CN108774151A - It is a kind of to induce azobenzene derivatives for realizing solid-liquid transformation and preparation method thereof and the application as photoswitch adhesive based on photo-thermal - Google Patents
It is a kind of to induce azobenzene derivatives for realizing solid-liquid transformation and preparation method thereof and the application as photoswitch adhesive based on photo-thermal Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/02—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides
- C07C245/06—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings
- C07C245/08—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings with the two nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings, e.g. azobenzene
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Abstract
The invention discloses a kind of azobenzene derivatives inducing realization solid-liquid transformation based on photo-thermal and preparation method thereof and as the application of photoswitch adhesive.The present invention, respectively with carboxyl azobenzene, gallic acid-derivate, final product is obtained by two step esterifications using two hydroxyls of bis-naphthol.Based on solid azobenzene melting point compound is relatively low and the luminous energy of absorption can be changed into heat by the longer property of absorption bands under the irradiation of green light, the raising of temperature leads to azobenzene derivatives fuse itself.It places when temperature is dropped under fusing point at room temperature, the azobenzene derivatives of liquid exist in the form of solid again, and possess very strong bond properties.It can be melted again after being irradiated again with green light, lose bond properties, become solid again when being cooled to room temperature, show bonding force.The photoswitch adhesive is highly soluble in common organic solvents, and recycling easy to clean is reusable, is a kind of environmentally protective and resource-effective adhesive.
Description
Technical field
The invention belongs to jointing material technical fields, it particularly relates to which a kind of realizing solid-liquid transformation based on photo-thermal induction
Azobenzene derivatives and preparation method thereof and application as photoswitch adhesive.
Background technology
Bridge of the adhesive as two kinds of materials of connection, all plays very important role in production and living.Bonding
Agent is the indispensable material in national economy field, and compared with other high molecular materials, purposes is wide, multi items, therefore also referred to as work
Industry monosodium glutamate becomes indispensable material in many modern industries.In life, adhesive is ubiquitous in being also, such as
You encountered such thing certainly：With adhesive tape or hook bonding thing, it is easy to use simple, but if improper make
With adhesive tape or hook are easy to fall off, and are glued again after falling off just fail to stick；Accidentally multi-use mucilage is dripped on hand
Or on clothing, quickly becomes solid-state and be difficult to wash off, and cannot reuse.It is tired that adhesive material is faced with recycling
Difficult, not re-usable problem, this also brings huge challenge to environment and resource.Therefore, development green can be recycled
Adhesive all have for chemical science, material science and resource-effective, environmental protection and important learning value and actually answer
Use meaning.
Azobenzene compound is a kind of simple in structure, relatively low organic molecule dyestuff of fusing point, in solid state
Under have obviously J clustering phenomenas, azobenzene compound can be made to absorb the light of more long wavelength in the solid state.Root
According to photo-thermal effect principle, light can be transformed into heat, and with lasting illumination, temperature is gradually increasing arrival fusing point, and phase becomes
Change, stops illumination, revert to solid-state again.Corresponding to two kinds of tacky states of adhesive：There is very strong bonding force when solid-state；Liquid
State loses bonding force.This phase transition process high reversible is recycled reciprocal use.In consideration of it, exploitation is a kind of to be based on photo-thermal
It is good that effect induces the photoswitch adhesive of azobenzene derivatives solid-liquid transformation to have in environmentally protective, resource-conserving field
Application prospect.
Invention content
In order to solve the above technical problems, the present invention provides a kind of induced based on photo-thermal to realize that the azobenzene of solid-liquid transformation spreads out
Biology and preparation method thereof and application as photoswitch adhesive, technical solution are as follows：
It is a kind of to induce the azobenzene derivatives for realizing solid-liquid transformation based on photo-thermal, which is characterized in that molecular structural formula is as follows：
Wherein, R1=-OCnH2n+1, n=1-18, and be integer；R2=-CnH2n+1, n=1-18, and for integer ,-I ,-
Br、-Cl、-NO2Or-NH2In any one.
The above-mentioned preparation method that the azobenzene derivatives for realizing solid-liquid transformation are induced based on photo-thermal, which is characterized in that use
With carboxyl azobenzene, gallic acid-derivate, final product is obtained by two step esterifications respectively for two hydroxyls of bis-naphthol.
