Synthesis of a Fluorescent Solvatochromic Resin Using Suzuki-Miyaura Cross-Coupling and Its Optical Waveguide Spectra to Measure the Solvent Polarity on the Surface

Yu Otsuka; Guanglei Li; Hiromi Takahashi; Hisashi Satoh; Koji Yamada

doi:10.3390/ma13204483

Synthesis of a Fluorescent Solvatochromic Resin Using Suzuki-Miyaura Cross-Coupling and Its Optical Waveguide Spectra to Measure the Solvent Polarity on the Surface

Materials (Basel). 2020 Oct 10;13(20):4483. doi: 10.3390/ma13204483.

Authors

Yu Otsuka¹, Guanglei Li², Hiromi Takahashi³, Hisashi Satoh⁴, Koji Yamada^{1

5}

Affiliations

¹ Division of Materials Science, Graduate School of Environmental Science, Hokkaido University, Sapporo, Hokkaido 060-0810, Japan.
² School of Food Science and Technology, Nanjing University of Finance & Economic, Nanjing 210023, China.
³ ATR Scientists Partners Inc., 3-27-13, Maehara, Koganei, Tokyo 184-0013, Japan.
⁴ Division of Environmental Engineering, Faculty of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan.
⁵ Division of Materials Science, Faculty of Environmental Earth Science, Hokkaido University, Sapporo, Hokkaido 060-0810, Japan.

Abstract

We have established a novel analytical method for solvent polarity on resin surface by combining the synthesis of fluorescent solvatochromic resin with optical waveguide spectrometry. The fluorescent solvatochromic resin was obtained via Suzuki-Miyaura cross-coupling between 4-iodobenzoic acid immobilized on Wang resin and 5-[4-(N,N-dihexylamino)phenyl]-2-thienylboronic acid N-methyl-iminodiacetic acid (MIDA) ester. The optical waveguide spectrometry studies on the resin showed a strong fluorescent solvatochromism in various organic solvents.

Keywords: Suzuki–Miyaura cross-coupling; optical waveguide spectrometry; solid-phase synthesis.