CN1470512A - Asymmetric diaryl ethylene photochromic compound, and its preparing method and use - Google Patents
Asymmetric diaryl ethylene photochromic compound, and its preparing method and use Download PDFInfo
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- CN1470512A CN1470512A CNA021252726A CN02125272A CN1470512A CN 1470512 A CN1470512 A CN 1470512A CN A021252726 A CNA021252726 A CN A021252726A CN 02125272 A CN02125272 A CN 02125272A CN 1470512 A CN1470512 A CN 1470512A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 15
- 238000000034 method Methods 0.000 title claims description 7
- -1 diaryl ethylene Chemical compound 0.000 title abstract description 10
- 239000005977 Ethylene Substances 0.000 title abstract description 3
- YBMDPYAEZDJWNY-UHFFFAOYSA-N 1,2,3,3,4,4,5,5-octafluorocyclopentene Chemical compound FC1=C(F)C(F)(F)C(F)(F)C1(F)F YBMDPYAEZDJWNY-UHFFFAOYSA-N 0.000 claims abstract description 32
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- 230000003287 optical effect Effects 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims abstract description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 claims description 11
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 238000000746 purification Methods 0.000 claims description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 238000001816 cooling Methods 0.000 abstract 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 3
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000931526 Acer campestre Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000001988 diarylethenes Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The present invention discloses a kind of asymmetric diaryl ethylene photochromic compound, its preparation method and application. Said invention provides its molecular structure formula, and its preparation method includes: 1) making equivalent perfluorocyclopentene and 5-lithium-2-substituent-4- methyl thiophene or benzothiophene implement reaction to prepare correspondent monosubstituted perfluorocyclopentene; and 2). cooling 3-bromine-5-substituent-2 methyl thiophene to -76 deg.C to -80 deg.C, adding n-Buli, making low-temp. reaction for 0.5-1.5 hr, then adding the equivalent monosubstituted perfluorocyclopentene obtained by step 1, reacting for 1-3 hr. and separating to obtain the invented product which can be used as erase write optical storage media and molecular switch, etc.
Description
Technical field
The present invention relates to a kind of diaryl ethylene compounds and preparation method thereof and application in the organic photochromic material field.
Background technology
The arrival of information age means the annual growth at faster speed of global quantity of information, and fast development of computer technology has proposed one and another challenge to information storage, and high-density, high-performance, low price optical disc storage have the market development potentiality.Magneto-optical that has come out and inversion of phases erasable optical disk are owing to material expensive processed complex, erasable speed wait shortcoming slowly, and application is restricted.Advantages such as organic optical memory material (photon type storage) is highly sensitive with it, response speed fast, organic synthesis can be adjusted, be easy to optical property by the change molecular structure become the focus of research.
Photochromic material has important application prospects in erasable optical storage.The reversibility of this class material use photochromic reactions can be carried out repeatedly erasable to recorded information.In various photochromic compound systems, the diarylethene of band hetero-aromatic ring, particularly the diaryl perfluoro cyclopentene compound has favorable photo-thermal stability and fatigue resistance, be used for optical storage media have one of photochromic molecules of application potential most.
At present existing a large amount of diarylvinylene compound is produced and studies, but their closed loop attitude is often responsive to the light ratio of 500～700nm scope.Yet along with reading and writing optical maser wavelength further shortens, it is very important that the diarylvinylene compound of exploitation and 400～500nm semiconductor laser coupling is used for short wavelength's record.
Summary of the invention
The purpose of this invention is to provide a kind of diarylvinylene compound with asymmetrical type of favorable photo-thermal stability and fatigue resistance.
Asymmetrical type diarylvinylene compound provided by the invention has the molecular structural formula of formula I or formula II:
Formula I formula II
Wherein, R
1, R
2, R
3, R
4Being respectively carbonatoms is the alkyl of 1-4, cycloalkyl or the aryl that carbonatoms is 3-6.
Another object of the present invention provides a kind of method for preparing above-mentioned formula I and formula II compound.
