Siloles. Part 2: Silaindenes (Benzosiloles) and Silafluorenes (Dibenzosiloles): Synthesis, Characterization, and Applications

Advances in Organometallic Chemistry

Volumn 59, Issue , 2011, Pages 181-328

  Corey, Joyce Y ^a  

^a UNIVERSITY OF MISSOURI ST LOUIS   (United States)

Author keywords

Devices; Dilithio reagents; Dithienosiloles; FETs and solar cells; Oligomers; PCs; Polymers; Reactivity; Silafluorenes; Silaindenes; Transition metal catalysis; WLEDs

Indexed keywords

EID: 82555165192     PISSN: 00653055     EISSN: None     Source Type: Book Series    
DOI: 10.1016/B978-0-12-378649-4.00002-2     Document Type: Chapter

References (174)

1. Corey J.Y. Adv. Organomet. Chem 2011, 59:1.
2. Zhan X., Barlow S., Marder S.R. Chem. Commun. 2009, 1948.
3. Beaupré S., Boudreault P.-L.T., Leclerc M. Adv. Mater. 2010, 22:E6.
4. Dubac J., Laporterie A., Manuel G. Chem. Rev. 1990, 90:215.
5. Dubac J., Guerin C., Meunier P. Chem. Org. Silicon Compd. 1998, 2(Pt. 3):1961.
6. Rausch M.D., Klemann L.P. J. Am. Chem. Soc. 1967, 89:5732.
7. Rausch M.D., Klemann L.P., Boon W.H. Synth. React. Inorg. Met. Org. Chem. 1985, 15:923.
8. Chernyshev E.A., Komalenkova N.G., Bashkirova S. J. Organometal. Chem. 1984, 271:129.
9. Barton T.J., Juvet M. Tetrahedron Lett. 1975, 3893.
10. Barton T.J., Burns G.T. Organometallics 1982, 1:1455.
11. Barton T.J., Groh B.L. Organometallics 1985, 4:575.
12. Choi S.-B., Boudjouk P., Wei P. J. Am. Chem. Soc. 1998, 120:5814.
13. Choi S.-B., Boudjouk P. J. Chem. Soc. Dalton Trans. 2000, 841.
14. Illies L., Tsuji H., Sato Y., Nakamura E. J. Am. Chem. Soc. 2008, 130:4240.
15. Xu C., Wakamiya A., Yamaguchi S. Org. Lett. 2004, 6:3707.
16. Wang C., Luo Q., Sun H., Guo X., Xi Z. J. Am. Chem. Soc. 2007, 129:3094.
17. Bauer W., Feigel M., Müller G., Schleyer P.v.R. J. Am. Chem. Soc. 1988, 110:6033.
18. Xu C., Yamada H., Wakamiya A., Yamaguchi S., Tamao K. Macromolecules 2004, 37:8978.
19. Yamaguchi S., Xu C., Tamao K. J. Am. Chem. Soc. 2003, 125:13662.
20. Matsuda T., Kadowaki S., Murakami M. Chem. Commun. 2007, 2627.
21. Matsuda T., Yamaguchi Y., Murakami M. Synlett 2008, 561.
22. Matsuda T., Yamaguchi Y., Isida N., Murakami M. Synlett 2010, 2743.
