Liquid crystal compound containing morpholine cation group, synthesis and uses thereof

A technology of liquid crystal compounds and ionic groups, used in chemical instruments and methods, liquid crystal materials, organic chemistry, etc.

Inactive Publication Date: 2009-05-13
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In 2000, Ivan J.B.Lin et al. reported the ionic liquid crystal of N-alkylimidazolium (Ching K.Lee, Hsin W.Huang and Ivan J.B.Lin., Chem.Commun., 2000, 1911), in 2004 Huen.Lee. et al. A room temperature ionic liquid (K.S.Kim, S.Choi, D.Demberelnyamba, H.Lee., Chem.Commun., 2004, 828) with morpholine as a cationic group has been synthesized, but the synthesis route is not yet simple, High-yield, low-cost thermotropic liquid crystal compounds containing morpholine cationic groups reported

Method used

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  • Liquid crystal compound containing morpholine cation group, synthesis and uses thereof
  • Liquid crystal compound containing morpholine cation group, synthesis and uses thereof
  • Liquid crystal compound containing morpholine cation group, synthesis and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Preparation of N-decyl-N-methyl-morpholine ammonium chloride

[0033] 10.12 grams (0.1mol) of N-methyl-morpholine, 176.1 grams (1mol) of chlorodecane and 150 grams of solvent ethanol were added to the reaction device, the reaction temperature was 150 ° C, and the pressure was 1 atmosphere and reacted for 100 hours. After the reaction was completed (chromatographic detection), the solvent was evaporated. The N-decyl-N-methyl-morpholine ammonium chloride compound can be obtained after the reaction product is recrystallized from acetonitrile, which is stable to air and easy to absorb water, with a yield of 94%. The liquid crystal temperature ranges from 42°C to 73°C.

[0034] 1 H-NMR (300MHz, D 2 O): δ=3.91(s, 4H), 3.38(m, 6H), 3.08(s, 3H), 1.67(s, 2H), 1.18(m, 14H), 0.73(m, 3H).Anal.Calcd .for C 15 h 32 CINO: C, 69.67; H, 12.25; N, 4.42%. Found: C, 69.99; H, 12.55; N, 4.36%. MS (ESI): m / z=242.3 (M + ).

Embodiment 2

[0036] Preparation of N-undecyl-N-ethyl-morpholine ammonium bromide

[0037] Add 11.51 grams (0.1mol) of N-ethyl-morpholine, 24.58 grams (0.105mol) of bromoundecane and 150 grams of solvent acetonitrile into the reaction device, the reaction temperature is 50 ° C, the pressure is 10 atmospheres, and the reaction time is After 10 hours, after the reaction was completed (chromatographic detection), the solvent was distilled off. The reaction product is recrystallized from acetonitrile to obtain N-undecyl-N-ethyl-morpholine ammonium bromide compound, which is stable to air and easy to absorb water, with a yield of 93%. The liquid crystal temperature ranges from 67°C to 86°C.

[0038] 1 H-NMR (300MHz, D 2 O): δ=3.81(m, 4H), 3.40(m, 6H), 3.28(m, 2H), 1.77(s, 2H), 1.18(m, 19H), 0.73(m, 3H).Anal.Calcd .for C 17 h 36 BrNO: C, 58.27; H, 10.36; N, 4.00%. Found: C, 58.10; H, 10.45; N, 4.16%. MS (ESI): m / z = 270.3 (M + ).

Embodiment 3

[0040] Preparation of N-tridecyl-N-ethyl-morpholine ammonium fluorophosphate

[0041] Add 11.51 grams (0.1mol) of N-ethyl-morpholine, 78.64 grams (0.3mol) of bromotridecane, and 200 grams of propanol into the reaction device. The reaction temperature is 100°C, the pressure is 5 atmospheres, and the reaction time is After 60 hours, after the reaction (chromatographic detection), 16.3 grams (0.1 mol) of ammonium fluorophosphate was added to the above reaction solution, and the reaction was carried out at 35°C for 50 hours, and the reaction product was recrystallized from acetonitrile to obtain N-tridecane Base-N-ethyl-morpholine ammonium fluorophosphate compound, stable to air and water, yield 96%. The liquid crystal temperature ranges from 73°C to 87°C.

[0042] 1 H-NMR (300MHz, CDCl 3 ): δ=3.84(m, 4H), 3.43(m, 6H), 3.28(m, 2H), 1.81(s, 2H), 1.22(m, 23H), 0.73(m, 3H).Anal.Calcd. for C 19 h 40 f 6 NOP: C, 51.46; H, 9.09; N, 3.16%. Found: C, 51.17; H, 9.45; N, 3.18%. MS (E...

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Abstract

The invention relates to a compound containing morpholine cation radical, a method for synthesizing the same and application thereof. The structural formula of the compound is shown on the right, wherein R1 is methyl or ethyl group, R2 is alkyl group of C10 to C16; X is Cl<->, Br<->, BF4<-> and PF6<->, and Y is Cl<->, Br<->, BF4<->, PF6<->, CH3SO3<-> and CH3C6H4SO3<->. The compound is a thermotropic liquid crystal material which is crystal at room temperature, and can form anisotropic liquid crystal phase when heated. The compound has the advantages of simple synthesis route, high yield and low cost. The compound can be used as ionic liquid in fields: ionic conduction material at the molecular level; order reaction medium in a chemical reaction; and a template in the synthesis of nano material.

Description

technical field [0001] The invention relates to a compound containing morpholine cationic groups, a synthesis method and application thereof, and belongs to the technical field of organic synthesis. Background technique [0002] Ionic liquid crystals (ionic liquid crystals) refer to salts composed only of ions that exhibit thermotropic liquid crystal behavior under rising or falling temperatures, referred to as ILCs. There are only anions and cations in ionic liquids, and there are no neutral molecules. Its main feature is that its ionic properties make it different from traditional molecular liquid crystals, especially its anion and cation interactions, which usually make it tend to form a stable anisotropic layer. Like liquid crystal phase, but also form other structures, such as nematic. Due to the structure of ionic liquids and the properties of thermotropic liquid crystals, ionic liquid crystals can be considered as materials that combine the properties of liquid cryst...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K19/34C09K19/40C07D295/037
Inventor 周晓海余巍张海波
Owner WUHAN UNIV
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