CN109400894B - Hyperbranched polytriazole functional polymer material and preparation method thereof - Google Patents

Hyperbranched polytriazole functional polymer material and preparation method thereof Download PDF

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CN109400894B
CN109400894B CN201811156670.7A CN201811156670A CN109400894B CN 109400894 B CN109400894 B CN 109400894B CN 201811156670 A CN201811156670 A CN 201811156670A CN 109400894 B CN109400894 B CN 109400894B
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azidoethoxy
ethane
functional polymer
polymer material
hyperbranched
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CN109400894A (en
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岳宝华
王胜楠
严六明
曾广波
胡益栋
张梦影
张宇
潘婷
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University of Shanghai for Science and Technology
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
    • C08G83/002—Dendritic macromolecules
    • C08G83/005—Hyperbranched macromolecules
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/0605—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms

Abstract

The invention relates to a hyperbranched polytriazole functional polymer material and a preparation method thereof. The structural formula of the functional polymer material is one of the following:a.
Figure DEST_PATH_IMAGE002
b.
Figure DEST_PATH_IMAGE004
using a bis-azido monomer
Figure DEST_PATH_IMAGE006
(1-azido-2- (2-azidoethoxy) ethane) or
Figure DEST_PATH_IMAGE008
(1, 2-bis (2-azidoethoxy) ethane) and Trienealkyne monomer B3(1, 3, 5-tri (2-propynyl-1-oxy) benzene) as raw material and 'A' as2+B3'click polymerization by method' to obtain two hyperbranched polytriazole functional polymer materialshbPTri1 andhbPTri 2. By controlling
Figure 164028DEST_PATH_IMAGE006
Monomers and
Figure DEST_PATH_IMAGE010
the ratio of the amount of the monomer substances and the reaction time to obtain a series of hyperbranched polytriazole functional polymer materialshbPTri1, and characterizing its structure and molecular weight. The raw materials of the invention are all industrial products, the price is low, the preparation process is simple, and the large-scale production is easy to realize.

Description

Hyperbranched polytriazole functional polymer material and preparation method thereof
Technical Field
The invention relates to two hyperbranched polytriazole functional polymer materials and a preparation method thereof.
Background
With the development of science and technology and the continuous improvement of the living standard of people, the variety of novel functional materials required by social production and people's life is more and more. As a novel functional material, the hyperbranched polytriazole functional polymer material can be used as a biomedical material, a photoelectric functional material, a surface modification material and the like, and has important research significance and great commercial value.
The hyperbranched polymer is a large class of high molecular substances containing a large number of branching units, and has the structural characteristics of intramolecular topological cavities, multiple branching points, multifunctional end groups and the like. Hyperbranched polymers can also be regarded as special dendrimers, but possess more random branching structures and weaker regularity. The hyperbranched polymer can be prepared by a one-step polymerization method, and has the advantage of easy batch synthesis.
The hyperbranched polymer can be prepared by a single monomer process (
Figure DEST_PATH_IMAGE001
By a process comprisingnA functional group A andmmonomers having B functional groups
Figure 123530DEST_PATH_IMAGE001
Synthesis and preparation by the Bimonomer Process (
Figure 301571DEST_PATH_IMAGE002
By means of a process comprisingnMonomers having A functional groups
Figure DEST_PATH_IMAGE003
And comprisemMonomers having B functional groups
Figure 705132DEST_PATH_IMAGE004
Synthesis). Customary bimonomers "A2+B3The "method" is to use monomers A containing 2A functional groups2And monomers B containing 3B functional groups3An example of the synthesis of hyperbranched polymer molecules.
In recent years, extensive research has been conducted on the azide and terminal alkyne cycloaddition reaction (so-called click reaction) catalyzed by monovalent cu (i) due to the advantages of mild reaction conditions, high conversion rate, environmental friendliness, simple method and the like. If proper polyfunctional azide and terminal alkyne are used as the raw materials of the click reaction, the hyperbranched polytriazole can be obtained. By adjusting the mass proportion and the reaction time of the monomers, a series of isomeric structures of the hyperbranched polytriazole can be obtained.
Disclosure of Invention
The invention aims to provide two hyperbranched polytriazole functional polymer materials.
