CN102079742B - Photochromic naphthalene-thiophene hybrid type perfluorinated cyclopentene compound and synthesis method and application thereof - Google Patents
Photochromic naphthalene-thiophene hybrid type perfluorinated cyclopentene compound and synthesis method and application thereof Download PDFInfo
- Publication number
- CN102079742B CN102079742B CN2010105271321A CN201010527132A CN102079742B CN 102079742 B CN102079742 B CN 102079742B CN 2010105271321 A CN2010105271321 A CN 2010105271321A CN 201010527132 A CN201010527132 A CN 201010527132A CN 102079742 B CN102079742 B CN 102079742B
- Authority
- CN
- China
- Prior art keywords
- photochromic
- thiophene
- compound
- naphthalene
- type perfluorinated
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Images
Abstract
The invention discloses a photochromic naphthalene-thiophene hybrid type perfluorinated cyclopentene compound and a synthesis method and application thereof. The photochromic material can keep good photochromic property in solution or a thin film; the photochromic material has remarkable properties, such as excellent chemical property and thermostability, good sensitivity and the like both in an open-loop state (colorless state) and a closed-loop state (colored state); in the open-loop state, the photochromic material has stronger fluorescence within a range of 350 to 550 nanometers, and in the closed-loop state, the photochromic material has no fluorescence at all; therefore, the photochromic naphthalene-thiophene hybrid type perfluorinated cyclopentene compound can be applied to fluorescence detection and fluorescence light-operated switches and simultaneously used for high-density holographic light storage in an erasable photon manner, and has wide application prospect.
Description
Technical field
The present invention relates to a kind of photochromic naphthalene nucleus-thiophene hybrid-type perfluorinated cyclopentene compound and compound method and application.
Technical background
Organic photochromic diarylethene material is owing to have advantages such as photoelectric characteristic and controllable structure, has characteristics such as thermostability, antifatigue, noise spectra of semiconductor lasers sensitivity and response speed that excellence is arranged be fast simultaneously.Therefore, in high-density, can wipe and rewrite photon type optical information field of storage and receive much concern.And in numerous photochromic compounds, the Perfluorocyclopentene diaryl ethylene compounds has plurality of advantages such as good photochromic performance, thermostability, fatigue resistence and response speed be fast, is one of photochromic material of at present tool application prospect.In numerous diarylethene photochromic molecules; The diarylethene Perfluorocyclopentene photochromic compound that has the hetero-aromatic ring group has excellent more photo and thermal stability, chemicalstability; And good fatigue resistence; Its photochromic reactions causes to such an extent that physicochemical property such as absorbed, emission, oxidation-reduction quality can take place reversible changely under light-operated condition, and these running parameters have boundless application prospect aspect optical storage and the novel photoelectric device.At present; In the Perfluorocyclopentene diaryl ethylene compounds; The aromatic ring that the ethylene double bond two ends are connected mainly is thiophene and two kinds of aromatic base (Irie of thionaphthene usually; M.Chem.Rev.100 (2000) 1685), in addition, few part is also arranged with heterocyclic substituted thiophene such as thiazole, pyrroles, indoles and cumarone or thionaphthene and form new Diarene compound.
Summary of the invention
The object of the invention just provides a kind of photochromic naphthalene nucleus-thiophene hybrid-type perfluorinated cyclopentene compound and compound method and application.
The general formula of molecular structure of photochromic naphthalene nucleus-thiophene hybrid-type perfluorinated cyclopentene compound of the present invention is following:
Wherein R is groups such as Wasserstoffatoms, methyl, methoxyl group, cyanic acid, trifluoromethyl.
The universal synthesis method of photochromic naphthalene nucleus-thiophene hybrid-type perfluorinated cyclopentene compound of the present invention is: (1), be raw material with the 2-thiotolene; Bromination under condition of ice bath; Then through reacting with n-Butyl Lithium (n-BuLi) and tributyl borate; Generate 2-methyl-3-bromo-5-boronate thiophene, make catalyzer with four triphen phosphorus palladiums again, through linked reaction various substituted halogeno-benzenes and thiphene ring are coupled together and obtain various substituted thiophene-based midbodys; (2), under the n-Butyl Lithium effect, with 1-bromo-2-methylnaphthalene and the mono-substituted Perfluorocyclopentene of Perfluorocyclopentene reaction generation; (3), under the low temperature nitrogen protective condition, use n-Butyl Lithium, preparation in the step (2) single replaced the midbody that obtains in Perfluorocyclopentene midbody and the step (1) reacts, thereby obtain target compound like the general formula of molecular structure class.
