New sugar-based gelators with an amino group, the gelatin ability of which is remarkably reinforced by the hydrogen bond and the metal coordination

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Amanokura, Natsuki and Kanekiyo, Yasumasa and Shinkai, Seiji and Reinhoudt, David N. (1999) New sugar-based gelators with an amino group, the gelatin ability of which is remarkably reinforced by the hydrogen bond and the metal coordination. Journal of the Chemical Society. Perkin transactions II, 1999 (10). pp. 1995-2000. ISSN 0300-9580

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Abstract:Three sugar-integrated gelators bearing a p-aminophenyl group which are expected to exert a hydrogen-bonding effect and a metal coordination effect on the gelation ability were synthesised. -D-Galactose-based 2b was only soluble or precipitated and -D-glucose-based 4b gelated only two of 15 solvents tested herein whereas -D-glucose-based 1b acted as an excellent gelator which could gelate 8 solvents. The sol–gel phase-transition temperature (Tgel) values for 1b were higher by 41–78 °C than those for -D-glucose-based 1a bearing a p-nitrophenyl group. The spectral studies indicated that this gel reinforcement is due to the hydrogen-bonding interaction including the amino group. The Tgel values for the ethanol gel of 1b were markedly improved by the addition of AgNO3, CoCl2 or CdCl2. The detailed examination of a 1b + CoCl2 gel system in ethanol showed that the gel is stabilised by the cross-link of 1b molecules by the Co(II)–amino group interaction. This is the first and a convenient method for the metal reinforcement of organic gels.
Item Type:Article
Copyright:© 1999 Royal Society of Chemistry
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Link to this item:http://purl.utwente.nl/publications/11623
Official URL:http://dx.doi.org/10.1039/a903298c
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Metis ID: 106255