23. Tobisu M., Onoe M., Kita Y., Chatani N. J. Am. Chem. Soc. 2009, 131:7506.
24. Matsuda T., Kadowaki S., Yamaguchi Y., Murakami M. Chem. Commun. 2008, 2744.
25. Matsuda T., Kadowaki S., Goya T., Murakami M. Org. Lett. 2007, 9:133.
26. Maercker A., Bodenstedt H., Brandsma L. Angew. Chem. Int. Ed. 1992, 31:1339.
27. Katkevics M., Yamaguchi S., Toshimitsu A., Tamao K. Organometallics 1998, 17:5796.
28. Kurita J., Ishii M., Yasuike S., Tsuchiya T. Chem. Commun. 1993, 1309.
29. Ashe A.J., Savla P.M. J. Organometal. Chem. 1993, 461:1.
30. Korneev S.M., Kaufmann D.E. Synthesis 2002, 491.
31. Xi Z., Zhang W.-X. Synlett 2008, 17:2557.
32. Ubayama H., Xi Z., Takahashi T. Chem. Lett. 1998, 517.
33. Xi C., Huo S., Afifi T.H., Hara R., Takahashi T. Tetrahedron Lett. 1997, 38:4099.
34. Sudo T., Asao N., Yamamoto Y. J. Org. Chem. 2000, 65:8919.
35. Ilies L., Tsuji H., Nakamura E. Org. Lett. 2009, 11:3966.
36. Saito M., Yoshioka M. Coord. Chem. Rev. 2005, 249:765.
37. Ilies L., Tsuji H., Sato Y., Nakamura E. J. Am. Chem. Soc. 2009, 131:13596.
38. Yamaguchi S., Xu C., Okamoto T. Pure Appl. Chem. 2006, 78:721.
39. Fukazawa A., Yamaguchi S. Chem. Asian J. 2009, 4:1386.
40. Yamaguchi S., Tamao K. Chem. Lett. 2005, 34:2.
41. Wong W.W.H., Hooper J.F., Holmes A.B. Aust. J. Chem. 2009, 62:393.
42. Chen J., Cao Y. Macromol. Rapid Commun. 2007, 28:1714.
43. Xu C., Wakamiya A., Yamaguchi S. J. Am. Chem. Soc. 2005, 127:1638.
44. Yamaguchi S., Xu C., Yamada H., Wakamiya A. J. Organometal. Chem. 2005, 690:5365.
45. Gilman H., Gorsich R. J. Am. Chem. Soc. 1955, 77:6380.
46. Gilman H., Gaj B.J. J. Org. Chem. 1957, 22:447.
47. Chan K.L., Watkins S.E., Mak C.S.K., McKiernan M.J., Towns C.R., Pascu S.I., Holmes A.B. Chem. Commun. 2005, 5766.
48. Wang E., Li C., Peng J., Cao Y. J. Polym. Sci. A Polym. Chem. 2007, 45:4941.
49. Agou T., Hossain Md.D., Kawashima T. Chem. Eur. J. 2010, 16:368.
50. Chan K.L., McKierman M.J., Towns C.R., Holmes A.B. J. Am. Chem. Soc. 2005, 127:7662.
51. Usta H., Lu G., Facchetti A., Marks T.J. J. Am. Chem. Soc. 2006, 128:9034.
52. Chen R., Zhu R., Zheng C., Fan Q.-L., Huang W. Sci. Chin. Chem. 2010, 53:2329.
53. Mo Y., Tian R., Shi W., Cao Y. Chem. Commun. 2005, 4925.
54. Chen R.-F., Fan Q.-L., Zheng C., Huang W. Org. Lett. 2006, 8:203.
