CN100427479C - Photochromic perfluoro cyclopentene diaryl ethylene schiff base compound, and its preparing method and use - Google Patents
Photochromic perfluoro cyclopentene diaryl ethylene schiff base compound, and its preparing method and use Download PDFInfo
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- CN100427479C CN100427479C CNB2004100607909A CN200410060790A CN100427479C CN 100427479 C CN100427479 C CN 100427479C CN B2004100607909 A CNB2004100607909 A CN B2004100607909A CN 200410060790 A CN200410060790 A CN 200410060790A CN 100427479 C CN100427479 C CN 100427479C
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Abstract
The present invention discloses a diaryl ethene Schiff base compound of photochromic octafluorocyclopentene, a preparation method thereof and the application thereof. The compound has the characteristics of diaryl ethene molecules and Schiff base and can be directly used for preparing optical discs, used in the technical field of erasable and rewritable organic-photon optical information memory with super-high density and super-high speed, used for preparing photoelectric molecular switches and molecular wire elements, used for preparing photochromic luminescent devices, and used for preparing plant growth regulators, antiviral drugs and the like in the biochemical technical field.
Description
Technical field
The present invention relates to a kind of photochromic Perfluorocyclopentene class diarylethene schiff base compound and preparation method thereof.
Background technology
In the rapid expansible of global quantity of information today, how to keep properly the urgent task and the important topic that become areas of information technology with these a large amount of useful informations of convenient search.For this reason, the optical information memory technology develops and becomes the mainstay industry in information science field rapidly.
For optical storage technology, storage medium is not only its center integral part, and its tempo is relatively slow and become the bottleneck in this field.Therefore, the optical disk medium of exploring new super-high density remains the key of optical storage technology development.At present, inorganic materials such as magneto-optic and phase change material have been used widely, and organic erasable optical storage media also is in the primary stage of research and development.Magneto-optic or phase change medium belong to photo-thermal type record, because the irregular fever character of material itself makes measuring point also be irregularly shaped, thereby causes this class material to have resolution limit, the very difficult storage density that further improves; Advantage such as organic optical memory material has the storage density height, heat conductance is little, signal to noise ratio is big, fusing point and softening temperature adjustability low, that higher recording sensitivity, molecular structure are arranged are big is expected to realize molecular memory.Therefore, organic optical information storage medium of research and development photon type is trend of the times, has extremely wide application prospect.
Diaryl ethylene photochromic compound has unusual excellent in chemical thermostability, fatigue resistance, higher photoisomerization quantum yield and the adjustable amplitude of absorbing wavelength of broad.Simultaneously, the trunk structure of this compounds is carried out the molecule modification, also can make it have different photochemistry and photophysical property and become functional molecular with different qualities by introducing different substituents.In addition, in the photoisomerization process, the specific refractory power of diarylethene, specific inductivity, oxidation/reduction potential and geometric configuration etc. also change, and these change of properties are very favourable in the erasable optical information storage of high-density.Therefore, the diarylethene material has been subjected to increasing concern and attention in technical fields such as the storage of high-density optical information, molecular switch and photoelectric display.
In addition, since finding that schiff bases and title complex thereof have significant biological activity and oxygen carrier function, people are active day by day to the research of this type of material.Studies show that in a large number schiff bases and title complex thereof all are with a wide range of applications in fields such as biological chemistry, catalytic chemistry, synthetic chemistry and macromolecular chemistries.
Summary of the invention
Purpose of the present invention just provides a kind of photochromic Perfluorocyclopentene class diarylethene schiff base compound with diarylethene molecule and schiff bases characteristic, and its preparation method is provided.
The general structure of photochromic Perfluorocyclopentene class diarylethene schiff base compound of the present invention is as follows:
N=0,1 wherein, R1 is H atom or methyl, R is the C atomicity less than 10 alkyl, cycloalkyl, aryl etc. can be following group as R:
The preparation method of photochromic Perfluorocyclopentene class diarylethene schiff base compound of the present invention is:
When n=0; its general synthetic method is: with 5-methyl-2 thiophenecarboxaldehyde is raw material; bromination at first at ambient temperature; protect by aldol reaction then; generate the diarylethene that contains aldehyde radical with n-Butyl Lithium and Perfluorocyclopentene reaction posthydrolysis again, utilize the Perfluorocyclopentene class diarylethene schiff base compound of aldehyde radical and various amine generation condensation reaction generation shown in general formula at last.
When n=1, its general synthetic method is: be the diarylethene of feedstock production band phenyl aldehyde with 2-thiotolene, liquid bromine, normal-butyl, tributyl borate and Perfluorocyclopentene etc. at first, utilize the Perfluorocyclopentene class diarylethene schiff base compound of aldehyde radical and various amine generation condensation reaction generation shown in general formula at last.