The main application of photochromic naphthalene nucleus-thiophene hybrid-type perfluorinated cyclopentene compound of the present invention has: mix up macromolecular material or process diaphragm, be useful for VHD, erasable organic photon type information storage material; Be used to prepare the photoswitch element; Be used to prepare photochromic luminescent device etc.
The advantage of photochromic naphthalene nucleus-thiophene hybrid-type perfluorinated cyclopentene compound of the present invention mainly contains the following aspects:
1, naphthalene nucleus-thiophene hybrid-type perfluorinated cyclopentene photochromic material all can keep the good photochromic performance in solution or film, and open loop attitude (colourless attitude) and equal tool good chemical of closed loop attitude (colour generation attitude) and high-performances such as thermostability and good sensitivity;
2, the open loop attitude of naphthalene nucleus-thiophene hybrid-type perfluorinated cyclopentene photochromic material has stronger fluorescence in the 350-500nm scope, and the closed loop attitude does not have fluorescence, thereby can be used for fluoroscopic examination and fluorescence photoswitch;
3, the Perfluorocyclopentene class two fragrant alkene photochromic materials that contain the hetero-aromatic ring group of the present invention successfully are used for the High-Density Holographic optical storage, and its memory attribute is erasable photon type storage.
4, with symmetrical thiophene or benzothiophene Perfluorocyclopentene material compared, the cost of its preparation material is relatively low, and application prospect is bigger.
Description of drawings
Fig. 1 is the general formula of molecular structure of photochromic naphthalene nucleus-thiophene hybrid-type perfluorinated cyclopentene compound;
Fig. 2 is the photochromic reactions principle schematic of compound 1a of the present invention, 2a, 3a;
Fig. 3 is compound 1a, 2a, the abosrption spectrogram of 3a before and after hexane solution medium ultraviolet rayed;
Fig. 4 is compound 1a, 2a, the abosrption spectrogram of 3a before and after PMMA film medium ultraviolet rayed;
Fig. 5 be compound 1a, 2a and 3a in hexane solution fluorescence emission spectrum with the ultraviolet lighting time variation diagram;
Fig. 6 be compound 1a, 2a and 3a in the PMMA diaphragm fluorescence emission spectrum with the ultraviolet lighting time variation diagram.
The practical implementation method
Embodiment 1: [compound 1a]:
In general formula of molecular structure, when R is methoxyl group, promptly constitute photochromic compound 1a, its name is called: [1-(2-dimethylnaphthalene-1-yl), 2-(2-methyl-5-m-methoxyphenyl-thiene-3-yl-)] Perfluorocyclopentene (1a), structural formula is following:
Shown in the synthetic schemes Scheme 1 of this novel diaryl perfluoro cycolpenfene photochrmism compounds: Scheme 1:
Its concrete synthesis step is described below:
1,3,5-two bromo-2-thiotolenes (2)
Under condition of ice bath, (25.617g 261.4mmol) is dissolved in the acetate, drips the acetate that contains the liquid bromine down in whipped state, continues ice bath reaction 8h, adds moisture liquid, and water is used Na with 2-thiotolene (1)
2CO
3After the neutralization, use extracted with diethyl ether again, merge organic phase, use saturated Na
2CO
3Wash anhydrous MgSO successively with the aqueous solution
4Drying filters, and revolves to boil off solvent, and underpressure distillation obtains light yellow liquid 55.69g, productive rate: 83.25%.
Structure is identified: IR (cm
-1) 780,810,949,1010,1138,1301,1450,1535,2785,3080.
2,2-methyl-3-bromo-5-boronate thiophene (3)
Reach under-78 ℃ of conditions at nitrogen, (20.6g 80.52mmol) is dissolved in the anhydrous diethyl ether with compound 5; Stir, slowly inject n-BuLi (84.5mmol), low-temp reaction is after half a hour; Add tributyl borate, heat up naturally behind the continuation reaction 1.5h, add rare HCl stopped reaction; Separatory is abandoned water, with rare NaOH extracted organic phase, till water is acidified to neutrality and no longer produces white precipitate with rare HCl solution.Filter, rare HCl washing precipitation, vacuum-drying obtain compound 6 light yellow solid 11.8g, productive rate: 66.7%.
