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Fast decoloration of spironaphthooxazine bound to a poly(dimethylsiloxane) network

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Abstract

Spironaphthooxazine (SNO) was attached to a three-dimensional network of polysiloxane through the allyloxygroup on C-7 of the naphthalene ring of SNO, and the photochemical coloration and thermal decoloration behaviors of this material (Film-P) were examined by comparing their properties with those of model SNO having a 7-propyloxynaphthylgroup in solution, in a doped polysiloxane film (Film-D), and in a doped PMMA film. For Film-P, the SNO units were connected to a part of the vinyl groups on the Si atoms of a linear polysiloxane by hydrosilylation, and the remaining vinyl groups were bridged by the bifunctional linear polysiloxane possessing two hydrosilylgroups at both ends of the chain. While Film-P containing 1.7 × 10−3 mol dm−3 of the SNO unit formed a transparent film, Film-D containing more than 1.2 × 10−3 mol dm−3 could not form a transparent film but segregation of SNO occurred. A transparent Film-D was prepared at 0.54 × 10−3 mol dm−3SNO concentration. The decoloration reaction rate of Film-D was faster than those for Film-P, solutions, and PMMA. However, due to the low concentration, the coloration of Film-D was weak. When the concentration of SNO in Film-P was increased 5.7 times, the decoloration rate became 3.6 times faster. Its half-life time was 0.9 s, which is 3.1 times as fast as that of corresponding solution in hexamethyldisiloxane.

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Authors and Affiliations

  1. Department of Advanced Materials Chemistry, Graduate School of Enginieering, Yokohama National University, Yokohama, Japan, 240-8501

    Tsuyoshi Gushiken, Takashi Ubukata & Yasushi Yokoyama

  2. Photochemical Materials Department, Information Media Materials Development Laboratory, ADEKA Co., Tokyo, Japan, 116-8553

    Masako Saito

Authors
  1. Tsuyoshi Gushiken
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  2. Masako Saito
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  3. Takashi Ubukata
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  4. Yasushi Yokoyama
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Correspondence to Yasushi Yokoyama.

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This paper is part of a themed issue on synthetic and natural photoswitches.

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Gushiken, T., Saito, M., Ubukata, T. et al. Fast decoloration of spironaphthooxazine bound to a poly(dimethylsiloxane) network. Photochem Photobiol Sci 9, 162–171 (2010). https://doi.org/10.1039/b9pp00113a

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