AU2017418044B2 - Monoselenide polymer and preparation method thereof - Google Patents

Monoselenide polymer and preparation method thereof Download PDF

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AU2017418044B2
AU2017418044B2 AU2017418044A AU2017418044A AU2017418044B2 AU 2017418044 B2 AU2017418044 B2 AU 2017418044B2 AU 2017418044 A AU2017418044 A AU 2017418044A AU 2017418044 A AU2017418044 A AU 2017418044A AU 2017418044 B2 AU2017418044 B2 AU 2017418044B2
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monoselenide
polymer
reaction
preparing
diselenide
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Xiaowei AN
Xiangqiang PAN
Dong XING
Jian Zhu
Xiulin ZHU
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Suzhou University
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/681—Polyesters containing atoms other than carbon, hydrogen and oxygen containing elements not provided for by groups C08G63/682 - C08G63/698
    • 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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/78—Preparation processes

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Abstract

The present invention relates to a method for preparing a monoselenide polymer. The method comprises the steps of: reacting a selenolactone with an unsaturated monohydric alcohol in the presence of a catalyst at 40-70°C, to obtain an alkenyl ester diselenide; dissolving the alkenyl ester diselenide in an organic solvent; adding sulfonyl chloride at -20 to -10°C to perform a reaction; then raising the temperature to 0 to 10°C to continue the reaction, to obtain the monoselenide polymer. The invention further provides a monoselenide polymer prepared by the above method. The method in the present invention is simple, efficient, and convenient in operation. As compared with a conventional method, the polymerization ofnon-active monomers is achieved in the present method.

Description

Monoselenide polymer and preparation method thereof
Field of the Invention
The present invention relates to the field of organic chemical synthesis, and more particularly to a monoselenide polymer and a preparation method thereof.
Description of the Related Art
Selenium is the third element in the oxygen family. Compared with oxygen and sulfur, the selenium atom has special outer electron structure and atomic properties, so a selenium-containing compound has unique redox property, coordination responsiveness and other functions. After the introduction of selenium into a polymer, the polymer exhibits sensitive redox responsiveness. These unique properties allow the selenium-containing polymers to have broad application prospects in the fields of drug controlled-release carriers, semiconductor materials, and stimuli-responsive materials.
Although the selenium-containing polymers have novel properties and broad application prospects, there are few reports on the preparation methods of selenium-containing polymers, and this greatly limits the use of selenium-containing polymers. Moreover, these limited methods mostly focus on the synthesis of diselenide polymers. The diselenide bond is very weak and easy to break to form a selenium free radical to participate in other reactions, which limits the use of diselenide polymers to some extent.
Monoselenide polymers are relatively more stable than diselenide polymers, thus, the development of an efficient, simple method for the synthesis and preparation of mono-selenium polymers is of great importance.
Currently few methods for synthesizing monoselenides are reported in the literatures, mainly including the following:
(1) Polymerization of selenium containing monomers: Diphenyl diselenide is polycondensed with diphenylethylene or diphenyl acetylene respectively to obtain a linear monoselenide polymer (Eiichi Kobayashi, Journal of Polymer Science: Part A Polymer Chemistry, Vol. 32, 1994, 1609-1617). The polymer synthesized by this method has poor solubility, and the synthesis and storage of the monomer are difficult.
(2) Iniferter polymerization initiated by selenide compound: Diphenyl diselenide is added to a styrene polymerization system, to attach monoselenide to the end of the polymer (Kondo S. Journal of Macromolecular Science, Part A, 1997, 34, 1553-1567). This kind of polymers is characterized by wide molecular weight distribution, which is not conducive to the design of polymer structures, and the use of selenide is limited due to the exclusive attachment o to the end of the polymer.
(3) Modification of polymers: A small molecular monoselenide is synthesized with sodium hydrogen selenide and then introduced into a polymer by terminal modification. In such a method for synthesizing polymers, the steps are cumbersome and the polymer components are complex.
(4) Synthesis of polymers containing monoselenide in backbones with seleno-resin: A polymer with a controlled molecular weight and a narrow molecular weight distribution is obtained by living polymerization, which reacts with a seleno-resin to obtain a monoselenide polymer. This method is simple, rapid, and efficient, but further functional modification of the polymer is difficult.
