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Circularly polarized luminescence (CPL) characteristics of hydrophobic pyrene derivatives/γ-cyclodextrin (γ-CD) complexes in aqueous solution dissolved by grinding

Journal of Inclusion Phenomena and Macrocyclic Chemistry volume 102, pages 133–142 (2022)Cite this article

Abstract

Circularly polarized luminescence (CPL) organic dyes are currently receiving a great interest, but there are still not many reported observations of CPL spectra of hydrophobic dyes from aqueous solution. We have prepared hydrophobic pyrene derivatives and dissolved them into aqueous solutions with γ-cyclodextrin (γ-CD) by using grinding technique. Among these derivatives, (pyrene-1-carbonyl)serine (PySer) forms a spatially restricted dimer in the hydrophobic chiral cavity of γ-CD and exhibits excimer emission with a high quantum yield of Φf = 0.68. In addition, circular dichroism and CPL signals were induced for the complex. The strong gCPL value of gCPL = + 2.2 × 10−3 was obtained, which may be attributed to the interaction between the hydroxyl groups in the side chain of PySer with those of γ-CD and it strengthens the chiral dimeric structure.

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Acknowledgements

This work is supported by JSPS KAKENHI Grant Number JP20K05567, the “ZE Research Program IAE(ZE2021A-04)”, the Murata Science Foundation, the Nara Women’s University Intramural Grant for Project Research and JST CREST (JPMJCR2001), Japan. The computations were performed using the resources at the Research Center for Computational Science, Okazaki, Japan. We thank Dr. Naokazu Yoshikawa for his assistance of X-ray analysis.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Nara Women’s University, Nara, 630-8506, Japan

    Mika Sawai, Sayaka Matsumoto & Hiroshi Takashima

  2. Department of Applied Chemistry, Faculty of Science and Engineering, Kindai University, Osaka, 577-8502, Japan

    Yuki Mimura & Yoshitane Imai

  3. Department of Chemistry, Nara University of Education, Nara, 630-8528, Japan

    Shoko Yamazaki

  4. Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Osaka, 565-0871, Japan

    Nobuko Kanehisa & Norimitsu Tohnai

  5. Nakata Institute of Advanced Energy, Kyoto University, Kyoto, 611-0011, Japan

    Eiji Nakata

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Sawai, M., Matsumoto, S., Mimura, Y. et al. Circularly polarized luminescence (CPL) characteristics of hydrophobic pyrene derivatives/γ-cyclodextrin (γ-CD) complexes in aqueous solution dissolved by grinding. J Incl Phenom Macrocycl Chem 102, 133–142 (2022). https://doi.org/10.1007/s10847-021-01108-z

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