Development of New Fluorine-containing Ferroelectric Liquid Crystals

新型含氟铁电液晶的研制

• 批准号: 06555277
• 负责人: NAKAI Takeshi
• 金额: $ 3.71万
• 依托单位: Tokyo Institute of Technology
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Developmental Scientific Research (B)
• 财政年份: 1994
• 资助国家: 日本
• 起止时间: 1994 至 1995
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-06555277/
• 关键词: Ferroelectric Liquid Crystal; Fluorine Compound; Claisen Rearrangment; Asymmetric Synthesis; Spontaneous; Optically Active Compound; Liquid Crystal; 応答時間

The purposes of this project are to develop a new and efficient synthetic method for optically active organofluorine compounds and, by using these as chiral building blocks, to develop new types of ferroelectric liquid crystals.First, the Tokyo Inst.Tech.group has developed the new, silyl triflate-mediated procedure for the Claisen rearrangement and successfully applied this Claisen procedure to asymmetric synthesis of alpha-fluoro-alpha-methyl and alpha-fluoro-alpha-trifluoromethyl carboxylic acid derivatives. Of particular interest is that the senses of asymmetric transmission observed with the fluorinated substrates are opposite to those observed with the non-fluorinated counterparts. Second, the Japan Energy Co.group has prepared a variety of liquid crystals by using the optically active fluorine compounds as the chiral building blocks and evaluated their functional properties as ferroelectric LC's. Notable findings are : (I) the fluorinated liquid crystals provide a larger degree of the spontaneous polarization than the non-fluorinated counterparts in general, (2) Liquid crystal with the alpha-fluoro-alpha-methyl chiral center show a greater spontaneous polarization than the liquid crystals with alpha-fluoro-alpha-CF_3 chiral center, and (3) The liquid crystal with a pyrimidine ring in the core part and alpha-fluoro-alpha-methyl ester moiety in the chiral part is shown to provide a greater than 400 nC/cm^2 of spontaneous polarization.

本项目的目的是开发一种新的有效的光学活性有机氟化合物的合成方法，并通过使用这些化合物作为手性结构单元，开发新型铁电液晶。首先，东京Inst.Tech.group开发了新的，甲硅烷基三氟甲磺酸酯介导的Claisen重排的程序，并成功地将此Claisen程序应用于α-氟-α-甲基和α-氟-α-甲基的不对称合成。三氟甲基羧酸衍生物。特别令人感兴趣的是，用氟化基材观察到的不对称透射的意义与用非氟化对应物观察到的意义相反。第二，Japan Energy Co.group通过使用光学活性氟化合物作为手性结构单元制备了各种液晶，并评价了它们作为铁电LC的功能特性。值得注意的调查结果是：（2）含α-氟-α-甲基手性中心的液晶比含α-氟-α-CF_3手性中心的液晶显示出更大的自发极化，以及（3）在核心部分具有嘧啶环且在手性部分具有α-氟-α-甲酯部分的液晶显示出提供大于400 nC/cm ^2的自发极化。

项目成果

Atsushi Yoshizawa: "New Chiral Dopants Based on the 2-Fluoro-2-methylalkoxy Tail for Use in Ferroelectric Liquid Crystal Mixtures" Mol.Cryst.& Liq.Cryst.263. 217-222 (1995)

Atsushi Yoshizawa：“基于 2-氟-2-甲基烷氧基尾部的新型手性掺杂剂，用于铁电液晶混合物”Mol.Cryst。

吉沢 篤: "Interlayer Correlation in Semectic Phases Induced by Chiral Twin Molecules" Mol. Cryst. &Liq. Cryst.260. 403 (1995)

Atsushi Yoshizawa：“手性孪生分子诱导的层间相关性”Cryst.260 (1995)。

Takeshi Nakai: "Claisen Rearrangementof alpha- (F-alkyl) enol Ethers Prepared via Wittig Olefination of Allyl Perfluoroalkanoates" Tetrahedron Lett.35, [18]. 2907-2910 (1994)

Takeshi Nakai：“通过全氟链烷酸烯丙酯的 Wittig 烯化制备 α-（F-烷基）烯醇醚的克莱森重排”Tetrahedron Lett.35，[18]。

Atsushi Yoshizawa: "Decrease in Apparent Viscosity in Electric Fields in Chiral Smectic Liquid Crystals" Ferroelectrics. 147. 395-409 (1993)

Atsushi Yoshizawa：“手性近晶液晶电场中表观粘度的降低”铁电体。

中井武: "Claisen Rearrangements of Fluorinated Enol Ethers : New Entries to α-Monofluoro and α,α-Difluro Acids" Journal of Fluorine Chemistry. 54. 68 (1992)

Takeshi Nakai：“氟化烯醇醚的克莱森重排：α-单氟酸和 α,α-二氟酸的新条目”《氟化学杂志》54. 68 (1992)。