CN108623543A - The class photochromic material of triaryl-ethylene containing furan derivatives and its synthetic method and application - Google Patents
The class photochromic material of triaryl-ethylene containing furan derivatives and its synthetic method and application Download PDFInfo
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- CN108623543A CN108623543A CN201810234482.5A CN201810234482A CN108623543A CN 108623543 A CN108623543 A CN 108623543A CN 201810234482 A CN201810234482 A CN 201810234482A CN 108623543 A CN108623543 A CN 108623543A
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- derivatives
- triaryl
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- photochromic material
- furan
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- 0 *B(c1c(cccc2)c2ccc1)O Chemical compound *B(c1c(cccc2)c2ccc1)O 0.000 description 1
- HEVJQAUMWQPCHR-UHFFFAOYSA-N BrC(Br)=Cc1ccc[o]1 Chemical compound BrC(Br)=Cc1ccc[o]1 HEVJQAUMWQPCHR-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N c1ccc(cccc2)c2c1 Chemical compound c1ccc(cccc2)c2c1 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/36—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
- C09K9/02—Organic tenebrescent materials
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
Abstract
The invention discloses a kind of class photochromic material of triaryl-ethylene containing furan derivatives and its synthetic method and applications, it is on the basis of traditional triphenylethylene photochromic material, by introducing the better Furan and its derivatives group of conjugacy, and optimum synthesis route, have greatly expanded the controllable range of material, synthetic method craft is simple, it is easy purifying, the change color stability of the series material is improved while greatly improving its photochromic properties emphatically, Modulatory character, and effectively reduce the production cost of material, it is suitable as memory storage material, wearable device of intelligence etc..Further, since the raw materials used industrial chemicals for being all made of technical maturity, furthermore simple synthesis, purification step, huge potentiality are provided for the system material mass market application.
Description
Technical field
The present invention relates to field of new materials, especially a kind of class photochromic material of triaryl-ethylene containing furan derivatives and
Its synthetic method and application in the fields such as optical information storage, wearable device, light control materials, safe-guarding and anti-counterfeiting, biological detection.
Background technology
In recent years, photochromism refers to that reversible color occurs under the conditions of absorption of electromagnetic radiation for certain chemical substance
Variation.Compound is usually moistened along with index of refraction, dielectric constant, dissolubility, luminous, surface in two states interconversion processes
The change of a series of chemistry such as humidity or mechanical effect and physical property.Therefore, photochromic material it is anti-fake, detection, it is non-
The fields application potentials such as linear optics, information storage, unimolecule logic gate and molecule machine are huge.That reports at present is organic photic
Off-color material is mainly the following：Spiro-pyrans class, azo, fulgides, triphenylmethane and diarylethene
Close object.However traditional organic photochromic material is mostly in the presence of design synthesis is complicated, material cost is high, oxidizable and cycle is secondary
The problems such as number difference.Triaryl-ethylene class compound structure is simply easily modified, and has excellent chemically and physically stability, good
The advantages that fatigue resistance, Chi etc. have obtained excellent light by introducing contraposition chlorine atom on two phenyl ring of triphenylethylene homonymy
Cause triphenylethylene derivatives (Ou D, et.al.Chemical Science, 2016,7 (8) of discoloration:5302-5306),
However this kind of brand-new material still has some defects in real-time monitoring and long-acting memory storage etc., needs further to be changed
Into.
Invention content
The object of the present invention is to provide a kind of class of triaryl-ethylene containing furan derivatives photochromic materials, have
Discoloration memory persistently reliable, outstanding erasable property and can in real time light-operated quick response the advantages that
It is a further object to provide the conjunctions of the above-mentioned class of triaryl-ethylene containing furan derivatives photochromic material
At method, these method and processes are simple, and yield is high, is easy to purify, and can adjust final product by introducing different functional groups
Recognizable optical wavelength response range, discoloration, the performances such as emission wavelength.
A further object of the invention is to be applied to the above-mentioned class of triaryl-ethylene containing furan derivatives photochromic material
The fields such as optical information storage, wearable device, light control materials, safe-guarding and anti-counterfeiting, biological detection.
To achieve the above object, a kind of class photochromic material of triaryl-ethylene containing furan derivatives provided by the invention,
Shown in its general formula of molecular structure such as general formula (1)：
General formula (1)：
Wherein, R0For furan nucleus or derivatives thereof；R1And R2It is identical or different, it is aromatic rings, heteroaromatic or derivatives thereof.
