CN112409342A - Organic photochromic material based on furfural and preparation method thereof - Google Patents
Organic photochromic material based on furfural and preparation method thereof Download PDFInfo
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- CN112409342A CN112409342A CN201910785797.3A CN201910785797A CN112409342A CN 112409342 A CN112409342 A CN 112409342A CN 201910785797 A CN201910785797 A CN 201910785797A CN 112409342 A CN112409342 A CN 112409342A
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- 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
- C07D405/02—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 two hetero rings
- C07D405/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Abstract
The invention discloses an organic photochromic compound and a synthesis method thereof, wherein, malonic acid ring (isopropylidene) reacts with furfural to synthesize a compound I, then a synthesized compound II, namely pyridine-2-ethylamine, is added to generate a target compound III, and the target compound III is recrystallized in a methanol solution to synthesize an isomer IV. And adding a proper amount of alkali into the water solution of the target compound III to convert the target compound III into the isomer V. The invention uses organic solvent with lower toxicity to carry out condensation reaction under certain conditions, obtains organic photochromic compound with high yield and high content, does not need to use catalyst, effectively reduces production cost, and has wide application in the fields of molecular electron and information processing, light-operated catalysis, molecular materials, drug delivery, imaging and control of biological systems, and the like.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and mainly relates to a preparation method of a photochromic material.
Background
The ability of organic photochromic compounds to reversibly undergo changes in spectral absorption, volume and solubility is of particular importance in energy storage and chemical sensing applications, as well as in controlling the conformation and activity of biomolecules.
Among organic photochromic materials, azobenzene, spiropyran and diolefin are attracting attention due to their excellent properties and wide use. In particular, azobenzene has been widely used due to its volume change caused by isomerization from trans to cis under irradiation. Likewise, changes in the spectral properties of spiropyrans and diolefins across optical switches are also utilized in many applications. Despite the popularity and widespread use of photochromism, these specialized photochromic molecules typically require the use of high-energy ultraviolet light to trigger their photochemical reactions. This hinders their potential applications in biomedical applications and material science, as uv light can damage healthy cells and cause degradation of many macromolecular systems. Fatigue resistance is also a major problem for ultraviolet-based photochromic switches.
A common design principle to solve this problem is to synthetically modify these known photochromic compounds to allow the use of visible light. One new class of photochromic molecules is the donor-acceptor substrate adducts (DASA) reported in 2014. The compounds are photoisomerized under the irradiation of visible light, are linearly converted from colored neutral into colorless amphoteric rings, have high molar absorptivity, are used for efficient and reversible photoswitch, and have good fatigue resistance. These easily synthesized molecules have been the subject of computational and mechanical research and have proven compatible with the performance of other photochromic molecules as orthogonal optical switches. At the same time, these compounds have found applications in polymer science, such as controlling wettability, light-induced micelle collapse, allowing targeted drug release, and temperature localization after impact loading such as bullet impact in explosives. To date, reversible switching behavior in DASAs has been limited to systems in toluene, dioxane, or polymer matrices. The irreversible linear-cyclic switch was demonstrated in methanol and water to stabilize the closed-loop zwitterionic structure. Thermal cycle-linear inversion (and very limited linear-cycle photoisomerization) has been demonstrated in dichloromethane, and similar behavior has also been reported in other halogenated solvents. Such photochromic compounds require use in a wider range of solvents, reversible switching being a more widely used option. The compound switch is converted from a conjugated, colored and hydrophobic structure into a closed-loop, colorless and zwitterionic structure under the irradiation of visible light, has higher fatigue resistance and good linear and cyclic solubility, and performs visible light photochromic behavior in common organic solvents such as methanol, ethanol, toluene and the like.
Disclosure of Invention
In order to overcome the defects of difficult raw material availability, harsh reaction conditions, low yield, need of using ultraviolet light to trigger photochemical reaction and the like in the prior art, the invention aims to provide an organic photochromic material and a synthesis method thereof.
An organic photochromic material iii (dasa) having the structure:
the synthesis method of the organic photochromic material III comprises the following steps:
(1) reacting isopropylidene malonate and furfural in H2A step of preparing a compound I by nucleophilic substitution reaction in O,
(2) a step of preparing a compound II by aldehyde-amine condensation reaction of pyridine formaldehyde and ethylamine in a methanol solvent,
(3) a step of carrying out nucleophilic addition reaction on a compound I and a compound II in a THF solvent to prepare a target product III,
further, in step (1), in terms of molar ratio, malonic acid cyclo (ylidene) isopropyl ester, furfural ═ 1: 1.
further, in the step (1), the reaction temperature is 75 +/-5 ℃, and the reaction time is not less than 2 hours.
Further, in step (2), in terms of molar ratio, the ratio of pyridine formaldehyde: ethylamine 1: 2.