A kind of method for preparing the described compound of claim 1 may further comprise the steps:
1) with the Perfluorocyclopentene of equivalent and 5-lithium-2-substituting group-4-thiotolene or the corresponding single Perfluorocyclopentene that replaces of thionaphthene prepared in reaction;
2) 3-bromo-5-substituting group-2-thiotolene is cooled to-76 ℃--80 ℃, add n-BuLi, low-temp reaction 0.5-1.5 hour, add single Perfluorocyclopentene that replaces of the equivalent that step 1) obtains then, react after 1～3 hour, separate product.
Described step 1) is that 2-R base-4-thiotolene or 3-methylbenzene thiophthene are dissolved in the anhydrous tetrahydro furan, adds n-BuLi at 0 ℃, rises to room temperature reaction then 1 hour; Be cooled to 0 ℃ again, add the Perfluorocyclopentene of equivalent, continued low-temp reaction 2-3 hour, rise to room temperature, stopped reaction is purified to such an extent that list replaces Perfluorocyclopentene through separation, and described R is that carbonatoms is the alkyl of 1-4, cycloalkyl or the aryl that carbonatoms is 3-6.
Described step 2) be that 3-bromine (iodine)-5-R base-2-thiotolene is dissolved in the anhydrous tetrahydro furan, at N
2Protection is cooled to-78 ℃ down, adds the n-BuLi afterreaction 1 hour; The single Perfluorocyclopentene that replaces that adds the equivalent of step 1) preparation, continue low-temp reaction 2～3 hours, and rose to room temperature then, stopped reaction, get product after separating purification, described R is that carbonatoms is the alkyl of 1-4, cycloalkyl or the aryl that carbonatoms is 3-6.
Two kinds of photochromic isomer of asymmetrical type diarylvinylene compound provided by the invention have favorable photo-thermal stability and fatigue resistance, and photochromic reactions is rapid, and sensitivity is higher, has the good photochromic reactivity in solid film; The closed loop attitude has stronger absorption in 400 ~ 500nm scope, is suitable for this wavelength region optical storage.
Have good photochromic character in crystalline state and non-crystalline state, and two kinds of photoisomer photo and thermal stabilities are good, photoresponse is highly sensitive, and response is fast, is suitable for the photochromic molecules switch.
The present invention will be further described below in conjunction with specific embodiment.
Description of drawings
Fig. 1 is the UV-Vis absorption spectrum of 1-(2,5-dimethyl-thiene-3-yl-)-2-(3-methyl-5-(4-p-methoxy-phenyl) thiophene-2-yl) Perfluorocyclopentene open loop attitude and closed loop attitude.
Fig. 2 is the UV-Vis absorption spectrum of 1-(2,5-dimethyl-thiene-3-yl-)-2-(3-methyl-thionaphthene-2-yl) Perfluorocyclopentene.
Embodiment
Embodiment 1, synthetic 1-(2,5-dimethyl-thiene-3-yl-)-2-(3-methyl-5-(4-p-methoxy-phenyl) thiophene-2-yl) Perfluorocyclopentene
The synthetic route of 1-(2,5-dimethyl-thiene-3-yl-)-2-(3-methyl-5-(4-p-methoxy-phenyl) thiophene-2-yl) Perfluorocyclopentene is as follows:
Concrete synthesis step is:
1,2g 2, and the 5-thioxene is dissolved in the mixed solvent of 25ml acetate and tetrachloromethane (volume ratio 1: 1); Take by weighing 1.6g iodine and 0.7g acid iodide (being dissolved in the 2ml deionized water) and add above-mentioned solution, stir and heating.After keeping refluxing 2 hours reactant is poured in the frozen water,, merged organic phase, use saturated aqueous sodium carbonate, sodium thiosulfate solution, deionized water wash successively, and use anhydrous magnesium sulfate drying with chloroform extraction (25ml * 3).Revolve boil off behind the solvent with silica gel chromatographic column purify 3-iodo-2, the about 3.5g of 5-thioxene, productive rate is about 83%, light red liquid,
1H NMR (CDCl
3) δ=1.81 (s, 3H), 2.41 (s, 3H), 6.707 (s, 1H);
2,3 methyl thiophene 1.5g is dissolved in the 50ml tetrahydrofuran (THF), at 0 ℃ of N
2Protection slowly drips n-BuLi hexane solution 9.2ml (1.6M) down, refluxes afterwards 1 hour; Be cooled to 0 ℃ again, add tributyl borate 4.5ml, rise to room temperature naturally and continue reaction 1 hour.In the previous step reactant, add 3.13g para-bromoanisole, 0.4gPd (PPh respectively
3)
4, refluxed 5 hours.Be cooled to room temperature then, separatory, water merge with organic phase after with extracted with diethyl ether, use MgSO
4Dry.Revolve and boil off solvent, vacuum-drying separates with silica gel chromatographic column, 4-methyl-2-(4-p-methoxy-phenyl) thiophene 2.26g, productive rate is 71.74%.White crystal, mp 56-57 ℃,
1HNMR (CDCl
3) δ=2.273 (s, 3H), 3.827 (s, 3H), 6.787 (s, 1H), 6.907 (d2H), 7.013 (s, 1H), 7.512 (d, 2H), Anal.:Calcd:C, 70.41; H, 6.02%Found:C, 70.54; H, 5.92%
3,1.55g4-methyl-2-(4-p-methoxy-phenyl) thiophene is dissolved in the anhydrous tetrahydro furan, puts into ice bath, add n-BuLi 4.67ml (1.6M), room temperature reaction 1 hour; Be cooled to 0 ℃ then, add Perfluorocyclopentene 0.5ml, continued low-temp reaction 2-3 hour, rise to room temperature then with syringe, stopped reaction, through separation purify 3-methyl-5-(4-p-methoxy-phenyl) thiophene-2-base Perfluorocyclopentene 1.75g.Productive rate is 61.26%.Pale brown look crystal, mp61-62 ℃,
1H NMR (CDCl
3) δ=2.273 (s, 3H), 3.827 (s, 3H), 6.787 (s, 1H), 6.907 (d2H), 7.013 (s, 1H), 7.512 (d, 2H), Anal.:Calcd:C, 53.68; H, 1.84; N, 6.80% Found:C, 53.66; H, 1.85%
4, with 3-iodo-2,5-thioxene 0.11g is dissolved in the anhydrous tetrahydro furan, at N
2Protection is cooled to-78 ℃ approximately down, adds n-BuLi 0.29ml (1.6M) afterreaction 1 hour; 3-methyl-5-(4-p-methoxy-phenyl) thiophene-2-base Perfluorocyclopentene that adds equivalent, continued low-temp reaction 2～3 hours, rise to room temperature then, stopped reaction, after separating purification, get 0.094g1-(2,5-dimethyl-thiene-3-yl-)-and 2-(3-methyl-5-(4-p-methoxy-phenyl) thiophene-2-yl) Perfluorocyclopentene, productive rate is 41.87%.Clear crystal, mp 73-74 ℃,
1H NMR (CDCl
3) δ=1.727 (s, 3H), 1.913 (s, 3H), 2.425 (s, 3H), 3.838 (s, 3H), 6.903 (d, 2H), 6.734 (s, 1H), 6.942 (s, 1H), 7.492 (d, 2H), Anal.:Calcd:C, 56.56; H, 3.69%Found:C, 56.43; H, 3.58%.
Fig. 1 is the 1-(2 that obtains, 5-dimethyl-thiene-3-yl-)-the UV-Vis absorb light of 2-(3-methyl-5-(4-p-methoxy-phenyl) thiophene-2-yl) Perfluorocyclopentene open loop attitude and closed loop attitude, among the figure, solid line is the absorption spectrum of closed loop attitude, and dotted line is the absorption spectrum of open loop attitude.
