CN112409342B - Organic photochromic material based on furfural and preparation method thereof - Google Patents

Organic photochromic material based on furfural and preparation method thereof Download PDF

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CN112409342B
CN112409342B CN201910785797.3A CN201910785797A CN112409342B CN 112409342 B CN112409342 B CN 112409342B CN 201910785797 A CN201910785797 A CN 201910785797A CN 112409342 B CN112409342 B CN 112409342B
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暴欣
蔡佑德
陈秀琴
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Nanjing University of Science and Technology
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    • 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
    • C07D405/02—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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    • C07D471/00—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
    • 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

Organic photochromic material based on furfural and preparation method thereof
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 photochromics, 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 ultraviolet 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 Adduct (DASA) reported in 2014. The compounds are photoisomerized under the irradiation of visible light, are converted into colorless amphoteric rings from colored neutral lines, have high molar absorptivity, are used for performing efficient and reversible optical switches by using the visible light, 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, photo-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. Irreversible linear-cycling switches were 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. The photochromic compound needs to be used in a wider range of solvents, and the reversible switch can be widely applied. 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:
Figure GDA0003893779170000021
the synthesis method of the organic photochromic material III comprises the following steps:
(1) Reacting isopropylidene malonate and furfural in H 2 A step of preparing a compound I by nucleophilic substitution reaction in O,
Figure GDA0003893779170000022
(2) A step of preparing a compound II by aldehyde-amine condensation reaction of pyridine formaldehyde and ethylamine in a methanol solvent,
Figure GDA0003893779170000023
(3) A step of preparing a target product III by nucleophilic addition reaction of a compound I and a compound II in a THF solvent,
Figure GDA0003893779170000024
Figure GDA0003893779170000031
further, in step (1), in terms of molar ratio, cyclopropane ring (methylene) 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.
Further, in the step (2), the reaction temperature is 20 +/-5 ℃, and the reaction time is not less than 5h.
Further, in step (3), the molar ratio of compound i: compound ii =1.
Further, in the step (3), the reaction temperature is 20 +/-5 ℃, and the reaction time is 10-15min.
The invention also provides another organic photochromic material IV, which has the following structure:
Figure GDA0003893779170000032
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 a compound IV,
Figure GDA0003893779170000033
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 extracted from plant by-products, which is renewable and readily available.
2. Condensation of cyclic 1, 3-dicarbonyl compounds in water simply activates furfural to provide an intermediate, which can undergo a ring-opening reaction with secondary amines at room temperature without the need for addition of catalysts or other reagents. This reaction has the property of being highly modular, synthesizing DASA material in high yield.
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 photochromism 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 spectrum of class III.
FIG. 4 is a two-dimensional COSY spectrogram of a compound III.
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 shows the NMR carbon spectrum of compound V.
FIG. 10 is a two-dimensional COSY spectrum of class compound V.
FIG. 11 is an IR chart of group 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 plot of absorbance as a function of illumination 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 drawings and examples.
Preparation of compound (I)
Example 1:
the molecular structure of the compound I is shown as follows:
Figure GDA0003893779170000051
the preparation of the compound of this example 1 comprises the following steps:
adding cyclopropyl (isopropylidene) malonate and furfural into H in sequence 2 And (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 finished (TLC), hexane: ethyl acetate = 3). The precipitated solid was collected by vacuum filtration and washed twice with cold water. The collected solid was dissolved in dichloromethane and separately saturated NaHSO 3 、H 2 O, saturated NaHCO 3 And a brine wash. The organic layer was MgSO 4 After drying, filtration, the solvent was removed by rotary evaporator to give a bright yellow powder. The nuclear magnetic hydrogen spectrum is shown in figure 1.
Example 2:
the molecular structure of the compound II is shown as follows:
Figure GDA0003893779170000052
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 a further 2h, then extract the yellow reaction mixture three times with diethyl ether. Again using anhydrous MgSO 4 Drying, filtering, evaporating to dryness, and adding NaBH 4 Reduction to obtain yellow oily liquid. The nuclear magnetic hydrogen spectrum is shown in figure 2.
Example 3:
compound III, the molecular structure of which is shown below:
Figure GDA0003893779170000061
the preparation of the compound of this example 3 comprises the following steps:
in a two-necked flask, compound i: pyridylethylamine =1:1 was added to THF in succession. 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 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:
Figure GDA0003893779170000062
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.
Figure GDA0003893779170000063
The crystal data obtained after recrystallization of compound III are shown in tables 1-2 below.
