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Title: Facile synthesis of acyl chitosan isothiocyanates and their application to porphyrin-appended chitosan derivative.
Authors: Shibano, Masaya
Nishida, Shouko
Saito, Yasuko
Kamitakahara, Hiroshi  kyouindb  KAKEN_id  orcid (unconfirmed)
Takano, Toshiyuki  kyouindb  KAKEN_id
Author's alias: 高野, 俊幸
Keywords: Acylation
Issue Date: 26-Nov-2014
Publisher: Elsevier Ltd.
Journal title: Carbohydrate polymers
Volume: 113
Start page: 279
End page: 285
Abstract: Chitosan (1) was reacted with phenylisothiocyanate in 5% AcOH/H2O to give N-phenylthiocarbamoyl chitosan (2) with a degree of substitution (DS) of N-phenylthiocarbamoyl groups of 0.86 in 87.1% yield. The following acylation of compound 2 with hexanoyl chloride in the presence of pyridine afforded 3, 6-di-O-2, 3-hexanoyl chitosan isothiocyanate (4a) with a DS of the isothiocyanate groups of 0.70 in high yield, unexpectedly. Compound 4a exhibited high levels of reactivity toward various amines to give the corresponding N-thiocarbamoyl chitosan derivatives in high yields. Other acyl (decanoyl (4b), myristroyl (4c), stearoyl (4d), benzoyl (4e)) chitosan isothiocyanates were also prepared from chitosan (1) in high yields. To evaluate the potential applications of acyl chitosan isothiocyanates, N-(triphenylporphynyl)thiocarbamoyl chitosan derivative 6 with a DS of the triphenylporphynyl groups of 0.46 was prepared from compound 4b. The Langmuir-Blodgett monolayer film of compound 6 gave a good photon-to-electron conversion performance.
Rights: © 2014 Elsevier Ltd.
This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。
DOI(Published Version): 10.1016/j.carbpol.2014.05.099
PubMed ID: 25256486
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