Further, in the step (2), the reaction temperature is 20 +/-5 ℃, and the reaction time is not less than 5 hours.
Further, in step (3), the molar ratio of compound i: compound ii is 1: 1.
Further, in the step (3), the reaction temperature is 20 +/-5 ℃, and the reaction time is 10-15 min.
The invention also provides another organic photochromic material IV, which has the following structure:
the preparation method of the organic photochromic material IV comprises the steps of recrystallizing the compound III in methanol and standing for 1-2 days to obtain the compound IV,
compared with the prior art, the invention has the following advantages:
the synthetic design of DASA optical switches utilizes furfural as a starting material, a chemical that is extracted from plant by-products, is renewable and readily available.
2. The cyclic 1, 3-dicarbonyl compound is condensed in water to simply activate furfural to provide an intermediate, a catalyst or other reagents are not required to be added, and ring-opening reaction can be carried out on the cyclic 1, 3-dicarbonyl compound and secondary amine at room temperature. This reaction has the property of being highly modular, resulting in the synthesis of DASA materials in high yields.
3. The change in properties of the organic photochromic compound is triggered by light, which is the most widely available, non-invasive, environmentally friendly external stimulus. Expanding their potential applications in biomedical applications and material science.
4. The synthesized DASA compound has high molar absorptivity and shows photochromic property under low-energy visible light. And has high fatigue resistance.
Drawings
FIG. 1 shows the NMR spectrum of compound I.
FIG. 2 is the NMR spectrum of class II compound.
FIG. 3 is a NMR chart of class III.
FIG. 4 is a two-dimensional COSY spectrum of class III compound.
FIG. 5 is a nuclear magnetic resonance hydrogen spectrum of class IV compound.
FIG. 6 is a nuclear magnetic resonance carbon spectrum of class IV.
FIG. 7 is a two-dimensional COSY spectrum of a compound IV.
FIG. 8 is the NMR spectrum of class V compound.
FIG. 9 is the NMR carbon spectrum of class V compound.
FIG. 10 is a two-dimensional COSY spectrum of class compound V.
FIG. 11 shows IR charts of class III and IV compounds.
FIG. 12 is an XRD pattern of class IV compound.
FIG. 13 is a UV diagram of the conversion of a dichloromethane solution of class II to compound III under visible light irradiation, wherein a: photograph of solution, b: full spectrum of absorbance as a function of illumination time, c: graph of absorbance at 542nm as a function of irradiation time.
FIG. 14 is a UV chart of absorbance as a function of concentration for a dichloromethane solution of class II, wherein a: full spectrum of absorbance as a function of concentration, b: the absorbance and concentration are plotted linearly.
FIG. 15 is a UV diagram of the conversion of a toluene solution of class II to compound III under visible light irradiation, wherein a: photograph of solution, b: full spectrum of absorbance as a function of illumination time, c: absorbance at 546nm as a function of irradiation time.
FIG. 16 is a UV chart of absorbance of toluene solution of class II as a function of concentration, wherein a: full spectrum of absorbance as a function of concentration, b: the absorbance and concentration are plotted linearly.
FIG. 17 is a UV diagram of the conversion of a methanolic solution of class II to compound III under visible light irradiation, wherein a: photograph of solution, b: full spectrum of absorbance as a function of illumination time, c: absorbance at 524nm as a function of irradiation time.
FIG. 18 is a UV plot of absorbance as a function of concentration for a methanol solution of class II, wherein a: full spectrum of absorbance as a function of concentration, b: the absorbance and concentration are plotted linearly.
FIG. 19 is a UV diagram of the conversion of a DMSO solution of class II to compound III under visible light irradiation, wherein a: photograph of solution, b: full spectrum of absorbance as a function of illumination time, c: absorbance at 532nm as a function of irradiation time.
FIG. 20 is a UV plot of absorbance as a function of concentration for a DMSO solution of class II, wherein a: full spectrum of absorbance as a function of concentration, b: the absorbance and concentration are plotted linearly.
Detailed Description
The invention is further elucidated with reference to the figures and embodiments.
Preparation of compound (I)
Example 1:
the molecular structure of the compound I is shown as follows:
the preparation of the compound of this example 1 comprises the following steps:
adding cyclopropyl (isopropylidene) malonate and furfural into H in sequence2And (4) in O.The heterogeneous mixture was heated to 75 ℃ and stirred at this temperature for 2 hours, a yellow precipitate formed during the reaction. After the reaction was complete (TLC), the mixture was cooled to room temperature with hexane: ethyl acetate ═ 3: 1). The precipitated solid was collected by vacuum filtration and washed twice with cold water. The collected solid was dissolved in dichloromethane and separately saturated NaHSO3、H2O, saturated NaHCO3And a brine wash. The organic layer was MgSO4After drying, filtration and removal of the solvent by rotary evaporator, a bright yellow powder was obtained. The nuclear magnetic hydrogen spectrum is shown in figure 1.