The second purpose of the invention is to provide a preparation method of the functional polymer material. The process is carried out by2+B3Two novel hyperbranched polytriazole functional polymer materials are synthesized by a 'method click polymerization' one-pot method.
In order to achieve the purpose, the invention adopts the following technical scheme:
a hyperbranched polytriazole functional polymer material is characterized in that the structural formula of the functional polymer material is one of the following:
a.
Figure DEST_PATH_IMAGE005
b.
Figure 310426DEST_PATH_IMAGE006
。
a hyperbranched prepared by the methodThe method for preparing the polytriazole functional polymer material is characterized by comprising the following specific steps: under the protection of inert atmosphere, 1-azido-2- (2-azidoethoxy) ethane (2)
Figure DEST_PATH_IMAGE007
Monomer) or 1, 2-bis (2-azidoethoxy) ethane (b)
Figure 665184DEST_PATH_IMAGE008
Monomer) and 1,3, 5-tris (2-propynyl-1-oxy) benzene (A)
Figure DEST_PATH_IMAGE009
Monomer) is dissolved in the mixture according to the molar ratio of 1: 1-3: 1N,N-Dimethylformamide (DMF), copper sulphate pentahydrate is added in an amount of
Figure 142521DEST_PATH_IMAGE007
0.1 molar amount of monomer and sodium ascorbate in an amount of
Figure 899124DEST_PATH_IMAGE007
Reacting for 12-30 hours at room temperature, wherein the molar weight of the monomer is 0.3; dropwise adding the reacted solution into 0.035mol/L disodium ethylene diamine tetraacetate (EDTA-2 Na) aqueous solution to precipitate solid; finally, washing the solid with methanol, filtering and drying to obtain the hyperbranched polytriazole functional polymer material; the 1-azido-2- (2-azidoethoxy) ethane (b)
Figure 613002DEST_PATH_IMAGE007
Monomer) is of the formula:
Figure 658319DEST_PATH_IMAGE010
(ii) a The structural formula of the 1, 2-bis (2-azidoethoxy) ethane (monomer) is as follows:
Figure DEST_PATH_IMAGE011
(ii) a The 1,3, 5-tri (2-propynyl-1-oxyl) benzene (monomer) junctionThe structure formula is as follows:
Figure 378778DEST_PATH_IMAGE012
。
Figure 708129DEST_PATH_IMAGE007
Figure 470810DEST_PATH_IMAGE009
Figure 936427DEST_PATH_IMAGE007
Figure 195370DEST_PATH_IMAGE007
Figure 12016DEST_PATH_IMAGE007
Figure 811345DEST_PATH_IMAGE009
Figure 898512DEST_PATH_IMAGE008
Figure 328356DEST_PATH_IMAGE009
Figure 366719DEST_PATH_IMAGE008
Figure 969739DEST_PATH_IMAGE008
Figure 675527DEST_PATH_IMAGE008
in a word, the invention synthesizes two novel hyperbranched polytriazole functional materials in one step by a' one-pot methodhbPTri1 andhbthe PTri2 has the characteristics of easily obtained raw materials, simple process, convenient operation process and suitability for large-scale industrial production. The hyperbranched polytriazole prepared by the method is a new substance and is not reported in patents or documents at home and abroad.The invention utilizes the azide A with double functional groups2"monomeric and trifunctional terminal alkynes" B3"monomer, by" A2+B3"method for synthesizing two new hyperbranched polytriazoleshbPTri1 andhb-PTri 2) functional polymer material. The polymer containing triazole functional group can be used as a conjugated polymer, and shows wide research space in the aspect of detecting various metal ions by a fluorescence sensor. According to the inventionhbPTri1 andhbPTri2 as fluorescence sensor for Cr3+Detection of (3).
