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Preparation method of thienopyridine-type ionic rod-like liquid crystal and ionic liquid compound

An ionic liquid and compound technology, applied in organic chemistry methods, organic chemistry and other directions, can solve the problem of high price of pyridine and achieve the effect of rich chemical structure

Inactive Publication Date: 2019-07-12
SICHUAN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, the raw material thieno[3,2-c]pyridine involved in the synthesis of the thienopyridine-type ionic rod-shaped liquid crystal and ionic liquid is relatively expensive, and the domestic price is about 1500 yuan per gram.

Method used

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  • Preparation method of thienopyridine-type ionic rod-like liquid crystal and ionic liquid compound
  • Preparation method of thienopyridine-type ionic rod-like liquid crystal and ionic liquid compound
  • Preparation method of thienopyridine-type ionic rod-like liquid crystal and ionic liquid compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Embodiment 1: the synthesis of raw material thieno[3,2-c]pyridine

[0050] A preparation method of thieno[3,2-c]pyridine heterocyclic compound 3, comprising the following steps: (1) using 4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride Neutralization reaction occurs under alkaline conditions to obtain compound 2; (2) compound 2 and manganese dioxide are stirred and refluxed in toluene solvent to undergo aromatization reaction to obtain compound 3; the synthetic route is as follows:

[0051]

[0052] Add 4,5,6,7-tetrahydrothiophene[3,2-c]pyridine hydrochloride (1.0 g, 5.69 mmol) and sodium hydroxide (228 mg, 5.69 mmol) to water (20 mL) and dichloromethane (20mL), stirred and reacted at room temperature for 1-2 hours, extracted with dichloromethane, dried over magnesium sulfate and filtered, and distilled off the solvent (be careful not to depressurize, the product has sublimation properties); Manganese dioxide (3.5g, 39.8mmol) was activated at 230°C for 2-3 hou...

Embodiment 2

[0054] Example 2: Ionization of bromoperfluorohexylpropane, when X is Br -

[0055] A preparation method of a thienopyridine-type ionic rod-shaped liquid crystal compound, comprising the following steps: using thieno[3,2-c]pyridine as a raw material, and bromoperfluorohexylpropane (Br-C 3 h 6 C 6 f 13 ) heated and stirred to reflux, and reacted to obtain compound 4; its synthetic route is as follows:

[0056]

[0057] Thieno[3,2-c]pyridine (100mg, 0.74mmol) and Br-C 3 h 6 C 6 f 13 Add (978.77mg, 2.22mmol) into a small round bottom flask with a capacity of 10mL, add 2-3mL toluene as a solvent, heat and stir at 120°C, condense and reflux for about 12 hours, and use thin-layer chromatography to determine that the reaction of the raw materials is complete. Stop the reaction. After the reaction, it was purified by silica gel column chromatography (dichloromethane:ethanol=10:1) to obtain compound 4 (332 mg), with a yield of 77.89%; macroscopically, it was not easy to bec...

Embodiment 3

[0060] Embodiment 3: ion exchange, this moment X is I -

[0061] A preparation method of a thienopyridine-type ionic rod-shaped liquid crystal compound, comprising the following steps: using thieno[3,2-c]pyridine as a raw material, and bromoperfluorohexylpropane (Br-C 3 h 6 C 6 f 13 ) after ionization, use KI to perform ion exchange, and react to obtain compound 5; its synthetic route is as follows:

[0062]

[0063] Add compound 4 (100mg, 0.17mmol) and KI (144.05mg, 0.87mmol) into a small round bottom flask with a capacity of 10mL, add 2-3mL dichloromethane and 1-2mL water as solvents, and stir the reaction at room temperature After about 1-2 hours, the reaction is terminated after confirming that the raw materials are completely reacted by thin-layer chromatography. After the reaction, extract with dichloromethane (note that it cannot be chemically dried to prevent the introduction of impurity ions), then distill under reduced pressure on a rotary evaporator, and obs...

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Abstract

The invention discloses a preparation method of a thienopyridine-type ionic rod-like liquid crystal and ionic liquid compound. The thienopyridine-type ionic rod-like liquid crystal and ionic liquid compound have structures as shown in a general formula I, a general formula II and a general formula III. Asymmetric compounds represented by the general formula I show a liquid crystal phase in a certain temperature range, and different inorganic ions and organic ions can be regulated and controlled for carrying out ion exchange. On one hand, storage and release of the inorganic ions and organic ions can be realized in a liquid crystal phase range according to needs; on the other hand, conversion between ionic liquid crystals and ionic liquid is realized through ion regulation and control, anda directional reference is provided for design and application of ion battery materials, special molecular devices and the like. The compounds represented by the general formula II and the general formula III provides another probable design and synthesis idea for the thienopyridine-type rod-like (ion) liquid crystal (plastic crystal) compound. The preparation method is short in route and high inyield.

Description

technical field [0001] The invention relates to a preparation method of thienopyridine type ionic rod liquid crystal and ionic liquid compound. Background technique [0002] In the design and synthesis of lamellar and columnar phase liquid crystal compounds, thiophene is one of the most studied five-membered heterocyclic compounds. Due to its electron-rich properties, stable chemical properties, and easy processing, it has been widely used. Based on this, we designed an ionic rod-shaped liquid crystal and ionic liquid compound containing a thienopyridine structure. Because of its certain charge transport ability and ion transport ability, it is compatible with lithium salts and sodium salts. Devices, ion battery materials, etc. have broad application prospects. There have been many reports on liquid crystal compounds with lamellar, nematic, and columnar phases, but reports on the formation of smectic phases are limited. For ionic rod-like liquid crystals forming smectic p...

Claims

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Application Information

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IPC IPC(8): C07D495/04
CPCC07B2200/13C07D495/04
Inventor 林航赵可清赵可孝胡平汪必琴
Owner SICHUAN NORMAL UNIVERSITY
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