CN108484562A - The hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl and its application - Google Patents
The hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl and its application Download PDFInfo
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- CN108484562A CN108484562A CN201810258334.7A CN201810258334A CN108484562A CN 108484562 A CN108484562 A CN 108484562A CN 201810258334 A CN201810258334 A CN 201810258334A CN 108484562 A CN108484562 A CN 108484562A
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/38—Polycyclic condensed hydrocarbons containing four rings
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- 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
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/008—Supramolecular polymers
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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
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- C09K2211/1011—Condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
Abstract
It is that the hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl is made as raw material using the hexa-atomic melon ring of hexamethyl and neutral aqueous solution the invention discloses a kind of hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl and its application.The carrier is the porous framework structure based on the hexa-atomic melon ring Supramolecular self assembly of hexamethyl, the structure can be used for preparing many kinds of solids fluorescent material, the fluorescent material not only shows specific recognition reaction to specific escaping gas, and the fluorescent material of allotment different colours is can also be used for, extend the application of the hexa-atomic melon ring of hexamethyl；In addition, the fluorescent material of the present invention has preparation process simple, the low feature of manufacturing cost.
Description
Technical field
The present invention relates to a kind of applications of the hexa-atomic melon ring of hexamethyl, especially a kind of to be based on the hexa-atomic melon ring supermolecule of hexamethyl
The porous framework structure of self assembly and its application.
Background technology
Melon ring (Cucurbit [n] uril), also known as Cucurbituril, (abbreviation CB [n] or Q [n]) are obtained because structure is like pumpkin
Name, is the novel caged host compound of another class after the macrocyclic compound such as crown ether, cyclodextrin, calixarenes, from structural
From the point of view of in matter, melon ring tool is there are one the hydrophobic cavity of high degree of symmetry and both ends open and is covered with polar carbonylic oxygen atom,
The feature of this structure can be selective under solution state inclusion size dimension it is suitable organic and inorganic and biological
The small molecules such as molecule act on again or with hydrophilic complex occurs at port with dipole or ionic compound, with research
The deep progress of work, melon ring are applied to organic synthesis, molecular recognition, nano material, catalysis, separation etc. gradually.Pregnancy
The hexa-atomic melon ring of base, at the lower product of content in the process, hexamethyl is reported in Day seminar in 2003 for the first time as melon cyclization
The separation of hexa-atomic melon ring and characterization, but because of low yield, the factors such as hardly possible separation limit its development and application.And it is applied to
Fluorescent material has not been reported.
Meanwhile there are many existing fluorescent material type, but there are preparation process complexity, the high defects of processing cost.
Invention content
The object of the present invention is to provide a kind of hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl and its applications.It is described
Carrier is the porous framework structure based on the hexa-atomic melon ring Supramolecular self assembly of hexamethyl, which can be used for preparing many kinds of solids glimmering
Luminescent material, the fluorescent material not only show specific recognition reaction to specific escaping gas, but also can also be used for allocating
The fluorescent material of different colours extends the application of the hexa-atomic melon ring of hexamethyl；In addition, the fluorescent material of the present invention, which has, prepares work
Skill is simple, the low feature of manufacturing cost.
Technical scheme of the present invention：A kind of hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl, with the hexa-atomic melon ring of hexamethyl
It is that the hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl is made in raw material with neutral aqueous solution.
It is described with the hexa-atomic melon ring of hexamethyl and neutral water in the hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl above-mentioned
Solution is the obtained hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl of raw material；By being added in every 8-12mL neutral aqueous solutions
The hexa-atomic melon ring of hexamethyl is added in neutral aqueous solution 0.08-0.12mmol hexamethyls hexa-atomic melon ring, and concussion makes it dissolve, i.e.,
.
In the hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl above-mentioned, the hexa-atomic melon ring Supramolecular self assembly of hexamethyl
The molecular formula of carrier is：C42H106N24O41。
A kind of application of the hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl above-mentioned, is used to prepare fluorescent material.
In the application of the hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl above-mentioned, described is used to prepare fluorescent material
It is；The hexa-atomic melon ring of hexamethyl is added in neutral water, concussion makes it dissolve, and obtains the hexa-atomic melon ring Supramolecular self assembly of hexamethyl and carries
Body, the hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl are added loading solution and load organic fluorescence small molecule, and fluorescent material is made.
In the application of the hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl above-mentioned, the loading solution is acetonitrile solution.
In the application of the hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl above-mentioned, the organic fluorescence small molecule is Luo Dan
Bright B (G1), fluorescein (G2) or pyrene (G3).
In the application of the hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl above-mentioned, the fluorescent material is red fluorescence material
Material, green fluorescent material or blue fluorescent material.
