CN113480716B - Polyaromatic hydrocarbon with main chain containing perfluoroarene and perfluoroalkane and preparation method thereof - Google Patents
Polyaromatic hydrocarbon with main chain containing perfluoroarene and perfluoroalkane and preparation method thereof Download PDFInfo
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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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
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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
- C08G2261/12—Copolymers
- C08G2261/122—Copolymers statistical
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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
- 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
- C08G2261/146—Side-chains containing halogens
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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
- 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
Abstract
The invention discloses a polymer with a main chain containing perfluorinated aromatic hydrocarbon and a perfluorinated alkyl chain and a preparation method thereof, belonging to the technical field of synthesis of high polymer materials. The structure of the polymer simultaneously has perfluoroarene and perfluoroalkyl chain, and has a structural formula shown in a formula I. The preparation method comprises the following steps: the polymer is prepared by taking a fluorine-containing aromatic hydrocarbon monomer, a hexafluoroacetone monomer and an octafluoro-2-butanone monomer as raw materials and carrying out nucleophilic substitution reaction in an organic solvent in the presence of an acid catalyst. The polymer has better solubility in common organic solvents, higher glass transition temperature (>300 ℃) and higher thermal decomposition temperature (5% thermal weight loss temperature >450 ℃), is suitable for being used as a high-performance structural material, and can also be used as a composite material matrix resin or a functional film material.
Description
Technical Field
The invention belongs to the technical field of polymers, and particularly relates to a perfluorinated polyaromatic hydrocarbon material and a preparation method thereof.
Background
Perfluoropolymers, because of their many unique structures, exhibit a number of special properties, such as: fluorine atoms have low polarizability, strong electronegativity, small van der waals radius and strong C-F bond energy (485kJ/mol), so that the fluorocarbon polymer with high fluorine content has high heat resistance, chemical corrosion resistance, durability and weather resistance, especially the inertness to many solvents, hydrocarbons and various acids and bases, low capacitance, low flammability, low refractive index, low surface energy (neither oleophilic nor hydrophilic) and moisture absorption performance. Moreover, the strong C-F bond enables such polymers to have very strong stability to redox. The polymer is widely applied to the fields of industrial construction (used as an inner and outer wall coating and used for preventing ultraviolet rays and noise), petrochemical and automobile industries, aerospace industries (used for gaskets and films in the form of elastomers and used on containers required for containing liquid hydrogen for space shuttles at extremely low temperature), chemical engineering (used for high-performance films), optics (used for inner cores and attached layers of optical fibers), treatment of textile articles, treatment of cultural stone tablets, microelectronics and the like.
Most of the currently used perfluoro resins are made of fluoroolefin, TFE (tetrafluoroethylene), HFP (hexafluoropropylene), trifluoroethylene and the like, the number of carbon atoms of which is between 2 and 4, and the dispersion medium is usually a chlorofluorocarbon organic solvent, but these substances have a certain effect of destroying the ozone layer, and recently, methyl branched hydrocarbons such as 2, 3-dimethylbutane, 2, 3-dimethylpentane, 2,2, 4-trimethylpentane, 2,2,4,6, 6-pentamethylheptane and 2,2,4,4, 6-pentamethylheptane are mainly used, but these methylated hydrocarbons are not expensive and are not feasible from the viewpoint of industrialization. Furthermore, the above reaction requires the use of an initiator, a pH buffer, a polymerization regulator, etc., and also requires many requirements for reaction temperature, reaction pressure, and stirring rate, for example: the initial reaction temperature is preferably 10 to 80 ℃. The reaction pressure is preferably 4 to 30 kg/cm. The stirring rate is preferably 50 to 700 rpm. The reaction time is preferably 1 to 20 hours.
In order to expand the processing means and application range of the perfluorinated high polymer material and improve the use temperature of the material, aiming at exploring a novel aromatic perfluorinated structure, it is necessary to explore amorphous poly-perfluorinated aromatic hydrocarbon and alkyl-containing resin obtained by condensation polymerization of fluorine-containing aromatic hydrocarbon and perfluorinated ketone, and develop resin with excellent performances such as chemical corrosion resistance, atmospheric aging resistance, excellent dielectric property, unique low surface energy, wide use temperature range and the like, so that the comprehensive performance of the resin can be comparable with that of polytetrafluoroethylene and polyvinylidene fluoride, and the resin has excellent dissolution processability and can greatly improve the application field of the resin.