55. Li L., Xu C., Li S. Tetrahedron Lett. 2010, 51:622.
56. Perron Q., Praz J., Alexakis A. Tetrahedron: Asymmetry 2009, 20:1004.
57. Shimizu M., Tatsumi H., Mochida K., Oda K., Hiyama T. Chem. Asian J. 2008, 3:1238.
58. Geramita K., McBee J., Tilley T.D. J. Org. Chem. 2009, 74:820.
59. Geramita K., McBee J., Tao Y., Segalman R.A., Tilley T.D. Chem. Commun. 2008, 5107.
60. Hoshi T., Shionoiri H., Suzuki T., Ando M., Hagiwara H. Chem. Lett. 1999, 1245.
61. Hoshi T., Nakamura T., Suzuki T., Ando M., Hagiwara H. Organometallics 2000, 19:4483.
62. Boden N., Bushby R.J., Cammidge A.N., Duckworth S., Headdock G. J. Mater. Chem. 1997, 7:601.
63. Furukawa S., Kobayashi J., Kawashima T. Dalton Trans. 2010, 39:9329.
64. Boden N., Bushby R.J., Lu Z., Headdock G. Tetrahedron Lett. 2000, 41:10117.
65. Waldvogel S.R., Aits E., Holst C., Fröhlich R. Chem. Commun. 2002, 1278.
66. Kwong C.-Y., Chan T.-L., Chow H.-F., Lin S.-C., Leung M.-k. J. Chin. Chem. Soc. 1997, 44:211.
67. Lee S.H., Jang B.-B., Kafafi Z.H. J. Am. Chem. Soc. 2005, 127:9071.
68. Wang E., Li C., Mo Y., Zhang Y., Ma G., Shi W., Peng J., Yang W., Cao Y. J. Mater. Chem. 2006, 16:4133.
69. Wang Z., Fang H., Xi Z. Tetrahedron Lett. 2005, 46:499.
70. Liu Y., Stringfellow T.C., Ballweg D., Guzei I.A., West R. J. Am. Chem. Soc. 2002, 124:49.
71. Ballweg D., Liu Y., Guzei I.A., West R. Silicon Chem. 2002, 1:57.
72. Hudrlik P.F., Dai D., Hudrlik A.M. J. Organometal. Chem. 2006, 691:1257.
73. Mewes J., Lerner H.-W., Bolte M. Acta Crystallogr. 2009, E65:o451.
74. Kim C., Seo W., Oh M.-J. Bull. Korean Chem. Soc. 2007, 28:1963.
75. Lu G., Usta H., Risko C., Wang L., Facchetti A., Ratner M.A., Marks T.J. J. Am. Chem. Soc. 2008, 130:7670.
76. Hoshi T., Nakamura T., Suzuki T., Ando M., Hagiwara H. Organometallics 2000, 19:3170.
77. Yasuike S., Iida T., Okajima S., Yamaguchi K., Seki H., Kurita J. Tetrahedron 2001, 57:10047.
78. Chan K.L., Mak C.S.K., Evans N.R., Watkins S.E., Pascu S.I., Holmes A.B., Hayer A., Koehler A., Devi L.S., Friend R.H. Proc. SPIE Int. Soc. Opt. Eng. 2005, 5937. 59370B/1-59370B/9. CAN 145: 145846.
79. van Klink G.P.M., de Boer H.J.R., Schat G., Akkerman O.S., Bickelhaupt F., Spek A.L. Organometallics 2002, 21:2119.
