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Synthesis and properties of poly(tetramethyl-1,6-silpyrenylenesiloxane) derivative with phenyl groups on pyrenylene moiety

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Abstract

Poly(tetramethyl-1,6-silpyrenylenesiloxane) derivative with phenyl groups on pyrenylene moieties (P1) was prepared via polycondensation of disilanol monomer, i.e. 1,6-bis(dimethylhydroxysilyl)-3,8-diphenylpyrene (M1). P1 exhibited the very high glass transition temperature (T g) of 191 °C. The temperature at 5% weight loss (T d5) of P1 was 482 °C, indicating the relatively good thermostability of P1. P1 exhibited the bathochromic effect in the absorption and fluorescence spectra, indicating the expansion of π-conjugation by introducing phenyl groups onto pyrene skeleton as well as the σ–π and σ*–π* conjugation between pyrene and silyl moieties. In addition, P1 exhibited relatively weak excimer emission because of the inhibition of the excimer formation of pyrene skeleton by introduction of bulky phenyl groups onto pyrene skeleton. The fluorescence quantum yields (ΦFs) of M1 and P1 in chloroform were determined to be 0.46 and 0.37, respectively. It was revealed that M1 and P1 exhibited the higher fluorescence intensity than 1,6-diphenylpyrene, owing to the effect of the introduction of silyl moieties onto pyrene skeleton.

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Acknowledgments

The authors would like to appreciate Ms. Satoko Tokiwa and Ms. Nami Sugashima, Nihon University College of Engineering Worldwide Research Center for Advanced Engineering & Technology (NEWCAT), for performing NMR measurements; and Dr. Miki Hasegawa, School of Science and Engineering, Aoyama Gakuin University, for performing the fluorescence quantum yield measurement.

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Authors and Affiliations

  1. Department of Chemistry, School of Science and Engineering, Aoyama Gakuin University, Fuchinobe, Chuo-ku, Sagamihara, Kanagawa, 252-5258, Japan

    Kazutoshi Imai & Jiro Abe

  2. Department of Chemical Biology and Applied Chemistry, College of Engineering, Nihon University, Tamura-machi, Koriyama, Fukushima, 963-8642, Japan

    Takumi Sasaki & Nobukatsu Nemoto

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  1. Kazutoshi Imai
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  2. Takumi Sasaki
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  3. Jiro Abe
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  4. Nobukatsu Nemoto
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Correspondence to Nobukatsu Nemoto.

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Imai, K., Sasaki, T., Abe, J. et al. Synthesis and properties of poly(tetramethyl-1,6-silpyrenylenesiloxane) derivative with phenyl groups on pyrenylene moiety. Polym. Bull. 68, 1589–1601 (2012). https://doi.org/10.1007/s00289-011-0639-0

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  • DOI: https://doi.org/10.1007/s00289-011-0639-0

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