TABLE 1 Crystal parameters
Figure GDA0003893779170000071
TABLE 2 bond lengths between atoms
Figure GDA0003893779170000081
Figure GDA0003893779170000091
Example 5:
compound V, the molecular structure of which is shown below:
Figure GDA0003893779170000092
the preparation of the compound of this example 5 comprises 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 representation of the compound V is shown in figures 8-10.
Figure GDA0003893779170000093
Photophysical property test of (II) Compound III
1. Photophysical properties of Compound III in different solvents
(1) Methylene dichloride
Irradiation with visible light: (>535 nm), photoisomerization of compound ii to compound III (in dichloromethane, C =5.0 × 10) –5 mol/L). The performance characteristics are shown in FIGS. 13-14.
Referring to a in FIG. 13, under 535nm light irradiation, the color of the solution changes from purple to colorless. In conjunction with b in fig. 13, the absorbance of compound III decreased from 1.0 to 0 with light illumination for 720s, and the maximum absorption occurred at 542nm. In conjunction with c in fig. 13, the absorbance at 542nm decreases with longer irradiation time. This indicates that a solution of compound III in dichloromethane can be completely converted to compound IV under light conditions.
In combination with a in FIG. 14, the absorption spectrum of compound III in dichloromethane of different concentrations varies with the concentration, and the maximum absorbance is 542nm. In conjunction with b in FIG. 14, the absorbance at 542nm is linearly related to the concentration of compound III. This indicates that the dichloromethane solution of compound III has a good linear relationship and that the wavelength of maximum absorption does not vary with concentration.
(2) Toluene
Irradiation with visible light: (>535 nm), photoisomerization of compound III to compound IV (in toluene, C =1.0 × 10) – 5 mol/L). The performance characteristics are shown in FIGS. 15-16.
Referring to a in FIG. 15, under 535nm light irradiation, the solution changes color from purple to colorless. In connection with b in FIG. 15, the absorbance of compound III decreased from 1.0 to 0 with illumination for 90s and the maximum absorption occurred at 546nm. In conjunction with c in fig. 15, the absorbance at 546nm decreases with longer irradiation time. This indicates that a toluene solution of compound III can be rapidly converted to compound IV under light conditions.
Referring to a in FIG. 16, the absorption spectrum of compound II in toluene with different concentrations changes, and the maximum absorbance is 546nm. In conjunction with b in FIG. 16, the absorbance at 546nm is linear with compound III concentration. 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: (>535 nm) from compound II to compound III 3 In OH, C =1.0 × 10 – 5 mol/L). The performance characteristics are shown in FIGS. 17-18.
Referring to a in FIG. 17, under 535nm light irradiation, the color of the solution changes from red to colorless. In conjunction with b in fig. 17, the absorbance of compound III decreases from 1.0 to 0 with illumination of 1200s and the maximum absorption occurs at 524nm. In conjunction with c in fig. 17, the absorbance at 524nm decreases with longer irradiation time. This indicates that a solution of compound III in methanol can be completely converted to compound IV under light conditions.
In combination with a in FIG. 18, the absorption spectrum of compound III in methanol of different concentrations as a function of concentration has the maximum absorbance at 524nm. In conjunction with b in FIG. 18, the absorbance at 524nm is linear with the concentration of compound II. This indicates that the methanol solution of compound III has a good linear relationship and that the wavelength of maximum absorption does not vary with concentration.
(4)DMSO
Irradiation with visible light: (>535 nm) from compound III to compound IV (in DMSO, C =1.0 × 10) – 5 mol/L). The performance characteristics are shown in FIGS. 19-20.
Referring to a in FIG. 19, under 535nm light irradiation, the color of the solution changes from red to light yellow. In conjunction with b in FIG. 19, at 2040s illumination, the absorbance of compound III decreased from 0.9 to 0, and the maximum absorption occurred at 532 nm. This indicates that DMSO solutions of compound III can be completely converted to compound IV under light conditions.
In combination with a in FIG. 20, the absorption spectrum of compound II in DMSO at different concentrations as a function of concentration has a maximum absorbance at 531nm. In conjunction with b in FIG. 20, the absorbance at 531nm is linear with compound III concentration. This indicates that compound III in DMSO has a good linear relationship and that the wavelength of maximum absorption does not vary with concentration.

Claims (8)

1. An organic photochromic material IV is characterized by having the following structure:
Figure FDA0003893779160000011
2. the method for preparing the organic photochromic material iv according to claim 1, comprising:
(1) Reacting cyclopropane-isopropyl (methylene) malonate and furfural in H 2 A step of preparing a compound I by nucleophilic substitution reaction in O,
Figure FDA0003893779160000012
(2) A step of preparing a compound II by aldehyde-amine condensation reaction of pyridine formaldehyde and ethylamine in a methanol solvent,
Figure FDA0003893779160000013
(3) A step of preparing a target product III by nucleophilic addition reaction of a compound I and a compound II in a THF solvent,
Figure FDA0003893779160000014
(4) Recrystallizing the compound III in methanol, and standing for 1-2 days to obtain a compound IV,
Figure FDA0003893779160000021
3. the method of claim 2, wherein in step (1), the molar ratio of cyclopropanecarboxylic ring (ylidene) isopropyl ester is furfural =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.
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 =1.
8. The method of claim 2, wherein in the step (3), the reaction temperature is 20 ± 5 ℃ and the reaction time is 10-15min.
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