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Synthesis and characterization of optically active helical poly(α, β-unsaturated ketone) with bulky pendant of binaphthyl

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Abstract

The synthesis and chiroptical properties of a novel optically active helical polymers, poly[(S)-6-acryloyl-2,2′-bisalkoxy-1,1′-binaphthyl] (poly-3), were reported. All the monomers readily underwent anionic polymerization to yield the polymers displaying optical rotations and Cotton effects in the UV–vis absorption region of side groups distinct to monomers (3) and the corresponding model compounds such as (S)-6-propionyl-2,2′-bisalkoxy-1,1′-binaphthyl (4) and (S)-6-heptanoyl-2,2′-bisalkoxy-1,1′-binaphthyl (5), implying the formation of main-chain chirality, most probable helicity. Their helical conformations were quite stable as revealed by the almost unchanged chiroptical properties measured at different temperatures.

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Acknowledgments

We gratefully thank the National Science Foundation of China (21172186) and the Higher Education Doctoral Science Foundation of China (No. 20134301110004) for financial support of this work.

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Authors and Affiliations

  1. Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan, 411105, Hunan, People’s Republic of China

    Yehui Chen, Liwen Yang, Nianfa Yang, Jingyi Yan, Zhusheng Yang & Jian Zhang

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  1. Yehui Chen
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  2. Liwen Yang
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  3. Nianfa Yang
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  4. Jingyi Yan
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  5. Zhusheng Yang
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Correspondence to Nianfa Yang.

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Chen, Y., Yang, L., Yang, N. et al. Synthesis and characterization of optically active helical poly(α, β-unsaturated ketone) with bulky pendant of binaphthyl. Polym. Bull. 71, 2507–2521 (2014). https://doi.org/10.1007/s00289-014-1204-4

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