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Synthesis and properties of poly(1-phenyl-1-octyne)s containing stereogenic and chromophoric pendant groups

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Abstract

Poly(1-phenyl-1-octyne)s containing different stereogenic and chromophoric pendants {-[(C6H13)C= C(C6H4-p-CO2-R)] n -R = [(1S)-endo]-(−)-borneyl (P3), (1R,2S,5R)-(−)-menthyl (P4), -C6H4-p-(1R,2S,5R)-(−)-menthyl (P5), 2-napthyl (P6), 4-biphenylyl (P7)} have been designed and synthesized. The polymers are prepared in moderate yields by WCl6-Ph4Sn and possess high molecular weights (M w up to 64000). The structures and properties of the polymers are characterized and evaluated by NMR, TGA, UV, CD, PL, and EL analyses. All the polymers are thermally stable and their temperatures for 5% weight loss locate in the range of 300 to 416°C under nitrogen. The energy band gaps of all the polymers are ∼3.0 eV. Polymers P4 and P5 show CD absorptions associated with the helicity of the polymer segments. Excitation of the THF solutions of P3–P7 by UV irradiation gives strong blue lights of ∼485 nm with quantum yields higher than 20%. The thin films of the polymers also emit in the same spectral region, indicative of little aggregation-caused quenching of light emission. Multilayer EL devices with a configuration of ITO/Polymer:PVK/BCP/Alq3/LiF/Al are constructed, which emit blue lights of ∼487 nm. The maximum luminance and external quantum efficiency vary with the pendant groups, with P6 exhibiting the highest external quantum efficiency of 0.16%. The spectra stability of the EL devices is outstanding and the EL peak maximum experiences little change with the applied voltage.

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Authors and Affiliations

  1. Department of Chemistry, The Hong Kong University of Science & Technology, Hong Kong, China

    Jacky W. Y. Lam, AnJun Qin, Cathy K. W. Jim, Ping Lu, WangZhang Yuan, YongQiang Dong & Ben Zhong Tang

  2. Department of Polymer Science and Engineering, Key Laboratory of Macromolecular Synthesis and Functionalization of the Ministry of Education of China, Zhejiang University, Hangzhou, 310027, China

    AnJun Qin, YongQiang Dong & Ben Zhong Tang

  3. College of Materials Science & Engineering, Beijing Institute of Technology, Beijing, 100081, China

    YuPing Dong

  4. Center for Display Research, The Hong Kong University of Science & Technology, Hong Kong, China

    Hoi Sing Kwok

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  1. Jacky W. Y. Lam
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  2. AnJun Qin
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  3. Cathy K. W. Jim
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  4. Ping Lu
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  9. Ben Zhong Tang
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Correspondence to Ben Zhong Tang.

Additional information

Supported by the Research Grants Council of Hong Kong (Grant No. 603509, 603008, 601608, 602707 & CUHK2/CRF/08), the National Natural Science Foundation of China (Grant No. 20634020), and the Ministry of Science and Technology of China (Grant No. 2009CB623605). B. Z. T. thanks the support from the CAO GuangBiao Foundation of Zhejiang University.

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Lam, J.W.Y., Qin, A., Jim, C.K.W. et al. Synthesis and properties of poly(1-phenyl-1-octyne)s containing stereogenic and chromophoric pendant groups. Sci. China Ser. B-Chem. 52, 1691–1702 (2009). https://doi.org/10.1007/s11426-009-0228-3

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