Synthesis of chiral polyphenylenes through Bergman cyclization of enediynes with pendant chiral amino ester groups

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• 作者：Shiyuan Sun (1)
  Binlei Huang (1)
  Fei Li (1)
  Depeng Song (1)
  Aiguo Hu 鑳＄埍鍥?/a> (1)
  
  1. Shanghai Key Laboratory of Advanced Polymeric Materials ; School of Materials Science and Engineering ; East China University of Science and Technology ; Shanghai ; 200237 ; China
  
• 关键词：Enediyne ; Bergman cyclization ; Chiral polyphenylene ; MALDI ; TOF/MS
• 刊名：Chinese Journal of Polymer Science
• 出版年：2015
• 出版时间：May 2015
• 年：2015
• 卷：33
• 期：5
• 页码：743-753
• 全文大小：902 KB
• 参考文献：1. Ikeda, A, Terada, K, Shiotsuki, M, Sanda, F (2011) J. Polym. Sci., Part A: Polym. Chem. 49: pp. 3783 CrossRef
  2. Yashima, E, Maeda, K, Iida, H, Furusho, Y, Nagai, K (2009) Chem. Rev. 109: pp. 6102 CrossRef
  3. Goto, H, Akagi, K (2005) Macromolecules 38: pp. 1091 CrossRef
  4. Zhang, W, Yoshida, K, Fujiki, M, Zhu, X (2011) Macromolecules 44: pp. 5105 CrossRef
  5. Luo, X, Liu, X, Chen, B, Deng, J, Yang, W (2010) J. Polym. Sci., Part A: Polym. Chem. 48: pp. 5611 CrossRef
  6. Jeong, YS, Akagi, K (2011) Macromolecules 44: pp. 2418 CrossRef
  7. Maeda, K, Wakasone, S, Shimomura, K, Ikai, T, Kanoh, S (2012) Chem. Commun. 48: pp. 3342 CrossRef
  8. Oishi, T, Kagawa, K, Nagata, H (1997) Polymer 38: pp. 1461 CrossRef
  9. Oishi, T, Nagata, H, Tsutsumi, H (1998) Polymer 39: pp. 4135 CrossRef
  10. Isobe, Y, Onimura, K, Tsutsumi, H, Oishi, T (2001) Macromolecules 34: pp. 7617 CrossRef
  11. Zhang, Y, Onimura, K, Tsutsumi, H, Oishi, T (2004) Polym. J. 36: pp. 878 CrossRef
  12. Wang, L, Song, F, Hou, J, Li, J, Cheng, Y, Zhu, C (2012) Polymer 53: pp. 6033 CrossRef
  13. Mallakpour, S, Khani, M (2010) Chinese J. Polym. Sci. 28: pp. 859 CrossRef
  14. Okamoto, Y, Nakano, T (1994) Chem. Rev. 94: pp. 349 CrossRef
  15. Okamoto, Y, Nakano, T (2005) Asymmetric Polymerization. Catalytic Asymmetric Synthesis. pp. 757 CrossRef
  16. Zhu, N, Hu, W, Han, S, Wang, Q, Zhao, D (2008) Org. Lett. 10: pp. 4283 CrossRef
  17. Liu, JZ, Lam, JWY, Tang, BZ (2009) Chem. Rev. 109: pp. 5799 CrossRef
  18. Liu, D, Li, Y, Deng, J, Yang, W (2014) Polymer 55: pp. 840 CrossRef
  19. Schwartz, E, Koepf, M, Kitto, HJ, Nolte, RJ, Rowan, AE (2011) Polym. Chem. 2: pp. 33 CrossRef
  20. Takeshi, M, Takeshi, T, Yoshio, F, Toshikazu, T (2004) J. Polym. Sci., Part A: Polym. Chem. 42: pp. 4693 CrossRef
  21. Morgan, BJ, Xie, X, Phuan, PW, Kozlowski, MC (2007) J. Org. Chem. 72: pp. 6171 CrossRef
  22. Okamoto, Y (2009) J. Polym. Sci., Part A: Polym. Chem. 47: pp. 1731 CrossRef
  23. Nakano, T, Okamoto, Y (2001) Chem. Rev. 101: pp. 4013 CrossRef
  24. Bergman, RG (1973) Acc. Chem. Res. 6: pp. 25 CrossRef
