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Selective Synthesis and Application of Novel Liquid-Crystalline Diaryldiacetylenes

新型液晶二芳基二乙炔的选择性合成及应用

基本信息

批准号：
09450334
负责人：
KITAMURA Tsugio
金额：
$ 7.87万
依托单位：
KYUSHU UNIVERSITY
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (B).
财政年份：
1997
资助国家：
日本
起止时间：
1997 至 2000
项目状态：
已结题

项目摘要

(1) Selective Synthesis of Diaryldiacetylenes and Evaluation of Liquid Crystalline PropertiesArylethynyliodonium salts with long alkyl groups were prepared easily prepared by reaction of arylacetylenes and hydorxy(tosyloxy)iodobenzene. The reaction of the arylethynyliodonium salts with alkynylcopper reagents selectively provided diaryldiacetylenic compounds that exhibited liquid-crystalline properties. Liquid-crystalline thiophene derivatives were also synthesized from the diaryldiacelenes. Furthermore, chiral (S)-(2-methylbutoxy)phenylethynyliodonium tosylate was synthesized first and applied to chiral diaryldiacetylenic compounds by the reaction with arylethynylcopper reagents, affording chiral diaryldiacetylenic ferroelectric liquid crystals.(2) Synthesis of Liquid-Crystalline EnynesSynthesis of 1,4-diaryl-1-buten-3-ynes were synthesized by the palladium-catalyzed coupling reaction of arylacetylenes with styryl bromides having long alkyl groups. Thus prepared enyne derivatives showed smectic and nematic phases in a wide range of temperature.(3) Synthesis of 1,1 -Diethynylethenes and Tetraethynylethenes1,1 -Diethynylethenes and tetraethynylethenes have the structure that the π electronic system is delocalized on the molecular plane. 1,1 -Bis(arylethynyl)ethenes and tetrakis(4-decyloxyphenylethynyl)ethene were prepared but did not show mesogenic properties. The new charge-transfer complexes with trinitrofluorenone were obtained.

(1)芳基二乙炔的选择性合成及液晶性能评价芳基二乙炔与羟基（tosyloxy）碘苯反应制备了具有长烷基的芳基二乙炔钠盐。芳基乙基碘鎓盐与炔基铜试剂的反应选择性地提供了具有液晶性质的二芳基二乙基化合物。以二芳基二烯为原料合成了液晶噻吩衍生物。在此基础上，首次合成了手性(S)-（2-甲基丁氧基）苯乙基磺酰甲磺酸盐，并与芳乙基铜试剂反应，将其应用于手性二芳基二乙基化合物，得到了手性二芳基二乙基铁电液晶。(2)液晶炔的合成采用钯催化芳基乙炔与长烷基苯乙烯的偶联反应合成了1,4-二芳基-1-丁烯-3炔。由此制备的炔衍生物在较宽的温度范围内表现为近向相和向列相。(3) 1,1 -二乙基乙烯和四乙基乙烯的合成1,1 -二乙基乙烯和四乙基乙烯具有π电子体系在分子平面上离域的结构。制备了1,1 -二（芳基乙基）乙烯和四（4-癸氧基苯乙基）乙烯，但未表现出介生性质。得到了与三硝基芴酮的新型电荷转移配合物。