CN104327060B - Photochromic double (N-ethyl-1,8-naphthalimide) amine-benzothiophene hybrid-type perfluorinated cyclopentene compound and synthetic method and application - Google Patents
Photochromic double (N-ethyl-1,8-naphthalimide) amine-benzothiophene hybrid-type perfluorinated cyclopentene compound and synthetic method and application Download PDFInfo
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- CN104327060B CN104327060B CN201410536796.2A CN201410536796A CN104327060B CN 104327060 B CN104327060 B CN 104327060B CN 201410536796 A CN201410536796 A CN 201410536796A CN 104327060 B CN104327060 B CN 104327060B
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Abstract
The invention discloses a kind of photochromic double (N ethyls 1, 8 naphthalimides) synthetic method of amine benzothiophene hybrid-type perfluorinated cyclopentene compound and application, this photochromic material the most all can keep good photochromic properties, and open loop state (leuco-state) and closed loop state (colour generation state) all have the most chemically and thermally superior function such as stability and good sensitivity, can be used for fluoroscopic examination and fluorescence light-operated switch, High-Density Holographic optical storage, two ore control role in fluorescent molecule switch, pH chemical sensor, metal ion chemistry sensor etc., application prospect is vast.
Description
Technical field
The present invention relates to a kind of photochromic double (N-ethyl-1,8-naphthalimide) amine-benzothiophene series-parallel perfluoro rings
Amylene compound and synthetic method and application.
Background technology
In the system of the various photochromic compoundses of research at present, two virtue ene derivatives have prominent due to it
Heat irreversible, the characteristic such as good resisting fatigue, become in area information storage the optical memory material most with application potential.
These factors all make people pour into more enthusiasm and energy designs synthesis diaryl ene new, good properties and closes
Thing.It addition, two virtue ene derivatives have good optical physics and photochemical properties because of it so that in they many fields (such as:
Molecular switch), all there is the application prospect of desirable.Two virtue alkene of role in fluorescent molecule switch and chemical sensitisation have attracted generation
The concern of people, this new characteristic will be further driven to the development of two virtue alkene, and the general layout following to two virtue alkene and application bring entirely
New revolution.
So far, combine the research heat becoming new by the photochromic object identification concept with supramolecular chemistry
Point.Wherein carry out complex ion with two virtue alkene for part and present brand-new visual angle for design photochemical molecular lock.There is ion identification
The Multifunction Diarene compound of function and ion regulation photochromic properties is by substantial amounts of report out.In order to adapt to
Higher requirement meets multiple input, needs multiple signal focuses on a molecule, this also become current one important
Research topic.And the scientist of various countries has done unremitting effort for this, achieving significant achievement, these achievements are published in
The high-caliber periodical in the world.Two virtue alkene, as heliosensitivity organic substance, have sensitivity extremely to light, using two virtue alkene as mother
Other functional groups are also linked the role in fluorescent molecule switch constituting multiple response by body, and this compounds is by more and more
Report.Particularly two ore control two virtue alkene molecule, has been achieved for considerable achievement.In recent years, many researchers are entirely
Fluorine diarylethene side chain modification aspect has done substantial amounts of research work.Successively report double thiophene type, thiophene-benzothiophene
The various structures such as type, thiophene-benzene-type, thiophene-thiazole type, thiazole-benzene-type and thiophene-pyrroles's type, the light-induced variable that character is novel
Color system.Meanwhile, Song Yanlin and Tian He etc. utilize ester bond by two virtue alkene and naphthalimide couple together, compound initially by
Strong fluorescence is shown in naphthalimide, after cyclization, fluorescence cancellation the most completely；Further, Tian He etc. also synthesized have strong
Fluorogen naphthalimide and cholesteric symmetrical two virtue this good molecular switches of alkene, being applied to that these can be potential can
Erasing type optical information stores.But, up to now, with double (N-ethyl-1,8-naphthalimide) amine-benzothiophene series-parallel perfluoro
Cyclopentene compound there is not yet any document and patent report.
Summary of the invention
It is an object of the invention to provide a kind of photochromic double (N-ethyl-1,8-naphthalimide) amine-benzothiophenes to mix
Connection type perfluoro-cyclopentene compound and synthetic method and application.
