CN106749773A - The preparation method of the pure organic cyclodextrin main body derivative with efficient room temperature phosphorescent emissions - Google Patents
The preparation method of the pure organic cyclodextrin main body derivative with efficient room temperature phosphorescent emissions Download PDFInfo
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- CN106749773A CN106749773A CN201710011024.0A CN201710011024A CN106749773A CN 106749773 A CN106749773 A CN 106749773A CN 201710011024 A CN201710011024 A CN 201710011024A CN 106749773 A CN106749773 A CN 106749773A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; 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
- 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
- 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
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/145—Heterocyclic containing oxygen as the only heteroatom
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Abstract
The present invention relates to a kind of preparation method of the pure organic cyclodextrin main body derivative with efficient room temperature phosphorescent emissions, belong to luminous organic material field.The method carries out simple reaction using most of bromo aromatic ring phosphorescence group with beta cyclodextrin, prepares the corresponding cyclodextrin main body derivative with efficient room temperature phosphorescent emissions（It is not limited to following structure）, obtain the organic main body derivative amorphous solid materia with room temperature phosphorimetry transmitting.The present invention does not use the noble metal of costliness, and raw material is simple and easy to get, preparation method is simple, and resulting material emission function admirable and nontoxic, can apply to many fields.Cyclodextrin main body derivative with high efficiency phosphorescent transmitting（It is not limited to following structure）：Wherein,
Description
Technical field
The present invention relates to a kind of preparation method of the cyclodextrin main body derivative with efficiently organic room temperature phosphorimetry transmitting, category
In luminous organic material field.
Background technology
Organic room temperature phosphorimetry material suffers from being widely applied at aspects such as bio-imaging, chemical sensitisations, it is accordingly required in particular to have
A kind of easy preparation method and process；Current room temperature phosphor material is concentrated mainly on noble metal complexes aspect, and expensive
Metal is costly and harmful to organism, therefore develops pure organic room temperature phosphorimetry material and seem and be highly desirable to；It is currently pure to have
Machine room temperature phosphorimetry material is mainly crystalline state, and this needs strict condition of culture and process is uncontrollable, and material is also more fragile, holds
Easily lose luminosity.
The present invention mainly modifies beta-schardinger dextrin by bromo phosphorescence group so as to obtain with high efficiency phosphorescent emission characteristic
Amorphous powder, and post processing is simple, synthesis step is few；Compared with conventional metal-organic complex, the present invention is used
A purely organic system, reduces cost, and the product for obtaining is also nontoxic；Additionally, host compound phosphor material can be used to regulate and control solid
Luminous aspect, is greatly facilitated the progress of luminescent material.
The content of the invention
It is an object of the invention to pass through to modify the cyclodextrin that beta-schardinger dextrin obtains having efficiently organic room temperature phosphorimetry transmitting
Main body derivative.
Technical scheme：A kind of preparation of the cyclodextrin main body derivative with efficiently organic room temperature phosphorimetry transmitting
Method
, it is characterized in that by with the bromo phosphorescence group ring paste with the high efficiency phosphorescent characteristics of luminescence a kind of with beta cyclodextrin reaction generation
Smart main body derivative, comprises the following steps that：
（1）6-OTs- beta-schardinger dextrins（Compound H）Preparation；
Beta cyclodextrin and paratoluensulfonyl chloride are reacted i.e. available；
。
（2）The preparation of the cyclodextrin main body derivative with efficiently organic room temperature phosphorimetry transmitting；
By bromo phosphorescence group and 6-OTs- beta-schardinger dextrins（Compound H）It is dissolved in appropriate organic solvent, three is reacted at 90 DEG C
My god；Products therefrom is recrystallized by appropriate mixed solvent, obtains having the cyclodextrin of efficiently organic room temperature phosphorimetry transmitting after drying
Main body derivative（It is not limited to following structure）；
Wherein,
。
The step（2）In phosphorescence group in contain bromo aromatic ring, and reaction dissolvent be DMF.
Compared with prior art, the present invention has following significant advantage：
The Phosphorescent host compound prepared by the present invention has very strong phosphorescent emissions characteristic and in without fixed at ambient temperature
Shape pulverulence, the shortcoming for overcoming conventional pure organic room temperature phosphorimetry material to be lighted under low temperature, deoxygenation or crystalline state；It is amorphous
Pulverulence is beneficial to be processed further；Because no noble metal participates in reacting, reaction cost is greatly reduced；Can be by changing phosphorus
Light blob regulation transmitting light color；Also the glow color of powder by changing object, can be adjusted by interaction of host-guest.
Specific embodiment
With reference to example, the present invention is described in detail：
Phosphorescence unity structure：
Embodiment one：
The preparation method of the cyclodextrin main body derivative with efficiently organic room temperature phosphorimetry transmitting, comprises the following steps that：
Weigh 1g compound H, 0.207g compound 1,0.128g potassium carbonate to be dissolved in 20ml DMFs, in nitrogen
Under gas shielded, 90 DEG C are reacted three days, and then suction filtration removes potassium carbonate, by DMF vacuum distillation to 5ml, by
Drop is instilled in 200ml ethyl acetate, obtains crude product.Then crude product is recrystallized with first alcohol and water, obtains product A.
Its quantum yield is 5.95%, emission peak 512nm and 545nm or so, life-span 1.03ms.
