Molecular Design of "Super" Hydrogelators: Understanding the Gelation Process of Azobenzene-Based Sugar Derivatives in Water

Organic Letters

Volumn 4, Issue 9, 2002, Pages 1423-1426

  Kobayashi, Hideki ^a   Friggeri, Arianna ^a   Koumoto, Kazuya ^a   Amaike, Masato ^a   Shinkai, Seiji ^a   Reinhoudt, David N ^b  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^b UNIVERSITY OF TWENTE   (Netherlands)

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[No Author keywords available]

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ARTICLE;

EID: 0001011847     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025519+     Document Type: Article

References (30)

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2. For recent reviews, see: Terech, P.; Weiss, R. G. Chem. Rev. 1997, 97, 3133. van Esch, J. H.; Feringa, B. L. Angew. Chem., Int. Ed. 2000, 39, 2263, and references therein. Hafkamp, R. J. H.; Feiters, M. C.; Nolte, R. J. M. J. Org. Chem. 1999, 64, 412.
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20. Synthesis and gelation studies of all compounds in this library win be published as a full paper elsewhere.
21. gel is defined as the temperature at which the solvent begins to flow out of the gel (±3 °C). This temperature is lower than the temperature at which complete melting of the gel occurs. For the 0.05 and 0.06 wt % samples, inversion of the sample vials caused a small amount of water to flow out of the gels already at room temperature. This phenomenon is frequently observed for aqueous gels of low molecular weight compounds.
22. gel values are those at which the gel completely melted.
23. The solution sample had to be prepared in DMSO due to the low concentration at which 1 becomes soluble in water.
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27. The xerogel of 1 was obtained by freezing and pumping the gel of 1 tor 12 h.
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30. Energy minimization of 1 was carried out by MM3 using AccuMode 1.0 (Microsimulation, L. A. Systems, Inc.) on a Macintosh computer and by MOPAC PM3 using CS Chem-office Chem 3D (CambridgeSoft Corporation) on a NEC computer. The heat of formation calculated by MOPAC PM3 for the molecular structure shown in Scheme 2 was estimated to be -2131 kJ/mol.