Photochromic double (N-ethyl-1,8-naphthalimide) amine-benzothiophene hybrid-type perfluorinated cyclopentenes of the present invention
The molecular structural formula of compound is as follows:
Photochromic double (N-ethyl-1,8-naphthalimide) amine-benzothiophene hybrid-type perfluorinated cyclopentenes of the present invention
The universal synthesis method of compound is:
(1), with 2-methylthiophene as raw material, bromination under condition of ice bath, then by with n-BuLi (n-BuLi) and
Butyl borate reacts, and generates 2-methyl-3-bromo-5-boronate thiophene；Catalyst is made again with four triphen phosphorus palladiums, anti-by coupling
Halo 4-bromobenzaldehyde and thiphene ring should be coupled together and obtain substituted thiophene-based intermediate；(2), in n-BuLi effect
Under, bromo-for 1-2-methyl benzothiophene and perfluoro-cyclopentene are reacted the mono-substituted perfluoro-cyclopentene of generation；(3), by coupled product
Thiophene biphenyl aldehyde radical and ethylene glycol, react in reflux in toluene benzene methanesulfonic acid, carry out aldehyde radical protection；(4), protect at low temperature nitrogen
Under the conditions of protecting, use n-BuLi, the monosubstituted perfluoro-cyclopentene intermediate of preparation in step (2) is obtained in step (3)
Intermediate reaction；(5), the material deprotection that will obtain in step (4), then aldehyde radical is become hydroxyl, then hydroxyl is become bromine；
(6), 1.8-naphthalic anhydride and double-(2-ethylamine base amine) amine are heated to reflux in ethanol, double (the N-second of intermediate product
Base-1,8-naphthalimide) amine；(7) product finally given in double (N-ethyl-1,8-naphthalimide) amine and step (5), is incited somebody to action molten
Solution, in anhydrous acetonitrile, adds potassium carbonate, and KI, under argon shield, mixed solution is heated to reflux, and i.e. obtains end product.
Photochromic double (N-ethyl-1,8-naphthalimide) amine-benzothiophene hybrid-type perfluorinated cyclopentenes of the present invention
The main uses of compound has: mix up macromolecular material, is practically applicable to VHD, erasable organic photon type information storage material；
For preparing photoswitch element；For preparing photochromic luminescent device；For two ore control role in fluorescent molecule switch；PH chemistry
Sensor；Metal ion chemistry sensor.
Photochromic double (N-ethyl-1,8-naphthalimide) amine-benzothiophene hybrid-type perfluorinated cyclopentenes of the present invention
The advantage of compound mainly has the following aspects:
1, double (N-ethyl-1,8-naphthalimide) amine-benzothiophene hybrid-type perfluorinated cyclopentene photochromic materials are molten
Liquid can keep good photochromic properties, and open loop state (leuco-state) and closed loop state (colour generation state) all have well chemistry and
The superior function such as heat stability and good sensitivity；
2, the opening of double (N-ethyl-1,8-naphthalimide) amine-benzothiophene hybrid-type perfluorinated cyclopentene photochromic material
Ring state has stronger fluorescence in the range of 400-500 nm, and closed loop state does not has fluorescence, thus can be used for fluoroscopic examination and glimmering
Light light-operated switch；
3, the perfluoro-cyclopentene class two virtue alkene photochromic material containing double (N-ethyl-1,8-naphthalimide) amine of the present invention
Being used successfully to High-Density Holographic optical storage, its storage attribute is the storage of erasable photon type；
4, the present invention can be used for two ore control role in fluorescent molecule switch, pH chemical sensor, metal ion chemistry sensor etc.,
Application prospect is vast.
Accompanying drawing explanation
Fig. 1 is photochromic double (N-ethyl-1,8-naphthalimide) amine-benzothiophene series-parallel perfluoro rings penta of the present invention
The molecular formula of ene compound；
Fig. 2 is the compound photochromic reaction principle schematic diagram of the present invention；
Fig. 3 is the compounds of this invention color variation diagram in dichloromethane before and after photoreaction；
Fig. 4 is the abosrption spectrogram before and after dichloromethane solution medium ultraviolet light irradiates of the present invention；
Fig. 5 is that the fluorescence emission spectrum in tetrahydrofuran solution of the present invention is with ultraviolet lighting time variation diagram；
Fig. 6 is the fluorescence emission spectrogram adding trifluoroacetic acid in dichloromethane of the present invention；
Fig. 7 be the present invention in dichloromethane, add soda acid circulation figure；
Fig. 8 is that the fluorescence emission spectrum in dichloromethane after acid adding of the present invention is with ultraviolet lighting time variation diagram；
Fig. 9 is the fluorescence emission spectrum block diagram adding different ions in oxolane of the present invention；
Figure 10 is the ultraviolet resisting fatigue figure in oxolane of the present invention.