Structure is identified: IR (cm
-1) 690,789,832,1009,1132,1340,1473,1528,1290,3201.
3,3-bromo-2-methyl-5-p-methoxyphenyl thiophene (4)
Under nitrogen protection, will to the methoxyl group bromobenzene (2.12g, 11.3mmol) and Pd (PPh
3)
4(0.5g) be dissolved among the 80mlTHF, (2.5g is 2.0mol/L Na with concentration 11.3mmol) to add compound 3 behind the stirring 20min
2CO
3Solution 50ml, reflux 16h, stopped reaction is chilled to room temperature.Separatory, water is used extracted with diethyl ether, merges organic phase, anhydrous magnesium sulfate drying.Suction filtration, filtrating is revolved and is boiled off solvent, silica gel column chromatography (sherwood oil) separates, obtain white solid (1.7g, 6.0mmol), productive rate: 53.1%.
Structure is identified:
1H NMR (400MHz, CDCl
3): δ 2.43 (s, 3H), 3.86 (s, 3H), 6.86 (d, 1H, J=8.0Hz), 7.05 (s, 1H, J=8.0Hz), 7.13 (d, 2H, J=8.0Hz), 7.30 (d, 1H, J=8.0Hz).
4,1-(2-methylnaphthalene-1-yl) Perfluorocyclopentene (6)
(3.0g 13.5mmol) is dissolved among the 60ml THF, under nitrogen and-78 ℃ of conditions, stirs, and (5.9ml 14.9mmol), continues low temperature and stirs half a hour slowly to inject the n-BuLi of 2.5mol/L with compound 5.(2mL 14.9mmol) is injected in the reaction flask, continues reaction mixture is stirred 1h at low temperatures, rises to room temperature naturally, adds the suitable quantity of water termination reaction with the perfluoro cyclopentenes.Separatory is also used extracted with diethyl ether.Merge organic phase, distillation is desolvated, vacuum-drying.Resistates with the sherwood oil silica gel column chromatography separate obtain compound 6 water white transparency solids (4.3g, 12.8mmol), productive rate: 94.9%.
1HNMR(400MHz，CDCl
3)：δ2.45(s，3H，-CH3)，7.46(d，3H，naphthalene-H，J＝8.0Hz)，7.54(m，3H，naphthalene-H，J＝8.0Hz)，7.90(m，2H，naphthalene-H，J＝8.0Hz)。
5, [1-(2-methylnaphthalene-1-yl), 2-(2-methyl-5-p-methoxyphenyl thiene-3-yl-)] Perfluorocyclopentene (1a)
Reach under-78 ℃ of conditions at nitrogen, (0.98g 3.46mmol) is dissolved among the refining THF, stirs the hexane solution that adds n-BuLi and keeps low temperature stirring 0.5 hour with compound 4; (1.0g, THF solution 3.29mmol) join in the reaction flask, continue reaction mixture was stirred 1 hour at low temperatures, rise to room temperature naturally, add the suitable quantity of water termination reaction will singly to replace perfluoro cyclopentenes (6).Separatory is also used extracted with diethyl ether.Merge organic phase, distillation is desolvated, vacuum-drying.Resistates is with petrol ether/ethyl acetate=eluent obtained 1a faint yellow solid (0.87g, 1.68mmol) productive rate: 50.8% through the silica gel column chromatography separation in 8: 1.
Structure is identified:
1H NMR (400MHz, CDCl
3): δ 2.22 (s, 3H ,-CH3), δ 2.34 (s, 3H ,-CH3), δ 3.71 (s, 3H ,-CH3); δ 6.61 (s, 1H, thiophene-H), δ 6.73 (d, 1H, benzene-H, δ 6.80 (d, 2H, benzene-H); δ 7.15 (t, 1H, benzene-H), δ 7.31 (d, 1H, naphthalene-H), δ 7.47 (t, 1H, naphthalene-H); δ 7.53 (d, 1H, naphthalene-H), δ 7.68 (d, 1H, naphthalene-H), δ 7.80 (m, 2H, naphthalene-H).