Embodiment 2, synthetic 1-(2,5-dimethyl-thiene-3-yl-)-2-(3-methyl-thionaphthene-2-yl) Perfluorocyclopentene
The synthetic route of 1-(2,5-dimethyl-thiene-3-yl-)-2-(3-methyl-thionaphthene-2-yl) Perfluorocyclopentene is as follows:
Concrete synthesis step is as follows:
1,0.65g3-methylbenzene thiophthene is dissolved in the anhydrous tetrahydro furan, puts into ice bath, add n-BuLi2.8ml (1.6M) back room temperature reaction 1 hour; Be cooled to 0 ℃ then, add the 0.55ml Perfluorocyclopentene, continued low-temp reaction 2-3 hour, rise to room temperature then, stopped reaction, through separation purify 3-methylbenzene thiophthene-2-base Perfluorocyclopentene 0.89g, productive rate is 59.68%.The pale yellow oily liquid body,
1HNMR: δ=2.43 (s, 3H), 7.35-7.80 (m, 4H, Ar); Anal.:Calcd:C, 49.41; H, 2.06%, Found:C, 49.37; H, 2.12%
2, with 3-iodo-2,5-thioxene 0.15g is dissolved in the anhydrous tetrahydro furan, at N
2Protection is cooled to-78 ℃ approximately down, adds n-BuLi 0.4ml afterreaction 1 hour; Add 0.2g 3-methylbenzene thiophthene-2-base Perfluorocyclopentene, continued low-temp reaction 2-3 hour, rise to room temperature then, stopped reaction, after separating purification, get product 1-(2,5-dimethyl-thiene-3-yl-)-and 2-(3-methyl-thionaphthene-2-yl) Perfluorocyclopentene 0.088g, productive rate is 32.47%.Light yellow crystal, 132～133 ℃ of mp,
1H NMR: δ=1.97 (s, 3H), 1.97 (s, 3H), 2.35-2.45 (s, 2Me), 7.35-7.47 (m, 4H, Ar), 6.68 (s, 1H); Anal.:Calcd:C, 55.56; H, 3.24%Found:C, 56.23; H, 3.11%.Fig. 2 is the UV-Vis absorption spectrum of 1-(2,5-dimethyl-thiene-3-yl-)-2-(3-methyl-thionaphthene-2-yl) Perfluorocyclopentene of obtaining, and solid line is the absorption spectrum of closed loop attitude among the figure, and dotted line is the absorption spectrum of open loop attitude.
Claims (7)
1, the diarylvinylene compound of asymmetrical type, it has the molecular structural formula of formula I or formula II:
Formula I formula II
Wherein, R
1, R
2, R
3, R
4Being respectively carbonatoms is the alkyl of 1-4, cycloalkyl or the aryl that carbonatoms is 3-6.
2, a kind of method for preparing the described compound of claim 1 may further comprise the steps:
1) with the Perfluorocyclopentene of equivalent and 5-lithium-2-substituting group-4-thiotolene or the corresponding single Perfluorocyclopentene that replaces of thionaphthene prepared in reaction;
2) 3-bromo-5-substituting group-2-thiotolene is cooled to-76 ℃--80 ℃, add n-BuLi, low-temp reaction 0.5-1.5 hour, add single Perfluorocyclopentene that replaces of the equivalent that step 1) obtains then, react after 1～3 hour, separate product.
3, method according to claim 2 is characterized in that: described step 1) is that 2-R base-4-thiotolene or 3-methylbenzene thiophthene are dissolved in the anhydrous tetrahydro furan, adds n-BuLi at 0 ℃, rises to room temperature reaction then 1 hour; Be cooled to 0 ℃ again, add the Perfluorocyclopentene of equivalent, continued low-temp reaction 2-3 hour, rise to room temperature, stopped reaction is purified to such an extent that list replaces Perfluorocyclopentene through separation, and described R is that carbonatoms is the alkyl of 1-4, cycloalkyl or the aryl that carbonatoms is 3-6.
4, method according to claim 2 is characterized in that: described step 2) be that 3-bromo-5-R base-2-thiotolene is dissolved in the anhydrous tetrahydro furan, at N
2Protection is cooled to-78 ℃ down, adds the n-BuLi afterreaction 1 hour; The single Perfluorocyclopentene that replaces that adds the equivalent of step 1) preparation, continue low-temp reaction 2～3 hours, and rose to room temperature then, stopped reaction, get product after separating purification, described R is that carbonatoms is the alkyl of 1-4, cycloalkyl or the aryl that carbonatoms is 3-6.
