Glycine and l-glutamic acid-based dendritic gelators

• Published in: Tetrahedron Vol. 63; no. 36; pp. 8794 - 8800
• Main Authors: Li, Wu-Song, Jia, Xin-Ru, Wang, Bing-Bing, Ji, Yan, Wei, Yen
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 03.09.2007; Elsevier
• Subjects: Chemistry; Chemistry, Organic; Dendritic gelators; Glycine; l-Glutamic acid; Physical Sciences; Science & Technology; Self-assembly; Self-assembly; Glycine; l-Glutamic acid; Dendritic gelators; POLYMERS; RECOGNITION; PEPTIDIC DENDRIMERS; ONE-COMPONENT; 2-DIRECTIONAL CASCADE MOLECULES; BIOMATERIALS; ORGANIC LIQUIDS; GELATION; SUPRAMOLECULAR CHEMISTRY; GEL
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2007.06.028

Novel dendrons based on glycine and l-glutamic acid from the first generation ( G1) to the third generation ( G3) were synthesized and studied for their gelation properties by using transmission electron microscopy (TEM), atomic force microscopy (AFM), fluorescence, IR, circular dichroism (CD), and 1H NMR spectroscopy. It was found that the gelation capability of these dendrons increased from the first generation ( G1) to the third generation ( G3), and that G3 exhibited the highest efficiency in forming gels. Both the focal and peripheral groups of dendrons had great effects on the formation of organogels. Hydrogen bonding and π–π stacking interactions were proved to be the main driving forces to form the fibrous networks at low concentrations (0.5 wt %). Small-angle X-ray scattering (SAXS) and wide-angle X-ray diffraction (WAXD) measurements indicate that the xerogels of the second generation ( G2) from ethyl acetate and ethanol, and G3 xerogel from CH 2Cl 2 all display lamellar structures with the interlamellar spacing of ca. 36.0 Å for G2 and 40.5 Å for G3, respectively. [Display omitted]