Helical arrangement of a hydrogen-bonded columnar liquid crystal induced by a centered triphenylene derivative bearing chiral side-chains

被引:11
作者
Ishihara, Shinsuke [1 ]
Furuki, Yusuke [1 ]
Takeoka, Shinji [1 ]
机构
[1] Waseda Univ, Grad Sch Adv Sci & Engn, Shinjuku Ku, Tokyo 1698555, Japan
关键词
supramolecular chemistry; liquid crystal; hydrogen bonding; columnar structure; induced helicity;
D O I
10.1002/pat.1085
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
A hydrogen-bonded helical columnar liquid crystal was synthesized, in which the helical structure is induced by a centered triphenylene derivative bearing chiral side-chains. The triphenylene derivative, 2,6,10-tris(carboxymethoxy)-3,7,11-tris((S)-(-)-2-methyl-1-butanoxy)triphenylene (TPC4(S)), and a dendric amphiphile, 3,5-bis-(3,4-bis-dodecyloxy-benzyloxy)-N-pyridine-4-yl-benzamide (DenC12), were mixed in a 1:3 ratio to obtain a complex, TPC4(S)-DenC12. Analyses by H-1-NMR spectroscopy, diffusion ordered spectroscopy (DOSY), CD spectroscopy, infrared (IR) spectroscopy, polarized optical microscopy (POM), differential scanning calorimetry (DSC), and X-ray diffractometry revealed that TPC4(S)-DenC12 self-assembles to form helical columnar stacks in solution and a helical columnar liquid crystal in bulk. The hydrogen bonding between TPC4(S) and DenC12 is essential for the helical columnar organization, and the preference for a one-handed helical conformation is likely derived from the steric interaction between the chiral side-chains and the dendric amphiphiles in the packing of the hydrogen-bonded columnar assemblies. Copyright C(-) 2008 John Wiley & Sons, Ltd.
引用
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页码:1097 / 1104
页数:8
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