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Int. J. Mol. Sci. 2015, 16(12), 29093-29102; doi:10.3390/ijms161226153

Preparation of a Near-Infrared Ray Absorption Film from N-Phenylthiocarbamoyl Chitosan Derivative

Division of Forest and Biomaterials Science, Graduate School of Agriculture, Kyoto University, Kyoto 606-8502, Japan
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Author to whom correspondence should be addressed.
Academic Editors: Hitoshi Sashiwa and Shinsuke Ifuku
Received: 18 September 2015 / Revised: 19 November 2015 / Accepted: 27 November 2015 / Published: 4 December 2015
(This article belongs to the Special Issue Chitins 2015)
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Abstract

We recently observed that the decanoylation of N-phenylthiocarbamoyl chitosan (2) with a mixture of decanoic anhydride and pyridine at 60 °C for 24 h afforded N,N-(decanoyl)phenythiocarbamoyl-/2-isothiocynato chitosan decanoate (3b) rather than the expected product N,N-(decanoyl)phenylthiocarbamoyl chitosan decanoate (3a). This result suggested that some of the N,N-(decanoyl)phenylthiocarmbamoyl groups had been converted to isothiocyanate groups during the decanoylation process. The subsequent reaction of compound 3b with aniline gave N,N-(decanoyl)phenylthiocarbamoyl/N-phenylthiocarbamoyl chitosan decanoate (4) in high yield. A solution of compound 4 in CHCl3 was then added to a solution of copper decanoate (5) in the same solvent, and the resulting mixture was cast onto a glass plate to give a cast film. The film was annealed at 200 °C in an oven to give a greenish film, which showed good near-infrared absorption characteristic in the range of 800–2200 nm. View Full-Text
Keywords: chitosan; copper; decanoylation; near-infrared absorption; phenythiocarbamoyl chitosan; copper; decanoylation; near-infrared absorption; phenythiocarbamoyl
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Nishida, S.; Shibano, M.; Kamitakahara, H.; Takano, T. Preparation of a Near-Infrared Ray Absorption Film from N-Phenylthiocarbamoyl Chitosan Derivative. Int. J. Mol. Sci. 2015, 16, 29093-29102.

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