CN108623543B - Furan derivative-containing triaryl ethylene photochromic material and its synthesis method and use - Google Patents
Furan derivative-containing triaryl ethylene photochromic material and its synthesis method and use Download PDFInfo
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Abstract
The invention discloses a triaryl ethylene photochromic material containing furan derivatives, a synthesis method and application thereof, which greatly expand the adjustable range of the material by introducing furan and derivative groups thereof with better conjugation property and optimizing the synthesis route on the basis of the traditional triphenylethylene photochromic material. In addition, the raw materials are chemical raw materials with mature processes and are combined with simple synthesis and purification steps, so that great potential is provided for large-scale marketization application of the system material.
Description
Technical Field
The invention relates to the field of new materials, in particular to a furan derivative-containing triaryl ethylene photochromic material, a synthesis method thereof and application thereof in the fields of optical information storage, wearable devices, light-operated materials, safety anti-counterfeiting, biological detection and the like.
Background
In recent years, the phenomenon of photochromism refers to the reversible color change of certain chemical substances under the condition of absorbing electromagnetic radiation. The interconversion of the two states of a compound is usually accompanied by a series of chemical and physical changes in refractive index, dielectric constant, solubility, luminescence, surface wettability, or mechanical efficiency. Therefore, the photochromic material has great application potential in the fields of anti-counterfeiting, detection, nonlinear optics, information storage, single-molecule logic gates, molecular machines and the like. The organic photochromic materials reported at present mainly comprise the following materials: spiropyrans, azos, fulgides, triphenylmethanes and diarylethenes. However, most of the traditional organic photochromic materials have the problems of complex design and synthesis, high material cost, easy oxidation, poor cycle number and the like. The triaryl ethylene compound has the advantages of simple and easily modified structure, excellent chemical and physical stability, good fatigue resistance and the like, and Chi and the like obtain the triphenylethylene derivative (Ou D, et al. chemical Science,2016,7(8): 5302-.
Disclosure of Invention
The invention aims to provide a furan derivative-containing triaryl ethylene photochromic material which has the advantages of durable and reliable color-changing memory, excellent erasability, quick response of real-time light control and the like
Another object of the present invention is to provide methods for synthesizing the above triarylethylene photochromic materials containing furan derivatives, which have the advantages of simple process, high yield, easy purification, and adjustable wavelength response range, color change performance, and luminescence wavelength of the final product.
The invention also aims to apply the furan derivative-containing triaryl ethylene photochromic material to the fields of optical information storage, wearable devices, light-operated materials, safety anti-counterfeiting, biological detection and the like.
In order to achieve the above object, the present invention provides a triarylethylene photochromic material containing furan derivatives, which has a general molecular structure formula shown in formula (1):
general formula (1):
wherein R is0Is a furan ring or a derivative thereof; r1And R2The same or different, is an aromatic ring, an aromatic heterocycle or a derivative thereof.
The synthesis method of the furan derivative-containing triaryl ethylene photochromic material is characterized by comprising the following steps of: method (1): synthesizing a dibromo substituent by reacting a furan ring or a derivative thereof with a formaldehyde substituent at one end through Corey-Funchs; then carrying out Suzuki reaction on the aromatic compound or the heterocyclic compound containing boric acid or pinacol borate to obtain a target product; method (2): reacting benzophenone derivative with furan ring containing phosphoric acid diethyl ester group or its derivative to obtain target product by Wittig reaction.
The furan derivative-containing triaryl ethylene photochromic material is applied to the preparation of light-operated materials, optical information storage materials, wearable devices, chemical biological detection products, biological imaging products or anti-counterfeiting products.
The invention carries out structural innovation and performance optimization on the basis of the traditional triphenylethylene photochromic material, greatly expands the adjustable range of the material by introducing furan and derivative groups with better conjugation property and optimizing the synthesis route, has simple synthesis method and simple process, is easy to purify, greatly improves the photochromic performance, emphatically improves the photochromic stability and controllability of the series of materials, effectively reduces the production cost of the materials, obtains a series of quick response photochromic materials which can be controlled by light in real time, have good memory storage function and excellent erasability, simultaneously has considerable yield, cheap and easily obtained raw materials and mild synthesis conditions and endows the materials with larger market potential, so that the series of materials have light-operated material, optical information storage, chemical biological detection, biological imaging, The wearable device, the anti-counterfeiting and other fields have great development potential and excellent market competitiveness.