Drawings
FIG. 1 is a drawing of
Figure 568616DEST_PATH_IMAGE007
A monomer,
Figure 297537DEST_PATH_IMAGE009
Monomer and hyperbranched polytriazole functional polymer materialhbOf PTri11H NMR spectrum. Wherein the synthesis conditions of sample S1 are
Figure DEST_PATH_IMAGE013
Reacting for 12 hours; the synthesis conditions for sample S2 were
Figure 500985DEST_PATH_IMAGE013
Reacting for 24 hours; the synthesis conditions for sample S3 were
Figure 998963DEST_PATH_IMAGE013
Reacting for 30 hours; the synthesis conditions for sample S4 were
Figure 567347DEST_PATH_IMAGE014
Reacting for 24 hours; the synthesis conditions for sample S5 were
Figure DEST_PATH_IMAGE015
Reaction for 24 hours (solvent is DMSO-d)6）；
FIG. 2 is
Figure 409664DEST_PATH_IMAGE008
A monomer,
Figure 292169DEST_PATH_IMAGE009
Monomer and hyperbranched polytriazole functional polymer materialhbOf PTri21H NMR spectrum under the synthesis conditions of
Figure 706970DEST_PATH_IMAGE016
Reaction for 30 hours (solvent is DMSO-d)6）。
Detailed description of the invention
The present invention will be described in detail with reference to examples.
The first embodiment is as follows: this example controls the mass ratio between the monomers
Figure 711835DEST_PATH_IMAGE013
Changing the reaction time, and synthesizing by one-pot methodhbPTri1 (i.e. sample S1), the procedure was as follows:
(1) in a 25 mL two-necked flask, 0.1452 g were sequentially added
Figure 713551DEST_PATH_IMAGE007
Monomer (0.93 mmol), 0.1490 g
Figure 134168DEST_PATH_IMAGE009
Monomer (0.62 mmol), 0.0232 g CuSO4·5H2O (0.093 mmol), 0.0553 g NaAsc (0.28 mmol) and 4 mL DMF as solvents were stirred at 25 ℃ for 12 hours under nitrogen protection.
(2) The reacted solution was added dropwise to 0.035mol dm-3The aqueous solution of EDTA-2Na was stirred for 30 minutes and filtered to obtain a yellowish green powder. Washing the obtained yellowish green powder with 20 mL anhydrous methanol for 5 times, and vacuum drying at 60 deg.C for 24 hr to obtainhb-PTri1(S1)。
(3) Measurement of hyperbranched polytriazoleshb-molecular weight of PTri1 (S1). Will be provided withhbDissolving PTri1(S1) in DMF to give 2 mg mL-1Solution, determination of weight average molecular weight by gel chromatography (GPC) ((weight average molecular weight))
Figure DEST_PATH_IMAGE017
) And polydispersity index (PDI). The sample introduction rate of the measurement is 2.22 muL min-1The eluent was DMF and the measurements are shown in table 1.
Example two: this example controls the mass ratio between the monomers
Figure 731372DEST_PATH_IMAGE013
Changing the reaction time, and synthesizing by one-pot methodhbPTri1 (i.e. sample S2), the procedure was as follows:
(1) in a 25 mL two-necked flask, 0.2998 g of the solution was sequentially added
Figure 641559DEST_PATH_IMAGE007
Monomer (1.92 mmol), 0.3075 g
Figure 130571DEST_PATH_IMAGE009
Monomer (1.28 mmol), 0.0480 g CuSO4·5H2O (0.192 mmol), 0.1141 g NaAsc (0.58 mmol), 8.5 mL DMF as solvent, and the reaction was stirred at 25 ℃ for 24 hours under nitrogen protection.
(2) The reacted solution was added dropwise to 0.035mol dm-3The aqueous solution of EDTA-2Na was stirred for 30 minutes and filtered to obtain a yellowish green powder. Washing the obtained yellowish green powder with 45 mL anhydrous methanol for 5 times, and vacuum drying at 60 deg.C for 24 hr to obtainhb-PTri1(S2)。
(3) Testing of hyperbranched polytriazoleshbMolecular weight of PTri1(S2), the procedure was as in example one, and the results of the measurements are shown in table 1.
Example three: this example controls the mass ratio between the monomers
Figure 354879DEST_PATH_IMAGE013
Changing the reaction time, and synthesizing by one-pot methodhbPTri1 (i.e. sample S3), the procedure was as follows:
(1) in a 50mL two-necked flask, 1.0739 g were sequentially added
Figure 744272DEST_PATH_IMAGE007
Monomer (6.88 mmol), 1.1027 g
Figure 90940DEST_PATH_IMAGE009
Monomer (4.59 mmol), 0.1720 g CuSO4·5H2O (0.69 mmol), 0.4081 g NaAsc (2.06 mmol) and 30 mL DMF as solvents were stirred at 25 ℃ under nitrogen for 30 hours.
