Advertisement

Modern Synthetic and Application Aspects of Polysilanes: An Underestimated Class of Materials?

  • A. Feigl
  • A. Bockholt
  • J. Weis
  • B. RiegerEmail author
Chapter
Part of the Advances in Polymer Science book series (POLYMER, volume 235)

Abstract

Polysilanes can be synthesized by various methods still lacking satisfactory product control in respect to quality and purity. Nonetheless polysilanes are promising in a number of applications like e.g. organic electronic devices. This review summarizes recent progress in the synthesis and possible applications of polysilanes.

Keywords

Dehydocoupling Masked disilenes OLEDs ⋅OFEDs Polysilanes Polysilane synthesis Wurtz-Coupling 

References

  1. 1.
    Kipping FS (1921) J Chem Soc 119:830CrossRefGoogle Scholar
  2. 2.
    Kipping FS (1923) J Chem Soc 125:2291Google Scholar
  3. 3.
    Miller DR, Michl J (1989) Chem Rev 89:1359CrossRefGoogle Scholar
  4. 4.
    Stock A (1926) Z Elektrochem 32:341Google Scholar
  5. 5.
    Fehér F, Schinkitz D, Schaaf J (1971) Z Anorg Allg Chem 383:303CrossRefGoogle Scholar
  6. 6.
    Fehér F, Schinkitz D, Wronka G (1971) Z Anorg Allg Chem 384:226CrossRefGoogle Scholar
  7. 7.
    F Fehér, D Schinkitz, H Strack (1971) Z Anorg Allg Chem 358:202CrossRefGoogle Scholar
  8. 8.
    Fehér F, Baier H, Enders B, Krancher M, Laakmann J, Ocklenburg FJ, Skrodski D (1985) Z Anorg Allg Chem 530:191CrossRefGoogle Scholar
  9. 9.
    Auner GA, Bauch C, Lippold G, Deltschew R (2008) DE 102006034061 A1 CAN 115: 115263Google Scholar
  10. 10.
    Friedel C, Ladenburg A (1869) C R Hebd Seances Acad Sci 68:920Google Scholar
  11. 11.
    Kipping FS (1924) J Chem Soc 125:2291CrossRefGoogle Scholar
  12. 12.
    Ziegler JM, Rozell JM, Pannell KH (1987) Macromolecules 6:399Google Scholar
  13. 13.
    Fujino M, Hisaki T, Fujiki M, Matsumoto N (1992) Macromolecules 1079Google Scholar
  14. 14.
    Ziegler JM (1986) Polym Prepr 27:109CrossRefGoogle Scholar
  15. 15.
    Ziegler JM, Harrah LA (1987) Macromolecules 20:601CrossRefGoogle Scholar
  16. 16.
    Horguchi R, Onishi Y, Hayase S (1988) Macromolecules 21:304CrossRefGoogle Scholar
  17. 17.
    Miller DR, Sooriyakumaran R (1988) Macromolecules 21:3120CrossRefGoogle Scholar
  18. 18.
    Jones RG, Holder SJ (2000) Synthesis of polysilanes by the wurtz reductive-coupling reaction. In: Silicon-containing polymers. Kluwer, DordrechtGoogle Scholar
  19. 19.
    Jones RG, Holder SJ (2006) Polym Int 55:711CrossRefGoogle Scholar
  20. 20.
    Ziegler JM (1987) Polym Prepr 27:109Google Scholar
  21. 21.
    Cragg RH, Jones RG, Swain AC, Webb SJ (1990) J Chem Soc Chem Commun 1147Google Scholar
  22. 22.
    Miller MD, Ginsberg EJ, Thompson D (1993) Polym J 25:807CrossRefGoogle Scholar
  23. 23.
    Jones RG, Budnik U, Holder SJ, Wong WKC (1996) Macromolecules 29:8036CrossRefGoogle Scholar
  24. 24.
    Holder SJ, Achilleos M, Jones RG (2006) J Am Chem Soc 128:12418CrossRefGoogle Scholar
  25. 25.