80. Seesukphronrarak S., Takata T. Chem. Lett. 2007, 1138.
81. Yabusaki Y., Ohshima N., Kondo H., Kusamoto T., Yamanoi Y., Nishihara H. Chem. Eur. J. 2010, 16:5581.
82. Li L., Xu C., Li S. Tetrahedron Lett. 2010, 51:622.
83. Ureshino T., Yoshida T., Kuninobu Y., Takai K. J. Am. Chem. Soc. 2010, 132:14324.
84. Shimizu M., Mochida K., Hiyama T. Angew. Chem. Int. Ed. 2008, 47:9760.
85. Shimizu M., Mochida K., Katoh M., Hiyama T. J. Phys. Chem. C 2010, 114:10004.
86. Matsuda T., Kadowaki S., Goya T., Murakami M. Org. Lett. 2007, 9:133.
87. Furukawa S., Kobayashi J., Kawashima T. J. Am. Chem. Soc. 2009, 131:14192.
88. Tobisu M., Onoe M., Kita Y., Chatani N. J. Am. Chem. Soc. 2009, 131:7506.
89. Shimizu M., Mochida K., Katoh M., Hiyama T. J. Phys. Chem. C 2010, 114:10004.
90. Millevolte A.J., van den Winkel Y., Powell D.R., West R. Organometallics 1997, 16:5375.
91. Pietschnig R., West R., Powell D.R. Organometallics 2000, 19:2724.
92. Bock H., Sievert M., Bogdan C.L., Kolbesen B.O., Wittershagen A. Organometallics 1999, 18:2387.
93. Sanchez J.C., DiPasquale A.G., Rheingold A.L., Trogler W.C. Chem. Mater. 2007, 19:6459.
94. Choi S.-B., Boudjouk P. Tetrahedron Lett. 2000, 41:6685.
95. Toulokhonova I.S., Friedrichsen D.R., Hill N.J., Müller T., West R. Angew. Chem. Int. Ed. 2006, 45:2578.
96. Hong J.-H., Boudjouk P., Stoenescu I. Organometallics 1996, 15:2179.
97. Braddock-Wilking J., Corey J.Y., Trankler K.A., Dill K.M., French L.M., Rath N.P. Organometallics 2004, 23:4576.
98. Braddock-Wilking J., Corey J.Y., Dill K., Rath N.P. Organometallics 2002, 21:5467.
99. Braddock-Wilking J., Corey J.Y., Trankler K.A., Xu H., French L.M., Praingam N., White C., Rath N.P. Organometallics 2006, 25:2859.
100. Braddock-Wilking J., Bandrowsky T., Praingam N., Rath N.P. Organometallics 2009, 28:4098.
101. Shinohara A., McBee J., Tilley T.D. Inorg. Chem. 2009, 48:8081.
102. Matsuda T., Kadowaki S., Murakami M. Chem. Commun. 2007, 2627.
103. de Keijzer A.H.J.F., de Kanter F.J.J., Schakel M., Osinga V.P., Klumpp G.W. J. Organometal. Chem. 1997, 548:29.
104. Deerenberg S., Schakel M., de Keijzer A.H.J.F., Kranenburg M., Lutz M., Spek A.L., Lammertsma K. Chem. Commun. 2002, 348.
105. Couzijn E.P.A., van den Engel D.W.F., Slootweg J.C., de Kanter F.J.J., Ehlers A.W., Schakei M., Lammertsma K. J. Am. Chem. Soc. 2009, 131:3741.