(2) The reacted solution was added dropwise to 0.035mol dm-3The aqueous solution of EDTA-2Na was stirred for 30 minutes and filtered to obtain a yellowish green powder. Washing the obtained yellowish green powder with 150mL anhydrous methanol for 5 times, and vacuum drying at 60 deg.C for 24 hr to obtainhb-PTri1(S3)。
(3) Testing of hyperbranched polytriazoleshbMolecular weight of PTri1(S3), the procedure was as in example one, and the results of the measurements are shown in table 1.
Example four: this example varied the mass ratio between the monomers
Figure 503467DEST_PATH_IMAGE014
Synthesized by one-pot method in one stephbPTri1 (i.e. sample S4), the procedure was as follows:
(1) in a 25 mL two-necked flask, 0.1490 g were sequentially added
Figure 328203DEST_PATH_IMAGE007
Monomer (0.62 mmol), 0.0968 g
Figure 67708DEST_PATH_IMAGE009
Monomer (0.62 mmol), 0.0155 g CuSO4·5H2O (0.062 mmol), 0.0368 g NaAsc (0.19 mmol) and 4 mL DMF as solvents were stirred at 25 ℃ under nitrogen for 24 hours.
(2) The reacted solution was added dropwise to 0.035mol dm-3The aqueous solution of EDTA-2Na was stirred for 30 minutes and filtered to obtain a yellowish green powder. Washing the obtained yellowish green powder with 20 mL anhydrous methanol for 5 times, and vacuum drying at 60 deg.C for 24 hr to obtainhb-PTri1(S4)。
(3) Testing of hyperbranched polytriazoleshbMolecular weight of PTri1(S4), the procedure was as in example one, and the results of the measurements are shown in table 1.
Example five: this example varied the mass ratio between the monomers
Figure 522961DEST_PATH_IMAGE015
Synthesized by one-pot method in one stephbPTri1 (i.e. sample S5), the procedure was as follows:
(1) in a 25 mL two-necked flask, 0.9744 g were sequentially added
Figure 485100DEST_PATH_IMAGE007
Monomer (6.24 mmol), 0.4997 g
Figure 113528DEST_PATH_IMAGE009
Monomer (2.08 mmol), 0.1558 g of CuSO4·5H2O (0.62 mmol), 0.3709 g NaAsc (1.87 mmol) and 14 mL DMF as solvent, and the reaction was stirred at 25 ℃ under nitrogen for 24 hours.
(2) The reacted solution was added dropwise to 0.035mol-3The aqueous solution of EDTA-2Na was stirred for 30 minutes and filtered to obtain a yellowish green powder. Washing the obtained yellowish green powder with 75 mL anhydrous methanol for 5 times, and vacuum drying at 60 deg.C for 24 hr to obtainhb-PTri1(S5)。
(3) To be preparedhbMolecular weight testing of PTri1(S5) was carried out in the same manner as in example one, and the results are shown in Table 1.
Example six: this example varied the monomer species by controlling the mass ratio between the monomers
Figure 149617DEST_PATH_IMAGE016
Synthesized by one-pot method in one stephbPTri2, the specific procedure being as follows:
1. in a 50mL two-necked flask, 1.3767 g were sequentially added
Figure 838087DEST_PATH_IMAGE008
Monomer (6.88 mmol), 1.1027 g
Figure 788988DEST_PATH_IMAGE009
Monomer (4.59 mmol), 0.1720 g CuSO4·5H2O (0.69 mmol), 0.4081 g NaAsc (2.06 mmol) and 30 mL DMF as solvents were stirred at 25 ℃ under nitrogen for 30 hours.
