聚合物荧光微球及荧光凝胶的制备研究
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摘要
本文以4-Br-1, 8-萘酐为原料,经中间体4-Br-N-烯丙基-1, 8-萘酰亚胺合成了六种可聚合的1, 8-萘酰亚胺荧光单体,利用红外、核磁共振等技术对所合成的产物进行了结构确认,采用紫外-可见吸收光谱、荧光激发发射光谱表征了产物的荧光性质。利用无皂乳液聚合方法制备了苯乙烯与两种1, 8-萘酰亚胺荧光单体的共聚物微球。SEM照片显示共聚物的外形为表面光洁、粒径分布均匀的球形。荧光光谱和荧光显微镜照片都说明,得到的聚合物在紫外光照射下能发出蓝色荧光的微球。合成了N-苯基-4-(2-羟基乙基氨基)-1, 8-萘酰亚胺和N-(2-羟基乙基)-4-乙氧基-1, 8-萘酰亚胺两种荧光小分子化合物,通过红外光谱和核磁共振氢谱确证了其结构,测试了它们的荧光光谱。将合成的两种荧光小分子接枝到SMA的侧基上,红外、核磁共振等表征结果说明接枝是成功的。将接枝SMA溶解于氢氧化钠水溶液,以MMA为单体,在溶液中进行了乳液聚合。测试结果表明,乳液聚合得到了表面覆盖有接枝SMA的PMMA荧光微球。荧光来自苯乙烯-马来酸酐接枝荧光共聚物,说明利用合成的SMA荧光乳化剂通过乳液法制备聚合物荧光微球是可行的。进行了荧光水凝胶制备的初步研究,得到了具有荧光的PVA、PAM水凝胶。
Researches and applications of fluorescence material are one of important focus in material field nowadays. Fluorescence materials include organic or inorganic materials. Advantages of organic fluorescence materials are high fluorescence photons efficiency, widely luminescence wavelength and various varieties. Therefore, more attentions are about inorganic materials in investigation and application. Organic fluorescence materials were used as dyes and pigments for many products formerly. For instance, it acted as fluorescent brighteners for some plastic and fibre. And it often was used to dye in fibre as fluorescent dyes, for example nylon. Many new synthetic organic fluorescence materials have excellent photochemical and photophysical characteristic. They are not only used in dyes and pigments, but also are used in biology medication, electron information, engineering materials, environment protect, energy, agriculture and so on. For example, they may be used as DNA cleavers, solar cell, fluorescent probes and OLEDs. Along with studies on synthesize, relations of structure and capability, the excellent photoelectricity would be applied furthest in every fields.
Currently, synthesize of organic fluorescence materials are organic fluorescence molecule and fluorescence polymer mostly. Fluorescence emission wavelength and intensity relate to structure of molecule. The molecules often have fluorescence groups and auxochrome. Conjugate degree of molecule and property of substitute group have many influences to fluorescence. Classify of fluorescence materials base on structure of molecule, there are aroma condensed ring compound, intramolecule charge transfer compound with conjugate structure and some metal complex compound. The research of aroma condensed ring compounds are focus on perylene and derivatives. The studies on secondly kind compound are most broad and active. They include stilbene, coumarin derivatives, pyrazolone derivatives, 1,8-naphthalimide derivatives, anthraquinone derivatives and rhodamine derivatives. 8-oxyquinoline was studied most in metal complex compounds. After the relations between structure and fluorescence performance are confirmed, fluorescence molecules are synthesized by appropriate route according to demand of luminescent structure.
Polymer fluorescence material is one of important species in function polymer. There are obvious advantages to compare polymer fluorescence material with fluorescence molecule. The consistency of fluorescence molecule and backing is bad. Distributing of fluorescence molecules are not homogeneous, they are easy tofall off and separate from mixture. Fluorescence units are bonded to polymer chain, so they are stable and good at bearing water and organic solvent. The chromophores distributing very homogeneous and the content of chromophore is stable. There are two way to prepare fluorescence polymer. The first, responded active molecules are polymerized by free radical or condensation polymerization. The other way, fluorescence molecules are grafted on polymer chain. Physics mixing is method too. But the way have defect as above. The synthesis is according to structure and reaction condition through suit way.
During the last few years, luminescent material has become a focus of investigation. 1,8-naphthalimide derivatives substituted at the 4 position with electron-donating groups can have high fluorescent quantum yields, they have been applied in the many fields. They are used for fluorescent dyes, sensors, organic light emitting diodes (OLEDS), fluorescent probes and photochemical DNA cleavers. With the syntheses of polymerisable 1, 8-naphthalimides, studies and applications of their copolymers are increasing. Copolymers containing fluorescent structure unit have good film forming ability, heat-durability, solvent resistance and high fluorescent quantum yields.