To further illustrate the features and technical content of the present invention, please refer to the following drawings related to the present invention, which are for reference and illustration only and are not intended to limit the present invention.
Drawings
FIG. 1 is a comparison graph of UV absorption spectra before and after photochromism of a solution of the product of example 2 of the present invention, wherein the solid line is before photochromism and the dotted line is after photochromism;
FIG. 2 is a comparison graph of the UV absorption spectra before and after photochromism of the powder of the product of example 2 of the present invention, wherein the solid line is before photochromism and the dotted line is after photochromism;
FIG. 3 is a comparison graph of UV absorption spectra before and after powder photochromism of the product of example 3 of the present invention, wherein the solid line is before photochromism and the dotted line is after photochromism.
Detailed Description
The following detailed description of the present invention will be provided in order to more clearly illustrate the technical solution and other advantages of the present invention, with reference to the accompanying drawings.
The invention relates to a furan derivative-containing triaryl ethylene photochromic material, which has a molecular structure general formula shown in a general formula (1):
general formula (1):
wherein R is0Is a furan ring or a derivative thereof; r1And R2The same or different, is an aromatic ring, an aromatic heterocycle or a derivative thereof.
Preferably, R is0Selected from the following structures:
wherein: r3、R4、R5Identical or different, from the group consisting of hydrogen, alkyl, halogen, alkoxy, nitro, carboxyl, amino, carbazole, aldehyde groups or cyano groups.
Preferably, said R is1And R2Selected from the following structures:
wherein: r4、R5、R6、R7、R8Same or different and selected from hydrogen, alkyl, halogen, alkoxy, nitro, carboxyl
A group, an amino group, a carbazole, an aldehyde group, or a cyano group.
The synthesis method of the furan derivative-containing triaryl ethylene photochromic material comprises the following steps:
method (1): synthesizing a dibromo substituent by reacting a furan ring or a derivative thereof with a formaldehyde substituent at one end through Corey-Funchs; then the target product is obtained by Suzuki reaction with aromatic compound or heterocyclic compound containing boric acid or pinacol borate group. Preferably, the method (1) comprises the following steps: firstly, providing a furan ring or a derivative thereof with one end containing a formaldehyde substituent, and reacting at normal temperature in a dichloromethane solution under the action of triphenylphosphine and carbon tetrabromide to obtain a dibromo substituent; and secondly, catalyzing the dibromo substituent obtained in the step I and an aromatic compound or a heterocyclic compound containing boric acid or pinacol borate in a tetrahydrofuran solution under the action of potassium carbonate to obtain a target product through palladium tetratriphenylphosphine.
Method (2): reacting benzophenone derivative with furan ring containing phosphoric acid diethyl ester group or its derivative to obtain target product by Wittig reaction. Preferably, the method (2) comprises the following steps: provides a target product obtained by Wittig reaction of benzophenone derivative and furan ring containing phosphoric acid diethyl ester group or derivative thereof in tetrahydrofuran solution under the action of potassium tert-butoxide.
The furan derivative-containing triaryl ethylene photochromic material can be applied to preparation of light-operated materials, optical information storage materials, wearable devices, chemical biological detection products, biological imaging products or anti-counterfeiting products.
The present invention will be further illustrated by the following specific examples, but the present invention is not limited to these specific examples.
Example 1:
(1) synthesis of intermediate [ 2- (2, 2-dibromoethene) furan ]
A250 ml single-neck flask was charged with 60ml of dichloromethane, 4.76g of carbon tetrabromide (20mmol) and 10.49g of triphenylphosphine (40mmol), placed in an ice-water bath, reacted on a magnetic stirrer for 1 hour, then added with 0.96g of 2-furaldehyde (10mmol), and reacted at room temperature for 16 hours. A black solution was obtained and excess solvent was evaporated in a rotary evaporator to give an oily mixture. Then purifying by silica gel column chromatography, wherein the eluent is n-hexane. 2.28g of a white solid was obtained, yield 91.31%.
