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Nitrogen-containing discotic ionic liquid crystal compound and preparation method thereof

A technology of ionic liquid crystals and compounds, applied in chemical instruments and methods, liquid crystal materials, organic chemistry, etc., can solve the problems of complex synthesis and tedious characterization of discotic ionic liquid crystals, and achieve good application value and prospects, and the effect of good luminescent properties.

Inactive Publication Date: 2020-06-09
SICHUAN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reason for this may be the complex synthesis, characterization and tedious purification steps of discotic ionic liquid crystals

Method used

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  • Nitrogen-containing discotic ionic liquid crystal compound and preparation method thereof
  • Nitrogen-containing discotic ionic liquid crystal compound and preparation method thereof
  • Nitrogen-containing discotic ionic liquid crystal compound and preparation method thereof

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specific Embodiment approach

[0050] A specific embodiment of the present invention is: a nitrogen-containing discotic ionic liquid crystal compound, which has the structure of the following general formula I, wherein R 1 =C 6 h 13 , R 2 =C 6 h13 , X is an organic anion bistrifluoromethanesulfonimide ion.

[0051]

[0052] R in formula I 1 =C 6 h 13 , R 2 =C 6 h 13 , X is the preparation reaction formula of the nitrogen-containing discotic ionic liquid crystal compound of organic anion bistrifluoromethanesulfonimide ion as follows:

[0053]

[0054] In the reaction formula, THF is tetrahydrofuran; toluene is toluene; Tf 2 NLi is lithium bistrifluoromethanesulfonylimide.

[0055] The preparation of 3,4-dihexylphenylboronic acid is a prior art, see literature: Chun-Xia Liu, Hu Wang, Jun-Qi Du, Ke-Qing Zhao, Ping Hu, Bi-Qin Wang, Hirosato Monobe, BenoÎt Heinrich and Bertrand Donnio. Molecular design of benzothienobenzothiophene-cored columnar mesogens: facile synthesis, mesomorphism, and cha...

Embodiment 2

[0070] R in formula I 1 =C 6 h 13 , R 2 =C 6 h 13 , X is the preparation reaction formula of the nitrogen-containing discotic ionic liquid crystal compound of organic anion dodecylsulfonate ion as follows:

[0071]

[0072] Concrete preparation steps are as follows:

[0073] A. Suzuki coupling reaction

[0074] Add 1 molar part of 3,4-dibromopyridine, 2.5 molar parts of 3,4-dihexylphenylboronic acid, 10 molar parts of potassium carbonate, and 0.25 molar parts of tetrakis(triphenylphosphine)palladium to THF and h 2 In the mixed solution of O, under the protection of argon, the reaction was stirred at 70 ° C for 36 hours. After the reaction was completed, it was extracted with dichloromethane, the organic phase was dried with anhydrous magnesium sulfate, filtered, concentrated, and the concentrated residue was used for silica gel column layer Analysis, separation and purification (mobile phase: dichloromethane: ethyl acetate volume ratio = 10: 1) to obtain a viscous c...

Embodiment 3

[0086] R in formula I 1 =C 6 h 13 , R 2 =C 6 h 13 , X is the preparation reaction formula of the nitrogen-containing discotic ionic liquid crystal compound of chiral organic anion L-camphorsulfonate ion as follows:

[0087]

[0088] Concrete preparation steps are as follows:

[0089] A. Suzuki coupling reaction

[0090] Add 1 molar part of 3,4-dibromopyridine, 2.5 molar parts of 3,4-dihexylphenylboronic acid, 10 molar parts of potassium carbonate, and 0.25 molar parts of tetrakis(triphenylphosphine)palladium to THF and h 2 In a mixed solution of O, under the protection of argon, the reaction was stirred at 70°C for 24 hours. After the reaction was completed, it was extracted with dichloromethane, the organic phase was dried with anhydrous magnesium sulfate, filtered, concentrated, and the concentrated residue was applied to a silica gel column layer Analysis, separation and purification (mobile phase: dichloromethane: ethyl acetate volume ratio = 10: 1) to obtain a ...

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Abstract

The invention discloses a nitrogen-containing discotic ionic liquid crystal compound, which has liquid crystal performance, is wide in liquid crystal temperature range, high in clearing point temperature and good in thermal stability, can be used as a good liquid crystal material, also has a luminescence property, emits yellow light in a solution and a film, has good quantum efficiency, and can beused as an optical material. The precursor nitrogen-containing benzophenanthrene of the compound emits blue light in a solution, wherein the quantum yield is 75%, so that the compound can also be used as a luminescent material. The invention also discloses a synthesis method of the compound, wherein the compound is synthesized by adopting a Suzuki coupling reaction, an intramolecular aromatic hydrocarbon oxidative coupling reaction, an ionization reaction and an ion exchange reaction (metathesis reaction), and the preparation method is short in synthetic route and high in yield.

Description

technical field [0001] The invention relates to a nitrogen-containing discotic ionic liquid crystal compound and a preparation method thereof. Background technique [0002] Ionic liquid crystals (ILCs) are functional materials that combine partial properties of liquid crystals and ionic liquids, consisting only of cations and anions. Such unique properties make ionic liquid crystals have broad application prospects in ion-conducting materials, ordered reaction media, and functional nanomaterials. Ionic liquid crystals can adjust the properties of ionic liquid crystals (such as liquid crystal range, luminescence, etc.) by changing the types and sizes of anions and cations to meet the needs of different functions. ILCs were first reported in 1938, and so far, most studies on ILCs have mainly focused on rod-shaped ILCs, while there are few reports on disc-shaped ILCs with columnar mesophases. The reason may be the complex synthesis, characterization and tedious purification s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/18C09K19/34C09K11/06G01N33/00
CPCC07D221/18C09K19/3447C09K11/06G01N33/00C09K2211/1007C09K2211/1029
Inventor 代佳赵可清赵可孝胡平汪必琴
Owner SICHUAN NORMAL UNIVERSITY
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