Detailed description of the invention
Entitled: 1-(2-dimethyl-3-benzothienyl), { 2-[2-methyl-5-(4-((double (N-ethyl-1,8-naphthoyls
Imines) amine) methyl)-phenyl)]-3-thienyl perfluoro-cyclopentene, structural formula is as follows:
Shown in the synthetic schemes Scheme 1 of this Novel diaryl perfluoro cycolpenfene photochrmism compounds:
Scheme1:
Its concrete synthesis step is as described below:
1,1-(2-methyl benzothiophene-1-base) perfluoro-cyclopentene (3):
Compound 2 (3.0g, 13.5mmol) is dissolved in 60 ml THF, stirs under the conditions of nitrogen and-78 DEG C, slowly
Inject the n-BuLi (5.9ml, 14.9mmol) of 2.5 mol/L, continue low temperature and stir half an hour.By perfluoro cyclopentenes (2
ML, 14.9 mmol) it is injected in reaction flask, continue reactant mixture is stirred 1 h at low temperatures, be naturally warmed to room temperature,
Adding suitable quantity of water and terminate reaction, separatory also extracts with ether, merges organic facies, and solvent is removed in distillation, vacuum drying, residue stone
Oil ether silica gel column chromatography isolated 3 water white transparency solid (4.3g, 12.8mmol), productivity: 94.9%, product structure qualification:
M.p. 322−323K；
1H NMR (400 MHz, CDCl3): δ2.53 (s, 3H, −CH3), 7.41 (m, 2H,
benzothiophene−H), 7.45 (d, 1H, J = 8.0 Hz, benzothiophene−H), 7.83 (t, 1H, J
= 8.0 Hz, benzothiophene−H); IR (ν, KBr, cm−1): 722, 753, 828, 859, 967,
1027, 1139, 1206, 1283, 1331, 1352, 1387, 1433, 1462, 1538, 1705, 2934, 3468。
2,3-bromo-2-methyl-5-(4-aldehyde radical-phenyl) thiophene (5):
Pd (PPh by 2-bromobenzaldehyde (2.50 g, 13.57 mmol) with existing system3)4(0.15 g) is dissolved in 100 mL
THF is placed in 250 mL there-necked flasks, with argon shield, after 20 min are stirred at room temperature, by 2-methyl-3-bromo-5-boronate
Thiophene (3.00 g, 13.57 mmol) and the Na2CO3 aqueous solution of 50 mL 2 mol L-1, join above-mentioned there-necked flask
In Ping, stirring, back flow reaction 16 h, it is cooled to room temperature, rotary evaporation in vacuo removes THF solution, extracts 3 times with dichloromethane, closes
And organic facies, respectively with saturated aqueous common salt and distilled water wash 3 times, anhydrous MgSO4 is dried overnight, and rotary evaporation in vacuo goes molten
Agent, with petroleum ether as eluent, crosses silicagel column, obtains faint yellow solid product 3.00 g, productivity: 78.95%, and product structure is identified:
M.p. 111–112 ºC;
1H NMR (400 MHz, CDCl3, ppm): δ2.44 (s, 3H), 7.24 (s, 1H), 7.65 (d,
2H, J = 8.0 Hz), 7.87 (d, 2H, J = 8.0 Hz), 9.98 (s, 1H)。
3,3-bromo-2-methyl-5-(4-1,3-dioxolanyl-phenyl) thiophene (6):
By bromo-for 3-2-methyl-5-(2-aldehyde radical-phenyl) thiophene (2.00 g, 7.10 mmol), p-methyl benzenesulfonic acid
(0.02 g) and ethylene glycol (2.40 ml) are dissolved in 120 mL benzene and being placed in 250 mL single port flasks, connect cold with water knockout drum
Solidifying pipe, 120 DEG C are stirred at reflux reaction 16 h, are cooled to room temperature and add water termination reaction, and rotary evaporation in vacuo removes solvent, uses dichloromethane
Alkane extracts 3 times, and organic facies saturated sodium carbonate solution washs 3 times, and anhydrous MgSO4 is dried overnight, and rotary evaporation in vacuo removes solvent,
There are yellow solid product 1.95 g, productivity: 84.42%, product structure is identified:
M.p. 93–94 ºC;
1H NMR (400 MHz, CDCl3, ppm): δ2.41 (s, 3H), 3.94–4.15 (m, 4H), 5.81
(s, 1H), 7.12 (s, 1H), 7.46–7.53 (m, 4H)。
4,1-[(2-methyl-benzothlophene base)]-2-[2-methyl-5-(4-aldehyde radical phenyl)-3-thienyl] perfluor ring penta
Alkene (7):
Bromo-for 3-2-methyl-5-(4-1,3-dioxolanyl-phenyl) thiophene (1.49 g, 4.60 mmol) is dissolved in 50
