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2-Triethoxysilylazulene derivatives: Syntheses and optical properties, and hydrolysis—condensation of 2-triethoxysilylazulene

  • Original Paper: Sol–gel, hybrids and solution chemistries
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Abstract

As the raw materials of organic–inorganic dyes, 2-triethoxysilylazulene derivatives (2a–2d) were synthesized via a cross-coupling reaction between a 2-haloazulene derivative (1a–1d) and triethoxysilane in the presence of a rhodium catalyst. Compounds 2a–2d were obtained as colored liquids and characterized using NMR and mass spectroscopy. The UV–Vis spectra of 2a–2d were red-shifted as compared to that of hydrogen-substituted azulene derivatives (3a–3d). This was attributed to the extended conjugated system and specific properties of the azulene moiety. Compound 2a was polymerized via a hydrolysis–condensation reaction, and the resulting polymer (P2a) was characterized using GPC, 29Si NMR, and FT-IR spectroscopy. The UV–Vis spectrum of P2a was red-shifted as compared to that of 2a, which was attributed to the π–π interactions.

2-Triethoxysilylazulene derivatives show excellent chromogenic properties. The absorption wavelength is dependent on the type of functional groups located at the 1,3-position.

Highlights

  • 2-Triethoxysilylazulene derivatives were synthesized via a cross-coupling reaction between a 2-haloazulene derivative and triethoxysilane.

  • The UV–Vis spectra of these derivatives are dependent on the type of functional groups.

  • 2-Triethoxysilylazulene polymer was prepared via a hydrolysis–condensation reaction.

  • The UV–Vis spectrum of the polymer was slightly red-shifted as compared to that of the monomer.

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Authors and Affiliations

  1. Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba, 278-8510, Japan

    Ryohei Hayami, Tetsuro Izumiya, Takashi Kokaji, Hajime Nakagawa, Satoru Tsukada, Kazuki Yamamoto & Takahiro Gunji

  2. Advanced Automotive Research Collaborative Laboratory, Graduate School of Engineering, Hiroshima University, 1-4-1 Kagamiyama, Higashi-Hiroshima City, Hiroshima, 739-8527, Japan

    Satoru Tsukada

Authors
  1. Ryohei Hayami
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  2. Tetsuro Izumiya
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  3. Takashi Kokaji
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  4. Hajime Nakagawa
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  6. Kazuki Yamamoto
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Correspondence to Takahiro Gunji.

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Hayami, R., Izumiya, T., Kokaji, T. et al. 2-Triethoxysilylazulene derivatives: Syntheses and optical properties, and hydrolysis—condensation of 2-triethoxysilylazulene. J Sol-Gel Sci Technol 91, 399–406 (2019). https://doi.org/10.1007/s10971-019-04991-8

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  • DOI: https://doi.org/10.1007/s10971-019-04991-8

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