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Transition Metal σ-Acetylide Polymers Containing Main Group Elements in the Main Chain: Synthesis, Light Emission and Optoelectronic Applications

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Inorganic and Organometallic Macromolecules

This chapter highlights recent progress in the development of rigid-rod transition metal polyyne polymers and their molecular model oligomers containing selected group 14 and 16 main group elements in the molecular backbone. The research work involves the synthesis, spectroscopic and photophysical characterization, and possible optoelectronic applications of these luminescent polymeric materials. Considerable emphasis is placed on the optical spectroscopy, photoluminescent behavior, thermal stability and structural aspects of this class of polymetallaynes. A comprehensive account of the effects of these main group elements on the spatial extent of the lowest singlet and triplet excited states of these metal polyyne polymers is provided and the roles of these conjugation-interrupting units in governing the radiative decay rates for phosphorescence emissions are critically elucidated. The future developments of this research frontier in various domains are also discussed.

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References

  1. Manners I. (2004) Synthetic metal-containing polymers. Wiley, Weinheim, Germany.

    Google Scholar 

  2. Nguyen P, Gómez-Elipe P, Manners I. (1999) Chem. Rev. 99:1515.

    Article  CAS  Google Scholar 

  3. Manners I. (1996) Angew Chem Int Ed Engl. 35:1602.

    Article  Google Scholar 

  4. Abd-El-Aziz AS. (2002) Macromol Rapid Commun. 23:995.

    Article  CAS  Google Scholar 

  5. Yam VWW. (2004) J Organomet Chem. 689:1393.

    Article  CAS  Google Scholar 

  6. Long NJ, Williams CK. (2003) Angew Chem Int Ed. 42:2586.

    Article  CAS  Google Scholar 

  7. Fujikura Y, Sonogashira K, Hagihara N. (1975) Chem Lett. 1067.

    Google Scholar 

  8. Sonogashira K, Takahashi S, Hagihara N. (1977) Macromolecules. 10:879.

    Article  CAS  Google Scholar 

  9. Takahashi S, Kariya M, Yatake T, Sonogashira K, Hagihara N. (1978) Macromolecules. 11:1063.

    Article  CAS  Google Scholar 

  10. Sonogashira K, Kataoka S, Takahashi S, Hagihara N. (1978) J Organomet Chem. 160:319.

    Article  CAS  Google Scholar 

  11. Davies SJ, Johnson BFG, Khan MS, Lewis J. (1991) J Chem Soc. Chem Commun. 187.

    Google Scholar 

  12. Atherton A, Faulkner CW, Ingham SL, et al. (1993) J. Organomet. Chem. 462:265.

    Article  CAS  Google Scholar 

  13. Johnson BFG, Kakkar AK, Khan MS, Lewis J. (1991) J Organomet Chem. 409:C12.

    Article  CAS  Google Scholar 

  14. Davies SJ, Johnson BFG, Lewis J, Raithby PR. (1991) J Organomet Chem. 414:C51.

    Article  CAS  Google Scholar 

  15. Brédas JL, Cornil J, HeegerAJ. (1996) Adv Mater. 8: 447.

    Article  Google Scholar 

  16. Sariciftci NS (ed). (1997) Primary photoexcitations in conjugated polymers: molecular exciton vs semiconductor band model. World Scientific, Singapore.

    Google Scholar 

  17. Skotheim TA, Reynolds JR, Elsenbaumer RL (eds). (1998) Handbook of conducting polymers, 2nd ed. Marcel Dekker, New York.

    Google Scholar 

  18. Friend RH, Gymer RW, Holmes AB, Jet al. (1999) Nature. 397:121.

    Article  CAS  Google Scholar 

  19. Wilson JS, Dhoot AS, Seeley AJAB, Khan MS, Köhler A, Friend RH, (2001) Nature.. 413:828.

    Article  CAS  Google Scholar 

  20. Köhler A, Wilson JS, Friend RH. (2002) Adv. Mater. 14:701.

    Article  Google Scholar 

  21. Adachi C, Baldo MA, Thompson ME, Forrest SR. (2001) J Appl Phys. 90:5048.

    Article  CAS  Google Scholar 

  22. Lupton JM, Pogantsch A, Piok Y, List EJW, Patil S, Scherf U. (2002) Phys. Rev Lett. 89:167401.

    Article  CAS  Google Scholar 

  23. Romanovskii YV, Gerhard A, Schweitzer B, Scherf U, Personov RI, Bässler H. (2000) Phys. Rev Lett. 84:1027.

    Article  CAS  Google Scholar 

  24. Gong X, Ostrowski JC, Bazan GC, et al. (2003) Adv. Mater. 15:45.

    Article  CAS  Google Scholar 

  25. Dhoot AS, Greenham NC. (2002) Adv Mater. 14:1834.

    Article  CAS  Google Scholar 

  26. Brédas JL, Chance RR (eds). (1990) Conjugated polymeric materials: opportunities in electronics, optoelectronics and molecular electronics. Kluwer Academic Publishers, Dordrecht.

