CN114015435A - Cellulose thermotropic liquid crystal fluorescent material and preparation method thereof - Google Patents
Cellulose thermotropic liquid crystal fluorescent material and preparation method thereof Download PDFInfo
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- CN114015435A CN114015435A CN202111383876.5A CN202111383876A CN114015435A CN 114015435 A CN114015435 A CN 114015435A CN 202111383876 A CN202111383876 A CN 202111383876A CN 114015435 A CN114015435 A CN 114015435A
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- 239000000463 material Substances 0.000 title claims abstract description 50
- 239000004974 Thermotropic liquid crystal Substances 0.000 title claims abstract description 39
- 229920002678 cellulose Polymers 0.000 title claims abstract description 37
- 239000001913 cellulose Substances 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title abstract description 14
- -1 quaternary ammonium salt compound Chemical class 0.000 claims abstract description 12
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims abstract description 10
- JLZUZNKTTIRERF-UHFFFAOYSA-N tetraphenylethylene Chemical group C1=CC=CC=C1C(C=1C=CC=CC=1)=C(C=1C=CC=CC=1)C1=CC=CC=C1 JLZUZNKTTIRERF-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000001768 carboxy methyl cellulose Substances 0.000 claims abstract description 9
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 claims abstract description 8
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 claims abstract description 8
- 238000004108 freeze drying Methods 0.000 claims abstract description 4
- 239000006228 supernatant Substances 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 239000011259 mixed solution Substances 0.000 claims description 5
- 125000003147 glycosyl group Chemical group 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- 229920003123 carboxymethyl cellulose sodium Polymers 0.000 claims description 2
- 229940063834 carboxymethylcellulose sodium Drugs 0.000 claims description 2
- 230000005284 excitation Effects 0.000 abstract description 6
- 230000002776 aggregation Effects 0.000 abstract description 4
- 238000004220 aggregation Methods 0.000 abstract description 4
- 239000012620 biological material Substances 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 229920002521 macromolecule Polymers 0.000 description 6
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 108091005461 Nucleic proteins Proteins 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000005842 biochemical reaction Methods 0.000 description 1
- 238000012984 biological imaging Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/38—Polymers
- C09K19/3804—Polymers with mesogenic groups in the main chain
- C09K19/3819—Polysaccharides or derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K2019/528—Surfactants
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/145—Heterocyclic containing oxygen as the only heteroatom
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Abstract
The invention relates to the technical field of biological materials, and mainly relates to a cellulose thermotropic liquid crystal fluorescent material and a preparation method thereof. The preparation method of the cellulose thermotropic liquid crystal fluorescent material comprises the steps of preparing a compound from sodium carboxymethylcellulose and a quaternary ammonium salt compound containing tetraphenylethylene groups in a water phase through electrostatic acting force, centrifuging, discarding supernatant, freeze drying, purifying and the like. The cellulose thermotropic liquid crystal fluorescent material prepared by the invention is a biological material with aggregation-induced emission property, and can generate fluorescence phenomenon under the excitation of ultraviolet light. The cellulose thermotropic liquid crystal fluorescent material prepared by the invention can be applied to the relevant fields of biomedicine, fluorescent materials and the like.
Description
Technical Field
The invention relates to the technical field of biological materials, and mainly relates to a cellulose thermotropic liquid crystal fluorescent material and a preparation method thereof.
Background
The solvent-free thermal liquid crystal material based on biological macromolecules is a new class of biological materials developed in recent years. The material enables the biomacromolecule to exist in a flexible liquid crystal state in a solvent-free state, enhances the thermal stability of the biomacromolecule in an anhydrous environment, and has good application prospect in the field of biomedicine. The reported materials mainly comprise solvent-free nucleic acid and protein thermotropic liquid crystal materials.
The solvent-free thermotropic liquid crystal material based on the biomacromolecules is obtained by combining the biomacromolecules and surfactants with opposite charges through electrostatic acting force, and most of the currently developed materials do not have the fluorescence characteristic and are not beneficial to the application in the fields of biological imaging, biochemical reaction process tracking and the like. Most biological macromolecules do not have the fluorescent characteristic, so that a solvent-free biological macromolecule thermotropic liquid crystal material with the fluorescent property is developed, and a surfactant with the fluorescent property is required to be used. Because the solvent-free biological macromolecule thermotropic liquid crystal material is a condensed substance, the used surfactant with fluorescence property preferably has the property of aggregation-induced luminescence so as to ensure the fluorescence property of the solvent-free biological macromolecule thermotropic liquid crystal material.
