peet, J.; Bazan, G. C. J. Am. Chem. Soc. 2009, 131, 10802-10803
77. Welch, G. C.; Bazan, G. C. J. Am. Chem. Soc. 2011, 133, 4632-4644
78. Zalar, P.; Henson, Z. B.; Welch, G. C.; Bazan, G. C.; Nguyen, T.-Q. Angew. Chem., Int. Ed. 2012, 51, 7495-7498
79. Zalar, P.; Kuik, M.; Henson, Z. B.; Woellner, C.; Zhang, Y.; Sharenko, A.; Bazan, G. C.; Nguyen, T.-Q. Adv. Mater. 2013, 25, 1
80. Durmus, A.; Gunbas, G. E.; Camurlu, P.; Toppare, L. Chem. Commun. 2007, 31, 3246-3248
81. Cihaner, A.; Algi Adv. Funct. Mater. 2008, 18, 3583-3589
82. Zhu, S. S.; Swager, T. M. J. Am. Chem. Soc. 1997, 119, 12568-12577
83. Tsubata, Y.; Suzuki, T.; Miyashi, T.; Yamashita, Y. J. Org. Chem. 1992, 57, 6749
84. Yang, R.; Tian, R.; Yan, J.; Zhang, Y.; Jian Yang, Y.; Hou, Q.; Yang, W.; Zhang, C.; Cao, Y. Macromolecules 2005, 38, 244-253
85. Blouin, N.; Michaud, A.; Gendron, D.; Wakim, S.; Blair, E.; Neagu-Plesu, R.; Belletete, M.; Durocher, G.; Tao, Y.; Leclerc, M. J. Am. Chem. Soc. 2008, 130, 732-742
86. Tanimoto, A.; Yamamoto, T. Adv. Synth. Catal. 2004, 346, 1818-1823
87. Yalcinkaya, F.; Powner, E. T. Med. Eng. Phys. 1997, 19, 299-301
88. Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877
89. Kulkarni, A.; Tonzola, C.; Babel, A.; Jenekhe, S. Chem. Mater. 2004, 16, 4556-4573
90. D'Andrade, B. W.; Datta, S.; Forrest, S. R.; Djurovich, P.; Polikarpov, E.; Thompson, M. E. Org. Electron. 2005, 6, 11
91. Djurovich, P. I.; Mayo, E. I.; Forrest, S. R.; Thompson, M. E. Org. Electron. 2009, 10, 515
92. Cardona, C. M.; Li, W.; Kaifer, A. E.; Stockdale, D.; Bazan, G. C. Adv. Mater. 2011, 23, 2367
93. Frisch, M. J., Gaussian 09, Revision A.02; Gaussian, Inc.: Wallingford, CT, 2009.
94. Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
95. Koch, W.; Holthausen, M. C. Chemist's Guide to Density Functional Theory; Wiley-VCH: New York, 2000.
96. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B: Condens. Matter Mater. Phys. 1988, 37, 785
97. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
98. Patra, A.; Wijsboom, Y. H.; Zade, S. S.; Li, M.; Sheynin, Y.; Leitus, G.; Bendikov, M. J. Am. Chem. Soc. 2008, 130, 6734-6736
99. Wong, W-Y; Wang, X.; Zhang, H.-L.; Cheung, K.-Y.; Fung, M.-K.; Djurisic, A. B.; Chan, W.-K. J. Organomet. Chem. 2008, 693, 3603
100. Steckler, T. T.; Abboud, K. A.; Craps, M.; Rinzler, A. G.; Reynolds, J. R. Chem. Commun. 2007, 4904
101. Patra, A.; Bendikov, M. J. Mater. Chem. 2010, 20, 422-433
102. Wijsboom, Y. H.; Patra, A.; Zade, S. S.; Sheynin, Y.; Li, M.; Shimon, L. J. W.; Bendikov, M. Angew. Chem., Int. Ed. 2009, 48, 5443-5447
103. Wijsboom, Y. H.; Sheynin, Y.; Patra, A.; Zamoshchik, N.; Vardimon, R.; Leitus, G.; Bendikov, M. J. Mater. Chem. 2011, 21, 1368
104. Li, M.; Sheynin, Y.; Patra, A.; Bendikov, M. Chem. Mater. 2009, 21, 2482-2488