Embodiment 2: [compound 2a]:
In general formula of molecular structure, when R is methyl, promptly constitute photochromic compound 2a, its name is called: [1-(2-methylnaphthalene-1-yl), 2-(aminomethyl phenyl-thiene-3-yl-between 2-methyl-5-)] Perfluorocyclopentene, structural formula is following:
Shown in the synthetic schemes Scheme 2 of this novel diaryl perfluoro cycolpenfene photochrmism compounds: Scheme 2:
Its concrete synthesis step is described below:
1, aminomethyl phenyl thiophene (4) between 3-bromo-2-methyl-5-
Under nitrogen protection, with 3-brooethyl benzene (2.32g, 13.58mmol) and Pd (PPh
3)
4(0.5g) be dissolved among the 80ml THF, (3.0g is 2.0mol/LNa with concentration 13.58mmol) to add 3 behind the stirring 20min
2CO
3Solution 50ml, reflux 16h, stopped reaction is chilled to room temperature.Separatory, water is used extracted with diethyl ether, merges organic phase, anhydrous magnesium sulfate drying.Suction filtration, filtrating is revolved and is boiled off solvent, silica gel column chromatography (sherwood oil) separates, obtain faint yellow solid (2.9g, 10.85mmol), productive rate: 89.8%.
Structure is identified:
1H NMR (400MHz, CDCl
3): δ 2.38 (s, 3H), δ 2.43 (s, 3H), 7.12 (s, 1H), 7.14 (s, 1H, J=8.0Hz), 7.27 (s, 1H, J=8.0Hz), 7.29 (d, 2H, J=8.0Hz), 7.32 (d, 1H, J=8.0Hz).
2, [1-(2-methylnaphthalene-1-yl), 2-(aminomethyl phenyl-thiene-3-yl-between 2-methyl-5-)] Perfluorocyclopentene (2a)
Under nitrogen and-78 ℃ of conditions, (0.76g 2.83mmol) is dissolved among the refining THF, stirs, and (1.2ml 3.11mmol) keeps low temperature to stir 0.5 hour slowly to inject the n-BuLi of 2.5mol/L with 4; (0.9g, THF solution 2.69mmol) join in the reaction flask, continue reaction mixture was stirred 1 hour at low temperatures, rise to room temperature naturally, add the suitable quantity of water termination reaction will singly to replace perfluoro cyclopentenes (6).Separatory is also used extracted with diethyl ether.Merge organic phase, distillation is desolvated, vacuum-drying.Resistates with sherwood oil through silica gel column chromatography separate obtain 1a yellow-green colour solid 2a (0.46g, 0.92mmol).Productive rate: 31.7%.
Structure is identified:
1H NMR (400MHz, CDCl
3, ppm): δ 2.21 (s, 3H ,-CH
3), δ 2.30 (s, 3H ,-CH
3), δ 2.36 (s, 3H ,-CH
3), δ 6.82 (s, 1H, thiophene-H), δ 7.06 (t, 1H, benzene-H), δ 7.13 (m; 2H, benzene-H), δ 7.33 (d, 1H, benzene-H), δ 7.49 (m, 3H; Naphthalene-H), and δ 7.69 (d, 1H, naphthalene-H), δ 7.83 (t, 2H, naphthalene-H).
Embodiment 3: [compound 3a]
In general formula, when R is a trifluoromethyl, promptly constitute photochromic compound 3a, its name is called: [1-(2-methylnaphthalene-1-yl), 2-(2-methyl-5-is to fluorophenyl-thiene-3-yl-)] Perfluorocyclopentene (3a), structural formula is following:
Shown in the synthetic schemes Scheme 3 of this novel diaryl perfluoro cycolpenfene photochrmism compounds: Scheme 3:
Concrete synthesis step is described below:
1,3-bromo-2-methyl-5-m-trifluoromethylphenyl thiophene (4)
Under nitrogen protection, with 3-bromine trifluoromethylbenzene (3.06g, 13.58mmol) and Pd (PPh
3)
4(0.5g) be dissolved among the 80ml THF, (3.0g is 2.0mol/L Na with concentration 13.58mmol) to add 3 behind the stirring 20min
2CO
3Solution 50ml, reflux 16h, stopped reaction is chilled to room temperature.Separatory, water is used extracted with diethyl ether, merges organic phase, anhydrous magnesium sulfate drying.Suction filtration, filtrating is revolved and is boiled off solvent, silica gel column chromatography (sherwood oil) separates, obtain pistac liquid (2.9g, 9.03mmol), productive rate: 66.5%.