In summary, the existing methods can be used to synthesize monoselenide polymers, but there are some problems, such as narrow choices of monomers, cumbersome preparation process, and poor functionality of selenide sites, etc., and these limit the study and use of monoselenide polymers. Therefore, there is a need to develop a simple and efficient method for synthesizing a polymer containing a monoselenide structure, to greatly expand the use of monoselenide polymers.
SUMMARY OF THE INVENTION
To solve the above technical problems, an object of the present invention is to provide a monoselenide polymer, and a preparation method thereof. The method in the present invention is simple, efficient, and convenient in operation. Compared with a traditional method, the present method realizes the polymerization of non-active monomers.
For the above purpose, the invention utilizes the following technical solutions.
In one aspect, the present invention provides a method for preparing a monoselenide polymer, which comprises the steps of:
(1) reacting a selenolactone with an unsaturated monohydric alcohol in the presence of a catalyst at 40 -70°C for 6-12 h, to obtain an alkenyl ester diselenide; and (2) dissolving the alkenyl ester diselenide in an organic solvent; adding sulfonyl chloride at -20 to -10°Cto perform a reaction; and then raising the temperature to 0°C to continues the reaction for 24-48 hrs, to obtain the monoselenide polymer.
Preferably, in the step (1), the selenolactone is
Figure AU2017418044B2_D0001
Preferably, in the step (1), the unsaturated monohydric alcohol is selected from the group consisting of 3-buten-l-ol, 5-hexen-l-ol, oleyl alcohol, 4-penten-l-ol, 6-hepten-l-ol, 7-octen-l-ol and 5 -norbornen-2 -methanol.
Preferably, in the step (1), the catalyst is selected from the group consisting of triethyl amine, 1, 8-diazabicyclo[5.4.0]undec-7-ene(DBU), and 4-dimethylaminopyridine (DMAP).
Preferably, in the step (1), the molar ratio of the selenolactone to the unsaturated monohydric alcohol is 1 : 0.6 - 1.
Preferably, in the step (1), the molar ratio of the unsaturated monohydric alcohol to the catalyst is 1 : 0.05 - 0.2.
Preferably, in the step (1), the reaction is performed in tetrahydro furan, chloroform, dichloromethane or any combination thereof.
Preferably, in the step (2), the organic solvent is selected from the group consisting of chloroform, tetrahydrofuran and dichloromethane.
Preferably, in the step (2), the reaction is performed under a protective atmosphere.
Preferably, in the step (2), the sulfonyl chloride is slowly added dropwise. The reaction is continued for 2-3 h with stirring at -20 to -10°C.
Preferably, in the step (2), the molar ratio of the alkenyl ester diselenide to the sulfonyl chloride is 1 : 0.6 - 1. The molar ratio is controlled to obtain monoselenide polymers with various molecular weights.
In another aspect, the present invention also provides a monoselenide polymer prepared by the above method.
The reaction principle of the method of the present invention is as follows.
In step (1), since the C-Se bond in selenolactone is weak, generally a nucleophilic group such as a hydroxyl group can undergo nucleophilic substitution in the presence of a catalyst, to produce an ester intermediate terminated with selenol. The intermediate is prone to selenium-selenium coupling to eventually form an ester diselenide compound.
In step (2), the alkenyl ester diselenide first reacts with the sulfonyl chloride to form an intermediate with selenium chloride at one end and a non-active double bond at the other end. By means of the efficient electrophilic addition reaction of the selenium chloride and the non-active double bond, the self-polycondensation of the monomer is achieved to give the monoselenide polymer.
By means of the above technical solutions, the present invention has the following advantages.
In the present invention, a monoselenide polymer is synthesized through the electrophilic addition reaction of selenium chloride with an alkene. The process is simple, efficient and convenient in operation. Compared with a conventional method, the present method realizes the polymerization of non-active monomers, to introduce selenide into a monoselenide polymer. Furthermore, in the method of the present invention, the monomer for the polymerization is a diselenide containing an ester group, and the polymerized product contains an ester group, such that the product can also be regarded as a monoselenide polyester, and the polyester is biocompatible.