To verify beneficial effects of the present invention, inventor has carried out a large amount of experimental study, part Experiment process and result
It is as follows：
The making of red fluorescence material：By the hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl of the present invention (by embodiment 1 into
Row prepare) be added loading solution in load rhodamine B, be made red fluorescence material.The loading solution is acetonitrile solution.
The making of green fluorescent material：By the hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl of the present invention (by embodiment 1 into
It is prepared by row) load sieve fluorescein in loading solution is added, green fluorescent material is made.The loading solution is acetonitrile solution.
The making of blue fluorescent material：By the hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl of the present invention (by embodiment 1 into
Row prepare) be added loading solution in load pyrene, be made blue fluorescent material.The loading solution is acetonitrile solution.
Inventor mixes orange respectively using red fluorescence material, green fluorescent material and blue fluorescent material as primary colours
Color fluorescent material, yellow fluorescent material, hanced cyan fluorescent material, purple fluorescence material and white light phosphor, rainbow fluorogram is such as
Shown in Fig. 5.
For red fluorescence material, we immerse the organic solvent dichloromethane of effumability, chloroform, tetrachloro respectively
Change carbon, ether, acetonitrile, ethyl alcohol, methanol, acetone, with the increase of adsorption time, the solid in the presence of ether and carbon tetrachloride is glimmering
Light can fade away, as shown in Figure 6.
And for green fluorescent material, we immerse the organic solvent dichloromethane of effumability, chloroform, four respectively
Chlorination carbon, ether, acetonitrile, ethyl alcohol, methanol, acetone, with the increase of adsorption time, the solid in the presence of methanol and ethyl alcohol is glimmering
Light can gradually increase as shown in Figure 7；And the solid fluorescence of enhancing can be decreased back to initially again originally after desorbing gas
State, can recycle, as shown in Figure 8.
The result shows that the red fluorescence material of A by fluorescent quenching in response to ether and tetrachloromethane, so red fluorescence
Material can identify ether and carbon tetrachloride.And A Green fluorescent dyes by Fluorescence Increasing in response to methanol and ethyl alcohol, so green
Color fluorescent material can identify methanol and ethyl alcohol.
Compared with prior art, the invention has the advantages that：
1, the present invention can prepare red, green, blue fluorescent solid material, simultaneously by loading different organic fluorescence small molecules
It is glimmering that fluorescent orange material, hanced cyan fluorescent material, purple fluorescence material and white are made using red, green, blue fluorescent solid material
Luminescent material greatly expands the application of the hexa-atomic melon ring of hexamethyl to which the fluorescent solid material of multiple color be made.
2, red fluorescence material prepared by the present invention, can identify ether and carbon tetrachloride, solid fluorescence is made to quench；And it is green
Color fluorescent material can then identify methanol and ethyl alcohol, solid fluorescence is made to enhance, and can recycle.
3, the preparation method of fluorescent material of the present invention is convenient and efficient, and preparation process is simple, and manufacturing cost is low, is at present
There is a kind of extension of fluorescent material, and great to the application value for exploring melon ring, is with a wide range of applications.
Therefore, carrier of the present invention is the porous framework structure based on the hexa-atomic melon ring Supramolecular self assembly of hexamethyl, should
Structure can be used for preparing many kinds of solids fluorescent material, which not only shows specifically to know to specific escaping gas
It does not act on, and can also be used for the fluorescent material of allotment different colours, extend the application of the hexa-atomic melon ring of hexamethyl；In addition, this
The fluorescent material of invention has preparation process simple, the low feature of manufacturing cost.
Description of the drawings：
Fig. 1 is the structure chart of the hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl of the present invention；
Fig. 2 is rhodamine B molecular structural formula and its color change under daylight and ultraviolet light；
Fig. 3 is fluorescein molecule structural formula and its color change under daylight and ultraviolet light；
Fig. 4 is pyrene molecule structural formula and its color change under daylight and ultraviolet light；
Fig. 5 is white, orange, green, the purple four color fluorescence materials obtained for three kinds of solid fluorescent material manual mixings of RGB
Material, and its color contrast under daylight and ultraviolet light；
Fig. 6 is red solid fluorescent material to the color change under the response ultraviolet light of ether and carbon tetrachloride；
Fig. 7 is green solid fluorescent material to the color change under the response ultraviolet light of ether and carbon tetrachloride；
Fig. 8 is the circular response figure of green solid fluorescent material identification methanol and ethyl alcohol.
With reference to embodiment, the present invention is further illustrated, but is not intended as the foundation limited the present invention.
Specific implementation mode
Embodiment 1：
1, the hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl, structure chart are as shown in Figure 1；Its molecular formula is：
C42H106N24O41.Its crystal data and structure details are as shown in table 1.