106. Wakamiya A., Mishima K., Ekawa K., Yamaguchi S. Chem. Commun. 2008, 579.
107. Corey J.Y., John C.S., Ohmsted M.C., Chang L.S. J. Organometal. Chem. 1986, 304:93.
108. Couzijn E.P.A., Ehlers A., Schakel M., Lammertsma K. J. Am. Chem. Soc. 2006, 128:13634.
109. Berry R.S. J. Chem. Phys. 1960, 32:933.
110. Berry R.S. Rev. Mod. Phys. 1960, 32:447.
111. Muetterties E.L. J. Am. Chem. Soc. 1969, 91:4115.
112. Muetterties E.L. J. Am. Chem. Soc. 1969, 91:1636.
113. Xiao H., Leng B., Tian H. Polymer 2005, 46:5707.
114. Boudreault P.-L.T., Michaud A., Leclerc M. Macromol. Rapid Commun. 2007, 28:2176.
115. Chen J., Tanaka M., Sahoo A., Takeda M., Yada A., Nakao Y., Hiyama T. Bull. Chem. Soc. Jpn. 2010, 83:554.
116. Xiao H., Shen H., Lin Y., Su J., Tian H. Dyes Pigments 2007, 73:224.
117. Sanchez J.C., DePasquale A.G., Mrse A.A., Trogler W.C. Anal. Bianal. Chem. 2009, 395:387.
118. Ormsby J.L., Black T.D., Hilton C.L., King B.B.T. Tetrahedron 2008, 64:11370.
119. Sanchez J.C., Trogler W.C. J. Mater. Chem. 2008, 18:3143.
120. Li L., Xiang J., Xu C. Org. Lett. 2007, 9:4877.
121. Sanchez J.C., Trogler W.C. Macromol. Chem. Phys. 2009, 209:1527.
122. Chen J., Cao Y. Acc. Chem. Res. 2009, 42:1709.
123. Zhang X., Jiang C., Mo Y., Xu Y., Shi H., Cao Y. Appl. Phys. Lett. 2006, 88:051116/1.
124. Sanchez J.C., Urbas S.A., Toal S.J., DiPasquale A.G., Rheingold A.L., Trogler W.C. Macromolecules 2008, 41:1237.
125. Mo Y.-Q., Deng X.-Y., Jiang X., Cui Q.-H. J. Polym. Sci. A Polym. Chem. 2009, 47:3286.
126. Duan C., Cai W., Huang F., Zhang J., Wang M., Yang T., Zhong C., Gong X., Cao Y. Macromolecules 2010, 43:5262.
127. Wang E., Li C., Zhuang W., Peng J., Cao Y. J. Mater. Chem. 2008, 18:797.
128. Wang E., Wang L., Lan L., Luo C., Zhuang W., Peng J., Cao Y. Appl. Phys. Lett. 2008, 92:033307(3).
129. Zou Y., Gendron D., Neagu-Plesu R., Leclerc M. Macromolecules 2009, 42:6361.
130. Chen R.-F., Fan Q.-L., Liu S.-J., Zhu R., Pu K.-Y., Huang W. Synth. Metals 2006, 156:1161.
131. Xie L.-H., Zhu R., Qian Y., Liu R.-R., Chen S.-F., Lin J., Huang W. J. Phys. Chem. Lett. 2010, 1:272.
132. Wong W.W.H., Hooper J.F., Holmes A.B. Aust. J. Chem. 2009, 62:393.
133. Shimizu M., Hiyama T. J. Am. Chem. Soc. 2009, 131:8350.
134. Ohshita J., Lee K.-H., Kumura K., Kunai A. Organometallics 2004, 23:5622.
135. Mouri K., Wakamiya A., Yamada H., Kajiwara T., Yamaguchi S. Org. Lett. 2007, 9:93.
136. Yui K., Aso Y., Otsubo T., Ogura F. Bull. Chem. Soc. Jpn. 1989, 62:1539.
137. Kellogg R.M., Schaap A.P., Wynberg H. J. Org. Chem. 1969, 34:343.
138. Gronowitz S. Acta Chem. Scand. 1961, 15:1393.
139. Ohshita J., Nodono M., Kai H., Wantanabe T., Kunai A., Komaguchi K., Shiotani M., Adachi A., Okita K., Harima Y., Yamashita K., Ishikawa M. Organometallics 1999, 18:1453.
140. Ohshita J., Nodono M., Watanabe T., Ueno Y., Kunai A., Harima Y., Yamashita K., Ishikawa M. J. Organometal. Chem. 1998, 553:487.
141. Liu M.S., Luo J., Jen A.K.-Y. Chem. Mater. 2003, 15:3496.
142. Son H.-J., Han W.-S., Chun J.-Y., Kwon S.-N., Ko J., Kang S.O. Organometallics 2008, 27:2464.
143. Ohshita J., Kumura K., Lee K.-H., Kunai A., Kwak Y.-W., Son E.-C., Kunugi Y. J. Polym. Sci. A Polym. Chem. 2007, 45:4588.