Example 2:
the molecular structure of the compound II is shown as follows:
the preparation of the compound of this example 2 comprises the following steps:
mixing 2-pyridine formaldehyde and ethylamine according to a molar ratio of 1:2, add to methanol with mixing, stir at reflux for 2h, then stir at room temperature for 2h more, then extract the yellow reaction mixture three times with ether. Again using anhydrous MgSO4Drying, filtering, evaporating to dryness, and adding NaBH4Reduction to obtain yellow oily liquid. The nuclear magnetic hydrogen spectrum is shown in FIG. 2.
Example 3:
the molecular structure of the compound III is shown as follows:
the preparation of the compound of this example 3 comprises the following steps:
in a two-necked flask, compound i: pyridine ethylamine ═ 1:1 was added sequentially to THF. The mixture was stirred at 23 ℃ for 10 minutes and then cooled at 0 ℃ for 20 minutes. After the reaction was complete, the mixture was filtered and the solid was collected. The solid was washed with cold ether and dried under vacuum to give a red solid. The nuclear magnetic hydrogen spectrum is shown in FIGS. 3-4.
Example 4:
the molecular structure of the compound IV is shown as follows:
the preparation of the compound of this example 4 comprises the following steps:
recrystallizing the compound III in methanol, and standing for 1-2 days to obtain compound IV, wherein the structural representation is shown in figures 5-7, the IR is shown in figure 11, and the XRD is shown in figure 12.
The crystal data obtained after recrystallization of compound II are shown in tables 1-2 below.
TABLE 1 Crystal parameters
TABLE 2 bond lengths between atoms
Example 5:
compound V, the molecular structure of which is shown below:
the preparation of the compound of this example 5 included the following steps:
and adding 1 time equivalent of NaOH into the aqueous solution of the compound IV to obtain a compound V, wherein the structural characteristics of the compound V are shown in figures 8-10.
Photophysical property test of (II) compound
1. Photophysical properties of compound II in different solvents
(1) Methylene dichloride
Irradiation with visible light: (>535nm), photoisomerization of compound ii to compound iii (in dichloromethane, C ═ 5.0 × 10)–5mol/L). The performance characteristics are shown in FIGS. 13-14.
Referring to FIG. 13a, under 535nm light irradiation, the solution changes color from purple to colorless. In conjunction with FIG. 13b, the absorbance of compound II decreased from 1.0 to 0 at 720s illumination and the maximum absorbance at 542nm occurred. In conjunction with fig. 13c, the absorbance at 542nm decreases with longer irradiation time. This indicates that the dichloromethane solution of compound II can be completely converted to compound III under light.
Referring to FIG. 14a, the absorbance spectrum of compound II in different concentrations of dichloromethane as a function of concentration shows that the maximum absorbance is 542 nm. With reference to FIG. 14b, the absorbance at 542nm is linear with the concentration of compound II. This shows that the dichloromethane solution of compound II has a good linear relationship and that the maximum absorption wavelength does not vary with concentration.
(2) Toluene
Irradiation with visible light: (>535nm), photoisomerization of compound ii to compound iii (in toluene, C ═ 1.0 × 10)– 5mol/L). The performance characteristics are shown in FIGS. 15-16.
Referring to FIG. 15a, under 535nm light irradiation, the solution changes color from purple to colorless. Referring to FIG. 15b, the absorbance of compound II decreases from 1.0 to 0 at 90s illumination and shows a maximum absorption at 546 nm. In conjunction with fig. 15c, the absorbance at 546nm decreases with longer irradiation time. This indicates that the toluene solution of compound II can be rapidly converted to compound III under light conditions.
Referring to FIG. 16a, the absorption spectrum of compound II in toluene with different concentrations varies with the concentration, and the maximum absorbance is 546 nm. In conjunction with FIG. 16b, the absorbance at 546nm is linear with the concentration of compound II. This indicates that the toluene solution of compound II has a good linear relationship and that the wavelength of maximum absorption does not vary with concentration.
(3) Methanol
Irradiation with visible light: (>535nm) from compound II to compound III3In OH, C is 1.0X 10– 5mol/L). The performance characteristics are shown in FIGS. 17-18.
Referring to FIG. 17a, under 535nm light irradiation, the color of the solution changes from red to colorless. In conjunction with FIG. 17b, the absorbance of compound II decreased from 1.0 to 0 at 1200s of light, and the maximum absorbance occurred at 524 nm. In conjunction with fig. 17c, the absorbance at 524nm decreased with longer irradiation time. This indicates that the methanol solution of compound II can be completely converted to compound III under light conditions.