    Gauthier S, Worsford DJ (1989) Macromolecules 22:2213CrossRefGoogle Scholar
  26. 26.
    Kim HK, Matyjaszewski K (1988) J Am Chem Soc 110:3321CrossRefGoogle Scholar
  27. 27.
    Matyjaszewski K, Chen YL, Kim HK (1988) Inorganic and organometallic polymers. In: ACS Symp Series. ACS, Washington DCGoogle Scholar
  28. 28.
    Worsfold DJ (1988) Inorganic and organometallic polymers. In: ACS Symp Series. ACS, Washington DCGoogle Scholar
  29. 29.
    Gauthier S, Worsfold DJ (1990) Mechanistic studies in polysilane polymerization. In: Silicon-based polymer science: a comprehensive resource. In: ACS Series. ACS, Washington DCGoogle Scholar
  30. 30.
    Matyjaszewski K (1987) Polym Prepr 28:224CrossRefGoogle Scholar
  31. 31.
    Sakamoto K, Obata K, Hirata H, Nakajima M, Sakurai H (1989) J Am Chem Soc 111:7641CrossRefGoogle Scholar
  32. 32.
    Raabe G, Michl J (1989) The chemistry of organic silicon compounds, Part 2 Wiley, ChichesterGoogle Scholar
  33. 33.
    Roark DN, Peddle GJD (1972) J Am Chem Soc 94:5837CrossRefGoogle Scholar
  34. 34.
    Sakamoto K, Yoshida M, Sakurai H (1990) Macromolecules 23:4494CrossRefGoogle Scholar
  35. 35.
    Sakurai H, Yoshida M (2000) Synthesis of polysilanes by new procedures. Part 1: Ring opening polymerisations and the polymerisation of masked disilenes. In: Silicon-containing polymers. Kluwer, DorndrechtGoogle Scholar
  36. 36.
    Sakurai H, Sakamoto K, Funada Y, Yoshida M (1993) Polym Prepr 34:218CrossRefGoogle Scholar
  37. 37.
    Sanji T, Kawabata K, Sakurai H (2000) J Organomet Chem 611:32CrossRefGoogle Scholar
  38. 38.
    Sanji T, Isozaki S, Yoshida M, Sakamoto K, Sakurai H (2003) J Organomet Chem 685:65CrossRefGoogle Scholar
  39. 39.
    Sakurai H, Honbori R, Sanji T (2005) Organometallics 24:4119CrossRefGoogle Scholar
  40. 40.
    Li J, Li Z, Tang HD, Zeng HY, Qin JG (2003) J Organomet Chem 685:258CrossRefGoogle Scholar
  41. 41.
    Sakamoto K, Yoshida M, Sakurai H (1984) Polymer 35:4990CrossRefGoogle Scholar
  42. 42.
    Chandrasekhar V (2005) Polysilanes and other silicon containing Polymers. In: Inorganic and organometallic polymers. Springer, Berlin Heidelberg New YorkGoogle Scholar
  43. 43.
    Cypryrk M, Gupta Y, Matyjaszewski K (1991) J Am Chem Soc 113:1046CrossRefGoogle Scholar
  44. 44.
    Suzuki M, Kotani J, Gyobu S, Kaneko T, Saegusa T (1994) Macromolecules 27:2360CrossRefGoogle Scholar
  45. 45.
    Koe JR, Powell DR, Buffy JJ, Hayase S, West R (1998) Angew Chem 37:1441CrossRefGoogle Scholar
  46. 46.
    Grimmond BJ, Corey JY (2002) Inorg Chim Acta 330:89CrossRefGoogle Scholar
  47. 47.
    Imori T, Tilley TD (1994) Polyhedron 13:2231CrossRefGoogle Scholar
  48. 48.
    Banovetz JP, Suzuki H, Waymouth RM (1993) Organometallics 12:4700CrossRefGoogle Scholar
  49. 49.
    Hashimoto H, Obara S, Kira M (2000) Chem Lett 188Google Scholar
  50. 50.
    Obora Y, Tanaka M (2000) J Organomet Chem 595:1CrossRefGoogle Scholar
  51. 51.
    Mu Y, Harrod JF, John F (1991) Inorg Organomet Oligomers Polym, Proc IUPAC Symp Macromol 33:23Google Scholar
