CN106279677B - Rich in heteroatomic phosphine amidine quasi polymer and prepares the multicomponent polymerization of the polymer and apply - Google Patents
Rich in heteroatomic phosphine amidine quasi polymer and prepares the multicomponent polymerization of the polymer and apply Download PDFInfo
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- CN106279677B CN106279677B CN201610649024.9A CN201610649024A CN106279677B CN 106279677 B CN106279677 B CN 106279677B CN 201610649024 A CN201610649024 A CN 201610649024A CN 106279677 B CN106279677 B CN 106279677B
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- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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Abstract
The invention belongs to the technical field of organic chemistry, multicomponent polymerization and the application of the polymer are disclosed rich in heteroatomic phosphine amidine quasi polymer and prepared.The method are as follows: (1) under inert gas protection, using organic solvent as reaction medium, under the effect of the catalyst, end diine hydrocarbon monomer, end disulfonyl nitrine monomer, phosphinimine class monomer are subjected to polymerization reaction, obtain crude product;(2) after completion of the reaction, by crude product solvent dissolved dilution, filtering precipitates filtrate added drop-wise into precipitating reagent, collects sediment, dry to constant weight, obtains phosphine amidine quasi polymer.Polymerization of the invention carries out at normal temperature, and efficiently, Atom economy is high for reaction, and product is easily separated;The phosphine amidine quasi polymer of preparation has special photoelectric properties rich in hetero atoms such as N, O, S, P, has unique application value in biology, chemiluminescence detection and platinum group metal ion detection field.
Description
Technical field
The invention belongs to the technical fields of organic chemistry, are related to a kind of preparation side rich in heteroatomic phosphine amidine quasi polymer
Method, and in particular to it is a kind of rich in heteroatomic phosphine amidine quasi polymer and prepare the multicomponent polymerization of the phosphine amidine quasi polymer with
Using.
Background technique
The hetero atoms such as O, N, S, P are introduced in polymer molecular chain can make polymer have certain special performances.Such as
The addition of element sulphur can make polymer refraction index with higher.Introducing hetero-atoms can also change in conducting polymer
The photoelectric properties of material.Meanwhile certain hetero atoms are introduced in strand, metal coordinating polymer can be formed.It is some to contain miscellaneous original
Sub- polymer energy and metallic ion coordination, so as to develop the material for metal ion detection and enrichment.In polymer
Phosphorus atoms can have coordination with transition metal ions, therefore phosphorous polymer has potentially in transition metal ions context of detection
Application value.Just because of these polymer containing hetero atom have special performance, they cause the extensive concern of scientists.
Currently, building is usually used rich in method used in heteroatomic polymer, structure is complicated, is difficult to the monomer prepared, or
It is realized by multistep reaction.Therefore more efficient, the simpler new method of one kind is developed to synthesize rich in heteroatomic polymerization
Object is very necessary.
The reaction of current synthesis phosphorous polymer is varied, but is prepared using multicomponent polymerization rich in a variety of miscellaneous originals
The report of the phosphorous polymer of son is also rarely found.Compared to traditional polymerization, multicomponent polymerization inherits the excellent of multi-component reaction
Point, such as mild condition, efficient, easy to operate, structure are easily adjusted, are environmentally protective etc..Meanwhile alkynes is used frequently as primitive is constructed
In the synthesis of conjugation/heterocyclic polymer.Therefore it is polymerize using the multicomponent that alkynes participates in, can be used for various new function high score
The synthesis and exploitation of sub- material.
Summary of the invention
In order to solve the disadvantage that the above prior art and deficiency, it is rich in the primary purpose of the present invention is that providing a kind of prepare
The multicomponent polymerization of the alkynes of heteroatomic phosphine amidine quasi polymer, sulfonyl azide and phosphinimine.
Heteroatomic phosphine amidine quasi polymer is rich in another object of the present invention is to provide prepared by the above method.
A further object of the present invention is to provide the above-mentioned applications rich in heteroatomic phosphine amidine quasi polymer.The phosphine amidine class
Polymer is used for platinum group metal ion detection and fluorescence detection field.
