CN105924630A - Optically-active helix chain poly(phenyl isocyanide) and polymerization method thereof - Google Patents
Optically-active helix chain poly(phenyl isocyanide) and polymerization method thereof Download PDFInfo
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- CN105924630A CN105924630A CN201610305211.5A CN201610305211A CN105924630A CN 105924630 A CN105924630 A CN 105924630A CN 201610305211 A CN201610305211 A CN 201610305211A CN 105924630 A CN105924630 A CN 105924630A
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/143—Side-chains containing nitrogen
- C08G2261/1432—Side-chains containing nitrogen containing amide groups
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/16—End groups
- C08G2261/162—End groups comprising metal complexes
- C08G2261/1624—End groups comprising metal complexes of Os, Ir, Pt, Ru, Rh or Pd
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/312—Non-condensed aromatic systems, e.g. benzene
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/35—Macromonomers, i.e. comprising more than 10 repeat units
- C08G2261/352—Macromonomers, i.e. comprising more than 10 repeat units containing only carbon atoms
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Abstract
The invention discloses an optically-active helix chain poly(phenyl isocyanide) and a polymerization method thereof. The polymerization process is shown as the general formula in the description; in the formula, the structural formula of a chiral phosphine ligand is shown in the description. A palladium catalyst is adopted, the chiral phosphine ligand (S-or R-BINAP) is added to induce polymerization of achiral phenyl isocyanide, and the optically-active polymer with excessive one-handed helixes is obtained; obtained poly(phenyl isocyanide) has a high molecular weight and narrow molecular weight distribution.
Description
Technical field
The present invention relates to polymer reaction field, be specifically related to a kind of optical activity coiled strand polyphenyl isonitrile and gather
Conjunction method.
Background technology
Chirality is a kind of phenomenon being widely present in nature, and helical structure is also the core texture mould of biomolecule
Block, the double-spiral structure of DNA the most familiar to people and the α-helixstructure of protein.They
Chiral helical secondary structure and the structure of more high order that separately or cooperatively formed form organism, execution assembling
Conclusive effect is played during biological function.By the high molecular inspiration of spiral biological in nature, people
Spiral macromolecule is created continue and study interest widely.In spiral macromolecule, spiral polyphenyl isonitrile
On the main chain carbon of (poly (phenyl isocyanide)) containing pi-conjugated C=N make main polymer chain distortion from
And define helical structure, there is stable helical conformation, its stable in properties, monomer are easy to get, polymerization simple,
In the solution with all can well keep helical structure during solid-state, be one significantly synthetic polymerization
Thing.Optically active spiral polyphenyl isonitrile is in multiple researchs such as chiral Recognition, Chiral Separation and liquid crystal displays
There is important using value in field.
Optically active coiled strand polyphenyl isonitrile generally uses chiral catalyst (initiator) or chiral monomer polymerization
Obtain.But, these polyphenyl isonitrile the most all have complex chiral structure, such as: helical backbones, side
Chiral radicals on base and chirality end group etc..Therefore, developing new synthetic method, preparation comprises only screw hand
The polymer of property, and do not have the polyphenyl isonitrile of other chiral element to have important Research Significance.
Therefore, those skilled in the art is devoted to develop a kind of new catalysis activity height, stable in properties, synthesis
Readily catalyst and chiral ligand polymerization, for being catalyzed the living polymerization of isonitrile compounds, thus be
The optical activity polyphenyl isonitrile of synthesis unidextrality spiral excess provides new polymerization and polymerization system.
Summary of the invention
It is contemplated that: the preparation side of a kind of optical activity polyphenyl isonitrile with unidextrality spiral excess is provided
Method.For generating the optics with unidextrality spiral excess after in the present invention, chiral phosphine ligand is coordinated with palladium catalyst
Activity polyphenyl isonitrile, reaction efficiency is high and simple to operate, synthesis is easy, simplifies synthesis step.
In order to realize foregoing invention purpose, the technical solution used in the present invention is as follows:
A kind of optical activity coiled strand polyphenyl isonitrile, structural formula is as follows:
Its degree of polymerization m=20-100.
Further, the polymerization of described optical activity coiled strand polyphenyl isonitrile, according to the following steps operation:
(1) in polymerization bottle, add chiral phosphine ligand and palladium catalyst, after vacuum nitrogen filling gas, add and be dried
Oxolane, stirring at normal temperature 3-5h, obtain the mixture of palladium catalyst and chiral phosphine ligand；
(2) achirality benzene isonitrile monomer is dissolved in dry CHCl3In, add step the most under nitrogen atmosphere
Suddenly (1) gained mixture, no longer increases to strand 50-55 DEG C of back flow reaction, adds methanol cancellation,
Make polymer Precipitation, wash with methanol, precipitate obtained by centrifugation thing, be dried under vacuum to mass conservation, i.e.
