Metal-free polymerization of phenylsilane: Tris(pentafluorophenyl)borane- catalyzed synthesis of branched polysilanes at elevated temperatures

Chemistry - A European Journal

Volumn 19, Issue 37, 2013, Pages 12526-12536

  Feigl, Andreas ^a   Chiorescu, Ion ^a   Deller, Katrin ^a   Heidsieck, Sven U H ^a   Buchner, Magnus R ^a,c   Karttunen, Virve ^a,d   Bockholt, Andreas ^b   Genest, Alexander ^a   Rösch, Notker ^a   Rieger, Bernhard ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b WACKER CHEMIE AG   (Germany)

^c UNIVERSITY OF YORK   (United Kingdom)

^d UNIVERSITY OF JYVÄSKYLÄ   (Finland)

Author keywords

boranes; density functional calculations; Lewis acids; polymerization; silanes

Indexed keywords

BORANES; CATALYZED SYNTHESIS; DEGREE OF POLYMERIZATION; ELEVATED TEMPERATURE; LEWIS ACID; METAL-FREE SYNTHESIS; SUBSTITUTION PATTERNS; TRIS(PENTAFLUOROPHENYL) BORANE;

BORON COMPOUNDS; CATALYSIS; CHEMICAL BONDS; DENSITY FUNCTIONAL THEORY; HYDRIDES; METALS; MONOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; POLYMERS; POLYSILANES; SILANES; SILICON;

CATIONIC POLYMERIZATION;

EID: 84883447248     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201203139     Document Type: Article

References (79)

