CN108929443A - The covalent organic polymer material JLUE-H of hydrogen bondCThe synthetic method of OP - Google Patents

The covalent organic polymer material JLUE-H of hydrogen bondCThe synthetic method of OP Download PDF

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CN108929443A
CN108929443A CN201811029125.1A CN201811029125A CN108929443A CN 108929443 A CN108929443 A CN 108929443A CN 201811029125 A CN201811029125 A CN 201811029125A CN 108929443 A CN108929443 A CN 108929443A
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CN108929443B (en
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徐非凡
刘美君
李阳雪
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Jilin University
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Abstract

A kind of covalent organic polymer material JLUE-H of hydrogen bondCThe synthetic method of OP, this method are: by benzene -1,3, tri- hydrazides of 5- is dissolved in organic solvent dimethyl sulfoxide, and concentration 0.02mol/L is named as solution A；Terephthalic acid (TPA) is dissolved in solution A, concentration 0.03mol/L is named as B solution；4,4 '-diphenyl-dimethanals are dissolved in B solution, concentration 0.03mol/L, are named as C solution, the molar ratio of each substance in C solution are as follows: benzene -1,3, tri- hydrazides of 5-: terephthalic acid (TPA): 4,4 '-diphenyl-dimethanals=2:3:3.C solution is placed in thermostatical oil bath, 100 DEG C of heating are reacted 10 seconds, and yellow solid is obtained；Yellow solid is placed in bag filter, using distilled water as dialyzate, removes organic solvent, after 2-3 days, obtains obtaining object.It will acquire object to pour into beaker, freeze under cryogenic, be then freeze-dried, obtain the covalent organic polymer material JLUE-H of hydrogen bondCOP。JLUE‑HCOP has amorphous state undefined structure, has excellent thermal stability and biggish specific surface area.

