Phosphorus-containing materials for organic electronics

Chemistry - An Asian Journal

Volumn 9, Issue 5, 2014, Pages 1212-1225

  Stolar, Monika ^a   Baumgartner, Thomas ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

conjugated materials; electron acceptors; OLEDs; phosphorus; sensors

Indexed keywords

PHOSPHORUS COMPOUNDS; SENSORS;

CONJUGATED MATERIALS; ELECTRON ACCEPTOR; OLEDS; ORGANIC ELECTRONICS; ORGANOPHOSPHORUS COMPOUNDS; PHOSPHORUS-CONTAINING MATERIALS; SENSING APPLICATIONS; STRUCTURAL MODIFICATIONS;

PHOSPHORUS;

EID: 84899438818     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201301670     Document Type: Article

References (103)

1. Handbook of Conducting Polymers, 3rd ed. (Eds.:, T. A. Skotheim, J. R. Reynolds,), CRC Press, Boca Raton, FL, 2006
2. Organic Light Emitting Devices, eds. K. Müllen, U. Scherf, Wiley-VCH, Weinheim, 2005
3. Handbook of Thiophene-Based Materials, Vol. 1 and 2 (Eds.:, I. F. Perepichka, D. F. Perepichka,), Wiley, Chichester, 2009
4. J. R. Lakowicz, Principles of Fluorescence Spectroscopy, 3rd ed., Springer, New York, 2006
5. B. Valeur, Molecular Fluorescence, Principles and Applications, Wiley-VCH, Weinheim, 2002.
6. Z. Bao, J. A. Rogers, H. E. Katz, J. Chem. Mater. 1999, 9, 1895-1904
7. Z. Bao, Y. Feng, A. Dodabalapur, V. R. Raju, A. Lovinger, Chem. Mater. 1997, 9, 1299-1301
8. J. Bharathan, Y. Yang, Appl. Phys. Lett. 1998, 72, 2660-2662
9. T. R. Hebner, C. C. Wu, D. Marcy, M. H. Lu, J. C. Sturm, Appl. Phys. Lett. 1998, 72, 519-521
10. T. R. Hebner, J. C. Sturm, Appl. Phys. Lett. 1998, 73, 1775-1777
11. J. A. Rogers, Z. Bao, V. R. Raju, Appl. Phys. Lett. 1998, 72, 2716-2718.
12. Boron.
13. C. D. Entwistle, T. B. Marder, Angew. Chem. Int. Ed. 2002, 41, 2927-2931
14. Angew. Chem. 2002, 114, 3051-3056; Nitrogen
15. U. H. F. Bunz, Chem. Eur. J. 2009, 15, 6780-6789; Silicon
16. S. Yamaguchi, K. Tamao, J. Chem. Soc. Dalton Trans. 1998, 3693-3702.
17. F. Mathey, Phosphorus-Carbon Heterocyclic Chemistry: The Rise of a New Domain, Pergamon, 2001.
18. T. Baumgartner, R. Réau, Chem. Rev. 2006, 106, 4681-4727.
19. Y. Ren, T. Baumgartner, Dalton Trans. 2012, 41, 7792-7800.
20. M.-H. Ha-Thi, V. Souchon, A. Hamdi, R. Métivier, V. Alain, K. Nakatani, P. G. Lacroix, J.-P. Genêt, V. Michelet, I. Leray, Chem. Eur. J. 2006, 12, 9056-9065.
21. V. Alain-Rizzo, D. Drouin-Kucma, C. Rouxel, I. Samb, J. Bell, P. Y. Toullec, V. Michelet, I. Leray, M. Blanchard-Desce, Chem. Asian J. 2011, 6, 1080-1091.
22. H. Meier, B. Mühling, H. Kolshorn, Eur. J. Org. Chem. 2004, 1033-1042.
23. A. L. Von Ruden, L. Cosimbescu, E. Polikarpov, P. K. Koech, J. S. Swensen, L. Wang, J. T. Darsell, A. B. Padmaperuma, Chem. Mater. 2010, 22, 5678-5686.