    Google Scholar 

  27. Ho PKH, Kim JS, Burroughes JH, et al. (2000) Nature. 404:481.

    Article  CAS  Google Scholar 

  28. Cao Y, Parker ID, Yu G, Zhang C, Heeger AJ. (1999) Nature. 397:414.

    Article  CAS  Google Scholar 

  29. Cleave V, Yahioglu G, Le Barny P, Friend RH, Tessler N. (1999) Adv Mater. 11:285.

    Article  CAS  Google Scholar 

  30. Baldo MA, O’Brien DF, You Y, et al. (1998) Nature. 395:151.

    Article  CAS  Google Scholar 

  31. Baldo MA, Thompson ME, Forrest SR. (2000) Nature. 403:750.

    Article  CAS  Google Scholar 

  32. Martin RE, Diederich F. (1999) Angew Chem Int Ed. 38:1350.

    Article  Google Scholar 

  33. Stang PJ, Diederich F. (eds). (1995) Modern Acetylene Chemistry. Wiley, Weinheim, Germany.

    Google Scholar 

  34. Diederich F. (2001) Chem Commun 219.

    Google Scholar 

  35. Bunz UHF. (2000) Chem Rev. 100:1605.

    Article  CAS  Google Scholar 

  36. Wong W-Y. (2005) J Inorg Organomet Polym Mater. 15:197.

    Article  CAS  Google Scholar 

  37. Beljonne D, Wittmann HF, Köhler A, et al. (1996) J Chem Phys. 105:3868.

    Article  CAS  Google Scholar 

  38. Wong W-Y, Chan S-M, Choi K-H, Cheah K-W, Chan W-K. (2000) Macromol Rapid Commun. 21:453.

    Article  CAS  Google Scholar 

  39. Lewis J, Raithby PR, Wong W-Y. (1998) J Organomet Chem. 556:219.

    Article  CAS  Google Scholar 

  40. Wong W-Y, Lu G-L, Choi K-H, Shi J-X, (2002) Macromolecules. 35:3506.

    Article  CAS  Google Scholar 

  41. Wong W-Y, Wong W-K, Raithby P-R. (1998) J Chem Soc Dalton Trans. 2761.

    Google Scholar 

  42. Wong W-Y, Choi K-H, Lu G-L, Shi J-X. (2001) Macromol Rapid Commun. 22:461.

    Article  CAS  Google Scholar 

  43. Khan MS, Al-Mandhary MRA, Al-Suti MK, et al. (2003) Dalton Trans. 74.

    Google Scholar 

  44. Khan MS, Mandhary MRA, Al-Suti MK, et al. (2002) J Chem Soc. Dalton Trans. 2441.

    Google Scholar 

  45. Khan MS, Al-Mandhary MRA, Al-Suti MK, et al. (2002) J Chem Soc. Dalton Trans. 1358.

    Google Scholar 

  46. Wilson JS, Köhler A, Friend RH, et al. (2000) J. Chem. Phys. 113:7627.

    Article  CAS  Google Scholar 

  47. Wong W-Y, Poon S-Y, Wong C-K. (2005) Polymeric materials: science and engineering. 93:791.

    CAS  Google Scholar 

  48. Chawdhury N, Köhler A, Friend RH, Younus M, Long NJ, Raithby PR, Lewis J. (1998) Macromolecules. 31:722.

    Article  CAS  Google Scholar 

  49. Ho C-L, Wong W-Y. (2006) J Organomet Chem. 691:395.

    Article  CAS  Google Scholar 

  50. Wong W-Y, Liu L, Shi J-X. (2003) Angew Chem Int Ed. 42:4064.

    Article  CAS  Google Scholar 

  51. Wong W-Y, Liu L, Poon S-Y, Choi K-H, Cheah K-W, Shi, J-X (2004) Macromolecules. 37:4496.

    Article  CAS  Google Scholar 

  52. Wilson JS, Chawdhury N, Al-Mandhary MRA, et al. (2001) J Am Chem Soc. 123:9412.

    Article  CAS  Google Scholar 

  53. Gong X, Robinson MR, Ostrowski JC, Moses D, Bazan GC, Heeger AJ. (2002) Adv Mater. 14:581.

    Article  CAS  Google Scholar 

  54. Baldo MA, Thompson ME, Forrest SR. (1999) Pure Appl Chem. 71:2095.

    Article  CAS  Google Scholar 

  55. Corriu RJP. (2000) Angew Chem Int Ed. 39:1376.

    Article  CAS  Google Scholar 

  56. Abd-Aziz AS, Carraher CE Jr, Pittman CU, Jr. Sheats JE, Zeldin M. (eds). (2005) Macromolecules containing metal and metal-like elements, Vol. 4, Group IVA Polymers, Wiley, New Jersey,.

    Google Scholar 

  57. Zeigler JM, Gordon FW (eds). (1990) Silicon-based polymer science: A comprehensive resource, advances in chemistry series 224, ACS, Washington, DC.

    Google Scholar 

  58. Chicart P, Corriu RJP, Moreau JJE, Garnier F, Yassar A. (1992) In: Laine RM (Ed). Inorganic and Organometallic Polymers with Special Properties. Kluwer, p 179.

    Google Scholar 

  59. Birot M, Pillot JP, Dunoguès J. (1995) Chem Rev. 95:1443.

    Article  CAS  Google Scholar 

  60. Corriu RJP, Douglas WE, Yang Z-X (1990) J Polym Sci. Polym Lett Ed. 28:431.

    CAS  Google Scholar 

  61. Tamao K, Uchida M, Izumizawa T, Furukawa K, Yamaguchi, S. (1996) J Am Chem Soc. 118:11974.

    Article  CAS  Google Scholar 

  62. Loy DA, Shea KJ. (1995) Chem Rev. 95:1431.

    Article  CAS  Google Scholar 

  63. Matsuo T, Uchida K, Sekiguchi A, (1999) Chem Commun 1799.

    Google Scholar 

  64. Pschirer NG, Fu W, Adams RD, Bunz UHF. (2000) Chem Commun 87.

    Google Scholar 

  65. Corriu R, Douglas W, Yang ZX. (1993) J Organomet Chem. 455:69.

    Article  CAS  Google Scholar 

  66. Douglas WE, Guy DMH, Kar AK, Wang C, (1998) Chem Commun 2125.

    Google Scholar 

  67. Ishikawa M, Ohshita J. (1997) in: Nalwa HS (ed). Silicon and germanium containing conductive polymers in handbook of organic conductive molecules and polymers, Vol. 2. Wiley, New York, p 685,.

    Google Scholar 

  68. Adachi A, Manhart SA, Okita K, Kido J, Ohshita J, Kunai A. (1997) Synth Met. 91:333.

    Article  CAS  Google Scholar 

  69. Manhart SA, Adachi A, Sakamaki K, et al. (1999) J Organomet Chem. 592:52.

    Article  CAS  Google Scholar 

  70. Itoh M, Mitsuzaka M, Iwata K, Inoue K. (1997) Macromolecules. 30:694.

    Article  CAS  Google Scholar 

  71. Ohshita J, Shinpo A, Kunai A. (1999) Macromolecules. 38:5998.

    Article  CAS  Google Scholar 

  72. Ishikawa M, Nate K. (1988) Inorganic and organometallic polymers, M. Zeldin, K. J. Wynne, H. R. Allcock (Eds.), (1988) ACS Symp. Ser. 360, ACS, Washington, DC.

