Acta Phys. -Chim. Sin. ›› 2013, Vol. 29 ›› Issue (09): 2005-2012.doi: 10.3866/PKU.WHXB201306142

• SOFT MATTER • Previous Articles     Next Articles

Synthesis and Gelation Properties of Cholesterol-Based New Low-Molecular-Mass Gelators

XUE Min1,2, MIAO Qing2, FANG Yu2   

  1. 1 School of Chemistry and Chemical Engineering, Xi'an University of Arts and Science, Xi'an 710065, P. R. China;
    2 Key Laboratory of Applied Surface and Colloid Chemistry of Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062, P. R. China
  • Received:2013-03-27 Revised:2013-06-13 Published:2013-08-28
  • Contact: FANG Yu E-mail:yfang@snnu.edu.cn
  • Supported by:

    The project was supported by the National Natural Science Foundation of China (21273141).

Abstract:

Three novel dimeric cholesteryl-based low-molecular-mass gelators (LMMGs), which have the structure A(LS)2, were designed and synthesized. In the structures, 1,3-diaminopropane is a linker (L), A is a benzene ring, and S is cholesteryl. According to the positions of the substituents on the benzene ring, the as-prepared compounds are denoted by 1 (o-position), 2 (m-position), and 3 (p-position), respectively. Their gelation properties were evaluated in 30 solvents. It was revealed that the relative positions of the two cholesteryl moieties on the benzene ring play a crucial role in the gelation behaviors of the compounds. In terms of the number of solvents gelled by the tested compounds, compound 3 is a more versatile gelator than compounds 1 and 2; compounds 2 and 3 can form five gels at room temperature. Furthermore, the compound 2/xylene gel is transparent and flexible, and forms a supramolecular filmin the wet state. Fouriertransform infrared (FTIR) spectroscopy and 1H nuclear magnetic resonance (1H NMR) spectroscopy studies demonstrated that intermolecular hydrogen bonding and π-π stacking among the molecules of the gelators play important roles in the gelation process. X-ray diffraction (XRD) analysis showed that the aggregate of compound 1 from its benzene gel adopts a hexagonal packing mode as the elementary structure of the gel networks.

Key words: Low-molecular-mass gelator, Cholesterol, Self-assembly, Roomtemperature gelation, Gel film

MSC2000: 

  • O641.3