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

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

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

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. [Figure not available: see fulltext.]

Original languageEnglish
Pages (from-to)399-406
Number of pages8
JournalJournal of Sol-Gel Science and Technology
Volume91
Issue number2
DOIs
Publication statusPublished - 15 Aug 2019

Fingerprint

azulene
Optical properties
Derivatives
optical properties
nuclear magnetic resonance
cross coupling
synthesis
rhodium
Nuclear magnetic resonance
spectroscopy
Rhodium
mass spectroscopy
dyes
catalysts
Hydrogen
Infrared spectroscopy
Raw materials
Polymers
polymers
hydrogen

Keywords

  • Hydrolysis–condensation
  • Organic–inorganic dyes
  • Triethoxysilylazulene derivatives
  • UV–Vis spectra

Cite this

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abstract = "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. [Figure not available: see fulltext.]",
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2-Triethoxysilylazulene derivatives : Syntheses and optical properties, and hydrolysis—condensation of 2-triethoxysilylazulene. / Hayami, Ryohei; Izumiya, Tetsuro; Kokaji, Takashi; Nakagawa, Hajime; Tsukada, Satoru; Yamamoto, Kazuki; Gunji, Takahiro.

In: Journal of Sol-Gel Science and Technology, Vol. 91, No. 2, 15.08.2019, p. 399-406.

Research output: Contribution to journalArticle

TY - JOUR

T1 - 2-Triethoxysilylazulene derivatives

T2 - Syntheses and optical properties, and hydrolysis—condensation of 2-triethoxysilylazulene

AU - Hayami, Ryohei

AU - Izumiya, Tetsuro

AU - Kokaji, Takashi

AU - Nakagawa, Hajime

AU - Tsukada, Satoru

AU - Yamamoto, Kazuki

AU - Gunji, Takahiro

PY - 2019/8/15

Y1 - 2019/8/15

N2 - 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. [Figure not available: see fulltext.]

AB - 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. [Figure not available: see fulltext.]

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