In the THF that mL is refined, under conditions of argon shield and-78 DEG C of liquid nitrogen-acetone bath, add 2.4 M n-BuLi (2.10 mL,
5.06 mmol), after stirring 30 min, by compound 1-(2-methyl benzothiophene-1-base) perfluoro-cyclopentene (1.57g, 4.60
Mmol) THF solution adds in reaction bulb, continues stirring 2 h, is naturally warmed to room temperature, and adds appropriate water and terminates reaction, and rotation is steamed
Removing THF, separatory dichloromethane extracts, and merges organic facies, the product that rotation obtains after steaming and pyridine and p-methyl benzenesulfonic acid one
Rising and be dissolved in acetone and aqueous solution, 60 DEG C are stirred at reflux reaction 18 h, add water and terminate reaction, and vacuum rotation is evaporated off solvent, uses
Dichloromethane extracts 3 times, and organic facies saturated sodium bicarbonate solution washs 3 times, and anhydrous MgSO4 is dried, and rotary evaporation in vacuo removes
Remove solvent, with petroleum ether: ethyl acetate=8:1 crosses silicagel column isolated and there are pale solid material 1.09 g, productivity:
45.42%, product structure is identified:
1H NMR (400 MHz, CD Cl3): δ1.98 (s, 3H, -CH3), 2.31 (s, 3H, -CH3),
7.31-7.36 (m, 3H, thiophene-H, phenyl-H), 7.56 (d, 3H, J=8.4 Hz, phenyl-H),
7.74 (t, 1H, J =6.2 Hz, phenyl-H), 7.85 (d, 2H, J =8.4 Hz, phenyl-H), 9.98
(s, 1H, -CHO)。
5,1-(2-methyl-3-benzothienyl), 2-[2-methyl-5-(4-hydroxymethyl phenyl)-3-thienyl] perfluor ring
Amylene (8):
By compound 2(2.61 g, 5.00 mmol) it is dissolved in 20 mL THF and is sufficiently stirred for, add sodium borohydride (0.27
G, 7.00 mmol), after refluxing two hours, it is cooled to room temperature.The cancellation that adds water is reacted, and rotation steams THF, is extracted with ethyl acetate
Three times, merge organic facies.Saturated common salt washing organic facies twice, is washing organic facies with water twice, and anhydrous magnesium sulfate is dried, with stone
Oil ether/ethyl acetate (2:1) is that eluant crosses silicagel column, obtains white solid 3(2.43 g, 4.65 mmol), productivity: 93%,
Product structure is identified:
M.p. 342–343 K;
1H NMR (CDCl3, 400 MHz), δ (ppm): 1.93 (s, 3H), 2.30 (s, 3H), 4.69 (s,
2H), 7.17 (s, 1H), 7.29–7.35 (m, 4H), 7.48 (d, 2H, J = 8.0 Hz), 7.57 (d, 1H,J = 8.0 Hz), 7.74 (d, 1H, J = 8.0 Hz)。
6,1-(2-methyl-3-benzothienyl), 2-[2-methyl-5-(4-2-bromomethylphenyl)-3-thienyl] perfluor ring
Amylene (9):
Under condition of ice bath, by compound 3(1.57 g, 3 mmol) it is dissolved in 40 mL anhydrous methylene chlorides, add and use
The lithium bromide (1.05 g, 12 mmol) that THF has dissolved, adds triethylamine (0.78 mL), mesyl chloride (0.39 mL), and 30
Naturally being warmed to room temperature after minute, stirring reaction 8 hours, the cancellation that adds water is reacted, and rotation steams solvent, and ethyl acetate extracts three times, closes
And organic facies, saturated common salt washing organic facies twice, washing organic facies with water twice, anhydrous magnesium sulfate is dried, with petroleum ether/second
Acetoacetic ester (10:1) is that eluant crosses silicagel column, obtains white solid (1.58 g, 2.70 mmol), productivity: 90%, and product is tied
Structure is identified:
M.p. 335–336 K;
1H NMR (CDCl3, 400 MHz), δ (ppm): 1.93 (s, 3H), 2.29 (s, 3H), 4.52 (d,
2H, J = 32.0 Hz), 7.16 (s, 1H), 7.30–7.38 (m, 6H), 7.55 (d, 1H, J = 8.0 Hz),
7.73 (d, 1H, J = 8.0 Hz)。
7, double (N-ethyl-1,8-naphthalimide) amine (11):
By compound 1.8-naphthalic anhydride (0.198g, 1mmol) and double-(2-ethylamine base amine) amine (0.051g,
0.5mmol) in 50mL ethanol, it is heated to reflux 4h, is cooled to room temperature, have precipitation to generate, filter, wash with substantial amounts of ethanol, vacuum
