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Helix-sense-selective radical polymerization of (S)-6-acryloyl-2,2′-bisalkoxy-1,1′-binaphthyl

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Abstract

A series of (S)-6-acryloyl-2,2′-bisalkoxy-1,1′-binaphthyl 1 were radically polymerized to obtain polymers. The optical rotation and the circular dichroism (CD) signal intensity of the radically polymerized poly-1 were close to that of the anionically polymerized poly-1 indicating that the radically polymerized poly-1 should adopt stable preferred-handed helical conformation in solution just as the anionically polymerized poly-1.

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References

  1. Pouliquen M, Blanchet J, Paolis MD, Devi BR, Rouden J, Lasne MC, Maddaluno J (2010) Chiral 3-aminopyrrolidines as a rigid diamino scaffold for organocatalysis and organometallic chemistry. Tetrahedron Asymmetry 21:1511–1521

    Article  CAS  Google Scholar 

  2. Song HL, Yuan K, Wu XY (2011) Chiral phosphine-squaramides as enantioselective catalysts for the intramolecular Morita–Baylis–Hillman reaction. Chem Commun 47:1012–1014

    Article  CAS  Google Scholar 

  3. Garnier JM, Anstiss C, Liu F (2009) Enantioselective trifunctional organocatalysts for rate- enhanced aza-Morita–Baylis–Hillman reactions at room temperature. Adv Synth Catal 351:331–338

    Article  CAS  Google Scholar 

  4. Ikawa M, Stahmann MA, Link KP (1944) Studies on 4-hydroxycoumarins. V. The condensation of α,β-unsaturated ketones with 4-hydroxycoumarin. J Am Chem Soc 66:902–906

    Article  CAS  Google Scholar 

  5. Mukaiyama T (1977) Titanium tetrachloride in organic synthesis [new synthetic methods (21)]. Angew Chem Int Ed Engl 16:817–826

    Article  Google Scholar 

  6. Lippert AR, Kaeobamrung J, Bode JW (2006) Synthesis of oligosubstituted bullvalones: shapeshifting molecules under basic conditions. J Am Chem Soc 128:14738–14739

    Article  CAS  Google Scholar 

  7. Wu S, Yang NF, Yang LW, Cao J, Liu J (2010) A novel type of optically active helical polymers: synthesis and characterization of poly(α,β-unsaturated ketone). J Polym Sci, Part A Polym Chem 48:1441–1448

    Article  CAS  Google Scholar 

  8. Wu S, Yang NF, LiuYL Cao J, Hu H, Sun YK, Liu J (2011) Optically active helical polymer from radical polymerization of menthyl vinyl ketone. J Polym Sci Part A Polym Chem 49:293–299

    Article  CAS  Google Scholar 

  9. Chen YH, Yang LW, Yang NF, Zhang J (2014) Single-handed helical poly-(α,β-unsaturated ketone) synthesized via anionic polymerization of (S)-2′-methyloxy-2-acrylyl-1,1′-binaphthyl. Macromol Res 22:236–239

    Article  CAS  Google Scholar 

  10. Chen YH, Yang LW, Yang NF, Yang ZS, Zhang J (2014) Helical poly(α,β-unsaturated ketone) with bulky pendant of binaphthyl from anionic polymerization of (−)-menthyl (S)-6′-acrylyl-2′- methyloxy-1,1′-binaphthalene-2-carboxylate. Chin J Chem 32:241–247

    Article  CAS  Google Scholar 

  11. Yuki H, Okamoto Y, Okamoto I (1980) Resolution of racemic compounds by optically active poly (triphenylmethyl methacrylate). J Am Chem Soc 102:6356–6358

    Article  CAS  Google Scholar 

  12. Okamoto Y, Honda S, Okamoto I, Yuki H, Murata S, Noyori R, Takaya H (1981) Novel packing material for optical resolution: (+)-poly(triphenylmethy1 methacrylate) coated on macroporous silica gel. J Am Chem Soc 103:6971–6973

    Article  CAS  Google Scholar 

  13. Nakano T (2001) Optically active synthetic polymers as chiral stationary phases in HPLC. J Chromatogr A 906:205–225

    Article  CAS  Google Scholar 

  14. Natta G, Pino P, Corradini P, Danusso F, Mantica E, Nazzanti G, Moraglio G (1955) Crystalline high polymers of α-olefins. J Am Chem Soc 77:1708–1710

    Article  CAS  Google Scholar 

  15. Okamoto Y, Suzuki K, Ohta K, Hatada K, Yuki H (1979) Optically active poly(triphenylmethyl methacrylate) with one-handed helical conformation. J Am Chem Soc 101:4763–4765