The advantage of photochromic Perfluorocyclopentene class diarylethene schiff base compound of the present invention mainly contains the following aspects:
1, Perfluorocyclopentene class diarylethene schiff bases all can keep the good photochromic performance in the solid, liquid medium, and its open loop attitude (colourless attitude) and closed loop attitude (colour generation attitude) chemistry that all tool is good and thermostability, significant fatigue resistance, time of response and high high-performances such as sensitivity fast;
2, have higher cyclisation quantum yield and open loop quantum yield;
3, the adjustable amplitude absorbing wavelength that has broad changes different substituents, can control its absorbing wavelength scope well, thereby be complementary with the different wavelength of laser device, to be used for the development of different wave length optical storage media;
4, have good single photon fluorescent characteristic, and the existence of the photoluminescent property of open and close ring status can be used for the development of fluorescence molecule switch than big-difference.
Description of drawings
Fig. 1, be the photochromic reactions synoptic diagram of compound 1a, 2a, 3a in the embodiments of the invention;
Fig. 2, be abosrption spectrogram (concentration: C=1.0 * 10 of compound 1a before and after the chloroformic solution medium ultraviolet rayed among the embodiment 1
-5Mol/L);
Fig. 3, be abosrption spectrogram (concentration: C=2.1 * 10 of compound 2a before and after the chloroformic solution medium ultraviolet rayed among the embodiment 2
-5Mol/L);
Fig. 4, be abosrption spectrogram (concentration: C=1.6 * 10 of compound 3a before and after the chloroformic solution medium ultraviolet rayed among the embodiment 3
-5Mol/L);
Fig. 5, be fluorescence spectrum figure (concentration: C=1.0 * 10 of compound 1a in chloroformic solution among the embodiment 1
-5Mol/L);
Fig. 6, write voltage of signals and time chart with the 650nm laser apparatus for compound 1a diaphragm among the embodiment 1;
Fig. 7, be used for the diaphragm structure (directly using the diarylethene schiff bases) of high-density optical information storage as recording layer.
Embodiment
Embodiment 1:[compound 1a]:
In general formula, work as n=0, R
1Be hydrogen atom, when R is normal-butyl, promptly constitute photochromic Perfluorocyclopentene class diarylethene schiff base compound---1, two (2-methyl-5-methylene radical n-butyl amine base thiene-3-yl-) Perfluorocyclopentenes (1a) of 2-, its structural formula is as follows:
1, shown in the synthetic schemes Scheme 1 of two (2-methyl-5-methylene radical n-butyl amine base thiene-3-yl-) this diarylethene schiff bases of Perfluorocyclopentene (1a) of 2-:
Scheme?1：
Concrete synthesis step is as described below:
1,4-bromo-5-methyl-2 thiophene carboxaldehyde (3): under the room temperature, 5-methyl-2 thiophene carboxaldehyde (2) 6.3g (50mmol) is dissolved in the 35mL acetate, drips the mixed solution that contains 8mL acetate and 3mL liquid bromine down, continued room temperature reaction 8 hours in whipped state.Add moisture liquid, water Na
2CO
3Be neutralized to neutrality, extracted with diethyl ether merges organic phase, uses saturated Na
2CO
3Wash anhydrous MgSO successively with water
4Dried overnight filters, and revolves to boil off solvent, vacuum-drying.With silica gel chromatographic column (normal hexane: chloroform=1: 2) separate purification, obtain light yellow crystal product 9.7g, productive rate: 94.6%.Product structure is identified:
1HNMR (400MHz, CDCl
3): δ 2.47 (s, 3H), δ 7.57 (s, 1H), δ 9.75 (s, 1H).
2,4-bromo-5-methyl-2-(1, the 3-dioxolanyl) thiophene (4): under the Dean-Stark condition, 6.15g (30mmol) 4-bromo-5-methyl-2 thiophene carboxaldehyde, 4mL ethylene glycol and 0.1g p-methyl benzenesulfonic acid are dissolved in the 200mL benzene, stir, reflux 12 hours.Be chilled to room temperature, pour reaction mixture into an amount of saturated NaHCO
3In the aqueous solution, extracted with diethyl ether, and use NaHCO successively
3Solution and water washing, anhydrous MgSO
4Drying filters, and revolves to boil off solvent, and vacuum-drying need not to separate obtaining pale yellow oily liquid body product 7g, productive rate: 93.7%.Product structure is identified:
1HNMR (400MHz, CDCl
3): δ 2.45 (s, 3H), δ 4.02-4.16 (d, 4H), δ 6.03 (s, 1H), δ 7.29 (s, 1H).