    Google Scholar 

  73. Ohshita J, Ishikawa M. (1996) In: Salamone JC (ed). Polymeric materials encyclopedia. CRC Press, New York, p. 892.

    Google Scholar 

  74. Corriu R, Gerbier P, Guerin C, Henner B, Jean A, Mutin A. (1992) Organometallics. 11:2507.

    Article  CAS  Google Scholar 

  75. Garten F, Hilberer A, Cacialli F, et al. (1997) Adv Mater. 9:127.

    Article  CAS  Google Scholar 

  76. Silcoff ER, Sheradsky T, (1998) Macromolecules. 31:9116.

    Article  CAS  Google Scholar 

  77. Boyer-Elma K, Carrè FH, Corriu RJP, Douglas WE. (1995) J Chem Soc Chem Commun 725.

    Google Scholar 

  78. Kim ZD, Park JS, Kim HK, Lee TB, No KT. (1998) Macromolecules. 31:7267.

    Article  CAS  Google Scholar 

  79. Kim HK, Ryu MK, Lee SM. (1997) Macromolecules. 30:1236.

    Article  CAS  Google Scholar 

  80. Kim HK, Ryu MK, Kim KD, Lee SM, Cho SW, Park JW. (1998) Macromolecules. 31:1114.

    Article  CAS  Google Scholar 

  81. Gleiter R, Schäfer W, Sakurai H. (1985) J Am Chem Soc. 107:3046.

    Article  CAS  Google Scholar 

  82. Sakurai H, Sugiyama H, Kira M. (1990) J Phys. Chem. 94:1837.

    Article  CAS  Google Scholar 

  83. Yao J, Son DY. (1999) Organometallics. 18:1736.

    Article  CAS  Google Scholar 

  84. van Walree CA, Roest MR, Schuddeboom W, et al. (1996) J. Am. Chem. Soc. 118:8395.

