Acta Phys. -Chim. Sin. ›› 2014, Vol. 30 ›› Issue (9): 1688-1696.doi: 10.3866/PKU.WHXB201407041

• SOFT MATTER • Previous Articles     Next Articles

Two-Component Supramolecular Organogels Formed from L-Phenylalanine Derivatives and Aliphatic Amines

ZHONG Jin-Lian1,2, PAN Hong2, LUO Xu-Zhong2, HONG San-Guo1, ZHANG Ning1, HUANG Jian-Bin3   

  1. 1. Department of Chemistry, Nanchang University, Nanchang 330031, P. R. China;
    2. Key Laboratory of Orgaro-phamaceutical Chemistry of Jiangxi Province, Gannan Normal University, Ganzhou 341000, Jiangxi Province, P. R. China;
    3. College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, P. R. China
  • Received:2014-03-31 Revised:2014-07-03 Published:2014-08-29
  • Contact: LUO Xu-Zhong, HONG San-Guo, HUANG Jian-Bin E-mail:luoxuzhong@hotmail.com;nzhang@ncu.edu.cn;jbhuang@pku.edu.cn
  • Supported by:

    The project was supported by the National Natural Science Foundation of China (51268002), Natural Science Foundation of Jiangxi Province, China (201114BNB213008), Research Foundation of Education Bureau of Jiangxi Province, China (GJJ11707), and“Gan Po 555 Engineering Excellence”of Jiangxi Province, China.

Abstract:

A series of monochain L-phenylalanine derivatives were synthesized. L-Phenylalanine derivatives have no gelation abilities, but two-component systems consisting of L-phenylalanine derivatives and aliphatic amines can gelate various organic liquids. The structures of the aggregates in the organogels were investigated using Fourier-transform infrared spectroscopy (FT-IR), nuclear magnetic resonance (NMR) spectroscopy, smallangle X-ray scattering (SAXS), rheological methods, and scanning electron microscopy (SEM). The rheological measurements showed that the steady-state value of the storage elastic modulus (G') was about 10 times larger than that of the loss elastic modulus (G"), indicating that the organogels have good mechanical properties and gel-like characteristics. The SEM, FT-IR, and 1H NMR results showed that two-component organogels can self-assemble into fibrous or lamellar aggregates in organic liquids through acid-base interactions, intermolecular hydrogen bonding of amide groups, and van der Waals interactions of long alkyl chains. The FT-IR and NMR spectra showed that the hydrogen-bonding and acid-base interactions were the main driving forces for the formation of self-assembled gels. The SAXS results indicated that the gelator molecules assembled into ordered lamellar structures in organic liquids. The ordered lamellar aggregates are juxtaposed and interlocked by van der Waals interactions to form a fibrous superstructure and are finally immobilized in the organic liquid.

Key words: Two-component supramolecular gel, L-benzedrine acid derivatives, Self-assemble, Acid-base interaction, Hydrogen bonding

MSC2000: 

  • O648