Synthesis and Properties of Optically Active Helical Polyethers Bearing Indole or Carbazole Derivatives

Chunhui Zhao; Kunbing Ouyang; Nianfa Yang; Jin Zhang; Zhusheng Yang

Macromolecular Research, Vol.24, No.5, 393-399, May, 2016

DOI10.1007/s13233-016-4057-x Export Citation

Synthesis and Properties of Optically Active Helical Polyethers Bearing Indole or Carbazole Derivatives

Chunhui Zhao, Kunbing Ouyang^†, Nianfa Yang^†, Jin Zhang, and Zhusheng Yang

Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan, 411105, P. R. China

E-mail:,

Six optically active oxide propane monomers (1m-6m) were synthesized in a very facile way. The monomers were polymerized using potassium hydroxide (KOH) as an initiator to afford the corresponding polyethers (1p-6p). The polyether (R)-1p (specific rotation, [α] 365 25 =+331) exhibited optical rotation as large as fourfold that of the monomer (R)-1m ([α] 365 25 =-10). The specific optical rotation, circular dichroism (CD) and ultraviolet (UV)-visible spectra data showed that the obtained polymers can keep a prevailing helicity of the backbone in solution.

Keywords:indole;carbazole derivatives;anionic polymerization;helical polyethers

[References]

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Koeckelberghs G, Sioncke S, Verbiest T, Persoons A, Samyn C, Polymer, 44(14), 3785 (2003)
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[Referenced By]

[1] Tsuchida A, Hasegawa T, Kobayashi K, Yamamoto C, Okamoto Y, Bull. Chem. Soc. Jpn., 75, 2681 (2002)

[2] Dyer DJ, Schroder UP, Chan KP, Twieg RJ, Chem. Mater., 9, 1665 (1997)

[3] Green MM, Peterson NC, Sato T, Teramoto A, Cook R, Lifson S, Science, 268(5219), 1860 (1995)

[4] Kubota T, Yamamoto C, Okamoto Y, J. Polym. Sci. A: Polym. Chem., 41(22), 3703 (2003)

[5] Ashida Y, Sato T, Morino K, Maeda K, Okamoto Y, Yashima E, Macromolecules, 36(9), 3345 (2003)

[6] Maxein G, Keller H, Novak BM, Zentel R, Adv. Mater., 10(4), 341 (1998)

[7] Green MM, Park JW, Sato T, Teramoto A, Lifson S, Selinger RLB, Selinger JV, Angew. Chem.-Int. Edit., 38, 3138 (1999)

[8] Koeckelberghs G, Sioncke S, Verbiest T, Persoons A, Samyn C, Polymer, 44(14), 3785 (2003)

[9] KAURANEN M, VERBIEST T, MEIJER EW, HAVINGA EE, TEERENSTRA MN, SCHOUTEN AJ, NOLTE RJM, PERSOONS A, Adv. Mater., 7(7), 641 (1995)

[10] Fujiki M, Macromol. Rapid Commun., 22(8), 539 (2001)

[11] Yashima E, Maeda K, Nishimura T, Chemistry, 10, 42 (2004)

[12] Nakano T, Okamoto Y, Chem. Rev., 101(12), 4013 (2001)

[13] Cornelissen JJLM, Rowan AE, Nolte RJM, Sommerdijk NAJM, Chem. Rev., 101(12), 4039 (2001)

[14] Suginome M, Ito Y, Polym. Synth., 171, 77 (2004)

[15] Tian GL, Lu YJ, Novak BM, J. Am. Chem. Soc., 126(13), 4082 (2004)

[16] Wu S, Yang NF, Yang LW, Cao J, Liu J, J. Polym. Sci. A: Polym. Chem., 48(6), 1441 (2010)

[17] Wu S, Yang NF, Liu YL, Ca J, Hu H, Sun YK, Liu J, J. Polym. Sci. A: Polym. Chem., 49(1), 293 (2011)

[18] Chen YH, Yang LW, Yang NF, Zhang J, Macromol. Res., 22(3), 236 (2014)

[19] Unruh CC, J. Am. Chem. Soc., 86, 2964 (1964)

[20] Kern W, Angew. Chem.-Int. Edit., 76, 762 (1964)

[21] Bouloc N, Walshe N, Bradley M, J. Comb. Chem., 3, 6 (2001)

[22] Price CC, Osgan M, J. Am. Chem. Soc., 78, 4787 (1956)

[23] Steiner EC, Pelletier RR, Trucks RO, J. Am. Chem. Soc., 86, 4678 (1964)

[24] Cao J, Yang NF, Wang PD, Yang LW, Polym. Int., 57, 530 (2008)

[25] Cao J, Yang NF, Li JC, Yang LW, Polym. Bull., 59(4), 481 (2007)

[26] Sun YK, Yang NF, Liu J, Cao J, Gong H, Polymer, 51(24), 5712 (2010)

[27] Kumar AB, Anderson JM, Melendez AL, Manetsch R, Bioorg. Med. Chem. Lett., 22, 4740 (2012)

[28] Kimura T, Hosokawa-Muto J, Asami K, Murai T, Kuwata K, Eur. J. Med. Chem., 46, 5675 (2011)

[29] Bertini S, Asso V, Ghilardi E, Granchi C, Manera C, Minutolo F, Saccomanni G, Bortolato A, Mason J, Moro S, Macchia M, Bioorg. Med. Chem. Lett., 21, 6657 (2011)

[30] Okamoto Y, Adachi M, Shohi H, Yuki H, Polym. J., 13, 175 (1981)

[31] Cheng HN, in Catalysis in Polymer Synthesis, American Chemical Society, Washington, DC, 1992, Vol. 496, p 157.

[32] Singfield KL, Brown GR, Macromolecules, 28(4), 1290 (1995)

[33] Nishijima Y, J. Polym. Sci. C: Polym. Symp., 31, 353 (1970)

[34] Oster G, Nishijima Y, in Fortschritte Der Hochpolymeren-Forschung, Springer-Verlag, Berlin, 1964, pp 313-331.

[35] Vandeleene S, Verswyvel M, Verbiest T, Koeckelberghs G, Macromolecules, 43(18), 7412 (2010)

[36] Song F, Wei G, Wang L, Jiao J, Cheng Y, Zhu C, J. Org. Chem., 77, 4759 (2012)

[37] Wei G, Zhang S, Dai C, Quan Y, Cheng Y, Zhu C, Chemistry, 19, 16066 (2013)

[38] Zhang HC, Pu L, Macromolecules, 37(8), 2695 (2004)

[39] Wei J, Zhang X, Zhao Y, Li R, Macromol. Chem. Phys., 214, 2232 (2013)

[40] Song F, Fei N, Li F, Zhang S, Cheng Y, Zhu C, Chem. Commun., 49, 2891 (2013)