    Article  CAS  Google Scholar 

  16. Okamoto Y, Gamaike H, Yuki H (1981) Enantiomer-selective polymerization of PEMA. Macromol Chem 182:2732–2736

    Article  Google Scholar 

  17. Nakano T, Okamoto Y, Hatadat K (1992) Asymmetric polymerization of triphenylmethyl methacrylate leading to a one-handed helical polymer: mechanism of polymerization. J Am Chem Soc 114:1318–1329

    Article  CAS  Google Scholar 

  18. Habaue S, Ajiro H, Okamoto Y (2000) Anionic polymerization of o-substituted styrene derivatives: control of reactivity and stereochemistry by aminomethyl group. J Polym Sci Part A Polym Chem 38:4088–4094

    Article  CAS  Google Scholar 

  19. Cao J, Yang NF, Li JC, Yang LW (2007) Helical polymers from optically active epoxides with bulky pendants. Polym Bull 59:481–490

    Article  CAS  Google Scholar 

  20. Sun YK, Yang NF, Liu J, Cao J, Gong H (2010) Single-handed helical polyethers synthesized via anionic polymerization of optically active 3-(9-alkylfluoren-9-yl)propene oxides. Polymer 51:5712–5718

    Article  CAS  Google Scholar 

  21. Okamoto Y, Nakano T (1994) Asymmetric polymerization. Chem Rev 94:349–372

    Article  CAS  Google Scholar 

  22. Nakano T, Okamoto Y (2001) Synthetic helical polymers: conformation and function. Chem Rev 101:4013–4038

    Article  CAS  Google Scholar 

  23. Yashima E, Maeda K, Iida H, Furusho Y, Nagai K (2009) Helical polymers: synthesis, structures, and functions. Chem Rev 109:6102–6211

    Article  CAS  Google Scholar 

  24. Nakano T (2014) Tricks of light on helices: transformation of helical polymers by photoirradiation. Chem Rec 14:369–385

    Article  CAS  Google Scholar 

  25. Nakano T, Shikisai Y, Okamoto Y (1995) Helix-sense-selective polymerization of 1-phenyl-dibenzosuberyl methacrylate by free radical mechanism. Proc Japan Acad Ser B 71:251–255

    Article  Google Scholar 

  26. Nakano T, Shikisai Y, Okamoto Y (1996) Helix-sense-selective free radical polymerization of 1-phenyldibenzosuberyl methacrylate. Polym J 28:51–60

    Article  CAS  Google Scholar 

  27. Hoshikawa N, Hotta Y, Okamoto Y (2003) Stereospecific radical polymerization of n-triphenylmethylmethacrylamides leading to highly isotactic helical polymers. J Am Chem Soc 125:12380–12381

    Article  Google Scholar 

  28. Yu ZN, Wan XH, Zhang HL, Chen XF, Zhou QF (2003) A free radical initiated optically active vinyl polymer with memory of chirality after removal of the inducing stereogenic center. Chem Commun 8:974–975

    Article  Google Scholar 

  29. Cui JX, Liu AH, Zhi JG, Zhu ZG, Guan Y, Wan XH, Zhou QF (2008) Synthesis and chiroptical properties of vinyl polymers containing laterally attached 4,4″-digalactosyloxy-p-terphenyl side groups. Macromolecules 41:5245–5254

    Article  CAS  Google Scholar 

  30. Cui JX, Lu AH, Wan XH, Zhou QF (2009) Long-range chirality transfer in free radical polymerization of bulky vinyl monomers containing laterally attached p-terphenyl groups. Macromolecules 42:7678–7688

    Article  CAS  Google Scholar 

  31. Wang R, Li XF, Bai JW, Zhang J, Liu AH, Wan XH (2014) Chiroptical and thermotropic properties of helical styrenic polymers: effect of achiral group. Macromolecules 47:1553–1562

    Article  CAS  Google Scholar 

  32. Zhao ZY, Bai JW, Zhang J, Liu AH, Wan XH (2014) Helix-sense-selective radical polymerization of bulky styrenic monomers: chiral induction and liquid crystallinity. Sci China Chem 57:982–994

    Article  CAS  Google Scholar 

  33. Chen YH, Yang LW, Yang NF, Yan JY, Yang ZS, Zhang J (2014) Synthesis and characterization of optically active helical poly(α,β-unsaturated ketone) with bulky pendant of binaphthyl. Polym Bull 71:2507–2521

    Article  CAS  Google Scholar 

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Acknowledgments

We gratefully thank the National Science Foundation of China (21172186) and Doctor Student Research Foundation of Chinese Education Ministry (20134301110004) for financial support of this work.

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Correspondence to Nianfa Yang.

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Chen, Y., Yang, L., Yang, N. et al. Helix-sense-selective radical polymerization of (S)-6-acryloyl-2,2′-bisalkoxy-1,1′-binaphthyl. Polym. Bull. 72, 3183–3190 (2015). https://doi.org/10.1007/s00289-015-1460-y

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  • DOI: https://doi.org/10.1007/s00289-015-1460-y

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