The synthetic method of the above-mentioned class of triaryl-ethylene containing furan derivatives photochromic material, it is characterised in that including：Side
Method (1)：The furan nucleus or derivatives thereof that formaldehyde substituent group is contained in one end is synthesized its dibromo by Corey-Funchs reactions to take
For object；Mesh is obtained by the reaction by Suzuki with the aromatic compound containing boric acid or pinacol boric acid ester group or heterocyclic compound again
Mark product；Method (2)：Benzophenone derivative is reacted with the furan nucleus or derivatives thereof containing p diethylaminobenzoic acid ester group and is loved and respect one's elder brother by dimension
It is uncommon that target product is obtained by the reaction.
The above-mentioned class photochromic material of triaryl-ethylene containing furan derivatives be applied to prepare light control materials, optical information is deposited
Store up material, wearable device, chemical-biological detection product, bio-imaging product or anti-fake product.
The present invention has carried out structure innovation and performance optimization on the basis of traditional triphenylethylene photochromic material, passes through
The better Furan and its derivatives group of conjugacy, and optimum synthesis route are introduced, the controllable range of material is had greatly expanded,
Synthetic method craft is simple, is easy purifying, and the series material is improved emphatically while greatly improving its photochromic properties
Become color stability, Modulatory character and the production cost for effectively reducing material, obtained it is a series of can light-operated in real time, tool
Have good memory storage function and outstanding erasable property quick response photochromic material, at the same time, considerable yield,
The cheap raw material being easy to get and mild synthesis condition will also assign the market potential of such material bigger so that the series material
Material possesses pole in the multiple fields such as light control materials, optical information storage, chemical-biological detection, bio-imaging, wearable device, anti-fake
Big development potentiality and the excellent market competitiveness.
In order to further illustrate the present invention feature and technology contents, please refer to below in connection with the present invention attached drawing,
But attached drawing is only to provide reference and description, is not intended to limit the present invention.
Description of the drawings
Fig. 1 is the photochromic front and back ultra-violet absorption spectrum comparison diagram of the solution of 2 product of the embodiment of the present invention, and wherein solid line is
Before photochromic, after dotted line is photochromic；
Fig. 2 is the photochromic front and back ultra-violet absorption spectrum comparison diagram of the powder of 2 product of the embodiment of the present invention, and wherein solid line is
Before photochromic, after dotted line is photochromic；
Fig. 3 is the photochromic front and back ultra-violet absorption spectrum comparison diagram of the powder of 3 product of the embodiment of the present invention, and wherein solid line is
Before photochromic, after dotted line is photochromic.
Specific implementation mode
Below in conjunction with the accompanying drawings, detailed description of the present invention specific implementation mode, more clearly to express the present invention's
Technical solution and other beneficial effects.
One kind class photochromic material of triaryl-ethylene containing furan derivatives of the present invention, general formula of molecular structure such as general formula
(1) shown in：
General formula (1)：
Wherein, R0For furan nucleus or derivatives thereof；R1And R2It is identical or different, it is aromatic rings, heteroaromatic or derivatives thereof.
Preferably, the R0Selected from lower structure：
Wherein：R3、R4、R5It is identical or different, selected from hydrogen, alkyl, halogen, alkoxy, nitro, carboxyl, amino, carbazole, aldehyde
Base or cyano.
Preferably, the R1And R2Selected from lower structure：
Wherein：R4、R5、R6、R7、R8It is identical or different, selected from hydrogen, alkyl, halogen, alkoxy, nitro, carboxylic
Base, amino, carbazole, aldehyde radical or cyano.
The synthetic method of the above-mentioned class of triaryl-ethylene containing furan derivatives photochromic material, including following methods：
Method (1)：One end is contained to furan nucleus of formaldehyde substituent group or derivatives thereof, conjunction is reacted by Corey-Funchs
At its dibromo substituent；Pass through Suzuki with the aromatic compound containing boric acid or pinacol boric acid ester group or heterocyclic compound again
Target product is obtained by the reaction.Preferably, the method (1) includes the following steps：1. providing one end contains formaldehyde substituent group
Furan nucleus or derivatives thereof, in dichloromethane solution, triphenylphosphine and carbon tetrabromide effect under, normal-temperature reaction obtain secondly
Bromine substituent；2. by step 1. gained dibromo substituent and aromatic compound or heterocycle containing boric acid or pinacol boric acid ester group
Compound under potassium carbonate effect, is catalyzed to obtain target product by tetra-triphenylphosphine palladium in tetrahydrofuran solution.
Method (2)：Benzophenone derivative is reacted with the furan nucleus or derivatives thereof containing p diethylaminobenzoic acid ester group and passes through dimension
Target product is obtained by the reaction in Ti Xi.Preferably, the method (2) includes the following steps：Benzophenone derivative is provided and is contained
Furan nucleus of p diethylaminobenzoic acid ester group or derivatives thereof passes through witig reaction in tetrahydrofuran solution under potassium tert-butoxide effect
Obtain target product.