Obtain target product；
Wherein the structural formula of palladium catalyst is:
The structural formula of achirality benzene isonitrile monomer is:
Further, described chiral phosphine ligand is S-BINAP or R-BINAP, and concrete structure formula is as follows:
Further, when chiral phosphine ligand is S-BINAP, the mol ratio of S-BINAP and palladium catalyst is
(6-12): 1；When chiral phosphine ligand is R-BINAP, the mol ratio of R-BINAP and palladium catalyst is
(6-12):1。
Further, the concentration of described achirality benzene isonitrile monomer is 0.1-02M, achirality benzene isonitrile monomer
It is (20-100) with the mol ratio of palladium catalyst: 1.
Further, vacuum nitrogen filling gas 3-5 time in step (1), the number of times of methanol washing in step (3)
4-5 time.
Further, in step (2), return time is 18-20h.
Compared with the prior art, beneficial effects of the present invention is embodied in:
1, the synthesis of the optical activity coiled strand polyphenyl isonitrile in the present invention is simple, requires the harshest to experiment condition,
Simple to operate.
2, by adding chiral phosphine ligand induction achirality isonitrile polymerization, synthesis step can be simplified, it is possible to
To that comprise only unidextrality spiral excess and have optically active, and there is no the polyphenyl isonitrile of other chiral element
Polymer.
3, it is the optical active polymer that S-BINAP can obtain single left hand helix when chiral phosphine ligand,
When chiral phosphine ligand is the optical active polymer that R-BINAP can obtain single right-handed helix.
Accompanying drawing explanation
Fig. 1 is the gel permeation chromatography figure of polyphenyl isonitrile in the embodiment of the present invention 1 and 2, and wherein solid line is gel
Permeation chromatography records the curve (M of embodiment 1 polyphenyl isonitrilen=2.45 × 104, PDI=1.19)；Dotted line is solidifying
Glue penetration chromatograph records the curve (M of embodiment 2 polyphenyl isonitrilen=2.66 × 104, PDI=1.22).
Fig. 2 is the circular dichroism spectrogram of polyphenyl isonitrile in the embodiment of the present invention 1 and 2, and wherein solid line is circular dichroism spectra
Recording the curve of embodiment 1 polyphenyl isonitrile, at 364nm, the g value of polymer is+323.2；Dotted line is circle two
Chromatograph records the curve of embodiment 2 polyphenyl isonitrile, and at 364nm, the g value of polymer is-318.4.
Fig. 3 is the circular dichroism spectrogram of polyphenyl isonitrile in the embodiment of the present invention 3,4 and 5, and wherein, dotted line is round
Two chromatographs record the curve of embodiment 3 polyphenyl isonitrile, and at 364nm, the g value of polymer is+136.68；Dotted line
Being the circular dichroism spectra curve that records embodiment 4 polyphenyl isonitrile, at 364nm, the g value of polymer is+171.54；
Solid line is the curve that circular dichroism spectra records embodiment 5 polyphenyl isonitrile, and at 364nm, the g value of polymer is
+302.94。
Fig. 4 is the gel permeation chromatography figure of polyphenyl isonitrile in the embodiment of the present invention 3,4 and 5.Dotted line is gel
Permeation chromatography records the curve (M of embodiment 3 polyphenyl isonitrilen=2.56 × 104, PDI=1.18)；Dotted line is solidifying
Glue penetration chromatograph records the curve (M of embodiment 4 polyphenyl isonitrilen=2.76 × 104, PDI=1.21)；Solid line is
Gel permeation chromatography records the curve (M of embodiment 5 polyphenyl isonitrilen=2.63 × 104, PDI=1.20).
Detailed description of the invention
Embodiment 1
The polymerization of a kind of optical activity coiled strand polyphenyl isonitrile, according to the following steps operation:
1. chiral phosphine ligand (S-BINAP) is carried out under the conditions of strict anhydrous and oxygen-free with palladium catalyst, 10
ML polymerization bottle adds chiral phosphine ligand (S-BINAP) and palladium catalyst, S-BINAP and palladium catalyst
Mol ratio is 12:1, vacuum nitrogen filling gas 3 times, adds the oxolane that 0.3mL is dried, stirring at normal temperature 3
H, obtains the mixture of S-BINAP and palladium catalyst.