Description

The covalent organic polymer material JLUE-H of hydrogen bondCThe synthetic method of OP
Technical field
The invention belongs to nano materials and environmentally conscious materials preparation field, are related to the covalent organic polymer material JLUE- of hydrogen bond HCThe synthetic method of OP.
Background technique
Covalent organic polymer (Covalent Organic Polymers, COPs) is made of covalent bond, including crystal and Amorphous form, they have clearly illustrated its surprising evil spirit in environmental area, medical health field and energy related field Power.In general, being synthesized by for COPs forms limited connection using the monomer of limited one or two kinds of types to realize, wrap Include B-O key, C-N key, C-C key, N-N key etc., for constructing 2D/3D structure.Obviously, although obtain progress with nowadays the case where Identical, the type and structure type of COPs are related with dull component and special combination, this makes the satisfaction of COPs It is not fully up to expectations.In this way, it is that need not set that exploring, which has the novel C OPs necessity of a variety of connections and multifunction structure, Doubtful.
Dependent on weak interaction hydrogen bond organic backbone (Hydrogen-bonded Organic Frameworks, HOFs), such as Van der Waals force, hydrogen bond, pi-pi accumulation etc. have been increasingly becoming one newly since Chen Shi group in 2011 is put forward for the first time Height innovation theme.However, the weakness of HOFs weak stability has been more than the advantage of mild synthesis condition, this makes HOFs exist Practical application in environment is hindered.By the inspiration of Lin et al. pioneering work established, similar concept can produce to open It sends out while having the advantages that the covalent organic polymer (H of the hydrogen bond of COPs and HOFsCOPs)。
Summary of the invention
The purpose of the present invention is to provide a kind of covalent organic polymer material JLUE-H of hydrogen bondCThe synthetic method of OP, institute JLUE-H obtainedCOP material has big specific surface area, and has good thermal stability and aqueous stability.
A kind of covalent organic polymer material JLUE-H of hydrogen bondCThe synthetic method of OP, comprising the following steps:
Step 1: by benzene -1,3, tri- hydrazides of 5- (BTCH) is dissolved in organic solvent dimethyl sulfoxide (DMSO), keeps its dense Degree is 0.02mol/L, is named as solution A.
Step 2: terephthalic acid (TPA) (BDC) is dissolved in solution A, and keeping its concentration is 0.03mol/L, and it is molten to be named as B Liquid.
Step 3: 4,4 '-diphenyl-dimethanals (BPDA) are dissolved in B solution, and keeping its concentration is 0.03mol/L, name For C solution.
The molar ratio of each substance in above-mentioned C solution are as follows: three hydrazides of benzene -1,3,5-: terephthalic acid (TPA): 4,4 '-biphenyl diformazans Aldehyde=2:3:3.
Step 4: above-mentioned C solution is placed in thermostatical oil bath, and 100 DEG C of heating are reacted 10 seconds, and it is solid to obtain yellow Body；
Step 5: the yellow solid that step 4 is obtained is placed in bag filter, using distilled water as dialyzate, is removed organic Solvent takes out after occurring obvious layering after 2-3 days, in bag filter, obtains obtaining object.
Step 6: the acquisition object that step 5 obtains being poured into beaker, is freezed under cryogenic, and it is dry then to carry out freezing It is dry, obtain the covalent organic polymer material JLUE-H of hydrogen bondCOP。
The beneficial effects of the present invention are:
The covalent organic polymer material JLUE-H that synthetic method of the present invention obtainsCOP, with amorphous state undefined structure, Excellent thermal stability and biggish specific surface area.
Detailed description of the invention
Fig. 1 is the JLUE-H that the present invention synthesizesCThe synthesis schematic diagram of OP.
Fig. 2 is the JLUE-H of synthesis of the inventionCThe powder X-ray diffractogram of OP.
Fig. 3 is the JLUE-H that the present invention synthesizesCThe electron scanning micrograph of OP.
Fig. 4 is the JLUE-H that the present invention synthesizesCFourier transformation-infrared spectrogram of OP.
Fig. 5 is the JLUE-H that the present invention synthesizesCThe solid-state nuclear magnetic resonance of OP13C CP/MAS spectrogram.
Fig. 6 is the JLUE-H that the present invention synthesizesCThe thermogravimetric curve of OP in a nitrogen atmosphere.
Fig. 7 is the JLUE-H that the present invention synthesizesCThe nitrogen adsorption desorption curve of OP-.
Specific embodiment
Synthesize JLUE-HCRaw material used in OP is commercially available product.
As shown in Figure 1, a kind of covalent organic polymer material JLUE-H of hydrogen bondCThe synthetic method of OP.The following steps are included:
Step 1: it weighs three hydrazides (BTCH) of 50mg benzene -1,3,5- and is dissolved in 10mL organic solvent dimethyl sulfoxide (DMSO) In, keeping its concentration is 0.02mol/L, is named as solution A.
Step 2: weighing 100mg terephthalic acid (TPA) (BDC) and be dissolved in solution A, and keeping its concentration is 0.03mol/L, name For B solution.
Step 3: weighing 4,4 '-diphenyl-dimethanal (BPDA) of 40mg and be dissolved in B solution, and keeping its concentration is 0.03mol/ L is named as C solution.
The molar ratio of each substance in above-mentioned C solution are as follows: three hydrazides of benzene -1,3,5-: terephthalic acid (TPA): 4,4 '-biphenyl diformazans Aldehyde=2:3:3.
Step 4: above-mentioned C solution is placed in thermostatical oil bath, and 100 DEG C of heating are reacted 10 seconds, and it is solid to obtain yellow Body；
Step 5: the yellow solid that step 4 is obtained is placed in bag filter, using distilled water as dialyzate, is removed organic Solvent takes out after occurring obvious layering after 2-3 days, in bag filter, obtains obtaining object.
Step 6: the acquisition object that step 5 obtains being poured into beaker, is freezed under cryogenic, and it is dry then to carry out freezing It is dry, obtain the covalent organic polymer material JLUE-H of hydrogen bondCOP。
The JLUE-H that the present invention synthesizesCThe powder X-ray diffractogram of OP is as shown in Figure 2.
The JLUE-H that the present invention synthesizesCThe electron scanning micrograph of OP is as shown in Figure 3.
The JLUE-H that the present invention synthesizesCFourier transformation-infrared spectroscopy of OP is as shown in Figure 4.
The JLUE-H that the present invention synthesizesCThe solid-state nuclear magnetic resonance of OP13C CP/MAS spectrum is as shown in Figure 5.
The JLUE-H that the present invention synthesizesCThe thermogravimetric curve of OP in a nitrogen atmosphere is as shown in Figure 6.
The JLUE-H that the present invention synthesizesCThe nitrogen adsorption desorption curve of OP is as shown in Figure 7.
The JLUE-H that the present invention synthesizesCOP material advantage is:
1, amorphous state undefined structure, biggish specific surface area have strong adsorptivity to pollutant
2, with excellent thermal stability.