24. R. A. Baldwin, M. T. Cheng, J. Org. Chem. 1967, 32, 1572-1577.
25. P. K. Koech, E. Polikarpov, J. E. Rainbolt, L. Cosimbescu, J. S. Swensen, A. L. Von Ruden, A. B. Padmaperuma, Org. Lett. 2010, 12, 5534-5537.
26. S.-J. Su, T. Chiba, T. Takeda, J. Kido, Adv. Mater. 2008, 20, 2125-2130
27. H. Sasabe, E. Gonmori, T. Chiba, Y.-J. Li, D. Tanaka, S.-J. Su, T. Takeda, Y.-J. Pu, K.-I. Nakayama, J. Kido, Chem. Mater. 2008, 20, 5951-5953
28. S.-J. Su, H. Sasabe, T. Takeda, J. Kido, Chem. Mater. 2008, 20, 1691-1693.
29. H. Chen, W. Delaunay, L. Yu, D. Joly, Z. Wang, J. Li, Z. Wang, C. Lescop, D. Tondelier, B. Geffroy, Z. Duan, M. Hissler, F. Mathey, R. Réau, Angew. Chem. Int. Ed. 2012, 51, 214-217
30. Angew. Chem. 2012, 124, 218-221.
31. M. O. Bevierre, F. Mercier, L. Ricard, F. Mathey, Angew. Chem. Int. Ed. Engl. 1990, 29, 655-657
32. Angew. Chem. 1990, 102, 672-675
33. F. Laporte, F. Mercier, L. Ricard, F. Mathey, J. Am. Chem. Soc. 1994, 116, 3306-3311
34. M. Gouygou, O. Tissot, J.-C. Daran, G. G. A. Balavoine, Organometallics 1997, 16, 1008-1015.
35. P.-A. Bouit, A. Escande, R. Sz?cs, D. Szieberth, C. Lescop, L. Nyulászi, M. Hissler, R. Réau, J. Am. Chem. Soc. 2012, 134, 6524-6527.
36. L. Liu, B. Yang, T. J. Katz, M. K. Poindexter, J. Org. Chem. 1991, 56, 3769-3775.
37. H. Chen, W. Delaunay, J. Li, Z. Wang, P.-A. Bouit, D. Tondelier, B. Geffroy, F. Mathey, Z. Duan, R. Réau, M. Hissler, Org. Lett. 2013, 15, 330-333.
38. Y. Dienes, M. Eggenstein, T. Kárpáti, T. C. Sutherland, L. Nyulászi, T. Baumgartner, Chem. Eur. J. 2008, 14, 9878-9889.
39. M. D. Watson, A. Fechtenkötter, K. Müllen, Chem. Rev. 2001, 101, 1267-1300
40. M. Bendikov, F. Wudl, D. M. Perepichka, Chem. Rev. 2004, 104, 4891-4946
41. J. E. Anthony, Chem. Rev. 2006, 106, 5028-5048.
42. D. Hanifi, A. Pun, Y. Liu, Chem. Asian J. 2012, 7, 2615-2620.
43. A. Bruch, A. Fukazawa, E. Yamaguchi, S. Yamaguchi, A. Studer, Angew. Chem. Int. Ed. 2011, 50, 12094-12098
44. Angew. Chem. 2011, 123, 12300-12304.
45. H.-C. Su, O. Fadhel, C.-J. Yang, T.-Y. Cho, C. Fave, M. Hissler, C.-C. Wu, R. Réau, J. Am. Chem. Soc. 2006, 128, 983-995.
46. M. Shimizu, H. Tatsumi, K. Mochida, K. Oda, T. Hiyama, Chem. Asian J. 2008, 3, 1238-1247.
47. G. A. Olah, D. Hehemann, J. Org. Chem. 1977, 42, 2190-2190
48. A. A. Diaz, J. D. Young, M. A. Khan, R. J. Wehmschulte, Inorg. Chem. 2006, 45, 5568-5575
49. A. A. Diaz, B. Buster, D. Schomich, M. A. Khan, J. C. Baum, R. J. Wehmschulte, Inorg. Chem. 2008, 47, 2858-2863.
50. T. Hatakeyama, S. Hashimoto, M. Nakamura, Org. Lett. 2011, 13, 2130-2133.