    Article  Google Scholar 

  85. Wong W-Y, Wong C-K, Lu G-L, Cheah K-W Shi J-X, Lin S. (2002) J Chem Soc Dalton Trans. 4587.

    Google Scholar 

  86. Wong W-Y, Wong C-K, Lu G-L. (2003) J Organomet Chem. 671:27.

    Article  CAS  Google Scholar 

  87. Johnson BFG, Kakkar AK, Khan MS, et al. (1991) J Mater Chem. 1:485.

    Article  CAS  Google Scholar 

  88. Lewis J, Khan, MS Kakkar AK, Johnson BFG, et al. (1992) J Organomet Chem. 425:165.

    Article  CAS  Google Scholar 

  89. Wong W-Y, Lee AW-M, Wong C-K, et al. (2002) New J. Chem. 26:354.

    Article  CAS  Google Scholar 

  90. Wong W-Y, Wong C-K, Lu G-L, Lee AW-M, Cheah K-W, Shi J-X. (2003) Macromolecules. 36:983.

    Article  CAS  Google Scholar 

  91. Wong W-Y, Poon S-Y, Lee AW-M, Shi J-X, Cheah K-W. (2004) Chem Commun 2420.

    Google Scholar 

  92. Cummings SD, Eisenberg R. (1996) J Am Chem Soc. 118:1949.

    Article  CAS  Google Scholar 

  93. Wittmann HF, Friend RH, Khan MS, Lewis J. (1994) J Chem Phys. 101:2693.

    Article  CAS  Google Scholar 

  94. Demas NJ, Crosby GA. (1970) J Am Chem Soc. 92:7262.

    Article  Google Scholar 

  95. Turro NJ. (1991) Modern molecular photochemistry. University Science Books, Mill Valley, CA.

    Google Scholar 

  96. Wong W-Y, Wong C-K, Poon S-Y, Lee AW-M, Mo T, Wei X. (2005) Macromol Rapid Commun. 26:376.

    Article  CAS  Google Scholar 

  97. Yamaguchi S, Tamao K. (1998) J Chem Soc. Dalton Trans. 3693.

    Google Scholar 

  98. Yamaguchi S, Iimura K, Tamao K. (1998) Chem. Lett. 89.

    Google Scholar 

  99. Yamaguchi S, Endo T, Uchida M, Izumizawa T, Furukawa K, Tamao K. (2000) Chem Eur J. 6:1683.

    Article  CAS  Google Scholar 

  100. Chen H-Y, Lam WY, Luo JD, et al. (2002) Appl Phys. Lett. 81:574.

    Article  CAS  Google Scholar 

  101. Yamaguchi S, Endo T, Uchida M, Izumizawa T, Furukawa K, Tamao K. (2001) Chem Lett. 98.

    Google Scholar 

  102. Kakkar AK, Khan MS, Long NJ, et al. (1994) J Mater Chem. 4:1227.

    Article  Google Scholar 

  103. Zhan X, Liu Y, Wu X, Wang S, Zhu, D. (2002) Macromolecules. 35:2529.

    Article  CAS  Google Scholar 

  104. Kraft A, Grimsdale AC, Holmes AB. (1998) Angew Chem Int Ed. 37:402.

    Article  Google Scholar 

  105. Lee AWM, Yeung ABW, Yuen MSW, Zhang H, Zhao X, Wong W-Y. (2000) Chem Commun 75.

    Google Scholar 

  106. Leuninger J, Uebe J, Salbeck J, Gherghel L, Wang CS, Müllen K. (1999) Synth. Met. 100:79.

    Article  CAS  Google Scholar 

  107. Shahram MA, Yaghoub S, Mehdi H, Leila AF. (2005) Eur Polym J. 41:491.

    Article  CAS  Google Scholar 

  108. Kim JP, Lee WY, Kang JW, Kwon SK, Kim JJ, Lee JS. (2001) Macromolecules. 34:7817.

    Article  CAS  Google Scholar 

  109. Hwang SW, Chen Y. (2002) Macromolecules. 35:5438.

    Article  CAS  Google Scholar 

  110. Hale WF, Farnham AG, Johnson RN, Clendinning RA. (1967) J Polym Sci Part A: Polym Chem. 5:2399.

    Article  CAS  Google Scholar 