Disclosure of Invention
The perfluoro polyaromatic hydrocarbon of the invention uses the resin which is obtained by condensation polymerization of fluorine-containing aromatic hydrocarbon and perfluoro-substituted ketone and contains amorphous perfluoro aromatic hydrocarbon and alkyl, can endow the polymer with good solubility and excellent heat resistance and hydrophobicity (super-large hydrophobic angle), and can widen the application of the polymer in the fields of films, separation membranes, coatings, insulating paints and the like.
The purpose of the invention is realized by the following technical scheme:
the main chain of the polyaromatic alkane contains a perfluorinated aromatic hydrocarbon and a perfluorinated methylene structure, and the structure of the polyaromatic alkane simultaneously has a perfluorinated alkane substituent.
Among the above-mentioned polyarylalkanes, as a preferred embodiment, said polyarylalkanes have the structural formula represented by formula I:
wherein m is more than or equal to 0 and less than or equal to 1, n is more than or equal to 0 and less than or equal to 1, and m + n is equal to 1; ar is any one of structures (a) to (h):
r is one or two of (i) or (j):
in the above perfluoroaromatic resin, as a preferred embodiment, the perfluoroaromatic resin has a number average molecular weight of 1 x 10 as measured by GPC4～6*104。
The preparation method of the polyaromatic resin with the main chain perfluorinated aromatic hydrocarbon and the perfluoroalkyl group structure takes a fluorine-containing aromatic hydrocarbon monomer and a perfluoroalkyl group ketone monomer as raw materials, and obtains the perfluorinated polyaromatic resin through homopolymerization or copolymerization reaction in the presence of a catalyst and a solvent.
In the above production method, as a preferred embodiment, the fluorine-containing aromatic hydrocarbon monomer is one of 1,2,4, 5-tetrafluorobenzene, 2',3,3',5,5',6,6' -octafluorobiphenyl, 3,3 '-oxybis (1,2,4, 5-tetrafluorobenzene), 2',2 ", 3,3', 3", 5,5',5 ", 6,6',6 ″ -dodecafluoroterphenyl, 3,3' - (perfluoro-1, 4-phenyl) bis (oxy) bis (1,2,4, 5-tetrafluorobenzene), 1,2,3,4,6, 7-hexafluoronaphthalene, 1,2,3,5,6, 7-hexafluoronaphthalene, 1,2,3,4,5,6,7, 8-octafluoroanthracene.
In the above production method, as a preferred embodiment, the perfluoroalkanone monomer is one or both of hexafluoroacetone and octafluoro-2-butanone.
The invention also provides a preparation method of the polymer containing the perfluorinated aromatic hydrocarbon and the perfluorinated alkane, which takes 1,2,4, 5-tetrafluorobenzene, hexafluoroacetone and octafluoro-2-butanone as raw materials as a preferred embodiment, and the reaction formula is as follows:
in the above preparation method, as a preferred embodiment, the preparation method is specifically as follows: mixing a mol of fluorine-containing aromatic hydrocarbon monomer, b mol of hexafluoroacetone monomer (dichloroethane solution of hexafluoroacetone) and c mol of octafluoro-2-butanone with an acid catalyst and an organic solvent, controlling the temperature to be-30-20 ℃ (such as-30 ℃, 20 ℃, 10 ℃, 0 ℃, 10 ℃ and 20 ℃), then reacting for 1-48 h (such as 1h, 5h, 10h, 15h, 24h, 35h and 48h), and adding a precipitator; then filtering, separating, cleaning and drying to obtain the perfluorinated polyaryl alkane copolymer; wherein a is b + c, a is more than 0, b is more than or equal to 0, and c is more than or equal to 0.
In the above preparation method, as a preferred embodiment, the acid catalyst is one or more of methanesulfonic acid, p-toluenesulfonic acid and trifluoromethanesulfonic acid, and the molar ratio of the fluorinated aromatic hydrocarbon monomer to the acid catalyst is 1:0.01 to 0.20 (for example: 1:0.01, 1:0.03, 1:0.08, 1:0.12, 1:0.16 and 1: 0.20).
In the above preparation method, as a preferred embodiment, the solvent is one of dichloromethane, chloroform and dichloroethane, and the amount of the solvent is 1.0-50.0 mL/1 g of the fluoroarene and perfluoroalkyl ketone monomer mixture (e.g., 1mL/g, 5mL/g, 10mL/g, 20mL/g, 30mL/g, 40mL/g, 50 mL/g).
In the above preparation method, as a preferred embodiment, the precipitant is one or both of ethanol and methanol.
The invention has the beneficial effects that:
1. the polymer structure of the invention has perfluorinated aromatic hydrocarbon group and perfluoroalkyl group at the same time, and the content of the two groups can be regulated and controlled; the polymer containing the two structures in the main chain has good solubility in common organic solvents, has high glass transition temperature (>300 ℃) and high thermal decomposition temperature (5% thermal weight loss temperature >450 ℃) and excellent hydrophobicity, is suitable for being used as a high-performance structural material, can also be used as a composite material matrix resin or a functional film material, and the like.