  25. Kar, M, Basak, A (2007) Chem. Rev. 107: pp. 2861 CrossRef
  26. Chen, XH, Tolbert, LM, Hess, DW, Henderson, C (2001) Macromolecules 34: pp. 4104 CrossRef
  27. Bowles, DM, Palmer, GJ, Landis, CA, Scott, JL, Anthony, JE (2001) Tetrahedron 57: pp. 3753 CrossRef
  28. Xiao, Y, Hu, A (2011) Macromol. Rapid Commun. 32: pp. 1688 CrossRef
  29. John, JA, Tour, JM (1994) J. Am. Chem. Soc. 116: pp. 5011 CrossRef
  30. Sun, S, Zhu, C, Song, D, Li, F, Hu, A (2014) Polym. Chem. 5: pp. 1241 CrossRef
  31. Cheng, X, Ma, J, Zhi, J, Yang, X, Hu, A (2010) Macromolecules 43: pp. 909 CrossRef
  32. Smith, DW, Babb, DA, Snelgrove, RV, Townsend, PH, Martin, SJ (1998) J. Am. Chem. Soc. 120: pp. 9078 CrossRef
  33. Miao, C, Zhi, J, Sun, S, Yang, X, Hu, A (2010) J. Polym. Sci., Part A: Polym. Chem. 48: pp. 2187 CrossRef
  34. Faghihi, K, Feyzi, A (2012) Chinese J. Polym. Sci. 30: pp. 777 CrossRef
  35. Mifsud, N, Mellon, V, Perera, KPU, Smith, DW, Echegoyen, L (2004) J. Org. Chem. 69: pp. 6124 CrossRef
  36. Green, U, Aizenshtat, Z, Ruthstein, S, Cohen, H (2013) Phys. Chem. Chem. Phys. 15: pp. 6182 CrossRef
  37. McCaughey, B, Costello, C, Wang, DH, Hampsey, JE, Yang, ZZ, Li, CJ, Brinker, CJ, Lu, YF (2003) Adv. Mater. 15: pp. 1266 CrossRef
  38. Dubernet, M, Caubert, V, Guillard, J, Viaud-Massuard, MC (2005) Tetrahedron 61: pp. 4585 CrossRef
  39. Gao, H, Isobe, Y, Onimura, K, Oishi, T (2007) J. Polym. Sci., Part A: Polym. Chem. 45: pp. 3722 CrossRef
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Condensed Matter Physics
  Industrial Chemistry and Chemical Engineering
  Polymer Sciences
  Characterization and Evaluation of Materials
  
• 出版者：Chinese Chemical Society and Institute of Chemistry, CAS, co-published with Springer
• ISSN：1439-6203

文摘

Chiral enediynes with pendant chiral amino ester groups are synthesized through Sonogashira reactions and subjected to thermal triggered Bergman cyclization at elevated temperatures either in bulk or in solvents to produce chiral polyphenylenes. The disappearance of enediyne monomers are evidenced by FTIR and NMR spectroscopies. The formation of polyphenylenes is further confirmed by UV-Vis and MALDI-TOF mass spectroscopies (MS). Isotope pattern analysis of the MS spectra shows that the polymers prepared in solvents are terminated by the solvent molecules, whereas the chain ends of the polymers prepared in bulk consist of considerable amount of unmasked free radicals, which is further confirmed by EPR analysis. Circular dichroism (CD) spectra of the chiral polymers show blue shifts of the Cotton peaks, indicating the occurrence of the cycloaromatization reaction. A new set of peaks mirrored at the horizontal axis show up in the long wavelength range, which are assigned to main chain chirality of the polyphenylenes.