The object of the invention is achieved through the following technical solutions:
A kind of multicomponent polymerization prepared rich in heteroatomic phosphine amidine quasi polymer, including following preparation step:
(1) under inert gas protection, using organic solvent as reaction medium, under the effect of the catalyst, by end diine
Hydrocarbon monomer, end disulfonyl nitrine monomer, phosphinimine class monomer carry out polymerization reaction, obtain crude product;
(2) after completion of the reaction, by crude product solvent dissolved dilution, filtering sinks filtrate added drop-wise into precipitating reagent
It forms sediment, collects sediment, it is dry to constant weight, obtain phosphine amidine quasi polymer;
Shown in the general structure such as formula (II) of the end diine hydrocarbon monomer:
Shown in the general structure such as formula (III) of the end disulfonyl nitrine monomer:
N3O2S-R2-SO2N3(III);
Shown in the general structure such as formula (IV) of the phosphinimine class monomer:
R3N=PPh3(IV);
Formula (II), (III), R in (IV)1、R2、R3It is identical or different, R1、R2、R3For organic group.Wherein, R1、R2Selected from
Any one in lower chemical structural formula 1~19;R3Any one in following structural formula 20~23:
Wherein, the integer that m, h, k are 1~20, R ' and R 〞 are identical or different hydrogen, halogen atom, nitro, ester
Base, alkyl or alkoxy, X are selected from N, P, O, S or Si element, and * indicates the position of substitution.
Catalyst described in step (1) is cuprous catalysis agent, and the cuprous catalysis agent is cuprous iodide, stannous chloride or bromine
Change cuprous, preferably cuprous iodide.
The dosage of catalyst described in step (1) is the 5%~30% of end diyne monomer molar dosage.
Catalyst described in step (1) need to be used cooperatively with triethylamine, the triethylamine and end diyne monomer molar
Than for (1~3): 1.
The condition of polymerization reaction described in step (1) be at room temperature reaction 0.5~for 24 hours.
The molar ratio of end diine hydrocarbon monomer and end disulfonyl nitrine monomer and phosphinimine class monomer described in step (1)
For 1:1:(2~3), the molal volume ratio of the end diine hydrocarbon monomer and organic solvent is (0.01~0.6) mol:1L.
Organic solvent described in step (1) is anhydrous tetrahydro furan, anhydrous chloroform, anhydrous methylene chloride, anhydrous dimethyl base
One of formamide.
Solvent described in step (2) is chloroform or dimethylformamide, preferably chloroform.
Precipitating reagent described in step (2) is methanol.
Dry temperature described in step (2) is 30~60 DEG C.
Reaction equation of the invention is as follows:
One kind is rich in heteroatomic phosphine amidine quasi polymer using what the above method was prepared, and the polymer has formula
(I) general structure shown in:
Wherein, the integer that n is 2~200;R1、R2、R3For identical or different organic group.
In the formula (I), R1、R2Any one in following chemical structural formula 1~19;R3Selected from following structural formula
Any one in 20~23:
Wherein, the integer that m, h, k are 1~20, R ' and R 〞 are identical or different hydrogen, halogen atom, nitro, ester
Base, alkyl or alkoxy, X are selected from N, P, O, S or Si element, and * indicates the position of substitution.
Above-mentioned phosphine amidine quasi polymer has special photoelectric properties because rich in a variety of hetero atoms such as N, O, S, P, and
There can be coordination with metal ion, therefore there is application value in platinum group metal ion detection and fluorescence detection field.
Preparation method of the invention and obtained product have the following advantages that and the utility model has the advantages that
(1) polymerized monomer used in polymerization of the present invention is easy to get, polymer yield height (85%~98%),
Molecular weight height (weight average molecular weight is that 1~200,000, PDI is 1.5~3.8), refraction index is higher, and film forming is preferable;
(2) polymerization of the present invention carries out at normal temperature, and efficiently, Atom economy is high, and product is easily separated for reaction,
It is considered as the click-reaction (click polymerization reaction) of three components;
(3) phosphine amidine quasi polymer prepared by the present invention has special photoelectric properties rich in hetero atoms such as N, O, S, P,
Biology, chemiluminescence detection and platinum group metal ion detection field have unique application value.
Detailed description of the invention
Fig. 1 is a kind of hydrogen NMR spectrum of the obtained phosphine amidine quasi polymer of embodiment 1 in deuterated dimethyl sulfoxide;
Fig. 2 is a kind of refractive index curve chart for phosphine amidine quasi polymer that embodiment 1 obtains;
Fig. 3 is a kind of light of the obtained phosphine amidine quasi polymer of embodiment 1 in the dimethyl sulphoxide solution of different water contents
Cause fluorescence curve figure;
Fig. 4 is a kind of testing result of the obtained phosphine amidine quasi polymer of embodiment 1 to different metal ions.
Specific embodiment
Further specific detailed description, but implementation of the invention is made to the present invention with attached drawing combined with specific embodiments below
Mode is without being limited thereto, for not specifically specified technological parameter, can refer to routine techniques progress.
