CN113502152A - Photochromic material containing cucurbituril and dipyridyl vinyl compound, preparation method and application thereof - Google Patents
Photochromic material containing cucurbituril and dipyridyl vinyl compound, preparation method and application thereof Download PDFInfo
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- CN113502152A CN113502152A CN202110744594.7A CN202110744594A CN113502152A CN 113502152 A CN113502152 A CN 113502152A CN 202110744594 A CN202110744594 A CN 202110744594A CN 113502152 A CN113502152 A CN 113502152A
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- 239000000463 material Substances 0.000 title claims abstract description 39
- MSBXTPRURXJCPF-DQWIULQBSA-N cucurbit[6]uril Chemical compound N1([C@@H]2[C@@H]3N(C1=O)CN1[C@@H]4[C@@H]5N(C1=O)CN1[C@@H]6[C@@H]7N(C1=O)CN1[C@@H]8[C@@H]9N(C1=O)CN([C@H]1N(C%10=O)CN9C(=O)N8CN7C(=O)N6CN5C(=O)N4CN3C(=O)N2C2)C3=O)CN4C(=O)N5[C@@H]6[C@H]4N2C(=O)N6CN%10[C@H]1N3C5 MSBXTPRURXJCPF-DQWIULQBSA-N 0.000 title claims abstract description 37
- -1 dipyridyl vinyl compound Chemical class 0.000 title claims abstract description 26
- 229920002554 vinyl polymer Polymers 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 238000001035 drying Methods 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 239000005711 Benzoic acid Substances 0.000 claims description 8
- 235000010233 benzoic acid Nutrition 0.000 claims description 8
- VXXRMBQHVJKWIC-UHFFFAOYSA-N 2-(1-pyridin-2-ylethenyl)pyridine Chemical group C=1C=CC=NC=1C(=C)C1=CC=CC=N1 VXXRMBQHVJKWIC-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 238000005034 decoration Methods 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 230000001681 protective effect Effects 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 230000002146 bilateral effect Effects 0.000 description 6
- 239000005977 Ethylene Substances 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 238000005286 illumination Methods 0.000 description 4
- 238000001338 self-assembly Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 229910052724 xenon Inorganic materials 0.000 description 4
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 4
- 238000011160 research Methods 0.000 description 3
- HKEOCEQLCZEBMK-UHFFFAOYSA-N 2-(2-pyridin-2-ylethenyl)pyridine Chemical class C=1C=CC=NC=1C=CC1=CC=CC=N1 HKEOCEQLCZEBMK-UHFFFAOYSA-N 0.000 description 2
- 238000004435 EPR spectroscopy Methods 0.000 description 2
- 239000005976 Ethephon Substances 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000010504 bond cleavage reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
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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
- C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
- C09K9/02—Organic tenebrescent 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
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- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Abstract
The invention relates to the technical field of photochromic materials, in particular to a photochromic material containing cucurbituril and bipyridine vinyl compounds, a preparation method and application thereof, wherein the photochromic material is formed by self-assembling a seven-membered cucurbituril or eight-membered cucurbituril host and a bipyridine vinyl compound object, and the molar ratio of cucurbituril to a single-side substituted bipyridine vinyl compound is 1:1, in a molar ratio to the bilaterally substituted bipyridylethylene compound of 2: 1. when the photochromic material is prepared, a cucurbituril host and a dipyridyl vinyl compound object are mixed and stirred at room temperature according to a corresponding molar ratio and dissolved in water; the two compounds are self-assembled in the solution to form a host-guest compound, and the photochromic material is obtained after concentration and drying; solves the problem that most bipyridyl vinyl compounds have no good photochromic performance and can not be applied to photochromic materials.
Description
Technical Field
The invention relates to the technical field of photochromic materials, in particular to a photochromic material containing cucurbituril and bipyridyl ethylene compounds, a preparation method and application thereof.
Background
Photochromism refers to the reversible change of certain compounds between two physical or chemical states under the action of light of a certain wavelength and intensity, resulting in a corresponding change in the absorption peak, i.e., color, of the compound to the light. This can be expressed by the following equation:
wherein A and B represent two different colors of the same substanceA color status; lambda [ alpha ]1And λ2Respectively, representing two different wavelengths.
