Improving the gelation properties of 3,5-diaminobenzoate-based organogelators in aromatic solvents with additional aromatic-containing pendants

A family of 3,5-diaminobenzoate derivatives containing different Cbz-protected α- or β-amino side pendant chains and different aromatic-containing ester functionalities was prepared. It was found that the additional aromatic rings in the Cbz- and aromatic-containing ester moieties significantly impr...

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Bibliographic Details
Published in:Tetrahedron 2007-01, Vol.63 (2), p.363-373
Main Authors: Chow, Hak-Fun, Zhang, Jie, Lo, Chui-Man, Cheung, Siu-Yin, Wong, Ka-Wai
Format: Article
Language:English
Subjects:
Amino acids
H-bonding
Organogelators
π–π Aromatic stacking
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Summary:A family of 3,5-diaminobenzoate derivatives containing different Cbz-protected α- or β-amino side pendant chains and different aromatic-containing ester functionalities was prepared. It was found that the additional aromatic rings in the Cbz- and aromatic-containing ester moieties significantly improved the gelation properties of the resulting organogelators in aromatic solvents. Infrared and circular dichroism spectroscopy revealed that both H-bonding and π–π aromatic stacking interactions were the main driving forces for gelation. [Display omitted] The gelation property of amino acid-based organogelators can be significantly improved by the addition of aromatic-containing pendant groups.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2006.10.066