In this paper, we used 4-Br-1, 8-naphthalic anhydride as raw material. 4-Br-N-allyl-1, 8-naphthalimide was synthesized by the reaction of 4-Br-1, 8-naphthalic anhydride and allylamine. Then we used 4-Br-N-allyl-1, 8-naphthalimide together with alkyl alcohol to synthesize a series of 4-Alkoxy-N-allyl-1, 8-naphthalimide fluorescence derivatives. IR and 1HNMR were used to analyze the structure of the compound in order to insure that we have obtained the target product. UV-vis spectrum and the fluorescence spectrum were used to study the fluorescence property of the product. The fluorescence properties of monomers were studied, and we also compared the fluorescence properties among monomers in acetone solution or in film-forming process.
There are several traditional methods to prepare fluorescent microsphere:emulsion polymerization, dispersion polymerization and suspension polymerization. Emulsifier-free emulsion polymerization can be used to prepare surface clean and mono-disperse microspheres. The pollution of the environment from emulsifier is eliminated. Emulsifier-free emulsion polymerization becomes a focus of research. Especially, it is used in the field of adhesives and paint. In this paper, fluorescent polystyrene microspheres were prepared by emulsifier-free emulsion polymerization. The results showed that emulsifier-free emulsion polymerization was an effective method for the preparation of uniform polystyrene microspheres in micron-size. In order to prepare the polystyrene fluorescent microspheres with controllable sizes, the factors on polystyrene microspheres diameter and size distribution have been investigated and discussed, such as monomer concentration, initiator reagent, the ionic strength of electrolyte. The polymerisable fluorescent monomer, 4-ethoxyl-N-allyl-1, 8-naphthalimide, was synthesized and characterized using FT-IR spectra, 1H-NMR and fluorescence spectra. A copolymer of styrene and 4-ethoxyl-N-allyl-1, 8-naphthalimide was prepared by emulsifier-free emulsion polymerization and characterized using fluorescence spectra.
Fluorescent microspheres are a new type of functional polymer materials, widely used in biomedical engineering. At present, the application of the actual production of the fluorescent microspheres, all rely on imports. The study of the preparation of fluorescent microspheres method has important practical significance. Fluorescence refers to the diameter of microspheres in the nano-to micro-scope, load have fluorescent material, by an external stimulus to stimulate the energy of light solid particles. Its shape can be any shape, typical for the spherical shape. Carriers of fluorescent microsphere are organic or inorganic compound materials. In this paper, fluorescent microspheres of polymethyl methacrylate (PMMA) were prepared by emulsion preparation. Emulsifier is copolymer of styrene and maleic anhydride (SMA), which grafted with fluorescent monomer (1, 8 naphthalimide fluorescent units). The temperature was controlled around 78℃, potassium persulfate acted as initiator for emulsion polymerization, reaction time was 12 hours. The degree of hydrolysis of SMA was changed by adding different amount of alkali (NaOH). The best degree of hydrolysis of SMA was studied. Fluorescent nano-microspheres were obtained. The microspheres were confirmed and measured by FT-IR, fluorescence spectra, SEM and hondrometer. The same way was used to prepare polystyrene fluorescent nanospheres. The result shows that PMMA are microspheres and the surfaces of microspheres are not smooth. Particle size is about 100nm. The polymer mic0rosphere can emit an intense fluorescence.
Researches and applications of fluorescence material are one of important focus in material field nowadays. Fluorescence materials include organic or inorganic materials. Advantages of organic fluorescence materials are high fluorescence photons efficiency, widely luminescence wavelength and various varieties. Therefore, more attentions are about inorganic materials in investigation and application. Organic fluorescence materials were used as dyes and pigments for many products formerly. For instance, it acted as fluorescent brighteners for some plastic and fibre. And it often was used to dye in fibre as fluorescent dyes, for example nylon. Many new synthetic organic fluorescence materials have excellent photochemical and photophysical characteristic. They are not only used in dyes and pigments, but also are used in biology medication, electron information, engineering materials, environment protect, energy, agriculture and so on. For example, they may be used as DNA cleavers, solar cell, fluorescent probes and OLEDs. Along with studies on synthesize, relations of structure and capability, the excellent photoelectricity would be applied furthest in every fields.
Currently, synthesize of organic fluorescence materials are organic fluorescence molecule and fluorescence polymer mostly. Fluorescence emission wavelength and intensity relate to structure of molecule. The molecules often have fluorescence groups and auxochrome. Conjugate degree of molecule and property of substitute group have many influences to fluorescence. Classify of fluorescence materials base on structure of molecule, there are aroma condensed ring compound, intramolecule charge transfer compound with conjugate structure and some metal complex compound. The research of aroma condensed ring compounds are focus on perylene and derivatives. The studies on secondly kind compound are most broad and active. They include stilbene, coumarin derivatives, pyrazolone derivatives, 1,8-naphthalimide derivatives, anthraquinone derivatives and rhodamine derivatives. 8-oxyquinoline was studied most in metal complex compounds. After the relations between structure and fluorescence performance are confirmed, fluorescence molecules are synthesized by appropriate route according to demand of luminescent structure.