2. In the structure of the polymer, perfluorobenzene and perfluoroalkyl are connected through covalent bonds, but the solubility of the prepared polymer is also obviously improved because the two groups have larger free volumes; can be dissolved in common organic solvents such as chloroform, tetrahydrofuran, toluene and the like at normal temperature, and lays an important foundation for the application of the polymer in the aspects of membrane materials, epoxy toughening, coatings, high-temperature resistant coatings and the like.
3. In the preparation method, the temperature-resistant grade and the solubility of the polymer can be effectively regulated and controlled by regulating the proportion of hexafluoroacetone and octafluoro-2-butanone in the copolymer so as to adapt to the use requirements of different fields.
4. The polymer of the invention is a perfluoro-substituted polymer, so the polymer has the inertness of various acids and bases, low capacitance, low flammability, low refractive index, low surface energy (neither oleophilic nor hydrophilic) and moisture absorption performance. Moreover, the strong C-F bond enables such polymers to have very strong stability to redox.
Drawings
FIG. 1 is an IR spectrum of the product obtained in example 1;
FIG. 2 is a thermogravimetric analysis of the product obtained in example 1.
The specific implementation mode is as follows:
in order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
Example 1
Adding 1,2,4, 5-tetrafluorobenzene (0.01mol, 1.50g), 0.005mol of hexafluoroacetone/dichloroethane solution and 0.005mol of octafluoro-2-butanone into a three-neck flask with a mechanical stirrer, a thermometer, a condenser and a nitrogen protection at-30 ℃, adding 0.0001mol of methanesulfonic acid as a catalyst and 1.5mL of dichloromethane as a solvent, heating to 0 ℃ for reaction for 1h, precipitating the reaction liquid in ethanol, filtering, and collecting a filter cake; the precipitate was boiled in boiling water and filtered several times, the filter cake was collected and vacuum dried at 110 ℃ for 24h to obtain a white product. The infrared spectrum of the product is shown in figure 1, and the thermogravimetric analysis (TGA) spectrum of the product is shown in figure 2.
Example 2
Adding 2,2',3,3',5,5',6,6' -octafluorobiphenyl (0.01mol, 29.81g), 0.01mol of hexafluoroacetone/dichloroethane solution into a three-neck flask provided with a mechanical stirrer, a thermometer, a condenser and a nitrogen protection device at-30 ℃, adding 14.9mL of chloroform as a solvent into 0.0003mol of trifluoromethanesulfonic acid as a catalyst, heating to 10 ℃, reacting for 15 hours, precipitating the reaction solution in methanol, filtering and collecting a filter cake; the precipitate was boiled in boiling water and filtered several times, the filter cake was collected and vacuum dried at 110 ℃ for 24h to obtain a white product.
Comparative example:
adding biphenyl (0.01mol, 1.54g) and 0.01mol of trifluoroacetone into a three-neck flask with a mechanical stirrer, a thermometer, a condenser tube and a nitrogen protection device at the temperature of minus 30 ℃, adding 14.9mL of chloroform as a solvent by taking 0.0003mol of trifluoromethanesulfonic acid as a catalyst, heating to 10 ℃, reacting for 15h, precipitating the reaction solution in methanol, filtering, and collecting a filter cake; the precipitate was boiled in boiling water and filtered several times, the filter cake was collected and vacuum dried at 110 ℃ for 24h to obtain a white product.
Example 3
Adding 3,3' -oxydi (1,2,4, 5-tetrafluorobenzene) (0.01mol and 3.14g) and 0.01mol of hexafluoroacetone/dichloroethane solution into a three-neck flask provided with a mechanical stirrer, a thermometer, a condenser and a nitrogen protection device at the temperature of-30 ℃, adding 31.41mL of dichloroethane as a solvent by taking 0.0008mol of trifluoromethanesulfonic acid as a catalyst, heating to 20 ℃, reacting for 10 hours, precipitating the reaction solution in methanol, filtering and collecting a filter cake; the precipitate was boiled in boiling water and filtered several times, the filter cake was collected and vacuum dried at 110 ℃ for 24h to obtain a white product.