Referring to FIG. 18a, the absorption spectrum of compound II in methanol with different concentrations varies with the concentration, and the maximum absorbance is 524 nm. With reference to FIG. 18b, the absorbance at 524nm is linear with compound II concentration. This indicates that the methanol solution of compound II has a good linear relationship and that the wavelength of maximum absorption does not vary with concentration.
(4)DMSO
Irradiation with visible light: (>535nm) of compound II to compound III (in DMSO, C ═ 1.0X 10– 5mol/L). The performance characteristics are shown in FIGS. 19-20.
Referring to FIG. 19a, under 535nm light irradiation, the color of the solution changes from red to light yellow. In connection with FIG. 19b, the absorbance of compound II decreases from 0.9 to 0 with 2040s illumination and the maximum absorption occurs at 532 nm. This indicates that a DMSO solution of compound II can be completely converted to compound III under light conditions.
Referring to FIG. 20a, the absorbance spectrum of compound II in DMSO at different concentrations as a function of concentration shows a maximum absorbance at 531 nm. With reference to FIG. 20b, the absorbance at 531nm is linear with compound II concentration. This indicates that compound ii in DMSO has a good linear relationship and that the wavelength of maximum absorption does not vary with concentration.
Claims (10)
1. An organic photochromic material III is characterized in that the structure is as follows:
2. the method of synthesizing the organic photochromic material III according to claim 1, comprising the steps of:
(1) reacting isopropylidene malonate and furfural in H2A step of preparing a compound I by nucleophilic substitution reaction in O,
(2) a step of preparing a compound II by aldehyde-amine condensation reaction of pyridine formaldehyde and ethylamine in a methanol solvent,
(3) a step of carrying out nucleophilic addition reaction on a compound I and a compound II in a THF solvent to prepare a target product III,
3. the method of claim 2, wherein in step (1), the molar ratio of cyclopropane ring (ylidene) isopropyl ester to furfural is 1: 1.
4. the method of claim 2, wherein in the step (1), the reaction temperature is 75 ± 5 ℃ and the reaction time is not less than 2 hours.
5. The method of claim 2, wherein in step (2), the molar ratio of the pyridine-formaldehyde: ethylamine 1: 2.
6. The method of claim 2, wherein in the step (2), the reaction temperature is 20 ± 5 ℃ and the reaction time is not less than 5 hours.
7. The method of claim 2, wherein in step (3), the molar ratio of compound i: compound ii is 1: 1.
8. The method of claim 2, wherein in the step (3), the reaction temperature is 20 ± 5 ℃ and the reaction time is 10-15 min.
9. An organic photochromic material IV is characterized by having the following structure:
10. the method for producing the organic photochromic material IV according to claim 9, which comprises the steps of recrystallizing the compound III in methanol and allowing the compound III to stand for 1 to 2 days to obtain the compound IV,
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114573544A (en) * | 2022-03-04 | 2022-06-03 | 南京理工大学 | Molecular switch with multiple stimulus responses and synthesis method thereof |
| CN115160824A (en) * | 2022-07-01 | 2022-10-11 | 四川大学 | Method for preparing multicolor dye from single polymer |
Citations (2)
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| CN101460453A (en) * | 2006-04-11 | 2009-06-17 | 埃科特莱茵药品有限公司 | Novel sulfonamide compounds |
| WO2017189700A1 (en) * | 2016-04-26 | 2017-11-02 | The Regents Of The University Of California | Negative photochromic materials with tunable properties |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101460453A (en) * | 2006-04-11 | 2009-06-17 | 埃科特莱茵药品有限公司 | Novel sulfonamide compounds |
| WO2017189700A1 (en) * | 2016-04-26 | 2017-11-02 | The Regents Of The University Of California | Negative photochromic materials with tunable properties |
Non-Patent Citations (2)
| Title |
|---|
| SAMEH HELMY,等: "Design and Synthesis of Donor-Acceptor Stenhouse Adducts:A Visible Light Photoswitch Derived from Furfural", 《THE JOURNAL OF ORGANIC CHEMISTRY》 * |
| SAMEH HELMY，等: "Photoswitching Using Visible Light: A New Class of Organic Photochromic Molecules", 《JOURNAL OF THE AMERICAN CHEMICAL SOCIETY》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114573544A (en) * | 2022-03-04 | 2022-06-03 | 南京理工大学 | Molecular switch with multiple stimulus responses and synthesis method thereof |
| CN114573544B (en) * | 2022-03-04 | 2023-11-21 | 南京理工大学 | Molecular switch with multiple stimulus responses and synthesis method thereof |
| CN115160824A (en) * | 2022-07-01 | 2022-10-11 | 四川大学 | Method for preparing multicolor dye from single polymer |
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