1. F. S. Kipping, J. Chem. Soc. 1921, 119, 830-847
2. F. S. Kipping, J. Chem. Soc. 1924, 125, 2291-2297.
3. A. Feigl, A. Bockholt, J. Weis, B. Rieger, in Adv. Polym. Sci., Silicon Polymers, Vol. 235 (Ed.:, A. M. Muzafarov,), Springer, Berlin/Heidelberg, 2011, pp. 1-31.
4. J. Baumgartner, D. Frank, C. Kayser, C. Marschner, Organometallics 2005, 24, 750-761
5. S. Chtchian, R. Kempe, C. Krempner, J. Organomet. Chem. 2000, 613, 208-219
6. S. Fukao, M. Fujiki, Macromolecules 2009, 42, 8062-8067
7. J. B. Lambert, J. L. Pflug, H. W. Wu, X. Y. Liu, J. Organomet. Chem. 2003, 685, 113-121
8. J. B. Lambert, H. W. Wu, Organometallics 1998, 17, 4904-4909
9. W. Uhlig, J. Organomet. Chem. 1996, 516, 147-154
10. L. A. Vermeulen, K. Smith, J. B. Wang, Electrochim. Acta 1999, 45, 1007-1014.
11. R. G. Jones, S. J. Holder, in Silicon-Containing Polymers, Kluwer Academic, Dordrecht/Boston/London, 2000, pp. 353-373
12. R. G. Jones, S. J. Holder, Polym. Int. 2006, 55, 711-718.
13. V. Chandrasekhar, in Inorganic and Organometallic Polymers, Springer, Berlin/Heidelberg, 2005, pp. 249-295
14. M. Cypryk, Y. Gupta, K. Matyjaszewski, J. Am. Chem. Soc. 1991, 113, 1046-1047
15. J. R. Koe, D. R. Powell, J. J. Buffy, S. Hayase, R. West, Angew. Chem. 1998, 110, 1514-1515
16. Angew. Chem. Int. Ed. 1998, 37, 1441-1442
17. M. Suzuki, J. Kotani, S. Gyobu, T. Kaneko, T. Saegusa, Macromolecules 1994, 27, 2360-2363.
18. H. Sakurai, M. Yoshida, in Silicon-Containing Polymers, Kluwer Academic, Dordrecht/Boston/London, 2000, pp. 375-399
19. H. Sakurai, K. Sakamoto, Y. Funada, M. Yoshida, Polym. Prepr. 1993, 34, 218
20. H. Sakurai, R. Honbori, T. Sanji, Organometallics 2005, 24, 4119-4121
21. C. Aitken, J. F. Harrod, E. Samuel, J. Organomet. Chem. 1985, 279, C 11 -C 13
22. B. J. Grimmond, J. Y. Corey, Organometallics 2000, 19, 3776-3783
23. B. J. Grimmond, J. Y. Corey, Inorg. Chim. Acta 2002, 330, 89-94.
24. L. Rosenberg, C. W. Davis, J. Yao, J. Am. Chem. Soc. 2001, 123, 5120-5121.
25. J. D. Parks, M. J. Blackwell, E. W. Piers, J. Org. Chem. 2000, 65, 3090-3098
26. X.-H. Zhang, L. W. Chung, Z. Lin, Y.-D. Wu, J. Org. Chem. 2008, 73, 820-829.
27. S.-W. Hu, Y. Wang, X.-Y. Wang, T.-W. Chu, X.-Q. Liu, J. Phys. Chem. A 2003, 107, 9189-9196
28. W. A. Eger, A. Genest, N. Rösch, Chem. Eur. J. 2012, 18, 9106-9116.
29. T. Müller, Organometallics 1998, 17, 278-280
30. R. Damrauer, A. L. Noble, Organometallics 2008, 27, 1707-1715
31. I. S. Ignat′ev, T. A. Kochina, Russ. J. Gen. Chem. 2005, 75, 1221-1224.
32. S. Sakaki, T. Takayama, M. Sugimoto, Organometallics 2001, 20, 3896-3905
33. M. Ray, Y. Nakao, H. Sato, S. Sakaki, Organometallics 2007, 26, 4413-4423
34. M. Ray, Y. Nakao, H. Sato, H. Sakaba, S. Sakaki, Organometallics 2009, 28, 65-73.
35. C. Eaborn, P. D. Lickiss, S. T. Najim, W. A. Stanczyk, J. Chem. Soc. Chem. Commun. 1987, 1461-1462
36. B. Luo, V. G. Young Jr., W. L. Gladfelter, J. Organomet. Chem. 2002, 649, 268-275
37. N. Lühmann, H. Hirao, S. Shaik, T. Müller, Organometallics 2011, 30, 4087-4096
38. A. Schäfer, M. Reißmann, A. Schäfer, W. Saak, D. Haase, T. Müller, Angew. Chem. 2011, 123, 12845-12848
39. Angew. Chem. Int. Ed. 2011, 50, 12636-12638.
40. H.-G. Elias, in Macromolecules, Vol. 1, Wiley-VCH, Weinheim, 2005.
41. A. Bax, M. F. Summers, J. Am. Chem. Soc. 1986, 108, 2093-2094
42. T. Kusukawa, Y. Kabe, T. Erata, B. Nestler, W. Ando, Organometallics 1994, 13, 4186-4188.
43. A. Bax, R. Freeman, T. A. Frenkiel, J. Am. Chem. Soc. 1981, 103, 2102-2104
44. J. B. Lambert, E. Basso, N. Qing, S. H. Lim, J. L. Pflug, J. Organomet. Chem. 1998, 554, 113-116.
45. K. Hassler, U. Katzenbeisser, J. Organomet. Chem. 1991, 421, 151-157
46. K. Hassler, W. Köll, J. Organomet. Chem. 1997, 538, 145-150
47. H. C. Marsmann, in Encyclopedia of Magnetic Resonance, Wiley, New York, 2007.
48. J. P. Wesson, T. C. Williams, J. Polym. Sci. Polym. Chem. 1980, 18, 959-965.
49. S. Gauthier, D. J. Worsford, Macromolecules 1989, 22, 2213-2218.
50. S. Rendler, M. Oestreich, Angew. Chem. 2008, 120, 6086-6089
51. Angew. Chem. Int. Ed. 2008, 47, 5997-6000
52. M. Mewald, M. Oestreich, Chem. Eur. J. 2012, 18, 14079-14084
53. G. Erker, Dalton Trans. 2005, 1883-1890.
54. T. A. Kochina, D. V. Vrazhnov, E. N. Sinotova, M. G. Voronkov, Russ. Chem. Rev. 2006, 75, 95-110.
55. Y. Apeloig, P. von R. Schleyer, Tetrahedron Lett. 1977, 18, 4647-4650
56. T. Truong, M. S. Gordon, P. Boudjouk, Organometallics 1984, 3, 484-487.
57. W. S. Sheldrick, in The Chemistry of Organic Silicon Compounds, Part 1 (Eds.:, S. Patai, Z. Rappoport,), Wiley, New York, 1989, pp. 227-303.
58. P. von R. Schleyer, P. Buzek, T. Mueller, Y. Apeloig, H.-U. Siehl, Angew. Chem. 1993, 105, 1558-1561
59. Angew. Chem. Int. Ed. Engl. 1993, 32, 1471-1473.
60. L. Olsson, D. Cremer, Chem. Phys. Lett. 1993, 215, 433-443.
61. L. Pauling, Science 1994, 263, 983-984.
62. L. Olsson, C.-H. Ottosson, D. Cremer, J. Am. Chem. Soc. 1995, 117, 7460-7479.
63. J. B. Lambert, S. Zhang, C. L. Stern, J. C. Huffman, Science 1993, 260, 1917-1918.
64. S. P. Hoffmann, T. Kato, F. S. Tham, C. A. Reed, Chem. Commun. 2006, 767-769.
65. S. Grimme, J. Comput. Chem. 2006, 27, 1787-1799.
66. Gaussian 09, Revision A.02, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian, Inc. Wallingford CT, 2009.
67. J. P. Foster, F. Weinhold, J. Am. Chem. Soc. 1980, 102, 7211-7218
68. A. E. Reed, F. Weinhold, J. Chem. Phys. 1983, 78, 4066-4073.
69. C. J. Cramer, D. G. Truhlar, Chem. Rev. 1999, 99, 2161-2200
70. J. Tomasi, B. Menucci, R. Cammi, Chem. Rev. 2005, 105, 2999-3094.
71. A. Klamt, G. Schüürmann, J. Chem. Soc. Perkin Trans. 2 1993, 799-805.
72. V. Barone, M. Cossi, J. Phys. Chem. A 1998, 102, 1995-2001.
73. V. Barone, M. Cossi, J. Tomasi, J. Chem. Phys. 1997, 107, 3210-3221.
74. A. Bondi, J. Phys. Chem. 1964, 68, 441-451.
75. A. Ben-Naim, Y. Marcus, J. Chem. Phys. 1984, 81, 2016-2027.
76. D. R. Lide, CRC Handbook Chemistry ans Physics, 85 th ed., CRC, Boca Raton, USA, 2004, 6 -162- 6 -177.
77. A. E. Stearn, H. J. Eyring, J. Chem. Phys. 1937, 5, 113-124.
78. F. P. Rotzinger, Chem. Rev. 2005, 105, 2003-2038
79. S. Sakaki, Y.-Y. Ohnishi, H. Sato, Chem. Rec. 2010, 10, 29-45.