51. I. Danila, F. Biaso, H. Sidorenkova, M. Geoffroy, M. Fourmigué, E. Levillain, N. Avarvari, Organometallics 2009, 28, 3691-3699.
52. C. Romero-Nieto, T. Baumgartner, Synlett 2013, 920-937.
53. X.-M. He, J.-B. Lin, W. H. Kan, T. Baumgartner, Angew. Chem. Int. Ed. 2013, 52, 8990-8994
54. Angew. Chem. 2013, 125, 9160-9164.
55. X.-M. He, J. Borau-Garcia, A. Y. Y. Woo, S. Trudel, T. Baumgartner, J. Am. Chem. Soc. 2013, 135, 1137-1147
56. X.-M. He, T. Baumgartner, Organometallics 2013, 32, 7625-7628.
57. J. A. Letizia, M. R. Salata, C. M. Tribout, A. Facchetti, M. A. Ratner, T. J. Marks, J. Am. Chem. Soc. 2008, 130, 9679-9694.
58. A. W. Czarnik, Fluorescent Chemosensors for Ion and Molecule Recognition, ACS, Washington, 1993
59. A. P. de Silva, H. Q. N. Gunaratne, T. Gunnlaugsson, A. J. M. Huxley, C. P. McCoy, J. T. Rademacher, T. E. Rice, Chem. Rev. 1997, 97, 1515-1566
60. J. S. Kim, D. T. Quang, Chem. Rev. 2007, 107, 3780-3799
61. C. R. Wade, A. E. J. Broomsgrove, S. Aldridge, F. P. Gabbaï, Chem. Rev. 2010, 110, 3958-3984
62. D. Y. McQuade, A. E. Pullen, T. M. Swager, Chem. Rev. 2000, 100, 2537-2574
63. S. W. Thomas III., G. D. Joly, T. M. Swager, Chem. Rev. 2007, 107, 1339-1386.
64. D. Faye, H. Zhang, J.-P. Lefevre, J. Bell, J. A. Delairea, I. Leray, Photochem. Photobiol. Sci. 2012, 11, 1737-1743.
65. F. J. Sainz-Gonzalo, M. Casimiro, C. Popovici, A. Rodríguez- Diéguez, J. F. Fernández-Sánchez, I. Fernández, F. Lõpez-Ortiz, A. Fernández-Gutiérrez, Dalton Trans. 2012, 41, 6735-6748.
66. L. Armelao, S. Quici, F. Barigelletti, G. Accorsi, G. Bottaro, M. Cavazzini, E. Tondello, Coord. Chem. Rev. 2010, 254, 487-505
67. P. A. Tanner, C.-K. Duan, Coord. Chem. Rev. 2010, 254, 3026-3029.
68. X.-M. He, P. Zhang, J.-B. Lin, H. V. Huynh, S. E. Navarro Muñoz, C.-C. Ling, T. Baumgartner, Org. Lett. 2013, 15, 5322-5325.
69. X.-M. He, J.-B. Lin, W. H. Kan, P. Dong, S. Trudel, T. Baumgartner, Adv. Funct. Mater. DOI:.
70. Y. M. Zhang, M. Han, H. Z. Chen, Y. Zhang, Y. Liu, Org. Lett. 2013, 15, 124-127
71. T. Ogoshi, A. Harada, Sensors 2008, 8, 4961-4982.
72. X.-M. He, A. Y. Y. Woo, J. Borau-Garcia, T. Baumgartner, Chem. Eur. J. 2013, 19, 7620-7630.
73. M. A. Baldo, D. F. O'Brien, Y. You, A. Shoustikov, S. Sibley, M. E. Thompson, S. R. Forrest, Nature 1998, 395, 151-154
74. S. Reineke, F. Lindner, G. Schwartz, N. Seidler, K. Walzer, B. Lussem, K. Leo, Nature 2009, 459, 234-238.
75. H.-H. Chou, C.-H. Cheng, Adv. Mater. 2010, 22, 2468-2471.
76. C. Han, Z. Zhang, H. Xu, J. Li, G. Xie, R. Chen, Y. Zhao, W. Huang, Angew. Chem. Int. Ed. 2012, 51, 10104-10108
77. Angew. Chem. 2012, 124, 10251-10255.