Embodiment 1
A kind of multicomponent polymerization side of the alkynes prepared rich in heteroatomic phosphine amidine quasi polymer, sulfonyl azide and phosphinimine
Method, specific preparation process is as follows:
(1) under nitrogen protection, by 38mg diethylacetylene tetraphenylethylene monomer 24Bis- sulphur of 38mg
Acyl azide monomer 2588mg tetraphenyl ammonification phosphine monomer 26With 4mg cuprous iodide
It is added in 1mL tetrahydrofuran and dissolves, stir lower dropwise addition 20mg triethylamine, under stiring normal-temperature reaction 12h;
(2) after completion of the reaction, with 2mL chloroform solvent diluting reaction mother liquor, then it is added drop-wise to by absorbent cotton filtering
It is precipitated in 100mL methanol, collects sediment, 40 DEG C of dryings obtain polymer to constant weight.
The diethylacetylene tetraphenylethylene monomer 24 of the present embodiment is according to document [Polym.Chem.2012,3,1481] public affairs
The method preparation opened.
The structural formula of the phosphine amidine quasi polymer P1 of the present embodiment:
The polymer P 1 of the present embodiment, yield 92%, weight average molecular weight 70400, PDI 2.49.
Hydrogen NMR spectrum of the polymer P 1 of the present embodiment in deuterated dimethyl sulfoxide is as shown in Figure 1.It can from Fig. 1
Out, the solvent peak of deuterated dimethyl sulfoxide and water peak are located at 2.5 and 3.3ppm, are in addition to this hydrogen atom in polymer
Appearance.
It is as shown in Figure 2 that the refractive index curve chart after film is made in the polymer P 1 of the present embodiment.Fig. 2 is the result shows that gained is poly-
Close object refractive index with higher, the refractive index 630nm at is up to 1.70, for example than general polymer material polystyrene with
Polymethyl methacrylate etc. wants much higher.
The photoluminescence curve figure such as Fig. 3 of the polymer P 1 of the present embodiment in the dimethyl sulphoxide solution of different water contents
It is shown.Fig. 3 shows that polymer solution fluorescence in 50% water content is most strong.The polymer material has certain aggregation glimmering
Light enhances phenomenon.
The polymer P 1 of the present embodiment is as shown in Figure 4 to the testing result of different metal ions.Fig. 4 shows different metal
The fluorescent quenching degree of ion pair polymerization object P1 solution is different.The polymer has the performance to palladium ion selective response, can
To be used to detect and be enriched with palladium ion.
Embodiment 2
A kind of multicomponent polymerization side of the alkynes of the phosphine amidine quasi polymer prepared rich in atom, sulfonyl azide and phosphinimine
Method, specific preparation process is as follows:
(1) under nitrogen protection, by 45.6mg diine hydrocarbon monomer 2738mg disulfonyl
Nitrine monomer 2588mg tetraphenyl ammonification phosphine monomer 26Add with 4mg cuprous iodide
Enter into 1mL tetrahydrofuran and dissolve, under stiring, 20mg triethylamine is added dropwise, under stiring normal-temperature reaction 12h;
(2) after completion of the reaction, with 2mL chloroform diluting reaction mother liquor, then it is added drop-wise to 100mL first by absorbent cotton filtering
It is precipitated in alcohol, collects sediment, 40 DEG C of dryings obtain polymer P 2 to constant weight.
The structural formula of the phosphine amidine quasi polymer P2 of the present embodiment:
The polymer P 2 of the present embodiment, yield 91%, weight average molecular weight 85600, PDI 2.89.
The above embodiment of the present invention be only to clearly illustrate example of the present invention, and not be to the present invention
Embodiment restriction.For those of ordinary skill in the art, it can also make on the basis of the above description
Other various forms of variations or variation.There is no necessity and possibility to exhaust all the enbodiments.It is all of the invention
Made any modifications, equivalent replacements, and improvements etc., should be included in the protection of the claims in the present invention within spirit and principle
Within the scope of.
Claims (10)
1. a kind of multicomponent polymerization prepared rich in heteroatomic phosphine amidine quasi polymer, it is characterised in that: including following system
Standby step:
(1) under inert gas protection, using organic solvent as reaction medium, under the effect of the catalyst, by end diyne list
Body, end disulfonyl nitrine monomer, phosphinimine class monomer carry out polymerization reaction, obtain crude product;
(2) after completion of the reaction, by crude product solvent dissolved dilution, filtering precipitates filtrate added drop-wise into precipitating reagent, receives
Collect sediment, it is dry to constant weight, obtain phosphine amidine quasi polymer;
Shown in the general structure such as formula (II) of the end diine hydrocarbon monomer:
Shown in the general structure such as formula (III) of the end disulfonyl nitrine monomer:
N3O2S-R2-SO2N3(Ⅲ);
Shown in the general structure such as formula (IV) of the phosphinimine class monomer:
R3N=PPh3(Ⅳ);
Formula (II), (III), R in (IV)1、R2、R3It is identical or different, R1、R2、R3For organic group.