The crystal data of the hexa-atomic melon ring Supramolecular self assembly carrier of 1 hexamethyl of the present invention of table
2, the preparation of the hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl：The hexa-atomic melon ring of hexamethyl is added in neutral water,
Concussion, make it dissolve to get.
Embodiment 2.
The making of red solid fluorescent material：10mL neutral waters are added in the hexa-atomic melon ring (0.126g, 0.1mmol) of hexamethyl
In, concussion makes it dissolve, colourless crystallization is obtained in neutral water in 5 days, obtains the hexa-atomic melon ring Supramolecular self assembly of hexamethyl and carries
Body, yield are 0.102g (81%)；
The hexa-atomic melon ring Supramolecular self assembly carrier (10.0mg) of above-mentioned hexamethyl is added a concentration of the 5 × 10 of 0.5mL-3M
Rhodamine B acetonitrile solution in, rock, filtering red solid fluorescent material can be obtained.The molecular structural formula of the rhodamine B
It is as shown in Figure 2 with its color change under daylight and ultraviolet light.
Embodiment 3.
The making of green fluorescence solid material：10mL neutral waters are added in the hexa-atomic melon ring (0.126g, 0.1mmol) of hexamethyl
In, concussion makes it dissolve, colourless crystallization is obtained in neutral water in 5 days, obtains the hexa-atomic melon ring Supramolecular self assembly of hexamethyl and carries
Body, yield are 0.102g (81%)；
The hexa-atomic melon ring Supramolecular self assembly carrier (10.0mg) of above-mentioned hexamethyl is added a concentration of the 5 × 10 of 0.5mL-3M
Fluorescein acetonitrile solution in, rock, filtering green solid fluorescent material can be obtained.The molecular structural formula of the fluorescein and
Its color change under daylight and ultraviolet light is as shown in Figure 3.
Embodiment 4.
The making of blue solid fluorescent material：10mL neutral waters are added in the hexa-atomic melon ring (0.126g, 0.1mmol) of hexamethyl
In, concussion makes it dissolve, colourless crystallization is obtained in neutral water in 5 days, obtains the hexa-atomic melon ring Supramolecular self assembly of hexamethyl and carries
Body, yield are 0.102g (81%)；
The hexa-atomic melon ring Supramolecular self assembly carrier (10.0mg) of above-mentioned hexamethyl is added a concentration of the 5 × 10 of 0.5mL-3M
Pyrene acetonitrile solution in, rock, filtering blue solid fluorescent material can be obtained.The molecular structural formula of the pyrene is with it in daylight
And the color change under ultraviolet light is as shown in Figure 4.
Embodiment 5.
Red, green and blue solid fluorescent material is prepared respectively using embodiment 2-4 the methods, it then will be above-mentioned
Three kinds of color fluorescence materials allocate the fluorescent material of different solid colors, and the specific method is as follows：
A. red solid fluorescent material 4.2-5.1mg and yellow solid fluorescent material 2.9-3.7mg mixing preparations can be obtained
Orange solids fluorescent material, as shown in Fig. 5；
B. green solid fluorescent material 5.3-5.6mg and blue solid fluorescent material 5.9-6.1mg mixing preparations can be obtained
Cyan solid fluorescent material, as shown in Fig. 5；
C. red solid fluorescent material 3.9-4.4mg and blue solid fluorescent material 4.7-5.1mg mixing preparations can be obtained
Violet solid fluorescent material, as shown in Fig. 5；
D. by red solid fluorescent material 3.0-3.5mg, green solid fluorescent material 2.8-3.3mg and blue solid fluorescence
Material 3.1-3.5mg mixing preparations can obtain white solid fluorescent material, as shown in Fig. 5.
Claims (8)
1. the hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl, it is characterised in that：With the hexa-atomic melon ring of hexamethyl and neutral aqueous solution
The hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl is made for raw material.
2. the hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl as described in claim 1, it is characterised in that：It is described with pregnancy
The hexa-atomic melon ring of base is the obtained hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl of raw material with neutral aqueous solution；By in every 8-12mL
Property aqueous solution in 0.08-0.12 mmol hexamethyls hexa-atomic melon ring is added the hexa-atomic melon ring of hexamethyl is added in neutral aqueous solution, shake
Swing, make it dissolve to get.
3. the hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl as described in claim 1, it is characterised in that：The hexamethyl six
The molecular formula of first melon ring Supramolecular self assembly carrier is： C42H106N24O41 。
4. a kind of application of the hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl as claimed in any one of claims 1-3,
It is characterized in that：It is used to prepare fluorescent material.