The above-mentioned class of triaryl-ethylene containing furan derivatives photochromic material can be applied to prepare light control materials, optical information is deposited
Store up material, wearable device, chemical-biological detection product, bio-imaging product or anti-fake product.
Below by way of specific examples of the implementation, the invention will be further elaborated, but the present invention is not limited thereto particular case
Son.
Embodiment 1：
(1) intermediate【2- (2,2- dibromoethylenes) furans】Synthesis
60ml dichloromethane, 4.76g carbon tetrabromides (20mmol) and 10.49g triphenylphosphines are added in 250ml single-necked flasks
(40mmol), is positioned in ice-water bath, 0.96g 2 furan carboxyaldehydes (10mmol) is added after 1h is reacted on magnetic stirring apparatus, often
Temperature reaction 16h.Dark solution is obtained, steams excessive solvent in Rotary Evaporators, obtains oily mix products.Then silicon is utilized
The method of plastic column chromatography is purified, and leacheate is n-hexane.Obtain white solid 2.28g, yield 91.31%.
(2) synthesis of target product embodiment 1
1.25g 2- (2,2- dibromoethylenes) furans (5mmol) and 1.68g phenyl boric acids are added in 250mL there-necked flasks
(15mmol) appropriate THF is added in nitrogen environment, 3.45g K are added2CO3The 2mol/L aqueous solutions that (15.00mmol) is made into,
5 ‰ catalyst Pd (PPh are added3)4.It is warming up to reflux on magnetic stirring apparatus, reacts 12h.Reaction solution is cooled down later, is added
Dichloromethane and water extraction, are extracted 3 times with dichloromethane, are washed with water 3 times.Organic layer is dried with anhydrous sodium sulfate, is being revolved
Turn to be spin-dried in evaporimeter.Then it is purified using the method for silica gel column chromatography, leacheate is n-hexane.Obtain product as clear oil
0.60g, yield 48.77%.1H NMR(500MHz,DMSO-d6)δ7.54–7.42(m,4H),7.35–7.24(m,5H),
7.20-7.16 (m, 2H), 7.04 (s, 1H), 6.33-6.29 (m, 1H), 5.38 (d, J=3.4Hz, 1H)
Embodiment 2：
(2) synthesize target product embodiment 2, yield using 4- fluorobenzoic boric acids for phenyl boric acid with reference to the step of embodiment 1
88.24%.1H NMR(500MHz,DMSO-d6) δ 7.52 (d, J=1.4Hz, 1H), 7.35-7.27 (m, 4H), 7.26-7.19
(m, 2H), 7.19-7.12 (m, 2H), 7.01 (s, 1H), 6.37-6.31 (m, 1H), 5.55 (d, J=3.4Hz, 1H)
The present embodiment product is configured to concentration 1.0 × 10-3M tetrahydrofuran solutions, in 365nm LED ultraviolet source irradiations
Under, gradually turned yellow by colourless transparent solution, it is as shown in Figure 1 to measure photochromic front and back ultra-violet absorption spectrum comparison.
The present embodiment product gradually turns yellow under 365nm LED ultraviolet source irradiations, by white crystalline powder, measures photic
The front and back ultra-violet absorption spectrum comparison of discoloration is as shown in Figure 2.
Embodiment 3：
(2) synthesize target product embodiment 3, yield using 4- chlorophenylboronic acids for phenyl boric acid with reference to the step of embodiment 1
83.62%.1H NMR(500MHz,DMSO-d6)δ7.55–7.52(m,3H),7.41–7.34(m,2H),7.30–7.26(m,
2H), 7.23-7.19 (m, 2H), 7.08 (s, 1H), 6.39-6.36 (m, 1H), 5.68 (d, J=3.4Hz, 1H)
The present embodiment product gradually turns yellow under 365nm LED ultraviolet source irradiations, by white crystalline powder, measures photic
The front and back ultra-violet absorption spectrum comparison of discoloration is as shown in Figure 3.
Embodiment 4：
(2) synthesize target product embodiment 4 using 2- naphthalene phenyl boric acids for phenyl boric acid with reference to the step of embodiment 1, and yield is
77.45%.1H NMR (400MHz, DMSO-d6) δ 8.48 (d, J=8.1Hz, 1H), 8.04-7.94 (m, 4H), 7.87 (d, J=
8.0Hz, 1H), 7.62-7.54 (m, 3H), 7.53-7.47 (m, 2H), 7.47-7.37 (m, 2H), 7.34 (d, J=7.2Hz,
1H), 7.03 (s, 1H), 6.29-6.22 (m, 1H), 5.43 (d, J=3.2Hz, 1H)
Embodiment 5
(2) replace phenyl boric acid synthesis target product embodiment 4, production using 4- carbazole phenyl boric acids with reference to the step of embodiment 1
Rate is 61.04%.1H NMR(400MHz,DMSO-d6)δ8.35–8.24(m,4H),7.87–7.61(m,10H),7.58–7.42
(m, 8H), 7.38-7.31 (m, 4H), 6.49 (s, 1H), 5.78 (d, J=3.0Hz, 1H)
Table 1:Maximum emission wavelength, maximum discoloration UV absorption wavelength of the final product in solid in each embodiment
Note：The emission spectrum of solid is by Shimadzu RF-5301PC fluorescence spectrophotometer measurements；Ultra-violet absorption spectrum
By Hitachi U-3900 spectrophotometer measurements.
