A kind of polythiophene containing nitroxide free radical in side chain and its preparation method and application
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A technology of nitroxide radical and polythiophene, which is applied in the field of electrochemistry and can solve the problems of difficult product separation and the like
Active Publication Date: 2022-04-19
ZHEJIANG UNIV OF TECH
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But when this kind of nitrogen oxide radical is used as a homogeneous catalyst, it is not easy to separate from the product after the reaction.
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Embodiment 1
[0026] The synthesis of embodiment 1 TT-TEMPO
[0027] In a 100 mL round bottom bottle, 5 mmol of TTAA, 5 mmol of 4-OH-TEMPO, 2 mmol of DMAP, 50 mL of dichloromethane and 5 mmol of DCC were sequentially added, and the reaction was stirred at room temperature for 12 h. The reaction solution was filtered, and the filtrate was evaporated under reduced pressure to remove the solvent, and then separated by column chromatography, using a mixture of ethyl acetate / petroleum ether with a volume ratio of 1:5 as the eluent, and the eluate containing the target compound was collected and evaporated to remove the solvent. The solvent is the monomer TT-TEMPO. The isolated yield was 80%.
[0028] Due to the presence of free radicals in TT-TEMPO molecules, NMR cannot be used to characterize directly, so TT-TEMPO was reduced with isoascorbic acid, and then characterized by NMR and MS. 1 H NMR (500M, CDCl 3 )δ:7.33-7.01(m,7H),5.08(s,1H),3.70(s,2H),1.91(d,J=10.0Hz,2H),1.58(t,J=11.2Hz,2H), 1....
Embodiment 2
[0029] The synthesis of embodiment 2 TT-TEMPO
[0030] The reaction steps were the same as in Example 1, except that the amount of 4-OH-TEMPO was changed to 6 mmol, and the amount of DMAP was changed to 1 mmol. After 12 hours of reaction, the separation yield of TT-TEMPO was 72%.
Embodiment 3
[0031] The synthesis of embodiment 3 TT-TEMPO
[0032] The reaction steps are the same as in Example 1, except that the amount of 4-OH-TEMPO is changed to 6 mmol, the amount of DCC is changed to 6 mmol, and the reaction is 8 hours. The separation yield of TT-TEMPO is 83%.
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Abstract
The invention discloses a polythiophene with nitroxide free radicals in the side chain and its preparation method and application. ‑2,2,6,6‑tetramethylpiperidine nitroxide free radical is the reaction raw material, 4‑dimethylaminopyridine is the catalyst, and dicyclohexylcarbodiimide is the dehydrating agent. The reaction is carried out in the methyl chloride solvent for 8-12 hours. After the reaction is completed, the reaction liquid is post-treated to obtain TT-TEMPO; in the sodium perchlorate boron trifluoride ether solution, the obtained TT-TEMPO is added to perform electropolymerization; the electropolymerization is completed Finally, wash the electrode surface to obtain the polymer PTT-TEMPO attached to the electrode surface. The PTT-TEMPO has catalytic activity similar to TEMPO. It is used in the electrocatalytic oxidation of alcohol to prepare aldehyde, and the results show that it has good catalytic oxidation performance.
Description
technical field [0001] The invention belongs to the technical field of electrochemistry, and in particular relates to a polythiophene whose side chain contains nitroxide free radicals, a preparation method and application thereof. Background technique [0002] Conductive polymer refers to a conductive material formed by chemically or electrochemically doping a polymer containing a long-chain conjugated π bond structure. Conductive polymers not only have the characteristics of metals and semiconductors, but also retain the advantages of good flexibility, light weight, and processability of polymers. In addition, its biggest feature is that the conductivity can be changed in a wide range of insulator-semiconductor-metal state. Conductive polymers have attracted extensive attention in various fields because of their special structures and excellent physical and chemical properties. [0003] Conductive polymers that are currently being studied include polyaniline, polypyrrole,...
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