2, weigh in the polymerization bottle that 0.1mmol (34mg) achirality benzene isonitrile monomer adds 10mL, then add
Enter the CHCl that 0.8mL is dried3Dissolve, then weigh the S-BINAP of 0.9 μm ol and the mixing of palladium catalyst
Solution, adds polymerization bottle under nitrogen atmosphere, after 55 DEG C of back flow reaction 20h, adds 10mL methanol
Cancellation, makes polymer Precipitation, washs 4-5 time with methanol, centrifuged yellow green flocculent deposit, very
Sky is dried to mass conservation.Obtaining 29.0mg polyphenyl isonitrile, its number-average molecular weight is 2.56 × 104, molecular weight divides
Cloth is 1.21.It is+323.2 that CD measures the g value of polymer at 364nm.
Embodiment 2
The polymerization of a kind of optical activity coiled strand polyphenyl isonitrile, according to the following steps operation:
1. chiral phosphine ligand (R-BINAP) is carried out under the conditions of strict anhydrous and oxygen-free with palladium catalyst,
10mL polymerization bottle adds chiral phosphine ligand (R-BINAP) and palladium catalyst, R-BINAP and palladium chtalyst
The mol ratio of agent is 12:1, vacuum nitrogen filling gas 3 times, adds the oxolane that 0.3mL is dried, room temperature
Stirring 3h, obtains the mixture of R-BINAP and palladium catalyst.
2, weigh 0.1mmol (34mg) achirality benzene isonitrile monomer to add in 10mL polymerization bottle, add
The CHCl that 0.8mL is dried3Dissolving, the R-BINAP then weighing 0.9 μm ol is molten with the mixing of palladium catalyst
Liquid, adds polymerization bottle under nitrogen atmosphere, after 55 DEG C of back flow reaction 20h, adds 10mL methanol and quenches
Go out, make polymer Precipitation, wash 4-5 time with methanol, centrifuged yellow green flocculent deposit, vacuum
It is dried to mass conservation.Obtaining 29.4mg polyphenyl isonitrile, its number-average molecular weight is 2.66 × 104, molecular weight distribution
It is 1.21.It is-318.4 that CD measures the g value of polymer at 364nm.
Embodiment 3
The polymerization of a kind of optical activity coiled strand polyphenyl isonitrile, according to the following steps operation:
1. chiral phosphine ligand (S-BINAP) is carried out under the conditions of strict anhydrous and oxygen-free with palladium catalyst,
10mL polymerization bottle adds chiral phosphine ligand (S-BINAP) and palladium catalyst, S-BINAP and palladium catalyst
Mol ratio be 3:1, vacuum nitrogen filling gas 4 times, add the oxolane that is dried of 0.3mL, stirring at normal temperature
3h, obtains the mixture of palladium catalyst and S-BINAP.
2, weigh 0.1mmol (34mg) achirality benzene isonitrile monomer and add 10mL polymerization bottle, add
The CHCl that 0.8mL is dried3Dissolving, the S-BINAP then weighing 0.9 μm ol is molten with the mixing of palladium catalyst
Liquid, adds polymerization bottle under nitrogen atmosphere, after 55 DEG C of back flow reaction 20h, adds 10mL methanol and quenches
Go out, make polymer Precipitation, wash 4-5 time with methanol, centrifuged yellow green flocculent deposit, vacuum
It is dried to mass conservation.Obtaining 28.5mg polyphenyl isonitrile, its number-average molecular weight is 2.56 × 104, molecular weight distribution
It is 1.18.It is+136.68 that CD measures the g value of polymer at 364nm.
Embodiment 4
The polymerization of a kind of optical activity coiled strand polyphenyl isonitrile, according to the following steps operation:
1. chiral phosphine ligand (S-BINAP) is carried out under the conditions of strict anhydrous and oxygen-free with palladium catalyst,
The mol ratio adding S-BINAP and palladium catalyst, S-BINAP and palladium catalyst in 10mL polymerization bottle is 5:
1, vacuum nitrogen filling gas 3 times, add the oxolane that 0.3mL is dried, stirring at normal temperature 3h, obtain S-BINAP
Mixture with palladium catalyst.