BRIEF DESCRIPTION OF THE DRAWINGS
Fig. 1 is a ’H NMR spectrum of Hexene-ButdiSe according to embodiment 1 of the present invention;
Fig. 2 is a 13C NMR spectrum of Hexene-ButdiSe according to embodiment 1 of the present invention;
Fig. 3 is a 77Se NMR spectrum of Hexene-ButdiSe according to embodiment 1 of the present invention;
Fig. 4 is a 'H NMR spectrum of PHex according to embodiment 1 of the present invention;
Fig. 5 is a 13C NMR spectrum of PHex according to embodiment 1 of the present invention;
Fig. 6 is a 77Se NMR spectrum of PHex according to embodiment 1 of the present invention;
Fig. 7 is a 'H NMR of PBut according to embodiment 2 of the present invention; and
Fig. 8 is a gel permeation chromatogram of monoselenide polymers according to embodiments 1-3 of the present invention.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
The invention will be further illustrated in more detail with reference to the accompanying drawings and embodiments. It is noted that, the following embodiments only are intended for purposes of illustration, but are not intended to limit the scope of the present invention.
In the following embodiments of the present invention, the purity and source of the reagents used are as follows:
5-hexen-l-ol, Energy Chemical, 98%; 3-buten-l-ol, J&K Scientific, 98%; oleyl alcohol, Macklin, 80-85%; l,8-diazabicyclo[5.4.0]undec-7-ene (DBU), Macklin, 99%; sulfonyl chloride, Aladdin, 97%; tetrahydro furan (THF), Chinasun Specialty Products Co., Ltd., analytical grade; chloroform,
Yonghua Technology (Jiangsu) Co., Ltd., analytical grade; and acetone,
Yonghua Technology (Jiangsu) Co., Ltd., analytical grade.
In the following embodiments of the present invention, the test instruments and methods used are as follows:
The JH NMR and 13C NMR spectra are recorded on Bruker 300 MHz NMR Spectrometer, by dissolving a sample to be tested in deuterated chloroform (CDCh,) as a solvent and using tetramethylsilane (TMS) as an internal standard. The 77Se NMR spectrum is recorded on Agilent 400MHz NMR Spectrometer. The small molecule mass spectrometry (MS) is conducted in Bruker microTOF-Qin Mass Spectrometer by dissolving a sample to be tested in acetonitrile as a solvent and filtering. The Fourier transform infrared spectroscopy (FT-TR) is performed by Bruker TENSOR 27 FT-IR by dissolving a selenium-containing polyester in chloroform, and dripping onto a KBr disk. The UV-vis spectroscopy is performed by SHIMADZU UV-2600 by dissolving a selenium-containing polyester in chloroform and filling into a cuvette. The Differential scanning calorimetry (DSC) is performed by TA Instrument DSC Q200. The thermogravimetric analysis (TGA) is performed by PerkinElmer Pyris 1 TGA.
Embodiment 1 (1) Preparation of hexenyl butyrate diselenide (Hexene-ButdiSe) □ γ-butyroselenolactone (10.5 mmol), hexen-l-ol (10 mmol), DBU (1 mmol) and THF(10 mL) were added to a 50 mL three-neck flask, and the flask was not capped and placed in an oil bath at 70°C. The reaction process was followed by TLC. After the reaction was complete after 12 h, the □ γ-butyroselenolactone was substantially completely reacted. The reaction solution was naturally cooled and subjected to rotary evaporation to remove the solvent. The residue was then separated by chromatography on silica gel column (eluting with PE : EA — 20 : 1), to give a brownish red liquid, which is the product hexenyl butyrate diselenide (Hexene-ButdiSe). The reaction route is as follows.
O O se-^ -B,J,7I>“C»
Figs. 1-3 are respectively a ’H NMR spectrum (CDCh as a solvent), a 13C NMR spectrum (CDCI3 as a solvent), and a 77Se NMR spectrum (CDCI3 as a solvent) of Hexene-ButdiSe obtained in this embodiment. The MS data is as follows. MS m/z: [M+H]+ calculated: 499.0866, found: 499.0896.