  111. Johnson RN, Farnham AG, Clendinning RA, Hale WF, Merriman CN. (1967) J. Polym. Sci. Part A: Polym. Chem. 5:2375.

    Article  CAS  Google Scholar 

  112. Bottino FA, Pasquale GD, Scalia L, Pollicino A. (2001) Polymer. 42:3323.

    Article  CAS  Google Scholar 

  113. Jenks WS, Lee W, Shutters D. (1994) J Phys. Chem. 98:2282.

    Article  CAS  Google Scholar 

  114. Lee, W, Jenks WS. (2001) J Org Chem. 66:474.

    Article  CAS  Google Scholar 

  115. Poon S-Y, Wong W-Y, Cheah K-W, Shi J-X, (2006) Chem Eur J. 12:2550.

    Article  CAS  Google Scholar 

  116. Liu L, Poon S-Y, Wong W-Y. (2005) J Organomet Chem. 690:5036.

    Article  CAS  Google Scholar 

  117. Hertel S, Setayesh S, Nothofer HG, Scherf U, Mullen K, Bässler H. (2001) Adv Mater. 13:65.

    Article  CAS  Google Scholar 

  118. Monkman AP, Burrows HD, Hartwell LJ, Horsburgh LE, Hamblett I, Navaratnam S. (2001) Phys. Rev Lett. 86:1358.

    Article  CAS  Google Scholar 

  119. Zhang H, Lee AW-M, Wong W-Y, Yuen MS-M. (2000) J Chem Soc Dalton Trans. 3675.

    Google Scholar 

  120. Chawdhury N, Köhler A, Friend RH, et al. (1999) J Chem Phys. 110:4963.

    Article  CAS  Google Scholar 

  121. Lewis J, Long NJ, Raithby PR, Shields GP, Wong W-Y, Younus M. (1997) J Chem. Soc. Dalton Trans. 4283.

    Google Scholar 

  122. Cornil J, Beljonne D, dos Santos DA, Shuai Z, Brédas JL. (1996) Synth Met. 78:209.

    Article  CAS  Google Scholar 

  123. Beljonne D, Cornil J, Brédas JL, Friend RH. (1996) Synth Met. 76:61.

    Article  CAS  Google Scholar 

  124. Köhler A, Wittmann HF, Friend RH, Khan MS, Lewis J. (1994) Synth Met. 67:245.

    Article  Google Scholar 

  125. Younus M, Köhler A, Cron S, et al. (1998) Angew Chem Int Ed. 37:3036.

    Article  CAS  Google Scholar 

  126. Chawdhury N, Younus M, Raithby PR, Lewis J, Friend RH. (1998) Opt Mater. 9:498.

    Article  CAS  Google Scholar 

  127. Wong KM-C, Zhu S, Hung L-L, Zhu N, Yam VW-W, Kwok H-S. (2005) Chem Commun. 2906.

    Google Scholar 

  128. Lu W, Mi B-S, Chan MCW, et al. (2004) J Am Chem Soc. 126:4958.

    Article  CAS  Google Scholar 

  129. Lin Y-Y, Chan S-C, Chan MCW, et al. (2003) Chem Eur J. 9:1264.

    Google Scholar 

  130. Tutt LW, Kost A. (1992) Nature. 356:225.

    Article  CAS  Google Scholar 

  131. Zhou G-J, Wong W-Y, Cui D, Ye C, (2005) Chem Mater. 17:5209.

    Article  CAS  Google Scholar 

  132. Wong W-Y (2005) Comment Inorg. Chem. 26:39.

    Article  CAS  Google Scholar 

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Wong, WY. (2008). Transition Metal σ-Acetylide Polymers Containing Main Group Elements in the Main Chain: Synthesis, Light Emission and Optoelectronic Applications. In: Abd-El-Aziz, A.S., Carraher, C.E., Pittman, C.U., Zeldin, M. (eds) Inorganic and Organometallic Macromolecules. Springer, New York, NY. https://doi.org/10.1007/978-0-387-72947-3_3

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