Polymer fluorescence material is one of important species in function polymer. There are obvious advantages to compare polymer fluorescence material with fluorescence molecule. The consistency of fluorescence molecule and backing is bad. Distributing of fluorescence molecules are not homogeneous, they are easy tofall off and separate from mixture. Fluorescence units are bonded to polymer chain, so they are stable and good at bearing water and organic solvent. The chromophores distributing very homogeneous and the content of chromophore is stable. There are two way to prepare fluorescence polymer. The first, responded active molecules are polymerized by free radical or condensation polymerization. The other way, fluorescence molecules are grafted on polymer chain. Physics mixing is method too. But the way have defect as above. The synthesis is according to structure and reaction condition through suit way.
During the last few years, luminescent material has become a focus of investigation. 1,8-naphthalimide derivatives substituted at the 4 position with electron-donating groups can have high fluorescent quantum yields, they have been applied in the many fields. They are used for fluorescent dyes, sensors, organic light emitting diodes (OLEDS), fluorescent probes and photochemical DNA cleavers. With the syntheses of polymerisable 1, 8-naphthalimides, studies and applications of their copolymers are increasing. Copolymers containing fluorescent structure unit have good film forming ability, heat-durability, solvent resistance and high fluorescent quantum yields.
In this paper, we used 4-Br-1, 8-naphthalic anhydride as raw material. 4-Br-N-allyl-1, 8-naphthalimide was synthesized by the reaction of 4-Br-1, 8-naphthalic anhydride and allylamine. Then we used 4-Br-N-allyl-1, 8-naphthalimide together with alkyl alcohol to synthesize a series of 4-Alkoxy-N-allyl-1, 8-naphthalimide fluorescence derivatives. IR and 1HNMR were used to analyze the structure of the compound in order to insure that we have obtained the target product. UV-vis spectrum and the fluorescence spectrum were used to study the fluorescence property of the product. The fluorescence properties of monomers were studied, and we also compared the fluorescence properties among monomers in acetone solution or in film-forming process.
There are several traditional methods to prepare fluorescent microsphere:emulsion polymerization, dispersion polymerization and suspension polymerization. Emulsifier-free emulsion polymerization can be used to prepare surface clean and mono-disperse microspheres. The pollution of the environment from emulsifier is eliminated. Emulsifier-free emulsion polymerization becomes a focus of research. Especially, it is used in the field of adhesives and paint. In this paper, fluorescent polystyrene microspheres were prepared by emulsifier-free emulsion polymerization. The results showed that emulsifier-free emulsion polymerization was an effective method for the preparation of uniform polystyrene microspheres in micron-size. In order to prepare the polystyrene fluorescent microspheres with controllable sizes, the factors on polystyrene microspheres diameter and size distribution have been investigated and discussed, such as monomer concentration, initiator reagent, the ionic strength of electrolyte. The polymerisable fluorescent monomer, 4-ethoxyl-N-allyl-1, 8-naphthalimide, was synthesized and characterized using FT-IR spectra, 1H-NMR and fluorescence spectra. A copolymer of styrene and 4-ethoxyl-N-allyl-1, 8-naphthalimide was prepared by emulsifier-free emulsion polymerization and characterized using fluorescence spectra.
Fluorescent microspheres are a new type of functional polymer materials, widely used in biomedical engineering. At present, the application of the actual production of the fluorescent microspheres, all rely on imports. The study of the preparation of fluorescent microspheres method has important practical significance. Fluorescence refers to the diameter of microspheres in the nano-to micro-scope, load have fluorescent material, by an external stimulus to stimulate the energy of light solid particles. Its shape can be any shape, typical for the spherical shape. Carriers of fluorescent microsphere are organic or inorganic compound materials. In this paper, fluorescent microspheres of polymethyl methacrylate (PMMA) were prepared by emulsion preparation. Emulsifier is copolymer of styrene and maleic anhydride (SMA), which grafted with fluorescent monomer (1, 8 naphthalimide fluorescent units). The temperature was controlled around 78℃, potassium persulfate acted as initiator for emulsion polymerization, reaction time was 12 hours. The degree of hydrolysis of SMA was changed by adding different amount of alkali (NaOH). The best degree of hydrolysis of SMA was studied. Fluorescent nano-microspheres were obtained. The microspheres were confirmed and measured by FT-IR, fluorescence spectra, SEM and hondrometer. The same way was used to prepare polystyrene fluorescent nanospheres. The result shows that PMMA are microspheres and the surfaces of microspheres are not smooth. Particle size is about 100nm. The polymer mic0rosphere can emit an intense fluorescence.
引文
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