2, weigh 0.1mmol (34mg) achirality benzene isonitrile monomer and add 10mL polymerization bottle, add
The CHCl that 0.8mL is dried3Dissolving, the S-BINAP then weighing 0.9 μm ol is molten with the mixing of palladium catalyst
Liquid, adds polymerization bottle under nitrogen atmosphere, after 55 DEG C of back flow reaction 20h, adds 10mL methanol and quenches
Go out, make polymer Precipitation, wash 4-5 time with methanol, centrifuged yellow green flocculent deposit, vacuum
It is dried to mass conservation.Obtaining 27.4mg polyphenyl isonitrile, its number-average molecular weight is 2.76 × 104, molecular weight distribution
It is 1.21.It is+171.54 that CD measures the g value of polymer at 364nm.
Embodiment 5
The polymerization of a kind of optical activity coiled strand polyphenyl isonitrile, according to the following steps operation:
1. chiral phosphine ligand (S-BINAP) is carried out under the conditions of strict anhydrous and oxygen-free with palladium catalyst,
10mL polymerization bottle adds chiral phosphine ligand (S-BINAP) and palladium catalyst, S-BINAP and palladium catalyst
Mol ratio be 10:1, vacuum nitrogen filling gas 3 times, add the oxolane that is dried of 0.3mL, room temperature stirs
Mix 3h, obtain the mixture of S-BINAP and palladium catalyst.
2, weigh 0.1mmol (34mg) achirality benzene isonitrile monomer and add 10mL polymerization bottle, add
The CHCl that 0.8mL is dried3Dissolving, the S-BINAP then weighing 0.9 μm ol is molten with the mixing of palladium catalyst
Liquid, adds polymerization bottle under nitrogen atmosphere, after 55 DEG C of back flow reaction 20h, adds 10mL methanol and quenches
Go out, make polymer Precipitation, wash 4-5 time with methanol, centrifuged yellow green flocculent deposit, vacuum
It is dried to mass conservation.Obtaining 27.2mg polyphenyl isonitrile, its number-average molecular weight is 2.63 × 104, molecular weight distribution
It is 1.20.It is+302.94 that CD measures the g value of polymer at 364nm.
In conjunction with accompanying drawing 1-4, it can be seen that the polyphenyl isonitrile of gained has from the data that embodiment 1-5 records
Higher molecular weight and narrower molecular weight distribution, obtain optically active polymerization with unidextrality spiral excess
Thing.
In embodiment 1-5:
The structural formula of palladium catalyst is:
The structural formula of achirality benzene isonitrile monomer is:
The concrete structure formula of S-BINAP, R-BINAP is as follows:
The polymerization process of the present invention is represented by the following general formula:
The preferred embodiment of the present invention described in detail above.Should be appreciated that the ordinary skill of this area without
Need creative work just can make many modifications and variations according to the design of the present invention.Therefore, all technology neck
In territory, technical staff is the most on the basis of existing technology by logical analysis, reasoning or limited
The available technical scheme of experiment, all should be in the protection domain being defined in the patent claims.
Claims (7)
1. an optical activity coiled strand polyphenyl isonitrile, it is characterised in that: structural formula is as follows:
Its degree of polymerization m=20-100.
2. a polymerization for optical activity coiled strand polyphenyl isonitrile as claimed in claim 1, its feature
It is: operation according to the following steps:
(1) in polymerization bottle, add chiral phosphine ligand and palladium catalyst, after vacuum nitrogen filling gas, add and be dried
Oxolane, stirring at normal temperature 3-5h, obtain the mixture of palladium catalyst and chiral phosphine ligand；
(2) achirality benzene isonitrile monomer is dissolved in dry CHCl3In, add step the most under nitrogen atmosphere
Suddenly (1) gained mixture, no longer increases to strand 50-55 DEG C of back flow reaction, adds methanol cancellation,
Make polymer Precipitation, wash with methanol, precipitate obtained by centrifugation thing, be dried under vacuum to mass conservation, i.e.
Obtain target product；
Wherein the structural formula of palladium catalyst is:
The structural formula of achirality benzene isonitrile monomer is:
3. the polymerization of optical activity coiled strand polyphenyl isonitrile as claimed in claim 2, it is characterised in that:
Described chiral phosphine ligand is S-BINAP or R-BINAP, and concrete structure formula is as follows:
4. the polymerization of optical activity coiled strand polyphenyl isonitrile as claimed in claim 3, it is characterised in that:
When chiral phosphine ligand is S-BINAP, the mol ratio of S-BINAP and palladium catalyst is (6-12): 1；When
When chiral phosphine ligand is R-BINAP, the mol ratio of R-BINAP and palladium catalyst is (6-12): 1.
