Synthesis, structure and properties of cholesterol-based A(LS) sub(2)- and A(LS) sub(3)-type gelators without hydrogen bond linkers

Dicholesteryl isophthalate (1m), dicholesteryl terephthalate (1p) and tricholesteryl trimesate (2) were synthesized as new cholesterol-based A(LS) sub(n)-type gelators (n=2 and 3) without hydrogen bond linkers. Their molecular structural details were investigated experimentally by super(1)H and supe...

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Bibliographic Details
Published in:Tetrahedron 2016-03, Vol.72 (12), p.1517-1523
Main Authors: Shimasaki, Toshiaki, Okamiya, Yuta, Sato, Ryota, Hara, Kazuyoshi, Nakamura, Taro, Teramoto, Naozumi, Shibata, Mitsuhiro
Format: Article
Language:English
Subjects:
Helical
Hydrogen bonds
Mathematical analysis
Molecular structure
Scanning electron microscopy
Self assembly
Solvents
Strands
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Summary:Dicholesteryl isophthalate (1m), dicholesteryl terephthalate (1p) and tricholesteryl trimesate (2) were synthesized as new cholesterol-based A(LS) sub(n)-type gelators (n=2 and 3) without hydrogen bond linkers. Their molecular structural details were investigated experimentally by super(1)H and super(13)C NMR, UV-vis and IR spectroscopies and theoretically by DFT calculations. Compounds 1p and 2 have relatively high degrees of symmetry and exhibit efficient gelation abilities, whereas compound 1m could not be gelated in any common organic solvents. The self-assembly behavior of the compound was largely affected by the type of solvent and the number and substitution positions of the cholesteryl groups, as revealed by scanning electron microscopy (SEM) measurements. Notably, the xerogel of 2 using benzene displayed an aggregated microfibrous strand structure that included helical fibers.
ISSN:0040-4020
DOI:10.1016/j.tet.2016.01.059