Structure is identified:
1H NMR (400MHz, CDCl
3): δ 2.45 (s, 3H), 7.19 (s, 1H), 7.52 (m, 2H, J=8.0Hz), 7.56 (d, 1H, J=8.0Hz), 7.75 (s, 1H).
2, [1-(2-methylnaphthalene-1-yl), 2-(2-methyl-5-is to fluorophenyl-thiene-3-yl-)] Perfluorocyclopentene (3a)
Under nitrogen and-78 ℃ of conditions, with compound 4 (0.91g 2.83mmol) is dissolved among the refining THF, stirs, slowly inject 2.5mol/L n-BuLi (1.2ml, 3.11mmol); (0.9g, THF solution 2.69mmol) join in the reaction flask, continue reaction mixture was stirred 1 hour at low temperatures, rise to room temperature naturally, add the suitable quantity of water termination reaction will singly to replace perfluoro cyclopentenes (6).Separatory is also used extracted with diethyl ether.Merge organic phase, distillation is desolvated, vacuum-drying.Resistates with petrol ether/ethyl acetate through silica gel column chromatography separate obtain the 3a yellow solid (0.45g, 0.81mmol), productive rate: 30.1%.
Structure is identified:
1H NMR (400MHz, CDCl
3, ppm): δ 2.25 (s, 3H ,-CH
3), δ 2.35 (s, 3H ,-CH
3), δ 6.84 (s, 1H, thiophene-H), δ 7.27 (s, 1H, benzene-H), δ 7.34 (m, 3H, benzene-H), δ 7.50 (m, 3H, naphthalene-H), δ 7.68 (d, 1H, naphthalene-H), δ 7.82 (t, 2H, naphthalene-H).
Claims (5)
1. photochromic naphthalene nucleus-thiophene hybrid-type perfluorinated cyclopentene compound, it is characterized in that: its molecular structural formula is following:
Wherein R is methyl or methoxy or trifluoromethyl.
2. photochromic naphthalene nucleus-thiophene hybrid-type perfluorinated cyclopentene compound as claimed in claim 1; Its compound method is: (1), be raw material with the 2-thiotolene; Bromination under condition of ice bath through reacting with n-Butyl Lithium (n-BuLi) and tributyl borate, generates 2-methyl-3-bromo-5-boronate thiophene then; Make catalyzer with four triphen phosphorus palladiums again, through linked reaction various substituted halogeno-benzenes and thiphene ring are coupled together and obtain various substituted thiophene-based midbodys; (2), under the n-Butyl Lithium effect, with 1-bromo-2-methylnaphthalene and the mono-substituted Perfluorocyclopentene of Perfluorocyclopentene reaction generation; (3), under-78 ℃ of nitrogen protection conditions, use n-Butyl Lithium, preparation in the step (2) single replaced the midbody that obtains in Perfluorocyclopentene midbody and the step (1) reacts, thereby obtain target compound like the general formula of molecular structure class.
3. photochromic naphthalene nucleus-thiophene hybrid-type perfluorinated cyclopentene compound as claimed in claim 1 is in the application of preparation VHD, erasable organic photon type information storage material.
4. photochromic naphthalene nucleus-thiophene hybrid-type perfluorinated cyclopentene compound as claimed in claim 1 is in the application of preparation photoswitch element.