78. J. Zhao, G.-H. Xie, C.-R. Yin, L.-H. Xie, C.-M. Han, R.-F. Chen, H. Xu, M.-D. Yi, Z.-P. Deng, S.-F. Chen, Y. Zhao, S.-Y. Liu, W. Huang, Chem. Mater. 2011, 23, 5331-5339
79. F.-M. Hsu, C.-H. Chien, C.-F. Shu, C.-H. Lai, C.-C. Hsieh, K.-W. Wang, P.-T. Chou, Adv. Funct. Mater. 2009, 19, 2834-2843.
80. R. Meerheim, K. Walzer, G. He, M. Pfeiffer, K. Leo, in Proc. SPIE, Vol. 6192, 1st ed. (Eds.: P. L. Heremans, M. Muccini, E. A. Meulenkamp), SPIE, Strasbourg, France, 2006, 61920P.
81. D. Yu, Y. Zhao, H. Xu, C. Han, D. Ma, Z. Deng, S. Gao, P. Yan, Chem. Eur. J. 2011, 17, 2592-2596.
82. D. Joly, D. Tondelier, V. Deborde, B. Geffroy, M. Hissler, R. Réau, New J. Chem. 2010, 34, 1603-1611.
83. D. Joly, D. Tondelier, V. Deborde, W. Delaunay, A. Thomas, K. Bhanuprakash, B. Geffroy, M. Hissler, R. Réau, Adv. Funct. Mater. 2012, 22, 567-576.
84. B. W. DAndrade, S. R. Forrest, Adv. Mater. 2004, 16, 1585-1595
85. K. T. Kamtekar, A. P. Monkman, M. R. Bryce, Adv. Mater. 2010, 22, 572-582.
86. P. J. Fagan, W. A. Nugent, J. C. Calabrese, J. Am. Chem. Soc. 1994, 116, 1880-1889.
87. A. Mishra, M. K. R. Fischer, P. Bäuerle, Angew. Chem. Int. Ed. 2009, 48, 2474-2499
88. Angew. Chem. 2009, 121, 2510-2536
89. H. Imahori, T. Umeyama, S. Ito, Acc. Chem. Res. 2009, 42, 1809-1818.
90. A. Kira, Y. Shibano, S. Kang, H. Hayashi, T. Umeyama, Y. Matano, H. Imahori, Chem. Lett. 2010, 39, 448-450.
91. Carboxylic acid
92. K. Hara, K. Sayama, H. Arakawa, Y. Ohga, A. Shinpo, S. Suga, Chem. Commun. 2001, 569-570
93. K. Tanaka, K. Takimiya, T. Otsubo, K. Kawabuchi, S. Kajihara, Y. Harima, Chem. Lett. 2006, 35, 592-593
94. S. Ito, H. Miura, S. Uchida, M. Takata, K. Sumioka, P. Liska, P. Comte, P. Péchy, M. Grätzel, Chem. Commun. 2008, 5194-5196; Sulfonic acid
95. T. Ma, K. Inoue, H. Noma, K. Yao, E. Abe, J. Photochem. Photobiol. A 2002, 152, 207-212; Phosphonic acid
96. M. K. Nazeeruddin, R. Humphry-Baker, D. L. Officer, W. M. Campbell, A. K. Burrell, M. Grätzel, Langmuir 2004, 20, 6514-6517.
97. J. Burschka, N. Pellet, S.-J. Moon, R. Humphry-Baker, P. Gao, M. K. Nazeeruddin, M. Grätzel, Nature 2013, 499, 316-319.
98. Y. Matano, A. Saito, Y. Suzuki, T. Miyajima, S. Akiyama, S. Otsubo, E. Nakamoto, S. Aramaki, H. Imahori, Chem. Asian J. 2012, 7, 2305-2312.
99. H. Tsuji, K. Sato, Y. Sato, E. Nakamura, J. Mater. Chem. 2009, 19, 3364-3366.
100. A. Saito, T. Miyajima, M. Nakashima, T. Fukushima, H. Kaji, Y. Matano, H. Imahori, Chem. Eur. J. 2009, 15, 10000-10004.
101. Y. Matano, A. Saito, T. Fukushima, Y. Tokudome, F. Suzuki, D. Sakamaki, H. Kaji, A. Ito, K. Tanaka, H. Imahori, Angew. Chem. 2011, 123, 8166-8170
102. Angew. Chem. Int. Ed. 2011, 50, 8016-8020
103. Angew. Chem. 2011, 123, 8166-8170.