It is dried；Product structure is identified:
1H NMR (CDCl3, 400 MHz): δ 3.10 (t, J = 6.2Hz, 4H), 4.33 (t, J =
6.2Hz, 4H), 7.66 (t, J = 7.8Hz, 4H), 8.17 (d, J = 7.8Hz, 4H), 8.39 ppm(d, J =
6.2 Hz, 4H)。
8,1-(2-dimethyl-3-benzothienyl), { 2-[2-methyl-5-(4-((double (N-ethyl-1,8-naphthalimides)
Amine) methyl)-phenyl)]-3-thienyl perfluoro-cyclopentene (1O):
By double (N-ethyl-1,8-naphthalimide) amine (0.120 g, 0.25 mmol) and compound 9(0.176 g,
0.300mmol) it is dissolved in 60 mL anhydrous acetonitriles, adds potassium carbonate (0.062 g, 0.45 mmol), KI(0.0498 g, 0.3
Mmol), under argon shield, mixed solution is heated to reflux 6 hours, and add water after cooling room temperature termination reaction, and rotation steams solvent, second
Acetoacetic ester extracts three times, merges organic facies, saturated common salt washing organic facies twice, is washing organic facies with water twice, anhydrous slufuric acid
Sodium is dried.It is that eluant crosses silicagel column with petrol ether/ethyl acetate (3:1), obtains the end product 1O(0.2 of Pink solid
G, 0.206 mmol), productivity: 86%, product structure qualification:
M.p. 497–498 K;
1H NMR (CDCl3, 400 MHz), δ(ppm): 1.91 (s, 3H), 2.31 (s, 3H), 2.93 (t,
4H, J = 9.4 Hz), 3.66–3.77 (m, 2H), 4.32 (t, 4H, J = 6.6 Hz), 6.51 (d, 2H, J
= 7.6 Hz), 6.82 (s, 1H), 6.93 (d, 2H, J = 7.6 Hz),7.30 (d, 1H, J = 10.4 Hz),
7.33-7.38 (m, 2H), 7.58 (t, 4H, J = 7.8 Hz), 7.76 (d, 1H, J = 8.4 Hz), 8.14
(d, 4H, J = 6.8 Hz), 8.17 (d, 4H, J = 11.2Hz)。
Claims (3)
1. photochromic double (N-ethyl-1,8-naphthalimide) amine-benzothiophene hybrid-type perfluorinated cyclopentene compounds, its
It is characterised by: its molecular structural formula is as follows:
。
Photochromic double (N-ethyl-1,8-naphthalimide) amine-benzothiophene series-parallel perfluoro rings the most as claimed in claim 1
Amylene compound, its synthetic method is: (1), with 2-methylthiophene as raw material, bromination under condition of ice bath, then by with just
Butyl lithium (n-BuLi) and butyl borate reaction, generate 2-methyl-3-bromo-5-boronate thiophene；Make with four triphenyl phasphine palladiums again
Catalyst, is coupled together halo 4-bromobenzaldehyde and thiphene ring by coupling reaction and obtains substituted thiophene-based intermediate；
(2), under n-BuLi effect, bromo-for 1-2-methyl benzothiophene and perfluoro-cyclopentene are reacted the mono-substituted perfluor ring of generation
Amylene；(3), by coupled product thiophene biphenyl aldehyde radical and ethylene glycol, benzene methanesulfonic acid is reacted in reflux in toluene, carries out aldehyde radical guarantor
Protect；(4), under low temperature nitrogen protective condition, n-BuLi is used, by the monosubstituted perfluoro-cyclopentene of preparation in step (2)
The intermediate reaction obtained in mesosome and step (3)；(5), the material deprotection that will obtain in step (4), then aldehyde radical is become
Hydroxyl, then hydroxyl is become bromine；(6), 1.8-naphthalic anhydride and double-(2-ethylamine base amine) amine are heated back in ethanol
Stream, obtains double (N-ethyl-1, the 8-naphthalimide) amine of intermediate product；(7), will double (N-ethyl-1,8-naphthalimide) amine and step
(5) product finally given in is dissolved in anhydrous acetonitrile, adds potassium carbonate, and KI, under argon shield, mixed solution heats back
Stream, i.e. obtains end product.
Photochromic double (N-ethyl-1,8-naphthalimide) amine-benzothiophene series-parallel perfluoro rings the most as claimed in claim 1
Amylene compound is preparing the application of two ore control role in fluorescent molecule switch.
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