Viologen derivative, preparation method thereof and electrochromic device
A derivative, viologen technology, applied in the field of electrochromic displays, can solve the problems that viologen materials are difficult to meet the multi-functional research needs, and achieve ultra-long cycle stability, stable fluorescence emission phenomenon, and enhanced fluorescence performance Effect
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[0053] The present invention also provides a preparation method of the viologen derivative, specifically:
[0054] The preparation method of the viologen derivatives shown in (I1) comprises the following steps:
[0055] A) reacting 4-pyridineboronic acid and a compound having a structure of formula (I11) under the action of a catalyst to obtain an initial reactant having a structure of formula (I12);
[0056] B) reacting the initial reactant with a compound having the structure of formula (I13) in a solvent to obtain a precursor having the structure of formula (I14);
[0057] C) anion-exchanging the precursor with a compound containing hexafluorophosphate to obtain a viologen derivative as shown in (I1);
[0058]
[0059] Among them, X 1 and X 2 independently selected from halogen;
[0060] R 1 It is selected from a substituted C1-C5 alkyl group or an unsubstituted C1-C5 alkyl group.
[0061] In the above preparation of the viologen derivatives shown in formula (I1), ...
Embodiment 1
[0089] Example 1 Synthesis of 4,4-(1,4-phenylene)bis(1-picoline) lithium hexafluorophosphate (PV)
[0090] Add 1,4-diiodobenzene (1.0g, 3.0mmol), 4-pyridineboronic acid (1.0g, 8.1mmol), potassium carbonate (1.2g, 8.6mmol), catalyst tetratriphenyl Phosphine palladium (0.28g, 0.24mmol) and a magnetic stirrer, protect the reaction system with argon, then inject 100mL of a mixed solvent of dioxane and water 4:1 into the round bottom flask, and the reaction system is refluxed and stirred for 48h;
[0091] After the reaction, the system was cooled to room temperature, deionized water was added, the organic phase was extracted with chloroform, dried over anhydrous sodium sulfate, and then the solvent chloroform was filtered and spin-dried to obtain a viscous crude product, which was then purified by column chromatography , to obtain a colorless oily liquid 1;
[0092] Add compound 1 (1g, 4.3mmol) and excess methyl iodide into a round bottom flask, add a magnetic stirrer, use chlorof...
Embodiment 2
[0096] Example 2 Synthesis of 4,4-(naphthalene-1,4-diyl)bis(1-methylpyridyl)hexafluorophosphate (NV)
[0097] Add 1,4-dibromonaphthalene (1.0g, 3.5mmol), 4-pyridineboronic acid (1.2g, 9.7mmol), potassium phosphate (2.2g, 10.3mmol) and a magnetic stirring bar in a 150mL round bottom flask, The reaction system was protected by argon, and tricyclohexylphosphine (0.1g, 0.35mmol) and catalyst tris(dibenzylidene ketone)dipalladium (0.16g, 0.17mmol) were dissolved in dioxane and water 4:1 Inject 100mL of mixed solvent into a round bottom flask, and stir the reaction system under reflux for 24h;
[0098] The post-treatment of the reaction, the methylation of the pyridine compound, and the anion exchange process were the same as the preparation process of Example 1, and compound NV was finally obtained. figure 2 is the H NMR spectrum of compound NV, 1 H NMR (300MHz, DMSO-d 6 ,ppm):δ9.261-9.239(d,4H),8.466-8.444(d,4H),8.028-7.994(m,2H),7.930(s,2H),7.855-7.824(m,2H),4.546 (s,6H).
...
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