화학공학소재연구정보센터
홈 로그인 로그아웃 연락처 사이트맵
Macromolecular Research, Vol.19, No.7, 729-733, July, 2011
DOI10.1007/s13233-011-0712-4  Export Citation
Preparation of Optically Active Poly(N-propargylamide) Gels and Their Application in Chiral Recognition
Dong Liu1, 2, Xiaoying Du1, 2, Yuanyuan Zhang1, 2, Jianping Deng1, 2, †, and Wantai Yang1, 2, †
  • 1State Key Laboratory of Chemical Resource Engineering, Beijing, 100029, China, Korea
  • 2College of Materials Science and Engineering, Beijing University of Chemical Technology, Beijing, 100029, China
E-mail:,
Optically active gels based on helical N-propargylamide polymers were prepared using a one-pot twostep methodology: the pre-formation of helical N-propargylamide copolymer (defined as N=N-HP) and the preparation of gels bearing the helical copolymers. To prepare N=N-HP, N-propargylamide M1, which contained -N=Nfunctional group, and M2, which provided helical polymer chains for the resulting copolymers, underwent copolymerizations in the presence of (nbd)Rh+B-(C6H5)4 as a catalyst. -N=N- groups in N=N-HP acted as an initiator to induce the free radical polymerization of styrene, yielding the designed gels. Trimethylol propane triacrylate (TMPTA) was used to improve the cross-linking degree of the gels. The obtained gels were characterized by Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM) and circular dichroism (CD) spectroscopy measurements. The gels showed high optically activity, resulting from the helical structures of the N-propargylamide polymer chains. Preferential adsorption towards (R)-(+)-1-phenylethylamine in the two enantiomers was observed in the obtained gels, demonstrating the potentials of such gels in chiral recognition and chiral resolution.
Keywords:N-propargylamide;gel;optical activity;chiral recognition.
  1. Cornelissen JJLM, Rowan AE, Nolte RJM, Sommerdijk NAJM, Chem. Rev., 101(12), 4039 (2001)
  2. Reggelin M, Schultz M, Holbach M, Angew. Chem.-Int. Edit., 41, 1614 (2002)
  3. Green MM, Park JW, Sato T, Teramoto A, Lifson S, Selinger RLB, Selinger JV, Angew. Chem.-Int. Edit., 38, 3138 (1999)
  4. Yamamoto T, Suginome M, Angew. Chem.-Int. Edit., 48, 539 (2009)
  5. Nakano T, Okamoto Y, Chem. Rev., 101(12), 4013 (2001)
  6. Khan A, Hecht S, J. Polym. Sci. A: Polym. Chem., 44(5), 1619 (2006)
  7. Yashima E, Maeda K, Iida H, Furusho Y, Nagai K, Chem. Rev., 109(11), 6102 (2009)
  8. Tsuji M, Azam AKMF, Kamigaito M, Okamoto Y, Macromolecules, 40(10), 3518 (2007)
  9. Amabilino DB, Serrano JL, Sierra T, Veciana J, J. Polym. Sci. A: Polym. Chem., 44(10), 3161 (2006)
  10. Suginome M, Ito Y, Adv. Polym. Sci., 17, 77 (2004)
  11. Tang HZ, Lu YJ, Tian GL, Capracotta MD, Novak BM, J. Am. Chem. Soc., 126(12), 3722 (2004)
  12. Mayer S, Zentel R, Prog. Polym. Sci, 26, 1973 (2001)
  13. Kim SY, Saxena A, Kwak G, Fujiki M, Kawakami Y, Chem. Commun., 538 (2004)
  14. Masuda T, J. Polym. Sci. A: Polym. Chem., 45(2), 165 (2007)
  15. Lam JWY, Tang BZ, Acc. Chem. Res., 38, 745 (2005)
  16. Rudick JG, Percec V, Acc. Chem. Res., 41, 1641 (2008)
  17. Omidian H, Rocca JG, Park K, J. Control. Release, 102, 3 (2005)
  18. Vintiloiu A, Leroux JC, J. Control. Release, 125, 179 (2008)
  19. Shankar BV, Patnaik A, J. Phys. Chem. B, 111(31), 9294 (2007)
  20. Du XY, Liu JB, Deng JP, Yang WT, J. Polym. Sci. A: Polym. Chem., 10, 1030 (2010)
  21. Zhao YL, Stoddart JF, Langmuir, 25(15), 8442 (2009)
  22. Gindl W, Emsenhuber G, Maier G, Keckes J, Biomacromolecules, 10(5), 1315 (2009)
  23. Deng W, Yamaguchi H, Takashima Y, Harada A, Angew. Chem.-Int. Edit., 46, 5144 (2007)
  24. Zhuo RX, Li W, J. Polym. Sci. A: Polym. Chem., 41(1), 152 (2003)
  25. Park TG, Hoffman AS, Biotechnol. Prog., 7, 383 (1991)
  26. Wang Y, Zhang JZ, Zhang WQ, Zhang MC, J. Org. Chem., 74, 1923 (2009)
  27. Sugiyama K, Rikimaru S, Okada Y, Shiraishi K, J. Appl. Polym. Sci., 82(1), 228 (2001)
  28. Goto H, Zhang HQ, Yashima E, J. Am. Chem. Soc., 125(9), 2516 (2003)
  29. Liu RY, Sanda F, Masuda T, J. Polym. Sci. A: Polym. Chem., 46(12), 4175 (2008)
  30. Nomura R, Yamada K, Tabei J, Takakura Y, Takigawa T, Masuda T, Macromolecules, 36(18), 6939 (2003)
  31. Liu XC, Dordick JS, J. Polym. Sci. A: Polym. Chem., 37(11), 1665 (1999)
  32. Habaue S, Satonaka T, Nakano T, Okamoto Y, Polymer, 45(15), 5095 (2004)
  33. Deng JP, Tabei J, Shiotsuki M, Sanda F, Masuda T, Macromolecules, 37(26), 9715 (2004)
  34. Deng JP, Tabei J, Shiotsuki M, Sanda F, Masuda T, Macromolecules, 37(5), 1891 (2004)
  35. Deng JP, Tabei J, Shiotsuki M, Sanda F, Masuda T, Macromolecules, 37(19), 7156 (2004)
  36. Deng JP, Zhao WG, Wang JM, Zhang ZG, Yang WT, Macromol. Chem. Phys., 208, 218 (2007)
  37. Ding L, Jiao XF, Deng JP, Zhao WG, Yang WT, Macromol. Rapid Commun., 30(2), 120 (2009)
  38. Zhang ZG, Deng JP, Zhao WG, Wang JM, Yang WT, J. Polym. Sci. A: Polym. Chem., 45(3), 500 (2007)
  39. Deng JP, Luo XF, Zhao WG, Yang WT, J. Polym. Sci. A: Polym. Chem., 46(12), 4112 (2008)
  40. Luo XF, Chang J, Deng JP, Yang WT, React. Funct. Polym., 70(2), 116 (2010)
  41. Deng JP, He QX, Wu ZL, Yang WT, J. Polym. Sci. A: Polym. Chem., 46(6), 2193 (2008)
  42. Schrock RR, Osborn JA, Inorg. Chem., 9, 2339 (1970)
  43. Luo XF, Liu XQ, Chen B, Deng JP, Yang WT, J. Polym. Sci. A: Polym. Chem., in press.
  44. Tabei J, Nomura R, Masuda T, Macromolecules, 35(14), 5405 (2002)
  45. Deng JP, Tabei J, Shiotsuki M, Sanda F, Masuda T, Macromolecules, 37, 5419 (2004)