  52. 52.
    Rosenberg L, Kobus DN (2003) J Organomet Chem 685:107CrossRefGoogle Scholar
  53. 53.
    Aitken C, Harrod JF, Samuel E (1985) J Organomet Chem 279:C11CrossRefGoogle Scholar
  54. 54.
    Shankar R, Saxena A, Brar AS (2001) J Organomet Chem 628:262CrossRefGoogle Scholar
  55. 55.
    Hengge E, Gspaltl P, Pinter E (1996) J Organomet Chem 521:145CrossRefGoogle Scholar
  56. 56.
    Woo HG, Tilley TD (1989) J Am Chem Soc 111:8043CrossRefGoogle Scholar
  57. 57.
    Corey JY, Zhu XH (1992) J Organomet Chem 439:1CrossRefGoogle Scholar
  58. 58.
    Corey JY (2004) Adv Organomet Chem 51:1CrossRefGoogle Scholar
  59. 59.
    Dioumaev VK, Harrod JF (1996) J Organomet Chem 521:133CrossRefGoogle Scholar
  60. 60.
    Grimmond BJ, Corey JY (2000) Organometallics 19:3776CrossRefGoogle Scholar
  61. 61.
    Gray GM, Corey JY (2000) Synthesis of polysilanes by new procedures. Part 2: Catalytic dehydropolymerisation of hydrosilanes. In: Silicon-containing polymers. Kluwer, DordrechtGoogle Scholar
  62. 62.
    Shaltout RM, Corey JY (1995) Tetrahedron 51:4309CrossRefGoogle Scholar
  63. 63.
    Shaltout RM, Corey JY (1995) Main Group Chem 1:115CrossRefGoogle Scholar
  64. 64.
    Minato M, Matsumoto T, Ichikawa M, Ito T (2003) Chem Commun 2968Google Scholar
  65. 65.
    Kim B, Woo HG, Kim W, Li H (2006) J Chem Technol Biotechnol 81:782CrossRefGoogle Scholar
  66. 66.
    Ojima I, Inaba S, Kogure T, Nagai Y (1973) J Organomet Chem 55:C7CrossRefGoogle Scholar
  67. 67.
    Berris C, Diefenbach SP (1992) U.S. 5003100 CAN 115:115263Google Scholar
  68. 68.
    Fontaine FG, Kadkhodazadeh T, Zargarian D (1998) Chem Commun 1253Google Scholar
  69. 69.
    Fontaine FG, Zargarian D (2002) Organometallics 21:401CrossRefGoogle Scholar
  70. 70.
    Tanaka M, Bannu P (1998) JP 10 67859 CAN 128:244528Google Scholar
  71. 71.
    Chauhan BPS, Shimizu T, Tanaka M (1997) Chem Lett 785Google Scholar
  72. 72.
    Sakakura T, Lautenschlager HJ, Nakajima M, Tanaka M (1991) Chem Lett 913Google Scholar
  73. 73.
    Kobayashi T, Sakakura T, Hayashi T, Yamura M, Tanaka M (1992) Chem Lett 1157Google Scholar
  74. 74.
    Aitken CT, Harrod JF, Samuel E (1986) J Am Chem Soc 108:4059CrossRefGoogle Scholar
  75. 75.
    Tilley TD (1993) Acc Chem Res 26:22CrossRefGoogle Scholar
  76. 76.
    Dioumaev VK, Harrod JF (1997) Organometallics 16:1452CrossRefGoogle Scholar
  77. 77.
    Dioumaev VK, Harrod JF (1996) J Organomet Chem 521:133CrossRefGoogle Scholar
  78. 78.
    Lunzer F, Marschner C, Landgraf S (1998) J Organomet Chem 568:253CrossRefGoogle Scholar
  79. 79.
    Ishifune M, Kashimura S, Kogai Y, Fukuhara Y, Kato T, Bu HB, Yamashita N, Murai Y, Murase H, Nishida R (2000) J Organomet Chem 611:26CrossRefGoogle Scholar
  80. 80.
    Wesson JP, Williams TC (1981) J Polym Sci A Polym Chem 19:65CrossRefGoogle Scholar
  81. 81.
    Fogarty HA, Ottosson CH, Michl J (2000) J Mol Struct 556:105CrossRefGoogle Scholar
  82. 82.