Cellulose is a biological macromolecule with abundant content in nature, and has the advantages of low economic cost, simplicity, easy obtainment and the like. The fluorescent material is developed into a solvent-free thermally induced liquid crystal fluorescent material, and a novel biological fluorescent material is provided for the fields of biomedicine and fluorescent materials. However, since cellulose molecules themselves do not have fluorescence characteristics, the currently developed cellulose-based fluorescent materials mainly adopt a mode of covalently modifying a fluorescent group to the cellulose molecules, and have the disadvantages of high synthesis requirements and easy occurrence of aggregation-induced fluorescence quenching. Therefore, the development of the solvent-free cellulose thermotropic liquid crystal fluorescent material with aggregation-induced emission properties has important fundamental research significance and practical application value.
Disclosure of Invention
In view of the above, the present invention provides a cellulose thermotropic liquid crystal fluorescent material and a preparation method thereof.
The technical scheme of the invention is as follows:
the invention provides a cellulose thermotropic liquid crystal fluorescent material, which is prepared from raw materials including sodium carboxymethylcellulose and a quaternary ammonium salt compound containing tetraphenylethylene groups.
In the present invention, the carboxymethyl cellulose sodium contains 500 glycosyl units.
In the invention, the quaternary ammonium salt compound containing tetraphenylethylene groups is N, N, N-trimethyl-8- (4- (2- (4-octyloxyphenyl) -1, 2-diphenylvinyl) phenoxy) octane-1-ammonium bromide.
In the invention, the preparation method of the cellulose thermotropic liquid crystal fluorescent material comprises the following steps:
adding the aqueous solution of sodium carboxymethylcellulose into the aqueous solution of a quaternary ammonium salt compound containing tetraphenylethylene groups for mixing, shaking the mixed solution for 2 minutes, centrifuging, discarding supernatant, and freeze-drying the obtained precipitate for 12 hours to obtain the cellulose thermotropic liquid crystal fluorescent material.
In the preparation method of the cellulose thermotropic liquid crystal fluorescent material, in the mixed solution, the molar ratio of the sodium carboxymethyl cellulose to the quaternary ammonium salt compound containing the tetraphenyl ethylene group is 1: 1-1: 5 in terms of the number of glycosyl units.
The invention provides a cellulose thermotropic liquid crystal fluorescent material and a preparation method thereof, wherein the cellulose thermotropic liquid crystal fluorescent material and the preparation method thereof have the following characteristics:
1. the cellulose thermotropic liquid crystal fluorescent material is an ionic compound obtained by combining carboxymethyl cellulose and a surfactant containing tetraphenylethylene groups.
2. The cellulose thermotropic liquid crystal fluorescent material obtained by the invention has strong fluorescence phenomenon under the excitation of ultraviolet light (365 nm).
3. The cellulose thermotropic liquid crystal fluorescent material obtained by the invention can be applied to the fields of biomedicine and fluorescent materials.
4. The preparation method of the cellulose thermotropic liquid crystal fluorescent material is a water-phase preparation method, and has the characteristics of low cost and easy obtainment of raw materials, simple and convenient preparation treatment process and the like.
Drawings
FIG. 1 is a fluorescence emission spectrum of the cellulose thermotropic liquid crystal fluorescent material described in example 1 under ultraviolet irradiation.
FIG. 2 is a fluorescence lifetime spectrum of the cellulose thermotropic liquid crystal fluorescent material of example 1.
Detailed Description
The invention provides a cellulose thermotropic liquid crystal fluorescent material and a preparation method thereof, and a person skilled in the art can realize the thermotropic liquid crystal fluorescent material by properly improving process parameters by referring to the content. It is noted that all such substitutions and modifications will be apparent to those skilled in the art and are intended to be included within the present invention. While the methods and applications of this invention have been described in terms of preferred embodiments, it will be apparent to those of ordinary skill in the art that variations and modifications in the methods and applications described herein, as well as other suitable variations and combinations, may be made to implement and use the techniques of this invention without departing from the spirit and scope of the invention.
The invention is further illustrated by the following examples:
example 1:
adding 102 mu L of 206.4 mu M aqueous solution of sodium carboxymethylcellulose (500 glycosyl units) into a centrifuge tube of 400 mu L of 26.4mM aqueous solution of N, N, N-trimethyl-8- (4- (2- (4-octyloxyphenyl) -1, 2-diphenylvinyl) phenoxy) octane-1-ammonium bromide, mixing, shaking for 2 minutes, centrifuging the mixed solution for 15 minutes under the condition that the relative centrifugal force is 6000g, discarding the supernatant, and freeze-drying the obtained precipitate for 12 hours to obtain the cellulose thermotropic liquid crystal fluorescent material.
The fluorescence emission spectrum of the prepared cellulose thermotropic liquid crystal fluorescent material under the excitation of ultraviolet light (365nm) is shown in figure 1, and the following results are obtained: the cellulose thermotropic liquid crystal fluorescent material has a fluorescence emission peak at a position of 400-600nm and a maximum emission peak at a position of about 482nm under the excitation of ultraviolet light (365 nm).