(2) Synthesis of the desired product example 1
A250 mL three-necked flask was charged with 1.25g of 2- (2, 2-dibromoethylene) furan (5mmol) and 1.68g of phenylboronic acid (15mmol), and under nitrogen, the appropriate amount of THF was added and 3.45g K was added2CO3(15.00mmol) is prepared into 2mol/L water solution, 5 per mill of catalyst Pd (PPh) is added3)4. The temperature is raised to reflux in a magnetic stirrer and the reaction lasts for 12 h. Then, the reaction solution was cooled, extracted with dichloromethane and water, extracted 3 times with dichloromethane, and washed 3 times with water. The organic layer was dried over anhydrous sodium sulfate and spun dry on a rotary evaporator. Then purifying by silica gel column chromatography, wherein the eluent is n-hexane. 0.60g of product is obtained as a clear oil, with a yield of 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).
Example 2:
the target product, example 2, was synthesized in 88.24% yield using 4-fluorobenzeneboronic acid instead of phenylboronic acid with reference to step (2) of example 1.1H NMR(500MHz,DMSO-d6)δ7.52(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 product of this example was formulated to a concentration of 1.0X 10-3The M tetrahydrofuran solution gradually turns yellow from the colorless transparent solution under the irradiation of 365nm LED ultraviolet light source, and the ultraviolet absorption spectrum pair before and after photochromism is measured, as shown in figure 1.
The product of this example gradually turned yellow from white crystal powder under the irradiation of 365nm LED uv light source, and the ultraviolet absorption spectrum pair before and after the measurement of photochromism is shown in fig. 2.
Example 3:
the objective product, example 3, was synthesized in 83.62% yield using 4-chlorobenzeneboronic acid instead of phenylboronic acid with reference to step (2) of example 1.1H 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 product of this example gradually turned yellow from white crystal powder under the irradiation of 365nm LED uv light source, and the ultraviolet absorption spectrum pair before and after the measurement of photochromism is shown in fig. 3.
Example 4:
synthesis of the objective product, example 4, using 2-naphthylphenylboronic acid instead of phenylboronic acid with reference to step (2) of example 1, was carried out in a yield of 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).
Example 5
The target product, example 4, was synthesized with reference to step (2) of example 1 using 4-carbazole phenylboronic acid instead of phenylboronic acid, in a yield of 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 fluorescence emission wavelength, maximum discoloration UV absorption wavelength of the final product in each example at solid
Note: the emission spectrum of the solid was measured by Shimadzu RF-5301PC fluorescence spectrophotometer; the ultraviolet absorption spectrum was measured by a Hitachi U-3900 spectrophotometer.
In conclusion, the invention relates to a furan derivative-containing triaryl ethylene photochromic material which has excellent photochromic performance, durable and reliable color-changing memory, excellent erasability and quick response, and is suitable for the fields of optical information storage, wearable devices, light-operated materials, safety anti-counterfeiting, biological detection and the like. As described above, the person skilled in the art can make other various corresponding changes and modifications according to the technical solution and the technical idea of the present invention, and all such changes and modifications should fall within the protection scope of the claims of the present invention.
Claims (4)
1. A furan derivative-containing triaryl ethylene photochromic material has a molecular structural formula as follows:
2. the method for synthesizing triarylethylene-based photochromic material containing furan derivatives as claimed in claim 1, which comprises: method (1): synthesizing a dibromo substituent of a furan ring with a formaldehyde substituent at one end by virtue of a Corey-Funchs reaction; then the target product is obtained by Suzuki reaction with aromatic compound or heterocyclic compound containing boric acid or pinacol borate group.
3. The method for synthesizing a triarylethylene-based photochromic material containing a furan derivative according to claim 2, wherein: the method (1) comprises the following steps: firstly, providing a furan ring with one end containing a formaldehyde substituent, and reacting at normal temperature in a dichloromethane solution under the action of triphenylphosphine and carbon tetrabromide to obtain a dibromo substituent; and secondly, catalyzing the dibromo substituent obtained in the step I and an aromatic compound or a heterocyclic compound containing boric acid or pinacol borate in a tetrahydrofuran solution under the action of potassium carbonate through palladium tetratriphenylphosphine to obtain a target product.
4. Application of furan derivative-containing triaryl ethylene photochromic material in preparation of light-operated material, optical information storage material, wearable device, chemical biological detection product, biological imaging product or anti-counterfeiting product, wherein the furan derivative-containing triaryl ethylene photochromic material is selected from
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