    Fogarty HA, Ottosson CH, Michl J (2000) J Mol Struct Theochem 506:243CrossRefGoogle Scholar
  83. 83.
    Jones RG, Wong WKC, Holder SJ (1998) Organometallics 17:59CrossRefGoogle Scholar
  84. 84.
    Yajima S, Hayashi J, Omori M (1975) Chem Lett 931Google Scholar
  85. 85.
    Michl J (1990) Acc Chem Res 23:127CrossRefGoogle Scholar
  86. 86.
    Michl J, West R (2000) Structure and spectroscopy of polysilanes. In: Silicon containing polymers. Kluwer, DordrechtGoogle Scholar
  87. 87.
    West R (1982) Organopolysilanes. In: Comprehensive organometallic chemistry. Pergamon, OxfordGoogle Scholar
  88. 88.
    Miller DR (1989) Angew Chem Int Ed Engl 28:1733CrossRefGoogle Scholar
  89. 89.
    West R (1986) J Organomet Chem 300:327CrossRefGoogle Scholar
  90. 90.
    Yajima S, Hasegawa Y, Hayashi J, Iimura M (1978) J Mater Sci 13:2569CrossRefGoogle Scholar
  91. 91.
    West R (1981) J Am Chem Soc 103:7352CrossRefGoogle Scholar
  92. 92.
    Orefice RL, Arnold JJ, Miller TM, Zamora MP, Brennan AB (1997) Polym Prepr 38:157Google Scholar
  93. 93.
    Matsuura K, Miura S, Naito H, Inoue H, Matsukawa K (2003) J Organomet Chem 230:6851Google Scholar
  94. 94.
    West R, Ikuo N, Xing-Hua Z (1984) Polym Prepr 25:4Google Scholar
  95. 95.
    Langguth K (1995) Ceram Int 21:237CrossRefGoogle Scholar
  96. 96.
    Langguth K, Bockhle S, Müller E, Röwer G (1995) J Mater Sci 30:5973CrossRefGoogle Scholar
  97. 97.
    Okamoto K, Shinohara M, Yamanishi T, Miyazaki S, Hirose M (1994) Appl Surf Sci 79:57CrossRefGoogle Scholar
  98. 98.
    Kotaro Y, Tazawa S, Kitsuno Y, Kawasaki K (1992) JP 6191821A2 CAN 121:219559Google Scholar
  99. 99.
    Fukujama K, Kitsuno Y, Sakawaki A, Takadera T, Kotaro Y (1998) JP 2000031066A2 CAN 132:95820Google Scholar
  100. 100.
    Yamamoto H, Takeuchi Y, Matsuki Y, Kato H, Hayakawa H, Endo M (2002) JP 2004186320A2 CAN 141:91765Google Scholar
  101. 101.
    Aoki T (2004) JP 2005219981A2 CAN 143:204477Google Scholar
  102. 102.
    Harrah LH, Ziegler JM (1985) J Polym Sci Polym Lett Ed. 23:209CrossRefGoogle Scholar
  103. 103.
    Trefonas P, Damewood JR, West R, Miller RD (1985) Organometallics 4:1318CrossRefGoogle Scholar
  104. 104.
    Peinado C, Alonso A, Catalina F, Schnabel W (2000) Macromol Chem Phys 201:1156CrossRefGoogle Scholar
  105. 105.
    Matsuura K, Matsukawa K, Kawabata R, Higashi N, Niwa M, Inoue H (2002) Polymer 43:1549CrossRefGoogle Scholar
  106. 106.
    Pyun J, Matyjaszewski K (2001) Chem Mater 12:3436CrossRefGoogle Scholar
  107. 107.
    Hamada Y, Tabei E, Mori S, Yamamoto Y, Noguchi N, Aramata M, Fukushima M (1998) Synth Metal 97:273CrossRefGoogle Scholar
  108. 108.
    Sakurai Y, Okuda S, Nagayama N, Yokoyama M (2001) J Mater Chem 11:1077CrossRefGoogle Scholar
  109. 109.
    Sakurai Y, Okuda S, Nishiguchi H, Nagayama N, Yokoyama M (2003) J Mater Chem 13:1862CrossRefGoogle Scholar
  110. 110.
    Hashimoto K, Nomura N (1991) JP 03139650 A CAN 116:245278Google Scholar
  111. 111.
    Kido J, Nagai K, Okamoto Y, Skotheim T (1991) Appl Phys Lett 59:2760CrossRefGoogle Scholar