2. The reacted solution was added dropwise to 0.035mol dm-3The aqueous solution of EDTA-2Na was stirred for 30 minutes and filtered to obtain a yellowish green powder. Washing the obtained yellowish green powder with 150mL anhydrous methanol for 5 times, and vacuum drying at 60 deg.C for 24 hr to obtainhb-PTri2。
TABLE 1 attached, hyperbranched polytriazoleshbMolecular weight of PTri1
hb-PTri1 S1 S2 S3 S4 S5
Figure DEST_PATH_IMAGE019
 3:2 3:2 3:2 1:1 3:1
Reaction time (hours) 12 24 30 24 24
Figure 955527DEST_PATH_IMAGE017
(Da) 		21,000 35,000 28,000 25,000 16,000
PDI 1.74 1.40 1.82 2.15 1.82
Yield (%) 79.6 69.0 90.2 44.2 46.2
Method for testing fluorescence properties
Preparation ofhbOf PTri1(S3)N,N-dimethylacetamide (DMAc) solution (concentrated)Degree: 1.0X 10-5moldm-3) And then standby. Preparation of acetonitrile (CH) of various metal ions using lithium carbonate and other various metal salts (chlorate)3CN) solution (concentration: 1.0X 10-3moldm-3) And then standby. 3.0 mL of the solution was taken outhbPTri1(S3) DMAc solution and equal amounts of various metal salt solutions were added to the polymer solution at room temperature and sonicated for 2 hours to give various polymer-metal complexes.hbPTri1(S3) and all polymer-metal complexes were subjected to spectrofluorimetry.hbThe fluorescence spectrum test of PTri2 and all its polymer-metal complexes refers to the procedure described above. The results of the measurements are shown in Table 2.
TABLE 2 attached hereto, hyperbranched polytriazoleshbPTri1(S3), hyperbranched polytriazoleshbEfficiency of fluorescence quenching of PTri2 at various metal ions
Quenching efficiency (%) Cd Cr K Li Na Ni Pb
hb-PTri1（S3） 44.0 91.3 45.1 42.9 45.8 68.9 46.5
hb-PTri2 58.7 83.2 60.6 60.1 57.6 72.3 60.4
Figure 111702DEST_PATH_IMAGE008
Figure 971074DEST_PATH_IMAGE009
Figure 206008DEST_PATH_IMAGE016
Figure 441817DEST_PATH_IMAGE007
Figure 452499DEST_PATH_IMAGE008
Figure 482772DEST_PATH_IMAGE009
Figure 641220DEST_PATH_IMAGE007
Figure 87245DEST_PATH_IMAGE009
Figure 781794DEST_PATH_IMAGE013
Figure 982968DEST_PATH_IMAGE013
Figure 566396DEST_PATH_IMAGE013
Figure 878429DEST_PATH_IMAGE014
Figure 863702DEST_PATH_IMAGE015
Figure 235778DEST_PATH_IMAGE008
Figure 509764DEST_PATH_IMAGE009
Figure 563171DEST_PATH_IMAGE016
。

Claims (2)

1. A hyperbranched polytriazole functional polymer material is characterized in that the structural formula of the functional polymer material is one of the following:
a.
Figure FDA0002734052270000011
b.
Figure FDA0002734052270000012
2. the method for preparing the hyperbranched polytriazole functional polymer material according to claim 1, wherein the method comprises the following steps:
under the protection of inert atmosphere, dissolving 1-azido-2- (2-azidoethoxy) ethane or 1, 2-bis (2-azidoethoxy) ethane and 1,3, 5-tris (2-propynyl-1-oxyl) benzene into N, N-dimethylformamide according to the molar ratio of 1: 1-3: 1, adding copper sulfate pentahydrate and sodium ascorbate, wherein the dosage of the copper sulfate pentahydrate is 0.1 time of the molar amount of the 1-azido-2- (2-azidoethoxy) ethane or 1, 2-bis (2-azidoethoxy) ethane, and the dosage of the sodium ascorbate is 0.3 time of the molar amount of the 1-azido-2- (2-azidoethoxy) ethane or 1, 2-bis (2-azidoethoxy) ethane, reacting for 12-30 hours at room temperature;
dropwise adding the reacted solution into 0.035mol/L disodium ethylene diamine tetraacetate aqueous solution to separate out solid; finally, washing the solid with methanol, filtering and drying to obtain the hyperbranched polytriazole functional polymer material; the structural formula of the 1-azido-2- (2-azidoethoxy) ethane is as follows:
Figure FDA0002734052270000021
the structural formula of the 1, 2-bis (2-azidoethoxy) ethane is as follows:
Figure FDA0002734052270000022
the structural formula of the 1,3, 5-tri (2-propynyl-1-oxyl) benzene is as follows:
Figure FDA0002734052270000023
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