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A kind of 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 small molecular weight, poor tolerance of functional groups, increased production costs, etc., and achieve the effect of mild reaction conditions and efficient methods

Active Publication Date: 2022-07-12
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • A kind of polynorbornene porous material containing azobenzene structure and preparation method thereof
  • A kind of polynorbornene porous material containing azobenzene structure and preparation method thereof
  • A kind of polynorbornene porous material containing azobenzene structure and preparation method thereof

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preparation example Construction

[0060] like figure 2 As shown, the 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, preparation of 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 shown in structural formula III Nitrophenyl ether;

[0062] Step 2, preparation of polynorbornene-p-nitrophenyl ether II: the disubstituted norbornene-p-nitrophenyl ether represented by the structural formula III, under the action of a ruthenium metal catalyst, undergoes an olefin ring-opening metathesis polymerization reaction to prepare the structural formula The polynorbornene p-nitrophenyl ether shown in II;

[0063] Step 3: Preparation of the azobenzene-containing polynorbornene porous material I: the polynorbornene p-nitrophenyl ether sho...

Embodiment 1

[0067] Example 1. Preparation of Endo-Configured Azobenzene-Linked Polynorbornene Porous Materials

[0068] Step 1: Preparation of Endo-configured norbornenediol with reference to related techniques

[0069] Measure DCPD (30mL, 0.35mol) in a 100mL flask with a measuring cylinder, heat up to 200°C, and obtain cyclopentadiene after distillation and condensation; Cis-1,4-butenediol (18 mL, 0.2 mol) was placed in a 250 mL sealed reaction tube, heated to 210° C. and reacted for 6 h. After cooling to room temperature, white crystals were precipitated, and the endo-configuration norbornene diol (14g, 45%) was obtained by filtration. The filtrate was dissolved in hot water (100ml, about 80°C), and the water was separated with a separatory funnel. The phase was concentrated under reduced pressure, and the oil was recrystallized to obtain endo-configuration norbornene diol (7.0 g, 23%). The overall yield was 68%).

[0070] Wherein, the DCPD is a cyclopentadiene dimer.

[0071] Step ...

Embodiment 2

[0089] Example 2. Synthesis of Endo-configured azobenzene-linked polynorbornene porous materials

[0090] Step 1: Preparation of Endo-Configured Norbornene Diols

[0091] Weigh norbornene anhydride (VI, 4.9 g, 30 mmol, 1 equiv.) with endo configuration, add it to anhydrous tetrahydrofuran (100 mL), stir to dissolve, and place it in an ice-water bath to cool; weigh out LiAlH 4 (3.6 g, 90 mmol, 3 equiv.) and slowly added to the above-mentioned mixed solution, maintained at low temperature and stirred for 0.5 hours, and 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, carry out suction filtration under reduced pressure, the filter residue was washed with ethyl acetate (3×50 mL), and the filtrate was washed with anhydrous MgSO 4 Dry, concentrate and dry with a rotary ev...

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Abstract

The invention provides a polynorbornene porous material containing an azobenzene structure and a preparation method thereof. The structural formula of the polynorbornene porous material containing the azobenzene structure is as follows: the method includes: norbornene diol and nitrohalobenzene in endo- and exo configurations to prepare disubstituted norbornene-p-nitro Phenyl ether; under the action of ruthenium metal catalyst, disubstituted norbornene-p-nitrophenyl ether undergoes ring-opening metathesis polymerization of olefins to prepare polynorbornene-p-nitrophenyl ether; polynorbornene-p-nitrophenyl ether Polynorbornene porous materials containing azobenzene structure were prepared by reductive coupling reaction. The preparation method fully combines the olefin ring-opening metathesis polymerization reaction and the azo coupling polymerization reaction through rational design, 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 and practicability, good physical and chemical stability, fast 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] Porous organic polymers (POPs) are new porous macromolecular materials with micropore, mesopore or hierarchical porous structure formed by covalent bonding of light elements such as C, H, O, N, etc. Due to 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 organic environmental pollutant treatment. [0003] The related technology mainly adopts metal (such as noble metal such as Au) catalyzed, potassium hydroxide-mediated polymerization of anilines and nitrobenzenes and strong oxidant (hypochlorous acid, etc.)-mediated oxidative coupling polymerization to prepare azo. Benzene porous polymer. In addition, diazonium salt addition polymerizati...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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