  112. 112.
    Suzuki H, Meyer H, Simmerer J, Yang J, Haarer D (1993) Adv Mater 5:743CrossRefGoogle Scholar
  113. 113.
    Kido J, Nagai K, Okamoto K (1993) J Alloys Compd 192:30CrossRefGoogle Scholar
  114. 114.
    Suzuki H, Meyer H, Hoshino S, Haarer D (1995) J Appl Phys Lett 78:2648Google Scholar
  115. 115.
    Suzuki H, Hoshino S (1996) J. Appl Phys Lett 79:8816CrossRefGoogle Scholar
  116. 116.
    Kamata N, Ishii R, Tonsyo S, Terunuma D (2002) Appl Phys Lett 81:4350CrossRefGoogle Scholar
  117. 117.
    Seoul C, Park J, Lee J (2003) Polym Prepr (Am Chem Soc, Div Polym Chem) 44:435Google Scholar
  118. 118.
    Hoshino S, Suzuki H (1996) Appl Phys Lett 69:224CrossRefGoogle Scholar
  119. 119.
    Fujii A, Yoshimoto K, Yoshido M, Ohomori Y, Moshino K (1995) Jpn J Appl Phys 34:L1365CrossRefGoogle Scholar
  120. 120.
    Ebihara K, Koshihara S, Miyazawa T, Kira M (1996) Jpn J Appl Phys 35:L1278CrossRefGoogle Scholar
  121. 121.
    Hattori R, Sugano T, Fujiki T (1996) Jpn J Appl Phys 35:L1509CrossRefGoogle Scholar
  122. 122.
    Xu Y, Fujino T, Naito H, Oka K, Dohmaru T (1998) Chem Lett 299Google Scholar
  123. 123.
    Yuan C, Hoshino S, Toyoda S, Suzuki H, Fujiki M, Matsumoto N (1997) Appl Phys Lett 71:3326CrossRefGoogle Scholar
  124. 124.
    Tokito S, Shirane K, Kamachi M (2003) WO 2003/092334 CAN 139:351099Google Scholar
  125. 125.
    Kanai M, Tanaka H, Sako S (1991) JP 03181184 A CAN 116:162057Google Scholar
  126. 126.
    Kanai M, Tanaka H, Sakou H (1991) DE 4039519 A1 CAN 116:95256Google Scholar
  127. 127.
    Lee J, Seoul C, Park J, Youk JH (2004) Synth Metal 145:11CrossRefGoogle Scholar
  128. 128.
    Rybak A, Jung J, Ciesielski W, Ulanski J (2006) Mater Sci 24:527Google Scholar
  129. 129.
    Haga Y, Harada Y (2001) Jpn J Appl Phys 1 40:855Google Scholar
  130. 130.
    Fukushima M, Aramata M, Mori S (1998) JP 3275736 B2 CAN 129:41835Google Scholar
  131. 131.
    Yamaguchi F, Ueda M, Fujisawa K (1999) JP 11012362 A CAN 130:154129Google Scholar
  132. 132.
    Furukawa M, Kaimoto T, Matsuo S (2004) JP 2004063238 CAN 140:184763Google Scholar
  133. 133.
    Ohshita J, Kangai S, Yoshida H, Kunai A, Kajiwara S, Ooyama Y, Harima Y (2007) J Organomet Chem 692:801CrossRefGoogle Scholar
  134. 134.
    Nakayama T, Naito K (1998) JP 10319450 A CAN 130:87978Google Scholar
  135. 135.
    Nishizawa H, Uchikoga S, Shuichi N, Yoshihiko H, Hayase S (1993) EP 528662 A1 CAN 119:215411Google Scholar
  136. 136.
    Ogier SD, Veres J, Zeidan M (2007) WO 2007082584 A1 CAN 147:224628Google Scholar
  137. 137.
    (1992) JP 5275695 A2 CAN 120:313472Google Scholar
  138. 138.
    Okumoto H, Yatabe T, Richter A, Peng J, Shimomura M, Kaito A, Minami N (2003) Adv Mater 15:716CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2009

Authors and Affiliations

  1. 1.Institut für Siliciumchemie, WACKER-Lehrstuhl für Makromolekulare ChemieTechnische Universität MünchenGarching b. MünchenGermany

Personalised recommendations