Photochromic materials include both inorganic and organic photo-reversible photochromic materials. The photochromism of organic systems is often accompanied by processes associated with photochemical reactions, leading to some modification of the structure of the compound, in a way that mainly consists of: valence bond isomerism, cis-trans isomerism, bond cleavage (including heterolytic and homolytic), polymerisation, oxidation-reduction, peri-reactions, etc. Organic photochromism has more researches on compounds including viologen, fulgide, spiropyran, spirooxazine, azobenzene and the like, and has wide application. The dipyridyl vinyl compound has very good thermal stability and chemical stability, and the research thereof is receiving more and more attention from domestic and foreign material workers. However, most bipyridylethylenes do not exhibit good photochromic properties by themselves.
In view of the above-mentioned drawbacks, the inventors of the present invention have finally obtained the present invention through a long period of research and practice.
Disclosure of Invention
The invention aims to solve the problem that most bipyridyl vinyl compounds have no good photochromic performance and cannot be applied to photochromic materials, and provides a photochromic material containing cucurbituril and bipyridyl vinyl compounds, a preparation method and application thereof.
In order to achieve the aim, the invention discloses a photochromic material containing cucurbiturils and dipyridyl vinyl compounds, which is a host-guest inclusion complex generated in a solution by any one of seven-membered cucurbiturils or eight-membered cucurbiturils and shell dipyridyl vinyl compounds according to a molar ratio.
The host compound is seven-membered cucurbituril or eight-membered cucurbituril, as shown in a general formula I, and the guest compound is one of bipyridyl ethylene compounds, as shown in a general formula II.
General formula I
General formula II
X-in the general formula II represents F-, Cl-, Br-, I-, PF 6-and other anions. R and R' may be an aromatic ring group such as phenyl, benzyl, naphthyl, furyl or thienyl, or a substituent group containing a carboxyl group such as 4-carboxy-benzylidene.
The dipyridyl ethenes compound is benzoic acid unilateral substituted dipyridyl ethene or benzyl bilateral substituted dipyridyl ethene.
The invention also discloses a preparation method of the photochromic material containing cucurbituril and dipyridyl vinyl compounds, which comprises the following steps:
s1: dissolving one of a seven-element cucurbituril or an eight-element cucurbituril as a main body and a guest dipyridyl vinyl compound in water, and uniformly stirring at room temperature to obtain a clear solution;
s2: and (4) concentrating and drying the clear solution obtained in the step (S1) at 40 ℃ by using a rotary evaporator to obtain the photo-reversible photochromic material.
In the step S1, the bipyridyl vinyl compound is benzoic acid unilateral substituted bipyridyl vinyl, and the molar ratio of the host to the guest is 1: 1.
In the step S1, the bipyridyl ethephon compound is benzyl bilateral substituted bipyridyl ethephon, and the molar ratio of the host to the guest is 2: 1.
The invention provides a photochromic material based on a host-guest inclusion compound and a synthesis method thereof by utilizing the inclusion effect of macrocyclic compound-cucurbituril on dipyridyl vinyl compounds. The color change mechanism of the photochromic material is as follows: under the light induction condition, electron transfer occurs between the bipyridyl ethylene compound object lacking electrons and the cucurbituril host rich in electrons to generate chromogenic free radicals, thereby realizing the change of color. When the dipyridyl vinyl compound is wrapped into the cavity of the cucurbituril to form a subject-guest compound, the cucurbituril can play a role in an electron donor and stabilizing the structure of the dipyridyl vinyl compound.
The invention also discloses application of the photochromic material containing cucurbituril and bipyridyl ethylene compounds in the fields of optical information storage, protection decoration, anti-counterfeiting, counterfeit identification and confidentiality.