3,1,2-is two, and ((2-(1 for 2-methyl-5-, the 3-dioxolanyl)) Perfluorocyclopentene (5) thiene-3-yl-): reach under-78 ℃ of conditions at nitrogen, 2.5g (10mmol) 4-bromo-5-methyl-2-dioxolanyl thiophene is dissolved in 50mL tetrahydrofuran (THF) (make with extra care and remove superoxide, dewater).Stir, and injection dropping n-Butyl Lithium (1.7mol/L, 10mmol), low-temp reaction 1 hour; Drip 0.68mL (5mmol) perfluoro cyclopentenes, continued low-temp reaction 3 hours, rise to room temperature naturally, add the suitable quantity of water termination reaction.Separatory, extracted with diethyl ether merges organic phase, and distillation removes and desolvates vacuum-drying.With silica gel column chromatography (normal hexane: chloroform=1: 5) separate purification, obtain colourless crystalline product 3.3g, productive rate: 64.4%.Product structure is identified: m.p.69-70 ℃; MS m/z (M
+) 513;
1HNMR (400MHz, CDCl
3): δ 2.47 (s, 6H), δ 3.99-4.13 (d, 8H), δ 6.09 (s, 2H), δ 7.33 (s, 2H); IR (cm-1): 745.2,980.2,1115.8,1264.6,1447.6,1559.9,1643.6,1682.0,2365.5,2897.5,2986.5
4,1, two (2-methyl-5-aldehyde radical thiene-3-yl-) Perfluorocyclopentene (6): 2.56g (5mmol) the two fragrant alkene 4 of 2-are dissolved in 20mL acetone (including 5mL water), add p-methyl benzenesulfonic acid pyridinium salt (PPTS), stir, and reflux 12 hours.Be chilled to room temperature, add an amount of water, the salt water washing of extracted with diethyl ether, organic phase, anhydrous MgSO
4Dry.Suction filtration revolves and boils off solvent.Separate purification with silica gel column chromatography (chloroform), obtain colourless crystalline product 2g, productive rate: 95.6%.Product structure is identified: m.p.181-183 ℃ (literature value: 182 ℃); MS m/z (M
+) 425;
1HNMR (400MHz, CDCl
3): δ 2.01 (s, 6H), δ 7.71 (s, 2H), δ 9.83 (s, 2H); IR (cm
-1): 858.8,985.9,1051.8,1154.0,1265.9,1330.3,1441.6,1466.0,1546.6,1664.8,2857.4,2964.9.
5,1, two (2-methyl-5-methylene radical n-butyl amine base thiene-3-yl-) Perfluorocyclopentenes (1a) of 2-: take by weighing 1, two (2-methyl-5-aldehyde radical thiene-3-yl-) Perfluorocyclopentene (6) 0.0850g (0.2mmol) of 2-are dissolved in the absolute dehydrated alcohol of 30mL, on put constant pressure funnel, in contain 0.1mL (1mmol) n-Butyl Amine 99 and 10mL dehydrated alcohol, stir, slowly drip n-Butyl Amine 99 and go in the flask.After dropwising, slowly refluxed 2 hours, be chilled to room temperature, revolve steaming and desolventize, separate and purify, get orange solid 0.0995g, productive rate: 93.0%.Product structure is identified:
1HNMR (400MHz, CDCl
3): δ 0.92-0.96 (m, 6H), δ 1.36-1.42 (m, 4H), δ 1.62-1.67 (m, 4H), δ 2.03 (s, 6H), δ 3.54-3.58 (m, 4H), δ 7.22 (s, 2H), δ 8.25 (s, 2H).
Embodiment 2:[compound 2a]:
In general formula, work as n=0, R
1Be hydrogen atom, when R is cyclohexyl, promptly constitute photochromic Perfluorocyclopentene class diarylethene schiff base compound---1, two (2-methyl-5-methylene radical hexamethylene aminothiophene-3-yl) Perfluorocyclopentenes (2a) of 2-, its structural formula is as follows:
1, shown in the synthetic schemes Scheme 2 of two (2-methyl-5-methylene radical hexamethylene aminothiophene-3-yl) this diarylethene schiff bases of Perfluorocyclopentene (2a) of 2-:
Scheme?2：
Concrete synthesis step is as described below:
1, two (2-methyl-5-methylene radical hexamethylene aminothiophene-3-yl) Perfluorocyclopentenes (2a) of 2-: take by weighing 1, two (2-methyl-5-aldehyde radical thiene-3-yl-) Perfluorocyclopentene (6) 0.1200g (0.3mmol) of 2-are dissolved in the absolute dehydrated alcohol of 45mL, on put constant pressure funnel, in contain 0.05mL (0.4mmol) n-Butyl Amine 99 and 15mL dehydrated alcohol, stir, slowly drip hexahydroaniline and go in the flask.After dropwising, 55 ℃ of isothermal reactions of water-bath 16 hours are chilled to room temperature, revolve to steam to desolventize, and separate and purify, and get orange solid 0.1543g, productive rate: 87.6%.Product structure is identified:
1HNMR (400MHz, CDCl
3): δ 1.25-1.35 (m, 4H), δ 1.54-1.67 (m, 8H), δ 1.71-1.83 (m, 8H), δ 1.93 (s, 6H), δ 3.12-3.25 (m, 2H), δ 7.22 (s, 2H), δ 8.27 (s, 2H).