The fluorescence lifetime spectrum of the prepared cellulose thermotropic liquid crystal fluorescent material under the excitation of ultraviolet light (365nm) is shown in figure 2, and the following results are obtained: the fluorescence lifetime of the prepared cellulose thermotropic liquid crystal fluorescent material under the excitation of ultraviolet light (365nm) is 4.31 ns.
The foregoing is only a preferred embodiment of this invention and it should be noted that modifications can be made by those skilled in the art without departing from the principle of the invention and these modifications should also be considered as the protection scope of the invention.
Claims (5)
1. The cellulose thermotropic liquid crystal fluorescent material is characterized in that the synthetic raw materials comprise sodium carboxymethylcellulose and a quaternary ammonium salt compound containing tetraphenylethylene groups.
2. The cellulose thermotropic liquid crystal fluorescent material of claim 1, wherein the carboxymethyl cellulose sodium contains 500 sugar-based units.
3. The cellulose thermotropic liquid crystal fluorescent material of claim 1, wherein the quaternary ammonium salt compound having a tetraphenylethylene group is N, N, N-trimethyl-8- (4- (2- (4-octyloxyphenyl) -1, 2-diphenylvinyl) phenoxy) octane-1-ammonium bromide.
4. The method for preparing the cellulose thermotropic liquid crystal fluorescent material according to any one of claims 1 to 3, comprising:
adding the aqueous solution of sodium carboxymethylcellulose into the aqueous solution of a quaternary ammonium salt compound containing tetraphenylethylene groups for mixing, shaking the mixed solution for 2 minutes, centrifuging, discarding supernatant, and freeze-drying the obtained precipitate for 12 hours to obtain the cellulose thermotropic liquid crystal fluorescent material.
5. The method for preparing the cellulose thermotropic liquid crystal fluorescent material of claim 4, wherein the molar ratio of the sodium carboxymethyl cellulose to the quaternary ammonium salt compound containing a tetraphenyl ethylene group is 1:1 to 1:5 in terms of the number of glycosyl units in the mixed solution.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114700112A (en) * | 2022-05-09 | 2022-07-05 | 青岛科技大学 | Gold nano catalyst loaded on cellulose material and preparation method thereof |
| CN114874341A (en) * | 2022-05-05 | 2022-08-09 | 东华大学 | Fluorescent nanoparticle with AIE characteristic, bionic nano composite hydrogel actuator, preparation method and application |
| CN116120472A (en) * | 2023-02-23 | 2023-05-16 | 中国科学院宁波材料技术与工程研究所 | Aggregation-induced emission cellulose and preparation method thereof |
| CN116655811A (en) * | 2023-06-28 | 2023-08-29 | 青岛科技大学 | Flexible cellulose material with triple stimulus response properties and preparation method thereof |
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| CN101935368A (en) * | 2010-09-27 | 2011-01-05 | 上海交通大学 | Composite method of liquid crystal supermolecule material containing double photosensitive units |
| WO2015192778A1 (en) * | 2014-06-18 | 2015-12-23 | The Hong Kong University Of Science And Technology | Light-emitting liquid crystal devices using aie materials |
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2021
- 2021-11-22 CN CN202111383876.5A patent/CN114015435A/en active Pending
Patent Citations (2)
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| CN101935368A (en) * | 2010-09-27 | 2011-01-05 | 上海交通大学 | Composite method of liquid crystal supermolecule material containing double photosensitive units |
| WO2015192778A1 (en) * | 2014-06-18 | 2015-12-23 | The Hong Kong University Of Science And Technology | Light-emitting liquid crystal devices using aie materials |
Non-Patent Citations (2)
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| 李宗植; 等: "四苯乙烯衍生物的应用研究进展", 有机化学, vol. 36, no. 10, 20 June 2016 (2016-06-20), pages 2317 - 2332 * |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114874341A (en) * | 2022-05-05 | 2022-08-09 | 东华大学 | Fluorescent nanoparticle with AIE characteristic, bionic nano composite hydrogel actuator, preparation method and application |
| CN114700112A (en) * | 2022-05-09 | 2022-07-05 | 青岛科技大学 | Gold nano catalyst loaded on cellulose material and preparation method thereof |
| CN116120472A (en) * | 2023-02-23 | 2023-05-16 | 中国科学院宁波材料技术与工程研究所 | Aggregation-induced emission cellulose and preparation method thereof |
| CN116655811A (en) * | 2023-06-28 | 2023-08-29 | 青岛科技大学 | Flexible cellulose material with triple stimulus response properties and preparation method thereof |
| CN116655811B (en) * | 2023-06-28 | 2024-06-11 | 青岛科技大学 | Flexible cellulose material with triple stimulus response properties and preparation method thereof |
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