Compared with the prior art, the invention has the beneficial effects that:
(1) the method is simple, the operation is simple and convenient, the required working procedures are less, and the required raw materials are simple and easy to obtain;
(2) the obtained photo-reversible color-changing material has excellent performance, and has the characteristics of high sensitivity, high response speed, high stability, high fatigue resistance and the like;
(3) the obtained photo-reversible color-changing material has the most outstanding advantage of fast fading speed, and the original color is recovered within 3 to 5 minutes generally.
Drawings
FIG. 1 is a schematic diagram of the structure of a host-guest compound obtained in example 1;
FIG. 2 is a solid UV diffuse reflectance chart before and after photochromism of the host-guest compound of example 2;
FIG. 3 is a solid UV diffuse reflectance chart before and after photochromism of the host-guest compound of example 3;
FIG. 4 is a one-electron spin resonance nuclear magnetic map of host and guest compounds of example 1 before and after photochromism.
Detailed Description
The above and further features and advantages of the present invention are described in more detail below with reference to the accompanying drawings.
Example 1
1. 0.1162g of seven-element cucurbituril and 0.0476g of unilateral benzoic acid substituted dipyridyl ethylene are respectively weighed and mixed and dissolved in about 30mL of aqueous solution at room temperature; the two can form a host-guest compound in a self-assembly mode in aqueous solution; the structure of the obtained host-guest compound is schematically shown in fig. 1, and a pyridine group and a vinyl group at one end of a guest molecule are wrapped in a hydrophobic cavity of a cucurbituril.
2. Drying the solution of the host-guest compound thoroughly at 40 ℃ by using a rotary evaporator to obtain the photochromic material based on seven-element cucurbituril and benzoic acid single-side substituted bipyridyl ethylene;
3. the photochromic material can be changed from light yellow to reddish brown within a very short time (2min) under the illumination of a full-wavelength xenon lamp. When the light was stopped, the reddish brown color quickly (5min) completely returned to pale yellow.
Example 2
1. 0.1328g of eight-membered cucurbituril and 0.0476g of unilateral benzoic acid substituted dipyridyl ethylene are respectively weighed and mixed and dissolved in 30mL of aqueous solution at room temperature; the two can form a host-guest compound in a self-assembly mode in aqueous solution;
2. spin-drying the solution of the host-guest compound by using a rotary evaporator at 40 ℃, and completely drying to obtain the photochromic material based on eight-membered cucurbituril and benzoic acid single-side substituted dipyridyl ethylene;
3. the photochromic material can be changed from light yellow to reddish brown within a very short time (1min) under the illumination of a full-wavelength xenon lamp. When the light was stopped, the reddish brown color quickly (5min) completely returned to pale yellow. Solid ultraviolet diffuse reflection patterns of the host compound and the guest compound before and after photochromism are shown in figure 2; the absorbance of the host-guest compound in the visible light range is obviously enhanced after illumination.
Example 3
1. 0.1162g of cucurbituril and 0.0525g of benzyl bilateral substituted dipyridyl ethylene are respectively weighed and mixed and dissolved in about 30mL of aqueous solution at room temperature; the two can form a host-guest compound in a self-assembly mode in aqueous solution;
2. spin-drying the solution of the host-guest compound by using a rotary evaporator at 40 ℃, and completely drying to obtain the photochromic material based on seven-membered cucurbituril and benzyl bilateral substituted bipyridyl ethylene;
3. the photochromic material can be changed into pink from light yellow in a very short time (2min) when being illuminated by a xenon lamp with full wavelength. When the light was stopped, the reddish brown color quickly (5min) completely returned to pale yellow. Solid ultraviolet diffuse reflection patterns of the host-guest compound before and after photochromism are shown in fig. 3, and the absorbance of the host-guest compound in a visible light range is enhanced after illumination.