5, method according to claim 2 is characterized in that: described step 2) be that 3-iodo-5-R base-2-thiotolene is dissolved in the anhydrous tetrahydro furan, at N
2Protection is cooled to-78 ℃ down, adds the n-BuLi afterreaction 1 hour; The single Perfluorocyclopentene that replaces that adds the equivalent of step 1) preparation, continue low-temp reaction 2～3 hours, and rose to room temperature then, stopped reaction, get product after separating purification, described R is that carbonatoms is the alkyl of 1-4, cycloalkyl or the aryl that carbonatoms is 3-6.
6, the described asymmetrical type diarylvinylene compound of claim 1 is as the application of erasable optical storage media.
7, the described asymmetrical type diarylvinylene compound of claim 1 is as the application of molecular switch.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007105620A1 (en) * | 2006-03-10 | 2007-09-20 | Kyoto University | Method for producing diarylethene compound and novel diarylethene compound |
| CN101602743B (en) * | 2009-07-09 | 2011-06-01 | 江西科技师范学院 | Photochromic thiazole hexatomic ring series-parallel asymmetric perfluoro-cyclopentene compound and preparation method and application thereof |
| CN101613883B (en) * | 2009-07-14 | 2012-02-15 | 江西科技师范学院 | U-type conjugated molecule single crystal and preparation method thereof |
| CN103333674A (en) * | 2013-07-16 | 2013-10-02 | 天津城建大学 | Diarylethene photochromic compound with electric field modulation function and synthesis method |
| CN104292234A (en) * | 2014-10-13 | 2015-01-21 | 江西科技师范大学 | Asymmetric perfluorocyclopentene photochromic fluorescent probe compound containing benzimidazole group as well as preparation method and application of asymmetric perfluorocyclopentene photochromic fluorescent probe compound |
| CN107652279A (en) * | 2017-10-31 | 2018-02-02 | 华中科技大学 | A kind of diarylethene role in fluorescent molecule switch, its preparation method and application |
| CN110218204A (en) * | 2019-06-11 | 2019-09-10 | 江南大学 | A kind of diaryl ethylene photochromic conjugated polymer and preparation method thereof |
-
2002
- 2002-07-22 CN CN 02125272 patent/CN1205206C/en not_active Expired - Fee Related
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007105620A1 (en) * | 2006-03-10 | 2007-09-20 | Kyoto University | Method for producing diarylethene compound and novel diarylethene compound |
| JP5216954B2 (en) * | 2006-03-10 | 2013-06-19 | 国立大学法人京都大学 | Method for producing diarylethene compound |
| CN101602743B (en) * | 2009-07-09 | 2011-06-01 | 江西科技师范学院 | Photochromic thiazole hexatomic ring series-parallel asymmetric perfluoro-cyclopentene compound and preparation method and application thereof |
| CN101613883B (en) * | 2009-07-14 | 2012-02-15 | 江西科技师范学院 | U-type conjugated molecule single crystal and preparation method thereof |
| CN103333674A (en) * | 2013-07-16 | 2013-10-02 | 天津城建大学 | Diarylethene photochromic compound with electric field modulation function and synthesis method |
| CN104292234A (en) * | 2014-10-13 | 2015-01-21 | 江西科技师范大学 | Asymmetric perfluorocyclopentene photochromic fluorescent probe compound containing benzimidazole group as well as preparation method and application of asymmetric perfluorocyclopentene photochromic fluorescent probe compound |
| CN104292234B (en) * | 2014-10-13 | 2017-03-22 | 江西科技师范大学 | Asymmetric perfluorocyclopentene photochromic fluorescent probe compound containing benzimidazole group as well as preparation method and application of asymmetric perfluorocyclopentene photochromic fluorescent probe compound |
| CN107652279A (en) * | 2017-10-31 | 2018-02-02 | 华中科技大学 | A kind of diarylethene role in fluorescent molecule switch, its preparation method and application |
| CN107652279B (en) * | 2017-10-31 | 2020-05-19 | 华中科技大学 | Diaryl ethylene fluorescent molecular switch, and preparation method and application thereof |
| CN110218204A (en) * | 2019-06-11 | 2019-09-10 | 江南大学 | A kind of diaryl ethylene photochromic conjugated polymer and preparation method thereof |
| CN110218204B (en) * | 2019-06-11 | 2021-06-15 | 江南大学 | Diaryl ethylene photochromic conjugated polymer and preparation method thereof |
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