(2) Preparation of monoselenide polymer
Hexene-ButdiSe (1.494 g, 3 mmol) prepared in Step (1) was weighed, dissolved in CHCI3 (2 ml) at room temperature, and stirred under argon atmosphere. SO2CI2 (0.45 g, 3 mmol) was slowly added dropwise at -20°C, and the reaction was performed for 3 h under stirring. The temperature was then raised to 0°C, and the reaction was continued for 24 h with stirring to obtain the monoselenide polymer PHex.
In the above reaction, Hexene-ButdiSe is firstly reacted with SO2CI2 to produce an intermediate with selenium chloride at one end and a non-active double bond at the other end. By means of the efficient addition reaction of the selenium chloride and the non-active double bond in the intermediate, polycondensation is effected to give the polymer PHex. Moreover, by controlling the molar ratio of Hexene-ButdiSe to SO2CI2, for example, at 3:2, 3:2.5, 3:2.8, 3:2.9, 3:3, monoselenide polymers of various molecular weights can be obtained. The reaction route is as follows.
Figure AU2017418044B2_D0002
Figs. 4-6 are respectively a Ή NMR spectrum (CDCh as a solvent), a 13C NMR spectrum (CDCh as a solvent), and a 77Se NMR spectrum (CDCI3 as a solvent) of PHex obtained in this embodiment.
Embodiment 2 (1) Preparation of butenyl butyrate diselenide (Butene-ButdiSe) γ-butyroselenolactone (10.5 mmol), buten-l-ol (10 mmol), DBU (1 mmol) and THF(10 mL) were added to a 50 mL three-neck flask, and the flask was not capped and placed in an oil bath at 70°C . The reaction process was followed by TLC. After the reaction was complete after 12 h, the γ-butyroselenolactone was substantially completely reacted. The reaction solution was naturally cooled and subjected to rotary evaporation to remove the solvent. The residue was then separated by chromatography on silica gel column (eluting with PE : EA = 20 : 1), to give a brownish red liquid, which is the product butenyl butyrate diselenide (Butene-ButdiSe). The reaction route is as follows.
Figure AU2017418044B2_D0003
(2) Preparation of monoselenide polymer (PBut)
Butene-ButdiSe (1.33 g, 3 mmol) prepared in Step (1) was weighed, dissolved in CHCI3 (2 ml) at room temperature, and stirred under argon atmosphere. SO2CI2 (0.45 g, 3 mmol) was slowly added dropwise at -20°C, and the reaction was performed for 3 h with stirring. The temperature was then raised to 0°C, and the reaction was continued for 24 h with stirring to obtain the monoselenide polymer PBut.
In the above reaction, the reaction principle is the same as that in embodiment 1.
The reaction route is as follows.
Figure AU2017418044B2_D0004
Fig. 7 is a *H NMR spectrum (CDC13 as a solvent) of PBut obtained in this example. It can be seen from Fig. 7 that all hydrogen atoms in PBut have been correspondingly attributed, and the actual number of hydrogen coincides with the theoretical number, and thus this further demonstrates that a monoselenide polymer is successfully prepared by the method of the present invention.
Embodiment 3 (1) Preparation of octadecenyl butyrate diselenide (OA-ButdiSe) γ-butyroselenolactone (10.5 mmol), oleyl alcohol (10 mmol), DBU (1 mmol) and THF(10 mb) were added to a 50 mL three-neck flask, and the flask was not capped and placed in an oil bath at 70°C. The reaction process was followed by TLC. After the reaction was complete after 12 h, the γ-butyroselenolactone was substantially completely reacted. The reaction solution was naturally cooled and subjected to rotary evaporation to remove
0 the solvent. The residue was then separated by chromatography on silica gel column (eluting with PE : EA = 20 : 1), to give a brownish red liquid, which is the product octadecenyl butyrate diselenide (OA-ButdiSe). The reaction route is as follows.
