2000 Fiscal Year Final Research Report Summary
Selective Synthesis and Application of Novel Liquid-Crystalline Diaryldiacetylenes
| Project/Area Number |
09450334
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| Research Category |
Grant-in-Aid for Scientific Research (B).
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
有機工業化学
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| Research Institution | KYUSHU UNIVERSITY |
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Principal Investigator |
KITAMURA Tsugio KYUSHU UNIVERSITY, Faculty of Engineering, Ass.Prof., 大学院・工学研究院, 助教授 (00153122)
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| Co-Investigator(Kenkyū-buntansha) |
NAGATA Kensuke KYUSHU UNIVERSITY, Faculty of Engineering, Research Ass., 大学院・工学研究院, 助手 (40264080)
TANIGUCHI Yuki KYUSHU UNIVERSITY, Faculty of Engineering, Research Ass., 大学院・工学研究院, 助手 (50217139)
FUJIWARA Yuzo KYUSHU UNIVERSITY, Faculty of Engineering, Prof., 大学院・工学研究院, 教授 (10029481)
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| Project Period (FY) |
1997 – 2000
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| Keywords | Diaryldiacetylene / Liquid Crystals / Thiophenes / Ferroelectric Liquid Crystals / Enynes / Diethynylethenes / Tetraethynylethenes / Charge-Transfer Complex |
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| Research Abstract |
(1) Selective Synthesis of Diaryldiacetylenes and Evaluation of Liquid Crystalline Properties
Arylethynyliodonium 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 Enynes
Synthesis 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 Tetraethynylethenes
1,1 -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.
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