2. preparing the multicomponent polymerization rich in heteroatomic phosphine amidine quasi polymer according to claim 1, feature exists
In: the R1、R2Any one in following chemical structural formula 1~19;R3It is any in following structural formula 20~23
It is a kind of;
Wherein, the integer that m, h, k are 1~20, R ' and R 〞 are identical or different hydrogen, halogen atom, nitro, ester group, alkane
Base or alkoxy, X are selected from N, P, O or S element, and * indicates the position of substitution.
3. preparing the multicomponent polymerization rich in heteroatomic phosphine amidine quasi polymer according to claim 1, feature exists
In: catalyst described in step (1) is cuprous catalysis agent.
4. preparing the multicomponent polymerization rich in heteroatomic phosphine amidine quasi polymer according to claim 3, feature exists
In: the cuprous catalysis agent is cuprous iodide, stannous chloride or cuprous bromide.
5. preparing the multicomponent polymerization rich in heteroatomic phosphine amidine quasi polymer according to claim 1, feature exists
In: the molar ratio of end diine hydrocarbon monomer described in step (1) and end disulfonyl nitrine monomer and phosphinimine class monomer is 1:
1:(2~3);
The dosage of catalyst described in step (1) is the 5%~30% of end diyne monomer molar dosage;
The molal volume ratio of end diine hydrocarbon monomer described in step (1) and organic solvent is (0.01~0.6) mol:1L.
6. preparing the multicomponent polymerization rich in heteroatomic phosphine amidine quasi polymer according to claim 1, feature exists
In: catalyst described in step (1) need to be used cooperatively with triethylamine, and the triethylamine and end diyne monomer mole ratio are (1
~3): 1;
The condition of polymerization reaction described in step (1) be at room temperature reaction 0.5~for 24 hours.
7. preparing the multicomponent polymerization rich in heteroatomic phosphine amidine quasi polymer according to claim 1, feature exists
In: organic solvent described in step (1) is anhydrous tetrahydro furan, anhydrous chloroform, anhydrous methylene chloride, anhydrous dimethyl formamide
One of;
Solvent described in step (2) is chloroform or dimethylformamide;Precipitating reagent described in step (2) is methanol;
Dry temperature described in step (2) is 30~60 DEG C.
8. one kind is rich in heteroatomic phosphine amidine quasi polymer using what any one of claim 1~7 the method was prepared,
Be characterized in that: the polymer has general structure shown in formula (I):
Wherein, the integer that n is 2~200;R1、R2、R3For identical or different organic group.
9. being rich in heteroatomic phosphine amidine quasi polymer according to claim 8, it is characterised in that: in the formula (I), R1、R2Choosing
From any one in following chemical structural formula 1~19;R3Any one in following structural formula 20~23;
Wherein, the integer that m, h, k are 1~20, R ' and R 〞 are identical or different hydrogen, halogen atom, nitro, ester group, alkane
Base or alkoxy, X are selected from N, P, O or S element, and * indicates the position of substitution.
10. being rich in the application of heteroatomic phosphine amidine quasi polymer according to claim 8 or claim 9, it is characterised in that: the phosphine amidine
Application of the quasi polymer in platinum group metal ion detection and fluorescence detection field.
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CN110183659B (en) * | 2018-02-21 | 2022-04-26 | 香港科技大学 | Polymer containing heterocyclic ring, preparation method and application thereof |
CN109161017B (en) * | 2018-07-26 | 2020-10-27 | 华南理工大学 | Multi-component polymerization method based on alkyne and sulfonyl azide, sulfonyl-containing polymer and application |
CN114805800B (en) * | 2022-06-09 | 2023-03-07 | 大连理工大学 | Preparation method and application of N-sulfonamidine polymer |
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CN105001419A (en) * | 2015-06-11 | 2015-10-28 | 华南理工大学 | Alkyne, sulfur and amine multi-component polymerization method for preparing poly-thioamide |
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CN105001419A (en) * | 2015-06-11 | 2015-10-28 | 华南理工大学 | Alkyne, sulfur and amine multi-component polymerization method for preparing poly-thioamide |
Non-Patent Citations (2)
Title |
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Recnet Advances in Alkyne-Based Multicomponent Polymerization;Rongrong Hu et al;《Macromol.Chem.Phys.》;20151117;213-224 |
Room Temperature Multicomponent Polymerizations of Alkynes,Sulfonyl Azides,and Iminophosphorane toward Heteroatom-Rich Multifunctional Poly(phosphorus amidines)s;Liguo Xu et al;《Macromolecules》;20170811;6043-6053 |
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