144. Ohshita J., Lee K.-H., Hamamoto D., Kunugi Y., Ikadai J., Kwak Y.-W., Kunai A. Chem. Lett. 2004, 33:892.
145. Lee K.-H., Ohshita J., Kimura K., Kunugi Y., Kunai A. J. Organometal. Chem. 2005, 690:333.
146. Kim D.-H., Ohshita J., Lee K.-H., Kunugi Y., Kunai A. Organometallics 2006, 25:1511.
147. Liao L., Dai L., Smith A., Durstock M., Lu J., Ding J., Tao Y. Macromolecules 2007, 40:9406.
148. He Y., Zhao G., Znang M., Min J., Li Y. Synth. Metals 2010, 160:1045.
149. Huo L., Chen H.-Y., Hou J., Chen T.L., Yang Y. Chem. Commun. 2009, 5570.
150. Hou J., Chen H.-Y., Zhang S., Li G., Yang Y. J. Am. Chem. Soc. 2008, 130:16144.
151. Chen C.-H., Hsieh C.-H., Dubosc M., Cheng Y.-J., Hsu C.-S. Macromolecules 2010, 43:697.
152. Lee K.-H., Ohshita J., Kunai A. Organometallics 2004, 23:5481.
153. Lin L.-Y., Tsai C.-H., Wong K.-T., Huang T.-W., Hsieh L., Liu S.-H., Lin H.-W., Wu C.-C., Chou S.-H., Chen S.-H., Tsai A.-I. J. Org. Chem. 2010, 75:4778.
154. Jung H., Hwang H., Park K.-M., Kum J., Kim D.-H., Kang Y. Organometallics 2010, 29:2715.
155. Beaujuge P.M., Pisula W., Tsao H.N., Ellinger S., Müllen K., Reynolds J.R. J. Am. Chem. Soc. 2009, 131:7514.
156. Lee I.-S., Kwak Y.-W., Kim D.-H., Cho Y., Ohshita J. J. Organometal. Chem. 2008, 693:3233.
157. Ohshita J., Kurushima Y., Lee K.-H., Kunai A., Ooyama Y., Harima Y. Organometallics 2007, 26:6591.
158. Lee T., Jung I., Song K.H., Lee H., Choi J., Lee K., Lee B.J., Pak J.Y., Lee C., Kang S.O., Ko J. Organometallics 2004, 23:5280.
159. Ohshita J., Kai H., Takata A., Iida T., Kunai A., Ohta N., Komaguchi K., Shiotani M., Adachi A., Sakamaki K., Okita K. Organometallics 2001, 20:4800.
160. Matsushita T., Uchida M. J. Photopolym. Sci. Technol. 2003, 16:315.
161. Zeng W., Cao Y., Bai Y., Wang Y., Shi Y., Zhang M., Wang F., Pan C., Wang P. Chem. Mater. 2010, 22:1915.
162. Ohshita J., Lee K.-H., Hashimoto M., Kunugi Y., Harima Y., Yamashita K., Kunai A. Org. Lett. 2002, 4:1891.
163. Boo B.H., Park J., Yeo H.G., Lee S.Y., Park C.J., Kim J.H. J. Phys. Chem. A 1998, 102:1139.
164. Ohshita J. Macromol. Chem. Phys. 2009, 210:1360.
165. Ohshita J., Kai H., Sumida T., Kunai A., Adachi A., Sakamaki K., Okita K. J. Organometal. Chem. 2002, 642:137.
166. Ohshita J., Hamamoto D., Kimura K., Kunai A. J. Organometal. Chem. 2005, 690:3027.
167. Ohshita J., Nodono M., Takata A., Kai H., Adachi A., Sakamaki K., Okita K., Kunai A. Macromol. Chem. Phys. 2000, 201:851.
168. Ding J., Song N., Li Z. Chem. Commun. 2010, 46:8668.
169. Hoven C.V., Dang X.-D., Coffin R.C., Peet J., Nguyen T.-Q., Bazan G.C. Adv. Mater. 2010, 22:63.
170. Zhang Z., Li J., Huang B., Qin J. Chem. Lett. 2006, 958.
171. Ohshita J., Sumida T., Kunai A. Macromolecules 2000, 33:8890.
172. Reyes-Reyes M., Kim K., Carroll D.L. Appl. Phys. Lett. 2005, 87:083506.
173. Shimizu M., Mochida K., Hiyama T. J. Phys. Chem. C 2011, 115:11265.
174. Scharber M.C., Mühlbacher D., Koppe M., Denk P., Waldauf C., Heeger A.J., Brabec C.J. Adv. Mater. 2006, 18:789.