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Polynorbornene porous material containing azobenzene structure and preparation method thereof

A technology of polynorbornene and porous materials, applied in the field of materials, can solve the problems of poor functional group tolerance, small molecular weight, long time for potassium hydroxide-mediated coupling polymerization reaction, etc., and achieves the effect of high efficiency and mild reaction conditions.

Active Publication Date: 2021-08-27
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the precious metals used in the metal-catalyzed method will increase the preparation cost; the coupling polymerization reaction mediated by potassium hydroxide takes a long time and consumes a lot of energy; strong oxidants require harsh reaction conditions and have poor tolerance to functional groups that are easily oxidized; The electrophilic addition polymerization of nitrogen salts is only suitable for monomers with high activity and low molecular weight

Method used

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  • Polynorbornene porous material containing azobenzene structure and preparation method thereof
  • Polynorbornene porous material containing azobenzene structure and preparation method thereof
  • Polynorbornene porous material containing azobenzene structure and preparation method thereof

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preparation example Construction

[0060] Such as figure 2 As shown, a flow chart of a preparation method of a polynorbornene porous material containing an azobenzene structure provided by the present invention may specifically include:

[0061] Step 1, preparing disubstituted norbornene p-nitrophenyl ether III: using norbornene diol shown in structural formula IV and nitrohalobenzene shown in structural formula V to prepare disubstituted norbornene p-nitrophenyl ether shown in structural formula III Nitrophenyl ether;

[0062] Step 2, preparation of polynorbornene p-nitrophenyl ether II: the disubstituted norbornene p-nitrophenyl ether shown in the structural formula III is prepared by olefin ring-opening metathesis polymerization under the action of a ruthenium metal catalyst Polynorbornene p-nitrophenyl ether shown in II;

[0063] Step 3, preparing polynorbornene porous material containing azobenzene structure I: the polynorbornene p-nitrophenyl ether shown in the structural formula II and a reducing agen...

Embodiment 1

[0067] Example 1, Preparation of azobenzene-linked polynorbornene porous material in Endo-configuration

[0068] Step 1: Prepare Norbornenediol of Endo-configuration with reference to related technology

[0069] Measure DCPD (30mL, 0.35mol) in a 100mL flask with a measuring cylinder, heat up to 200°C, distill and condense to obtain cyclopentadiene; Cis-1,4-butenediol (18mL, 0.2mol) was placed in a 250mL sealed reaction tube, heated to 210°C for 6h. Cool to room temperature to precipitate white crystals, obtain endo-configuration norbornenediol (14g, 45%) by filtration, dissolve the filtrate in hot water (100ml, about 80°C), separate the liquid with a separatory funnel, and dissolve the water The phase was concentrated under reduced pressure, and the oil was recrystallized to obtain endo-configured norbornene diol (7.0g, 23%). The two recrystallizations produced a total of endo-configuration norbornene diol (21g, Overall yield 68%).

[0070] Wherein, the DCPD is a cyclopenta...

Embodiment 2

[0089] Example 2, Synthesis of azobenzene-linked polynorbornene porous material in Endo-configuration

[0090] Step 1: Preparation of Norbornenediol in Endo-configuration

[0091] Weigh norbornene anhydride (VI, 4.9g, 30mmol, 1equiv.) in endo configuration, add it into anhydrous tetrahydrofuran (100mL) and stir to dissolve, place it in an ice-water bath to cool; weigh LiAlH 4 (3.6g, 90mmol, 3equiv.) and slowly added to the above mixture, maintained at low temperature and stirred for 0.5 hours, then slowly raised to room temperature and stirred for 12 hours. The reaction was cooled in an ice-water bath, ice water (8 mL) was slowly added to quench the reaction, and then 10% sodium hydroxide solution (10 mL) was slowly added. After the reaction was quenched, suction filtration under reduced pressure was carried out, the filter residue was washed with ethyl acetate (3x 50mL), and the filtrate was washed with anhydrous MgSO 4 Dried, concentrated and dried with a rotary evaporator...

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Abstract

The invention provides a polynorbornene porous material containing an azobenzene structure and a preparation method of the polynorbornene porous material. The structural formula of the polynorbornene porous material containing the azobenzene structure is shown in the specification. The method comprises the following steps: preparing disubstituted norbornene p-nitrophenyl ether from norbornene diol with endo-and exo configurations and nitro halobenzene; under the action of a ruthenium metal catalyst, carrying out olefin ring-opening metathesis polymerization reaction on the disubstituted norbornene p-nitrophenyl ether to prepare polynorbornene p-nitrophenyl ether; and carrying out reduction coupling reaction on the polynorbornene p-nitrophenyl ether to prepare the polynorbornene porous material containing the azobenzene structure. According to the preparation method, through rational design, an olefin ring-opening metathesis polymerization reaction and an azo coupling polymerization reaction are fully combined, so that the preparation method has the characteristics of high efficiency and practical production. In addition, the preparation method also has the characteristics of simplicity, feasibility, good physical and chemical stability, high reaction speed, mild reaction conditions and the like.

Description

technical field [0001] The invention relates to the field of materials, in particular to a polynorbornene porous material containing an azobenzene structure and a preparation method thereof. Background technique [0002] Organic porous polymers (POPs) are new polymer porous materials with microporous, mesoporous or hierarchical porous structures formed by covalently connecting light elements such as C, H, O, and N. With the advantages of low density and adjustable pore size, it has great potential in adsorption performance, and is widely used in the fields of gas storage, separation and treatment of organic environmental pollutants. [0003] Related technologies mainly use metal (such as noble metals such as Au) catalysis, potassium hydroxide-mediated polymerization of anilines and nitrobenzenes, and strong oxidants (hypochlorous acid, etc.) Benzene porous polymer. In addition, diazonium salt addition polymerization of anilines and reductive coupling polymerization of nitr...

Claims

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Application Information

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IPC IPC(8): C08G61/08C08G81/00B01J20/26B01J20/30B01D53/02
CPCC08G61/08C08G81/00B01J20/265B01D53/02C08G2261/11C08G2261/1424C08G2261/143C08G2261/148C08G2261/3325C08G2261/418B01D2257/504B01D2257/70Y02C20/40
Inventor 黄木华彭山青张志豪尤尼斯柴春鹏刘艳
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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