Embodiment two：
1g compound H, 0.219g compound 2,0.128g potassium carbonate is weighed to be dissolved in 20ml DMFs,
Under nitrogen protection, 90 DEG C are reacted three days, and reaction has solid to separate out, and add methyl alcohol to make solid dissolving, and insoluble matter suction filtration is removed, filter
To there is solid to separate out, suction filtration, again with methanol and water mixed solvent wash filter cake in a heated condition, and suction filtration is simultaneously done for liquid vacuum distillation
Product B is obtained after dry gained filter cake.
Its quantum yield is 2.89%, emission peak 497nm or so, life-span 0.66ms.
Embodiment three：
1g compound H and 0.911g compound 3 is weighed to be dissolved in 20ml DMFs, under nitrogen protection,
90 DEG C are reacted three days, are reacted three days, by DMF vacuum distillation to 5ml, dropwise instill 200ml ethyl acetate
In, obtain crude product.Then recrystallized with ethanol and methanol mixed solvent, obtained product C.
Its quantum yield is 4.16%, and emission peak is in 496nm or so, life-span 0.57ms.
Example IV：
1g compound H and 0.809g compound 4 is weighed to be dissolved in 20ml DMFs, under nitrogen protection,
90 DEG C are reacted three days, are reacted three days, by DMF vacuum distillation to 5ml, dropwise instill 200ml ethyl acetate
In, obtain crude product.Then recrystallized with ethanol and methanol mixed solvent, obtained product D.
Its quantum yield is 13.95%, and emission peak is in 520nm or so, life-span 1.45ms.
Claims (2)
1. a kind of preparation method of the pure organic cyclodextrin main body derivative with efficient room temperature phosphorescent emissions, it is characterized in that by bromine
For aromatic ring phosphorescence group and a kind of beta cyclodextrin reaction cyclodextrin main body derivative with efficient room temperature phosphorescent emissions characteristic of generation,
Comprise the following steps that：
（1）The preparation of 6-OTs- beta-schardinger dextrins；
Beta cyclodextrin and paratoluensulfonyl chloride are reacted i.e. available.
（2）The preparation method of the cyclodextrin main body derivative with efficiently organic room temperature phosphorimetry transmitting；
Bromo phosphorescence group is dissolved in appropriate organic solvent with 6-OTs- beta-schardinger dextrins, is reacted three days at 90 DEG C, gained is produced
Thing is recrystallized or washed by appropriate mixed solvent, obtains having the cyclodextrin main body of efficiently organic room temperature phosphorimetry transmitting after drying
Derivative.
2. the preparation method of Phosphorescent host compound according to claim 1, it is characterised in that step（2）In
Bromo aromatic ring is contained in phosphorescence group, and reaction dissolvent is DMF.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112011098A (en) * | 2020-09-04 | 2020-12-01 | 南开大学 | Supermolecule luminescent gel system constructed by sulfonated cyclodextrin-bromophenyl picolinate-amino clay and preparation method thereof |
| CN113088278A (en) * | 2021-04-12 | 2021-07-09 | 华东理工大学 | Room-temperature phosphorescent material and preparation method thereof |
Citations (2)
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| CN104673275A (en) * | 2013-10-15 | 2015-06-03 | 香港科技大学深圳研究院 | An activated luminescence material and a method for preparing the same |
| CN106188346A (en) * | 2016-06-27 | 2016-12-07 | 南开大学 | A kind of preparation method and applications of porosu solid luminescent material |
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- 2017-01-06 CN CN201710011024.0A patent/CN106749773B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104673275A (en) * | 2013-10-15 | 2015-06-03 | 香港科技大学深圳研究院 | An activated luminescence material and a method for preparing the same |
| CN106188346A (en) * | 2016-06-27 | 2016-12-07 | 南开大学 | A kind of preparation method and applications of porosu solid luminescent material |
Non-Patent Citations (4)
| Title |
|---|
| SANYOHAMAI: "Room-temperature phosphorescence of 6-bromo-2-naphthol in poly(vinyl alcohol) films containing cyclodextrins", 《JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A: CHEMISTRY》 * |
| YAN-QIANGZHAI: "Fluorescence and room temperature phosphorescence of 6-bromo-2-naphthol in β-cyclodextrin solution and its selective molecular recognition for cyclohexane", 《ANALYTICA CHIMICA ACTA》 * |
| 李志富 等: "《分析化学》", 31 August 2015, 华中科技大学出版社 * |
| 童林荟: "《环糊精化学——基础与应用》", 31 March 2001, 科学出版社 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112011098A (en) * | 2020-09-04 | 2020-12-01 | 南开大学 | Supermolecule luminescent gel system constructed by sulfonated cyclodextrin-bromophenyl picolinate-amino clay and preparation method thereof |
| CN112011098B (en) * | 2020-09-04 | 2022-04-29 | 南开大学 | Supermolecule luminescent gel system constructed by sulfonated cyclodextrin-bromophenyl picolinate-amino clay and preparation method thereof |
| CN113088278A (en) * | 2021-04-12 | 2021-07-09 | 华东理工大学 | Room-temperature phosphorescent material and preparation method thereof |
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Effective date of registration: 20200320 Address after: 444100 Yuyang office, Heping Village, Dangyang city, Yichang, Hubei (Jinqiao Industrial Park) Patentee after: Yichang innovation Materials Technology Co., Ltd Address before: 200237 East China University of Science and Technology, 130 Meilong Road, Shanghai, Xuhui District Patentee before: EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY |
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