In conclusion the present invention relates to the class photochromic material of triaryl-ethylene containing furan derivatives have it is excellent photic
Discoloration and lasting reliable, the outstanding erasable property of discoloration memory and fast-response, are suitably applied optical information storage, can wear
Wear the fields such as device, light control materials, safe-guarding and anti-counterfeiting, biological detection.The above, those skilled in the art can bases
Technical scheme of the present invention and technical concept make various other corresponding change and deformations, and all these change and distortions are all
The protection domain of the claims in the present invention should be belonged to.
Claims (7)
1. a kind of class photochromic material of triaryl-ethylene containing furan derivatives, shown in general formula of molecular structure such as general formula (1)：
General formula (1)：
Wherein, R0For furan nucleus or derivatives thereof；R1And R2It is identical or different, it is aromatic rings, heteroaromatic or derivatives thereof.
2. the class of triaryl-ethylene containing furan derivatives photochromic material according to claim 1, it is characterised in that：It is described
R0Selected from lower structure：
Wherein：R3、R4、R5It is identical or different, selected from hydrogen, alkyl, halogen, alkoxy, nitro, carboxyl, amino, carbazole, aldehyde radical or
Cyano.
3. the class of triaryl-ethylene containing furan derivatives photochromic material according to claim 1, it is characterised in that：It is described
R1And R2Selected from lower structure：
Wherein：R4、R5、R6、R7、R8It is identical or different, selected from hydrogen, alkyl, halogen, alkoxy, nitro, carboxyl, amino, carbazole,
Aldehyde radical or cyano.
4. the synthetic method of the class of triaryl-ethylene containing furan derivatives photochromic material, feature described in claim 1-3 exist
In including：Method (1)：One end is contained to furan nucleus of formaldehyde substituent group or derivatives thereof, synthesis is reacted by Corey-Funchs
Its dibromo substituent；It is anti-by Suzuki with the aromatic compound containing boric acid or pinacol boric acid ester group or heterocyclic compound again
It should obtain target product；Method (2)：Benzophenone derivative is reacted with the furan nucleus or derivatives thereof containing p diethylaminobenzoic acid ester group
Target product is obtained by witig reaction.
5. the synthetic method of the class of triaryl-ethylene containing furan derivatives photochromic material according to claim 4, special
Sign is：The method (1) includes the following steps：1. the furan nucleus or derivatives thereof that formaldehyde substituent group is contained in one end is provided,
In dichloromethane solution, under triphenylphosphine and carbon tetrabromide effect, normal-temperature reaction obtains its dibromo substituent；2. by step
1. gained dibromo substituent is with the aromatic compound containing boric acid or pinacol boric acid ester group or heterocyclic compound in tetrahydrofuran
In solution, under potassium carbonate effect, it is catalyzed to obtain target product by tetra-triphenylphosphine palladium.
6. the synthetic method of the class of triaryl-ethylene containing furan derivatives photochromic material according to claim 4, special
Sign is：The method (2) includes the following steps：There is provided benzophenone derivative and the furan nucleus containing p diethylaminobenzoic acid ester group or
Its derivative obtains target product under potassium tert-butoxide effect in tetrahydrofuran solution by witig reaction.
7. the class photochromic material of triaryl-ethylene containing furan derivatives described in claim 1-3 is applied to prepare light-operated material
Material, optical storage material, wearable device, chemical-biological detection product, bio-imaging product or anti-fake product.
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Cited By (3)
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| CN112047802A (en) * | 2019-06-05 | 2020-12-08 | 中国科学院上海有机化学研究所 | Polysubstituted ethylene compound, preparation method and application thereof |
| CN115404721A (en) * | 2022-06-21 | 2022-11-29 | 西北工业大学 | Preparation and application of photoresponse thermal printing paper |
| CN115404721B (en) * | 2022-06-21 | 2024-04-26 | 西北工业大学 | Preparation and application of photoresponse thermal printing paper |
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| CN115404721B (en) * | 2022-06-21 | 2024-04-26 | 西北工业大学 | Preparation and application of photoresponse thermal printing paper |
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| CN108623543B (en) | 2022-06-07 |
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