Example 4
Adding 2,2',3,3',5,5',6,6' -dodecafluoroterphenyl (0.01mol, 4.46g), 0.008mol of hexafluoroacetone/dichloroethane solution and 0.002mol of octafluoro-2-butanone into a three-necked flask with a mechanical stirrer, a thermometer, a condenser and a nitrogen gas protector at-30 ℃, adding 89.24mL of dichloromethane serving as a solvent with 0.0012mol of methanesulfonic acid serving as a catalyst, heating to 30 ℃ for reaction for 15 hours, precipitating the reaction solution into ethanol, filtering, and collecting a filter cake; the precipitate was boiled in boiling water and filtered several times, the filter cake was collected and vacuum dried at 110 ℃ for 24h to obtain a white product.
Example 5
Adding 3,3' - ((perfluoro-1, 4-phenyl) di (oxy) di (1,2,4, 5-tetrafluorobenzene) (0.01mol, 4.78g) and 0.01mol of octafluoro-2-butanone into a three-neck flask provided with a mechanical stirrer, a thermometer, a condenser tube and a nitrogen gas protector at the temperature of-30 ℃, adding 143.46mL of chloroform as a solvent by taking 0.0016mol of p-toluenesulfonic acid as a catalyst, heating to 0 ℃ for reaction for 24 hours, precipitating the reaction liquid into methanol, filtering, collecting a filter cake, putting the precipitate into boiling water, filtering for several times, collecting the filter cake, and drying in vacuum at the temperature of 110 ℃ for 24 hours to obtain a white product.
Example 6
Adding 1,2,3,4,6, 7-hexafluoronaphthalene (0.01mol, 2.36g), 0.005mol of hexafluoroacetone/dichloroethane solution and 0.005mol of octafluoro-2-butanone into a three-necked flask provided with a mechanical stirrer, a thermometer, a condenser and a nitrogen gas protector at-30 ℃, taking 0.0020mol of trifluoromethanesulfonic acid as a catalyst, adding 9.44mL of dichloromethane as a solvent, heating to 10 ℃, reacting for 35 hours, precipitating the reaction solution in ethanol, filtering, and collecting a filter cake; the precipitate was boiled in boiling water and filtered several times, the filter cake was collected and vacuum dried at 110 ℃ for 24h to obtain a white product.
Example 7
Adding 1,2,3,5,6, 7-hexafluoronaphthalene (0.01mol, 2.36g) and 0.01mol of hexafluoroacetone/dichloroethane solution into a three-necked flask with a mechanical stirrer, a thermometer, a condenser and a nitrogen protection device at the temperature of-30 ℃, adding 11.81mL of dichloroethane as a solvent by taking 0.0001mol of methanesulfonic acid as a catalyst, heating to-20 ℃ for reaction for 48 hours, precipitating the reaction solution in ethanol, filtering and collecting a filter cake; the precipitate was boiled in boiling water and filtered several times, the filter cake was collected and vacuum dried at 110 ℃ for 24h to obtain a white product.
Example 8
Adding 1,2,3,4,5,6,7, 8-octafluoroanthracene (0.01mol, 3.22g), 0.007mol of hexafluoroacetone/dichloroethane solution and 0.003mol of octafluoro-2-butanone into a three-neck flask with a mechanical stirrer, a thermometer, a condenser and a nitrogen protection at-30 ℃, adding 0.0003mol of trifluoromethanesulfonic acid as a catalyst and 20mL of chloroform as a solvent, heating to 20 ℃, reacting for 5 hours, precipitating the reaction solution in methanol, filtering and collecting a filter cake; the precipitate was boiled in boiling water and filtered several times, the filter cake was collected and vacuum dried at 110 ℃ for 24h to obtain a white product.
Example 9
Adding 1,2,4, 5-tetrafluorobenzene (0.01mol, 1.50g), 0.003mol of hexafluoroacetone/dichloroethane solution and 0.007mol of octafluoro-2-butanone into a three-neck flask provided with a mechanical stirrer, a thermometer, a condenser and a nitrogen protection device at the temperature of-30 ℃, adding 0.002mol of trifluoromethanesulfonic acid as a catalyst and 75.0mL of dichloroethane as a solvent, heating to 10 ℃, reacting for 20 hours, precipitating the reaction solution in ethanol, filtering, and collecting a filter cake; the precipitate was boiled in boiling water and filtered several times, the filter cake was collected and vacuum dried at 110 ℃ for 24h to obtain a white product.
The products obtained in examples 1 to 9 were compared for overall performance, and the results were as follows:
as can be seen from the above table: when the fluoroterphenyl is adopted, the glass transition temperature is obviously improved by more than 400 ℃, but the solubility is obviously reduced. The optimal result is that octafluorobiphenyl is used for reacting with perfluoroketone, so that the glass transition temperature can be increased, and the solubility and the hydrophobicity can be improved.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be able to cover the technical solutions and the inventive concepts of the present invention within the technical scope of the present invention.