Embodiment 3:[compound 3a]:
In general formula, work as n=1, R
1Be hydrogen atom, when R is n-propyl, promptly constitute photochromic Perfluorocyclopentene class diarylethene schiff base compound---1, two (2-methyl-5-(the 4-methylene radical n-propylamine base) phenyl) thiene-3-yl-s of 2-) Perfluorocyclopentene (3a), its structural formula is as follows:
1, two (2-methyl-5-(4-methylene radical n-propylamine base) phenyl) thiene-3-yl-s of 2-) shown in the synthetic schemes Scheme 3 of this diarylethene schiff bases of Perfluorocyclopentene (3a):
Scheme?3：
Concrete synthesis step is as described below:
1, two (2-methyl-5-(the 4-methylene radical n-propylamine base) phenyl) thiene-3-yl-s of 2-) Perfluorocyclopentene (3a): take by weighing 0.2000g (0.35mmol) 1,2-two (2-methyl-5-(4-aldehyde radical phenyl) thiene-3-yl-) Perfluorocyclopentene (7) (report in patent by concrete synthesis step of compound 7 and uses thereof, number of patent application is: 02125937.2.2002 and 02100681.4.2002) be dissolved in the absolute dehydrated alcohol of 50mL, on put constant pressure funnel, interior 0.1mL (1.2mmol) Tri N-Propyl Amine and the 20mL dehydrated alcohol contained stirs, slowly dripping n-Butyl Amine 99 goes in the flask.After dropwising, slowly refluxed 4 hours, be chilled to room temperature, revolve steaming and desolventize, separate and purify, get bluish voilet solid 0.1732g, productive rate: 75.1%.Product structure is identified:
1HNMR (400MHz, CDC1
3): δ 0.92-0.96 (m, 6H), δ 1.65-1.72 (m, 4H), δ 1.94 (s, 6H), δ 3.51-3.54 (m, 4H), δ 7.68-7.90 (m, 8H), δ 7.7.74 (s, 2H), δ 8.25 (s, 2H).
Claims (3)
1, a kind of photochromic Perfluorocyclopentene class diarylethene schiff base compound, its general structure is:
N=0,1 wherein, R1 is H atom or methyl, R is the C atomicity less than 10 alkyl, cycloalkyl, aryl.
2, photochromic Perfluorocyclopentene class diarylethene schiff base compound according to claim 1, it is characterized in that: R is one of following group:
3, the preparation method of photochromic Perfluorocyclopentene class diarylethene schiff base compound as claimed in claim 1, it is characterized in that: it may further comprise the steps: (1), when n=0, its general synthetic method is: with 5-methyl-2 thiophenecarboxaldehyde is raw material, bromination at first at ambient temperature, protect by aldol reaction then, generate the diarylethene that contains aldehyde radical with n-Butyl Lithium and Perfluorocyclopentene reaction posthydrolysis again, utilize aldehyde radical and n-Butyl Amine 99 at last, one or more material generation condensation reactions in hexahydroaniline and the Tri N-Propyl Amine generate the Perfluorocyclopentene class diarylethene schiff base compound shown in general formula; (2), when n=1, its general synthetic method is: be the diarylethene of feedstock production band phenyl aldehyde with 2-thiotolene, liquid bromine, normal-butyl, tributyl borate and Perfluorocyclopentene etc. at first, utilize the Perfluorocyclopentene class diarylethene schiff base compound of one or more material generation condensation reactions generations shown in general formula in aldehyde radical and n-Butyl Amine 99, hexahydroaniline and the Tri N-Propyl Amine at last.
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| CN103130846A (en) * | 2012-11-27 | 2013-06-05 | 江西科技师范大学 | Photochromic bi-thiophene six-sugar water-solubility symmetrical octafluorocyclopentene compound and preparation method and application |
| 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 |
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| CN111410624B (en) * | 2020-01-09 | 2022-05-06 | 江西科技师范大学 | Asymmetric naphthalene-pyrrole hybrid diarylethene compound and application thereof |
| CN111704626B (en) * | 2020-05-29 | 2022-07-29 | 江南大学 | Diaryl ethylene photochromic organic cage and preparation method thereof |
| CN114907312A (en) * | 2022-05-31 | 2022-08-16 | 中国计量大学 | Diaryl ethylene organic compound, preparation method thereof and application thereof in anti-counterfeiting |
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| US8697872B2 (en) | 2011-03-31 | 2014-04-15 | Queen's University At Kingston | Boron compounds and uses thereof |
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