The polymerization of optical activity coiled strand polyphenyl isonitrile the most according to claim 2, its feature exists
In: the concentration of described achirality benzene isonitrile monomer is 0.1-02M, achirality benzene isonitrile monomer and palladium catalyst
Mol ratio be (20-100): 1.
6. the polymerization of optical activity coiled strand polyphenyl isonitrile as claimed in claim 2, it is characterised in that:
Vacuum nitrogen filling gas 3-5 time in step (1), the number of times of methanol washing 4-5 time in step (3).
7. the polymerization of optical activity coiled strand polyphenyl isonitrile as claimed in claim 2, it is characterised in that:
In step (2), return time is 18-20h.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108395523A (en) * | 2018-03-29 | 2018-08-14 | 湖北科技学院 | A kind of isonitrile spiropolymer of Sulfide-containing Hindered side chain and preparation method thereof of oxidation helical conformation overturning |
| CN111471467A (en) * | 2020-05-14 | 2020-07-31 | 商丘师范学院 | Polymer type lyotropic liquid crystal material, preparation method thereof and application thereof in chiral drug resolution |
| CN112062901A (en) * | 2020-08-14 | 2020-12-11 | 合肥工业大学 | Spiral fluorescent isonitrile copolymer and preparation method thereof |
| CN114621417A (en) * | 2022-03-28 | 2022-06-14 | 合肥工业大学 | Optically active spiral polyfluorene block polyisonitrile copolymer and preparation method and application thereof |
| CN115286772A (en) * | 2022-08-30 | 2022-11-04 | 合肥工业大学 | Optically active spiral polyisonitrile block polyfluorene copolymer and preparation method and application thereof |
| CN115716737A (en) * | 2022-12-07 | 2023-02-28 | 黄庆华 | High-strength rubber concrete containing composite fiber interface filler and preparation method thereof |
| CN114989426B (en) * | 2022-06-20 | 2024-03-15 | 合肥工业大学 | Polymer brush of poly (isonitrile) grafted polyoxazoline and preparation method thereof |
-
2016
- 2016-05-06 CN CN201610305211.5A patent/CN105924630A/en active Pending
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Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108395523A (en) * | 2018-03-29 | 2018-08-14 | 湖北科技学院 | A kind of isonitrile spiropolymer of Sulfide-containing Hindered side chain and preparation method thereof of oxidation helical conformation overturning |
| CN108395523B (en) * | 2018-03-29 | 2020-05-01 | 湖北科技学院 | Oxidation helix conformation-reversed isonitrile helical polymer containing thioether side chain and preparation method thereof |
| CN111471467A (en) * | 2020-05-14 | 2020-07-31 | 商丘师范学院 | Polymer type lyotropic liquid crystal material, preparation method thereof and application thereof in chiral drug resolution |
| CN111471467B (en) * | 2020-05-14 | 2023-04-25 | 商丘师范学院 | Polymer type lyotropic liquid crystal material, preparation method thereof and application thereof in chiral drug resolution |
| CN112062901A (en) * | 2020-08-14 | 2020-12-11 | 合肥工业大学 | Spiral fluorescent isonitrile copolymer and preparation method thereof |
| CN112062901B (en) * | 2020-08-14 | 2023-03-21 | 合肥工业大学 | Spiral fluorescent isonitrile copolymer and preparation method thereof |
| CN114621417A (en) * | 2022-03-28 | 2022-06-14 | 合肥工业大学 | Optically active spiral polyfluorene block polyisonitrile copolymer and preparation method and application thereof |
| CN114621417B (en) * | 2022-03-28 | 2024-04-09 | 合肥工业大学 | Optically active spiral polyfluorene block polyisonitrile copolymer and preparation method and application thereof |
| CN114989426B (en) * | 2022-06-20 | 2024-03-15 | 合肥工业大学 | Polymer brush of poly (isonitrile) grafted polyoxazoline and preparation method thereof |
| CN115286772B (en) * | 2022-08-30 | 2024-03-15 | 合肥工业大学 | Optically active spiral polyisonitrile block polyfluorene copolymer and preparation method and application thereof |
| CN115286772A (en) * | 2022-08-30 | 2022-11-04 | 合肥工业大学 | Optically active spiral polyisonitrile block polyfluorene copolymer and preparation method and application thereof |
| CN115716737A (en) * | 2022-12-07 | 2023-02-28 | 黄庆华 | High-strength rubber concrete containing composite fiber interface filler and preparation method thereof |
| CN115716737B (en) * | 2022-12-07 | 2024-04-26 | 永清县优通建筑工程有限公司 | High-strength rubber concrete containing composite fiber interface filler and preparation method thereof |
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