Claims (8)
1. A polymer with a main chain containing a perfluorinated aromatic hydrocarbon and a perfluorinated alkyl chain structure is characterized in that the polymer structure simultaneously contains a perfluorinated aromatic hydrocarbon and a perfluorinated alkyl chain group; the polymer has a structural formula shown in formula I:
wherein m is more than or equal to 0 and less than or equal to 1, n is more than or equal to 0 and less than or equal to 1, and m + n is equal to 1; ar is any one of structures (a) to (h):
r is one or two of (i) or (j):
2. the polymer according to claim 1, characterized in that it has a number average molecular weight of 1 x 10 as determined by GPC4～6*104。
3. The method for preparing the polymer according to claim 1 or 2, wherein a fluorine-containing aromatic hydrocarbon monomer and a perfluoroalkyl ketone monomer are used as raw materials, and the polymer with a main chain containing a structure of the perfluoro-aromatic hydrocarbon and the perfluoroalkyl chain is obtained by homopolymerization or copolymerization reaction in an organic solvent in the presence of an acid catalyst.
4. The method according to claim 3, wherein the fluorine-containing aromatic hydrocarbon monomer is one of 1,2,4, 5-tetrafluorobenzene, 2',3,3',5,5',6,6' -octafluorobiphenyl, 3,3 '-oxybis (1,2,4, 5-tetrafluorobenzene), 2',3,3',5,5',6,6 '-dodecafluoroterphenyl, 3,3' - (perfluoro-1, 4-phenyl) bis (oxy) bis (1,2,4, 5-tetrafluorobenzene), 1,2,3,4,6, 7-hexafluoronaphthalene, 1,2,3,5,6, 7-hexafluoronaphthalene, 1,2,3,4,5,6,7, 8-octafluoroanthracene.
5. The method according to claim 3, wherein the perfluoroalkanone monomer is one or both of hexafluoroacetone and octafluoro-2-butanone.
6. The preparation method according to claim 3, which is specifically as follows: mixing a mol of fluorine-containing aromatic hydrocarbon monomer, b mol of hexafluoroacetone monomer and c mol of octafluoro-2-butanone with an acid catalyst and an organic solvent, controlling the temperature to be-30-20 ℃, reacting for 1-48 h, and adding a precipitator; filtering, separating, washing and drying to obtain the perfluoro polyaryl alkane copolymer; wherein a is b + c, a is more than 0, b is more than or equal to 0, and c is more than or equal to 0.
7. The preparation method of claim 6, wherein the acid catalyst is one or more of methanesulfonic acid, p-toluenesulfonic acid and trifluoromethanesulfonic acid, and the molar ratio of the fluorinated aromatic hydrocarbon monomer to the acid catalyst is 1: 0.01-0.20; the precipitant is one or two of ethanol and methanol.
8. The preparation method according to claim 3, wherein the organic solvent is one of dichloromethane, chloroform and dichloroethane, and the amount of the solvent is 1.0-50.0 mL/1 g of the monomer mixture of the fluoroarene and the perfluoroalkyl ketone.
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| JPH1077400A (en) * | 1996-08-30 | 1998-03-24 | Furukawa Electric Co Ltd:The | Polycarbonate resin composition and plastic optical waveguide using the same |
| CN101717465A (en) * | 2009-11-13 | 2010-06-02 | 山东东岳高分子材料有限公司 | Main-chain perfluorinated ion polymer and application of same as proton-exchange fiber material |
| CN104277216A (en) * | 2014-10-08 | 2015-01-14 | 广西大学 | Sulfonated perfluorocyclobutyl polyarylether polymers as well as preparation method and application thereof |
| CN111344318A (en) * | 2017-12-12 | 2020-06-26 | 国际商业机器公司 | Compounds with perfluoroaryl groups that promote post-synthesis functionalization |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH1077400A (en) * | 1996-08-30 | 1998-03-24 | Furukawa Electric Co Ltd:The | Polycarbonate resin composition and plastic optical waveguide using the same |
| CN101717465A (en) * | 2009-11-13 | 2010-06-02 | 山东东岳高分子材料有限公司 | Main-chain perfluorinated ion polymer and application of same as proton-exchange fiber material |
| CN104277216A (en) * | 2014-10-08 | 2015-01-14 | 广西大学 | Sulfonated perfluorocyclobutyl polyarylether polymers as well as preparation method and application thereof |
| CN111344318A (en) * | 2017-12-12 | 2020-06-26 | 国际商业机器公司 | Compounds with perfluoroaryl groups that promote post-synthesis functionalization |
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