5. the application of the hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl as claimed in claim 4, it is characterised in that：Described
Being used to prepare fluorescent material is；The hexa-atomic melon ring of hexamethyl is added in neutral water, concussion makes it dissolve, obtains the hexa-atomic melon of hexamethyl
Ring Supramolecular self assembly carrier, the hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl are added loading solution and load small point of organic fluorescence
Fluorescent material is made in son.
6. the application of the hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl as claimed in claim 5, it is characterised in that：It is described negative
Load solution is acetonitrile solution.
7. the application of the hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl as claimed in claim 5, it is characterised in that：It is described to have
Machine fluorescent small molecule is rhodamine B（G1）, fluorescein (G2) or pyrene (G3).
8. the application of the hexa-atomic melon ring Supramolecular self assembly carrier of hexamethyl as claimed in claim 5, it is characterised in that：It is described glimmering
Luminescent material is red fluorescence material, green fluorescent material or blue fluorescent material.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109111577A (en) * | 2018-11-01 | 2019-01-01 | 贵州大学 | Symmetric tetramethyl cucurbituril supermolecule frame material and its preparation method and application |
| CN109187476A (en) * | 2018-09-18 | 2019-01-11 | 贵州大学 | A kind of application of the supermolecule frame material based on ten yuan of melon rings in pyridine detection |
| CN109239035A (en) * | 2018-09-18 | 2019-01-18 | 贵州大学 | A kind of application of the supermolecule frame material based on ten yuan of melon rings in formaldehyde examination |
| CN109580567A (en) * | 2018-12-04 | 2019-04-05 | 贵州大学 | BF in a kind of detection water4-、H2PO4-And HSO4-Method |
| CN109647363A (en) * | 2018-11-23 | 2019-04-19 | 中山大学 | A kind of porous solid amine absorption granular materials and the preparation method and application thereof with fluorescence response |
| CN109897046A (en) * | 2019-02-15 | 2019-06-18 | 贵州大学 | A kind of preparation method and recognition methods of the fluorescent material that methanol gas can be detected |
| CN113461650A (en) * | 2021-06-15 | 2021-10-01 | 贵州大学 | Calixarene-rhodamine supramolecular assembly and preparation method and application thereof |
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| CN104383883A (en) * | 2014-11-28 | 2015-03-04 | 贵州大学 | Hexamethyl hexacucurbituril porous selective adsorption material as well as synthesis method and application |
| CN107446568A (en) * | 2017-07-12 | 2017-12-08 | 贵州大学 | A kind of fluorescent material |
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| CN104383883A (en) * | 2014-11-28 | 2015-03-04 | 贵州大学 | Hexamethyl hexacucurbituril porous selective adsorption material as well as synthesis method and application |
| CN107446568A (en) * | 2017-07-12 | 2017-12-08 | 贵州大学 | A kind of fluorescent material |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109187476A (en) * | 2018-09-18 | 2019-01-11 | 贵州大学 | A kind of application of the supermolecule frame material based on ten yuan of melon rings in pyridine detection |
| CN109239035A (en) * | 2018-09-18 | 2019-01-18 | 贵州大学 | A kind of application of the supermolecule frame material based on ten yuan of melon rings in formaldehyde examination |
| CN109187476B (en) * | 2018-09-18 | 2021-02-02 | 贵州大学 | Application of ten-element cucurbituril-based super-molecular framework material in pyridine detection |
| CN109239035B (en) * | 2018-09-18 | 2021-04-13 | 贵州大学 | Application of ten-element cucurbituril-based super-molecular framework material in formaldehyde detection |
| CN109111577A (en) * | 2018-11-01 | 2019-01-01 | 贵州大学 | Symmetric tetramethyl cucurbituril supermolecule frame material and its preparation method and application |
| CN109647363A (en) * | 2018-11-23 | 2019-04-19 | 中山大学 | A kind of porous solid amine absorption granular materials and the preparation method and application thereof with fluorescence response |
| CN109580567A (en) * | 2018-12-04 | 2019-04-05 | 贵州大学 | BF in a kind of detection water4-、H2PO4-And HSO4-Method |
| CN109580567B (en) * | 2018-12-04 | 2021-05-14 | 贵州大学 | Detect aquatic BF4-、H2PO4-And HSO4-Method (2) |
| CN109897046A (en) * | 2019-02-15 | 2019-06-18 | 贵州大学 | A kind of preparation method and recognition methods of the fluorescent material that methanol gas can be detected |
| CN113461650A (en) * | 2021-06-15 | 2021-10-01 | 贵州大学 | Calixarene-rhodamine supramolecular assembly and preparation method and application thereof |
| CN113461650B (en) * | 2021-06-15 | 2022-06-07 | 贵州大学 | Calixarene-rhodamine supramolecular assembly and preparation method and application thereof |
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| CN108484562B (en) | 2021-12-21 |
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