Citation: XUE Min, MIAO Qing, FANG Yu. Synthesis and Gelation Properties of Cholesterol-Based New Low-Molecular-Mass Gelators[J]. Acta Physico-Chimica Sinica, ;2013, 29(09): 2005-2012. doi: 10.3866/PKU.WHXB201306142 shu

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

XUE Min ^1,2 ,
MIAO Qing ² ,
FANG Yu ^2,

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 Date: 27 March 2013
Available Online: 14 June 2013
Fund Project: 国家自然科学基金(21273141)资助项目 (21273141)

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 hexa nal packing mode as the elementary structure of the gel networks.
- Low-molecular-mass gelator,
- Cholesterol,
- Self-assembly,
- Roomtemperature gelation,
- Gel film
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