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Preparation and photocatalyst application of dibenzothiophene diketo conjugated microporous polymers

A benzodithiophenedione-based, conjugated microporous technology, which is applied in the preparation of organic compounds, catalytic reactions, organic compound/hydride/coordination complex catalysts, etc., can solve the problems of general selectivity and achieve Wide application prospects, high conversion rate, high selectivity effect

Inactive Publication Date: 2018-02-16
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Kian Ping Loh's group reported that carbazole-based conjugated microporous polymers were used as photocatalysts in the oxidation of thioether, with a conversion rate of more than 99%, but the selectivity was average (ACS Catal, 2016, 6, 3594-3599)

Method used

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  • Preparation and photocatalyst application of dibenzothiophene diketo conjugated microporous polymers
  • Preparation and photocatalyst application of dibenzothiophene diketo conjugated microporous polymers
  • Preparation and photocatalyst application of dibenzothiophene diketo conjugated microporous polymers

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Weigh benzodithiophenedione (220mg, 1mmol) and dissolve in 30mL anhydrous CHCl 3 , quickly pipette the liquid bromine (400mg, 2.5mmol) mixed with 10mL anhydrous CHCl 3 Add to constant pressure dropping funnel, degas, N 2 Protection, slowly drop liquid bromine and anhydrous CHCl in a low-temperature reactor at -15°C 3 The mixed solution was stirred for 24 hours for 1 hour; saturated sodium thiosulfate solution was added to extract bromine, the organic layer was dried with anhydrous sodium sulfate for 2 hours, filtered, the organic layer was spin-dried, passed through the column quickly (PE:DCM=2:1), and collected Benzodithiophenedione bromide (M1) (198 mg, yield: 90%) was obtained as a bright yellow solid.

[0033] 1 H NMR (400MHz, CDCl 3 ):δ7.69(m,2H)

reference example 1

[0035] N,N-Dimethylthiophene-3-carboxamide (16.3g, 105.0mmol) and N-bromosuccinimide (NBS, 41.1g, 231.1mmol) were added to 150mL DMF, and stirred at room temperature for 2 hours in the dark. Then it was washed with water, extracted with ethyl acetate, and the organic phase was dried with anhydrous magnesium sulfate. After filtration, several layers were spin-dried and passed through the column. A yellow solid was obtained.

[0036] The yellow solid (4.9g, 15.4mmol, 40mL) was dissolved in ether, and tert-butyllithium (15.3mmol, 2.5M in hexane) was slowly added dropwise under ice-cooling conditions. Return to room temperature after the dropwise addition, then add saturated NH 4 Cl aqueous solution (30 mL), the precipitate was collected, and then passed through the column. Obtained yellow solid M1 (1.3 g, 37%)

Embodiment 2

[0038] Weigh monomer benzodithiophenedione bromide M1 (66mg, 0.17mmol) and 1,3,5-triynylbenzene (54mg, 0.36mmol) into a 25ml single-necked flask, add 12mL DMF and 36mL TEA, mix the solution to dissolve the powder, freeze the solution with liquid nitrogen and degas it, protect it with N2, thaw it with water at room temperature, repeat the above operations (freezing, degassing, thawing) three times in sequence, add Pd (pph 3 ) 4 (22mg, 6mol%), CuI (6mg, 10mol%), degassed, N 2 After protection, freezing, degassing, and thawing were repeated three times, the temperature was raised from room temperature to 100°C, benzodithiophenedione bromide (134 mg, 0.33 mmol) was added dropwise for one hour, and the reaction was stirred for 96 hours. After the device was cooled to room temperature, the turbid liquid was suction-filtered, and the filter residue was stirred in 5mol / L HCl solution for 2 hours and then suction-filtered. The filter residue was extracted with THF, chloroform, and ace...

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Abstract

The invention discloses novel dibenzothiophene diketo conjugated microporous polymers (CMPs), which can be prepared easily and have an excellent performance on catalyzing oxidation of thioether. For the first time, the inventor finds that at a room temperature, CMPs can catalyze oxidation of thioether under illumination. The prepared CMPs have the advantages of good performance on absorbing UV rays, large specific area, good thermal stability, and high chemical stability, can efficiently catalyze the oxidation of thioether, achieve high selectivity, can be used in circles, and have an important application value and application prospect in oxidation of thioether of organic synthesis.

Description

technical field [0001] The invention belongs to the field of preparation and application of catalytic functional materials. Specifically, it relates to the preparation of a class of benzodithiophenedione-based conjugated microporous polymers (CMPs), and their application as photocatalysts. Background technique [0002] As we all know, with the continuous development of the economy, the energy is becoming increasingly exhausted, and it has become the most important goal of scientists all over the world to find sustainable green new energy to change the current severe energy situation. Among the many existing new energy sources, solar energy has attracted widespread attention because of its abundant reserves on the earth, wide irradiation range, and clean and pollution-free advantages. In 2008, MacMillan's research group used Ru(bpy) under visible light conditions 3 Cl 2 As a photocatalyst, it successfully catalyzes the α-position asymmetric alkylation of aldehyde groups (S...

Claims

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Application Information

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IPC IPC(8): C08G61/12B01J31/06C07C315/02C07C317/14
CPCC07C315/02C08G61/126B01J31/06B01J2231/70C08G2261/124C08G2261/142C08G2261/3243C08G2261/18C08G2261/312C08G2261/415C08G2261/344B01J35/39C07C317/14
Inventor 潘春跃黄俏喻桂朋
Owner CENT SOUTH UNIV
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