Claims (1)

1. a kind of covalent organic polymer material JLUE-H of hydrogen bondCThe synthetic method of OP, comprising the following steps:
Step 1: by benzene -1,3, tri- hydrazides of 5- is dissolved in organic solvent dimethyl sulfoxide, and keeping its concentration is 0.02mol/L, life Entitled solution A；
Step 2: terephthalic acid (TPA) is dissolved in solution A, and keeping its concentration is 0.03mol/L, is named as B solution；
Step 3: 4,4 '-diphenyl-dimethanals are dissolved in B solution, and keeping its concentration is 0.03mol/L, are named as C solution；C is molten The molar ratio of each substance in liquid are as follows: three hydrazides of benzene -1,3,5-: terephthalic acid (TPA): 4,4 '-diphenyl-dimethanals=2:3:3；
Step 4: above-mentioned C solution is placed in thermostatical oil bath, and 100 DEG C of heating are reacted 10 seconds, obtains yellow solid；
Step 5: the yellow solid that step 4 is obtained is placed in bag filter, using distilled water as dialyzate, is removed organic molten Agent is taken out after occurring obvious layering after 2-3 days, in bag filter, obtains obtaining object；
Step 6: the acquisition object that step 5 obtains being poured into beaker, freezes, is then freeze-dried under cryogenic, Obtain the covalent organic polymer material JLUE-H of hydrogen bondCOP。
CN201811029125.1A 2018-09-05 2018-09-05 Synthesis method of hydrogen bond covalent organic polymer material JLUE-HCOP Active CN108929443B (en)

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CN110903478A (en) * 2019-12-13 2020-03-24 吉林大学 Synthesis method of hydrogen bond covalent organic polymer material HCOP-7
CN112979986A (en) * 2021-03-20 2021-06-18 吉林大学 Hydrogen bond covalent organic polymer material HcSynthesis method of OP-66
CN113402729A (en) * 2021-08-04 2021-09-17 吉林大学 Hydrogen bond covalent organic aerogel material HCMethod for synthesizing OA-3
CN115646463A (en) * 2022-11-01 2023-01-31 吉林大学 In-situ injection method for repairing levofloxacin polluted groundwater by multi-component covalent organic polymer based on competitive adsorption

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Publication number Priority date Publication date Assignee Title
CN110903478A (en) * 2019-12-13 2020-03-24 吉林大学 Synthesis method of hydrogen bond covalent organic polymer material HCOP-7
CN110903478B (en) * 2019-12-13 2022-02-25 吉林大学 Synthesis method of hydrogen bond covalent organic polymer material HCOP-7
CN112979986A (en) * 2021-03-20 2021-06-18 吉林大学 Hydrogen bond covalent organic polymer material HcSynthesis method of OP-66
CN112979986B (en) * 2021-03-20 2021-11-19 吉林大学 Hydrogen bond covalent organic polymer material HcSynthesis method of OP-66
CN113402729A (en) * 2021-08-04 2021-09-17 吉林大学 Hydrogen bond covalent organic aerogel material HCMethod for synthesizing OA-3
CN115646463A (en) * 2022-11-01 2023-01-31 吉林大学 In-situ injection method for repairing levofloxacin polluted groundwater by multi-component covalent organic polymer based on competitive adsorption
CN115646463B (en) * 2022-11-01 2023-12-05 吉林大学 In-situ injection method for repairing levofloxacin polluted groundwater by multicomponent covalent organic polymers based on competitive adsorption

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