Example 4
1. 0.1328g of eight-membered cucurbituril and 0.0528g of benzyl bilateral substituted dipyridyl ethylene are respectively weighed, mixed and stirred at room temperature and dissolved in 30mL of aqueous solution; the two can form a host-guest compound in a self-assembly mode in aqueous solution;
2. spin-drying the solution of the host-guest compound by using a rotary evaporator at 40 ℃, and completely drying to obtain the irreversible photochromic material based on eight-membered cucurbituril and benzyl bilateral substituted bipyridyl ethylene;
3. the photochromic material can be changed into pink from light yellow in a very short time (2min) when being illuminated by a xenon lamp with full wavelength. When the light was stopped, the reddish brown color quickly (5min) completely returned to pale yellow. The one-electron spin resonance nuclear magnetic map before and after the host-guest compound is photochromic is shown in fig. 4, and a free radical resonance peak caused by remarkable electron transfer appears after the host-guest compound is irradiated with light.
The foregoing is merely a preferred embodiment of the invention, which is intended to be illustrative and not limiting. It will be understood by those skilled in the art that various changes, modifications and equivalents may be made therein without departing from the spirit and scope of the invention as defined in the appended claims.
Claims (9)
1. A photochromic material containing cucurbituril and dipyridyl vinyl compounds is characterized in that a host-guest inclusion complex is generated in a solution by a molar ratio of any one of seven-membered cucurbituril or eight-membered cucurbituril and capsidyl vinyl compounds.
2. The photochromic material comprising cucurbituril and dipyridylethylene compounds according to claim 1, wherein said dipyridylethylene compounds have the formula
X in the general formula-Is F-，Cl-，Br-，I-，PF6 -R and R' are any substituent containing carboxyl, such as phenyl, benzyl, naphthyl, furyl, thienyl, 4-carboxyl-benzylidene and the like.
3. The photochromic material of claim 1 wherein the bipyridylethylene compound is a benzoic acid unilaterally substituted bipyridylethylene or a benzyl unilaterally substituted bipyridylethylene compound.
4. A method for preparing a photochromic material containing cucurbituril and dipyridyl vinyl compounds as claimed in any one of claims 1 to 3, comprising the steps of:
s1: dissolving one of a seven-element cucurbituril or an eight-element cucurbituril as a main body and a guest dipyridyl vinyl compound in water, and uniformly stirring at room temperature to obtain a clear solution;
s2: and (4) concentrating and drying the clear solution obtained in the step (S1) at 40 ℃ by using a rotary evaporator to obtain the photo-reversible photochromic material.
5. The method of claim 4, wherein the bipyridyl vinylene compound in step S1 is a benzoic acid mono-substituted bipyridyl vinylene, and the molar ratio of host to guest is 1: 1.
6. The method according to claim 4, wherein the bipyridyl vinylic compound in step S1 is benzyl-bilateral-substituted bipyridyl vinylic compound, and the molar ratio of host to guest is 2: 1.
7. Use of a photochromic material comprising cucurbituril and a bipyridylethylene compound as claimed in any one of claims 1 to 3 in the field of optical information storage.
8. Use of the photochromic material containing cucurbituril and dipyridyl vinyl compounds as claimed in any one of claims 1 to 3 in the field of protective decoration.
9. Use of the photochromic material containing cucurbituril and bipyridyl vinylic compounds as claimed in any one of claims 1 to 3 in the fields of anti-counterfeiting, counterfeit identification and confidentiality.
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| Application Number | Priority Date | Filing Date | Title |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110650977A (en) * | 2017-03-16 | 2020-01-03 | 奥伦·A·谢尔曼 | Deep eutectic solvent composition |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110650977A (en) * | 2017-03-16 | 2020-01-03 | 奥伦·A·谢尔曼 | Deep eutectic solvent composition |
Non-Patent Citations (3)
| Title |
|---|
| MASATO NANASAWA等: "Synthesis of Viologens with Extended π-Conjugation and Their Photochromic Behavior on Near-IR Absorption", 《J. ORG. CHEM.》 * |
| QIN WANG等: "Electron transfer photochromism of solid-state supramolecules constructed by cucurbit[n]uril (n = 5-8) and 1-(4-carboxybenzyl)-4-[2-(4-pyridyl)-vinyl]-pyridinium chloride", 《NEW JOURNAL OF CHEMISTRY》 * |
| TETSUO KUWABARA等: "Photochromism of Viologens Included in Crown Ether Cavity", 《PHOTOCHEMISTRY AND PHOTOBIOLOGY》 * |
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