Figure AU2017418044B2_D0005
Figure AU2017418044B2_D0006
DBU, 70 °C
O
Figure AU2017418044B2_D0007
O (2) Preparation of monoselenide polymer (POA)
OA-ButdiSe (2.50 g, 3 mmol) prepared in Step (1) was weighed, dissolved in CHCk (2 ml) at room temperature, and stirred under argon atmosphere. SO2CI2 (0.45 g, 3 mmol) was slowly added dropwise at -20°C, and the reaction was performed for 3 h with stirring. The temperature was then raised to 0°C, and the reaction was continued for 24 h with stirring to obtain the monoselenide polymer POA.
In the above reaction, the reaction principle is the same as that in Embodiment 1.
The reaction route is as follows.
Figure AU2017418044B2_D0008
The molecular weights of the products PHex, PBut and POA obtained in Examples 1-3 were tested. The results are shown in Fig. 8 and Table 1. Fig. 8 is a gel permeation chromatogram of the three products. Table 1 shows the test results by gel permeation chromatography (GPC) for the three products.
1
Table 1. Test results by GPC for PHex, PBut, and POA
Ratio Mi,GPC (g mol'1) D
Embodiment 1 1:1 9700 1.70
Embodiment 2 1:1 7100 1.62
Embodiment 3 1:1 4200 1.92
In Table 1, Ratio denotes the molar ratio of the alkenyl ester diselenide to the sulfonyl chloride; Mi,gpc denotes molecular weights of the products in 5 embodiments, and D denotes the molecular weight distribution of the products in embodiments.
The results show that the molecular weight of PHex is 9700 g/mol, the molecular weight of PBut is 7100 g/mol, and the molecular weight of POA is 4200 g/mol.
The above description is only preferred embodiments of the present invention and not intended to limit the present invention, it should be noted that those of ordinary skill in the art can further make various modifications and variations without departing from the technical principles of the present invention, and these modifications and variations also should be considered to be within the scope of protection of the present invention.

Claims (10)

What is claimed is:
1 3
(1) reacting a selenolactone with an unsaturated monohydric alcohol in the presence of a catalyst at 40-70°C, to obtain an alkenyl ester diselenide; and (2) dissolving the alkenyl ester diselenide in an organic solvent; adding sulfonyl chloride at -20 to -10°C to perform a reaction; and then raising the temperature to 0 to 10°C to continue the reaction, to obtain the monoselenide polymer.
1. A method for preparing a monoselenide polymer, comprising steps of:
2. The method for preparing a monoselenide polymer as claimed in claim 1, wherein in the step (1), the selenolactone is
Figure AU2017418044B2_C0001
3. The method for preparing a monoselenide polymer as claimed in claim 1, wherein in the step (1), the unsaturated monohydric alcohol is selected from the group consisting of 3-buten-l-ol, 5-hexen-l-ol, oleyl alcohol, 4-penten-l-ol, 6-hepten-l-ol, 7-octen-l-ol and 5-norbornen-2-methanol.
4. The method for preparing a monoselenide polymer as claimed in claim 1, wherein in the step (1), the catalyst is selected from the group consisting of 1, 8-diazabicyclo[5.4.0]undec-7-ene, 4-dimethylaminopyridine and triethyl amine.
5. The method for preparing a monoselenide polymer as claimed in claim 1, wherein in the step (1), the molar ratio of the selenolactone to the unsaturated monohydric alcohol is 1 : 0.6-1.
6. The method for preparing a monoselenide polymer as claimed in claim 1, wherein in the step (1), the molar ratio of the unsaturated monohydric alcohol to the catalyst is 1 : 0.05-0.2.
7. The method for preparing a monoselenide polymer as claimed in claim 1, 5 wherein in the step (2), the organic solvent is selected from chloroform, dichloromethane, tetrahydro furan and any combination thereof.
8. The method for preparing a monoselenide polymer as claimed in claim 1, wherein in the step (2), the reaction is carried out under a protective atmosphere.
10
9. The method for preparing a monoselenide polymer as claimed in claim 1, wherein in the step (2), the molar ratio of the alkenyl ester diselenide to the sulfonyl chloride is 1 : 0.6-1.
10. A monoselenide polymer prepared by the method as claimed in any one of claims 1 to 9.
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