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Organic radical modified DNA-cationic lipid complex and preparation method and application thereof

A cationic lipid and free radical technology, applied in electrical components, battery electrodes, circuits, etc., can solve the problems of difficult preparation of PTMA, reduce the molecular weight of polymers, reduce the performance of polymer organic free radical batteries, etc., and achieve a simple and feasible preparation process. , High physical and chemical stability, the effect of battery capacity is not easy to decay

Active Publication Date: 2013-02-06
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The first generation polymer organic free radical battery was the first use of poly 4-methacrylate-2,2,6,6-tetramethylpiperidine-1 nitrogen oxide radical (PTMA) in 2002 by Nakahara K of NEC Corporation of Japan. It is prepared as the positive electrode active material of lithium-ion batteries, but it is difficult to prepare PTMA, and the discharge capacity of the battery is less than 70% of the theoretical capacity of the polymer.
Because PTMA is synthesized by an indirect method, that is, the corresponding amine-based polymer precursor is first synthesized, and then the amine group is oxidized into nitrogen-oxygen free radicals. The oxidation reaction cannot completely convert the amine groups of the polymer precursor into nitrogen-oxygen free radicals. , the highest conversion rate is less than 70%, so that the concentration of free radicals bound to the polymer molecular chain cannot reach the theoretical value, such as the discharge capacity of a battery containing PTMA free radicals is 77Ah kg -1 , can only reach 70% of the theoretical battery capacity (theoretical value is 111Ahkg -1 )
In addition, the indirect synthesis method will also degrade the polymer, reduce the molecular weight of the polymer, and often introduce trace metal salt impurities (oxidants), etc., which will reduce the performance of the polymer organic free radical battery, and the polymer is difficult to degrade.

Method used

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  • Organic radical modified DNA-cationic lipid complex and preparation method and application thereof
  • Organic radical modified DNA-cationic lipid complex and preparation method and application thereof
  • Organic radical modified DNA-cationic lipid complex and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0045] (1) Preparation of cationic lipids containing organic free radicals: Add 11-bromo-12 acid (1.33g, 5.0mmol) to a mixture containing EDC.HCl (1.0g, 5.2mmol) and DMAP (60mg, 0.50mmol) in an ice-water bath ) in dichloromethane (45mL), reacted with 4-hydroxy-TEMPO (1.20g, 5.7mmol) at room temperature for 12h, then washed three times with 50mL water, and the organic phase was washed with MgSO 4 The dried, rotary evaporated crude product was purified by a silica gel column to obtain 1.96 g of an orange solid (85%). The orange solid was subjected to reflux reaction in pyridine solvent for 48h, the pyridine was removed by rotary evaporation, and the cationic lipid containing free radical was obtained by precipitation in diethyl ether [attached figure 2 Lipid(1)];

[0046] (2) Preparation of DNA-cationic lipid complexes modified by organic radicals (attached image 3 shown): Dissolve 2.0mmol of free radical-containing cationic lipid in 5ml THF, slowly add to deionized water to...

Embodiment 2

[0051] (1) Preparation of cationic lipids containing organic free radicals: Add 11-bromo-12 alcohol (1.33g, 5.0mmol) to a mixture containing EDC.HCl (1.0g, 5.2mmol) and DMAP (60mg, 0.50mmol) in an ice-water bath ) in dichloromethane (45mL), reacted with 3-carboxy PROXYL (1.20g, 5.7mmol) at room temperature for 12h, then washed three times with 50mL of water, and the organic phase was washed with MgSO 4 Drying. The crude product obtained by rotary evaporation was purified by a silica gel column to obtain 1.96 g of an orange solid (85%). The above product was reacted with pyridine for 48 hours under reflux, the pyridine was removed by rotary evaporation, and the cationic lipid containing free radicals was obtained by precipitation in diethyl ether [attached figure 2 lipid(L1-P)] in

[0052] (2) Preparation of DNA-cationic lipid complexes modified by organic radicals (attached image 3): Dissolve a small amount of free radical-containing cationic lipid [lipid(L1-P)] in 10ml TH...

Embodiment 3

[0057] (1) Preparation of cationic lipids containing organic free radicals: react 11-bromo-12 acid with L-glutamic acid-α,γ-dimethyl ester hydrochloride [Glu(OMe)-OMe·HCl], and the product desorbs Remove methyl to obtain carboxyl-containing product, react with 4 hydroxyl TEMPO then, prepare the lipid containing 2 TEMPO free radicals in each lipid molecular structure according to the method in example 1 (attachment figure 2 Lipid(L2-T) in.

[0058] (2) Preparation of DNA-cationic lipid complexes modified by organic radicals (attached image 3 ): Dissolve a small amount of free radical-containing cationic lipid [Lipid(L2-T)] in 10ml THF (30wt%), slowly add to deionized water to form a uniform and transparent aqueous solution (5wt%); 0.5gDNA-Na (base pair 10000) was dissolved in 100mL water (0.5wt%), and then the DNA-Na solution was slowly added to the lipid aqueous solution, the molar ratio of phosphate to lipid was 1.5, stirred for 24h, and the DNA-cation was precipitated Th...

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Abstract

The invention discloses an organic radical modified DNA (deoxyribonucleic acid)-cationic lipid complex and a preparation method and application thereof. The method comprises the following steps: nitroxide with stability of carboxyl, alcohol or acyl chloride and bromo longchain alcohol or acid react to prepare a bromo longchain compound with organic radical; then the bromo longchain compound with organic radical and pyridine react to prepare cationic lipid with organic radical; and finally, the cationic lipid with organic radical and a DNA-Na water solution are compounded to prepare the DNA-cationic lipid complex with stable organic radical. A lithium ion battery prepared by adopting the DNA-cationic lipid complex as the cathode material has second-order charge-discharge performance, has the discharge capacity reaching 124-195 percent of the theoretical value, and is quick in charge, and the charging time can be shortened to 60 minutes. According to the invention, the charge-discharge cycling stability of the lithium ion battery can be improved and the service life of the battery is prolonged.

Description

technical field [0001] The present invention relates to a DNA-cation lipid complex, in particular to an organic free radical modified DNA-cation lipid complex and a preparation method thereof. The DNA-cation lipid complex can be used as a lithium-ion battery The positive electrode material belongs to the technical field of energy materials. technical background [0002] Deoxyribonucleic acid (DNA) has stable physical and chemical properties and unique structure. In addition to arousing extensive research interest in the field of life sciences, DNA has been successfully applied to nanostructured materials. DNA is an anionic polyelectrolyte, dissolved in water in the form of DNA-Na salt, and precipitated by cationic lipids to form DNA-cationic lipid complexes. DNA-cationic lipid complexes provide useful non-viral gene carriers in the field of biotechnology and medical applications as gene therapy and vaccination. DNA-cationic lipid complexes have coiled or spherical supramol...

Claims

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Application Information

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IPC IPC(8): H01M4/60H01M4/137
CPCY02E60/122Y02E60/10
Inventor 瞿金清
Owner SOUTH CHINA UNIV OF TECH