5. the application of photochromic naphthalene nucleus-thiophene hybrid-type perfluorinated cyclopentene compound as claimed in claim 1 in the photochromic luminescent device of preparation.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010105271321A CN102079742B (en) | 2010-11-01 | 2010-11-01 | Photochromic naphthalene-thiophene hybrid type perfluorinated cyclopentene compound and synthesis method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010105271321A CN102079742B (en) | 2010-11-01 | 2010-11-01 | Photochromic naphthalene-thiophene hybrid type perfluorinated cyclopentene compound and synthesis method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102079742A CN102079742A (en) | 2011-06-01 |
| CN102079742B true CN102079742B (en) | 2012-11-14 |
Family
ID=44085963
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2010105271321A Expired - Fee Related CN102079742B (en) | 2010-11-01 | 2010-11-01 | Photochromic naphthalene-thiophene hybrid type perfluorinated cyclopentene compound and synthesis method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102079742B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9227986B2 (en) | 2011-09-30 | 2016-01-05 | Switch Materials, Inc. | Diarylethene compounds and uses thereof |
| CN105161634B (en) * | 2015-09-10 | 2017-11-24 | 京东方科技集团股份有限公司 | A kind of AMOLED devices and preparation method thereof, by its obtained display device |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101792435B (en) * | 2010-01-11 | 2012-03-14 | 江西科技师范学院 | Photochromic thiophene indole combined type asymmetric perfluoro cyclopentene compound as well as synthesizing method and application thereof |
-
2010
- 2010-11-01 CN CN2010105271321A patent/CN102079742B/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN102079742A (en) | 2011-06-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Dou et al. | Multistimuli-responsive benzothiadiazole-cored phenylene vinylene derivative with nanoassembly properties | |
| Devadiga et al. | Recent synthetic advances in pyridine-based thermotropic mesogens | |
| CN104098555B (en) | Method for synthesizing ultrashort-wavelength photochromic diarylethene compound by using imidazole-thiophene aromatic heterocycle and application of compound | |
| CN104558004B (en) | Organic second order non-linear optical chromophore and preparation method and use with D π A structures | |
| CN101845040B (en) | Organic second-order non-linear optical chromophore with D-Pi-A structure and decorated by tree-like group, synthesizing method and application thereof | |
| CN1978444B (en) | Photochromic thiophene pyrrole mixed linkage type dithienylethene compounds, and their synthesizing and use | |
| Utsumi et al. | Synthesis of a novel family of photochromic amorphous molecular materials based on dithienylethene, their photochromic properties and application for dual image formation | |
| CN107216320A (en) | A kind of organic second order non-linear optical chromophore and preparation method and use with double donor structures | |
| CN102079742B (en) | Photochromic naphthalene-thiophene hybrid type perfluorinated cyclopentene compound and synthesis method and application thereof | |
| CN101851232B (en) | Photochromic isoxazole thiophene hybrid-type perfluorinated cyclopentene compound as well as synthesis method and application thereof | |
| CN101602743B (en) | Photochromic thiazole hexatomic ring series-parallel asymmetric perfluoro-cyclopentene compound and preparation method and application thereof | |
| CN100427479C (en) | Photochromic perfluoro cyclopentene diaryl ethylene schiff base compound, and its preparing method and use | |
| CN101591334B (en) | Photochromic thiophene-thiazole heterocycle hybrid asymmetric perfluorocyclopentene compound, preparation method and application | |
| Guan et al. | Synthesis and properties of novel liquid crystalline materials with super high birefringence: styrene monomers bearing diacetylenes, naphthyl, and nitrogen-containing groups | |
| Kawamoto et al. | Thermo and photoresponsive behavior of liquid-crystalline helical structures with the aid of dual molecular motions | |
| CN106905354A (en) | A kind of D π A π D type BODIPY analog derivatives based on acetenyl bridging and preparation method thereof | |
| CN101792435B (en) | Photochromic thiophene indole combined type asymmetric perfluoro cyclopentene compound as well as synthesizing method and application thereof | |
| CN101845041B (en) | Photochromic benzofuran thiophene series-parallel perfluoro-cyclopentene compound as well as synthesizing method and application thereof | |
| CN106632438A (en) | Ethynyl bridging based A-phi-D-phi-A type BODIPY derivative and preparation method thereof | |
| CN102442999A (en) | Photochromic pyrimidine-thiophene mixed octafluorocyclopentene compound, synthesis method and application thereof | |
| TW201321479A (en) | Liquid crystal compounds, and liquid crystal displays and photochromic materials comprising the liquid crystal compounds | |
| Liang et al. | Activating Molecular Room-Temperature Phosphorescence by Manipulating Excited-State Energy Levels in Poly (vinyl alcohol) Matrix | |
| CN104327060B (en) | Photochromic double (N-ethyl-1,8-naphthalimide) amine-benzothiophene hybrid-type perfluorinated cyclopentene compound and synthetic method and application | |
| CN100402526C (en) | Lysotropic-photodiscolour diaryl ethylene and preparation and application thereof | |
| CN101402852B (en) | Carbazolyl-containing unsymmetrical photochromicsm di-fragrant alkene monomer or polymer and electrochemical polymerization preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C17 | Cessation of patent right | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20121114 Termination date: 20131101 |