Further, the preparation method that the azobenzene derivatives for realizing solid-liquid transformation are induced based on photo-thermal, including with
Lower specific steps:
1) gallicins and bromo pentane silane are with 1:The molar ratio of 3-4 is added in two mouthfuls of reaction tubes, adds K2CO3,
K2CO3Molar ratio with gallicin is 1:Then acetone solvent, nitrogen atmosphere is added in 2-4, the TBAB of catalyst equivalent
Under stir evenly after react 48h-72h at 70 DEG C -90 DEG C；Postcooling that the reaction was complete rotates acetone solvent to room temperature, uses
Dichloromethane and water extraction, concentrate organic phase, and then silicagel column purifies, and obtained product is denoted as a1-COOCH3；
2) is by the product a1-COOCH of step 1)3With potassium hydroxide in molar ratio 1:1-2 is added in reaction tube, then adds
Enter alcohol solvent, reacts 4h-6h at 70 DEG C -90 DEG C after being stirred evenly under nitrogen atmosphere；Postcooling that the reaction was complete is dilute to room temperature
Hydrochloric acid adjusts product pH to 1, filters and is rinsed solid product to neutrality with deionized water, obtained product is denoted as a1-COOH；
3) by azobenzene derivative COOH-AZO and bis-naphthol with 1:The molar ratio of 4-6 is added in two mouthfuls of reaction tubes, then
The molar ratio that EDC and DMAP, EDC and azobenzene derivative COOH-AZO is added is 1:1-2, the DMAP of catalyst equivalent, so
Dichloromethane is added afterwards and reacts 24 h-48h at room temperature after being stirred evenly under all reactants dissolving, nitrogen atmosphere；Instead
It is poured into after answering completely in beaker and adds water and dichloro extraction organic phase, revolving removing dichloromethane, silicagel column purification, obtained product
It is denoted as a1-OH；
4) by the product a1-COOH of step 2) and the product a1-OH of step 3) with 1:The molar ratio of 1-2 is added two mouthfuls instead
Ying Guanzhong, adds EDC and DMAP, and the molar ratio of EDC and a1-COOH are 1:1-2, the DMAP of catalyst equivalent, is then added
Dichloromethane is dissolved up to all reactants, reacts -48h for 24 hours at room temperature after being stirred evenly under nitrogen atmosphere；After the reaction was complete
It pours into beaker plus water and dichloro extraction organic phase, revolving removes dichloromethane, silicagel column purification, obtains described luring based on photo-thermal
Lead the azobenzene derivatives for realizing solid-liquid transformation.
Further, described induced based on photo-thermal realizes that the molecular structural formula of the azobenzene derivatives of solid-liquid transformation is as follows：
Further, the structural formula of the azobenzene derivative COOH-AZO, bis-naphthol and gallicin from
Left-to-right is followed successively by：
Above-mentioned induced based on photo-thermal is realized that the azobenzene derivatives of solid-liquid transformation are used as that there is reversible photoswitch to glue
Mixture.
Further, the solid-state and possess bond properties photoswitch adhesive under the irradiation of green light, can will absorb
Luminous energy be changed into heat, the raising of temperature leads to azobenzene derivatives fuse itself and without bond properties；It places warm at room temperature
After degree drops under fusing point, the azobenzene derivatives of liquid exist in the form of solid again, and possess bond properties.
5mg or so azobenzene derivatives P1 is taken to be placed on sheet glass, acted on green light makes its fusing or direct above
Heating fusing, then covers another sheet glass on liquid, cooling at room temperature until P1 becomes solid-state, two glass again
Glass piece is closely bonded in one piece, and can be used for lifting the weight that quality is 2200,000 times of P1 itself.It is shone when with green light
It penetrates when on the P1 for bonding two sheet glass, P1 fusings, adhesive loses bond properties, and when dropping to room temperature again, P1 becomes
Solid-state shows very strong bond properties again.Green light is as the switch for determining adhesive strength power, this process high reversible.Knot
The adhesive for closing this photoswitch described above is highly soluble in the common organic solvents such as dichloromethane, recycling easy to clean,
The technical advantage of the present invention：
1) have in green Region under the azo-based benzene analog derivative photoswitch adhesive solids state of present invention design synthesis
Green light efficiently can be transformed into heat by very strong absorption, P1, there is extraordinary photo-thermal effect.The present invention design synthesis based on idol
For pyridine analog derivative photoswitch adhesive fusing point in 44 degrees centigrades, the heat that green light is transformed into can melt P1, be not necessarily to heat source
Heating, simple green light irradiate the variation that can cause phase.
2) state pair of azo-based benzene analog derivative photoswitch two kinds of adhesive strengths of adhesive of present invention design synthesis
The solid-state and liquid of answering P1 is can be controlled by the irradiation of green light, and phase transformation is pure physical change, therefore high
It spends reversible.The azo-based benzene analog derivative photoswitch adhesive that the present invention designs synthesis can pass through photo-thermal effect high reversible
Control phase-state change, therefore the adhesive can be recycled for multiple times, and have in environmentally protective, resource-conserving field
Good application prospect.
3) the azo-based benzene analog derivative photoswitch adhesive of present invention design synthesis is common organic in dichloromethane etc.
Dissolubility is very good inside solvent, easily removes, recycles, reusable, can be applied to environmentally protective, resource-effective bonding
Agent field.
Description of the drawings
Fig. 1 is the structural formula of azobenzene derivative and the like, R1=-OCnH2n+1, n=1,2,3 ... 18, R2
=-CnH2n+1(n=1,2,3 ... 18) ,-I ,-Br ,-Cl ,-NO2、-NH2。
Fig. 2 is the reacting flow chart of P1 in embodiment 1.
Fig. 3 is the UV absorption spectrograms of P1 in the solid state in Application Example 1.
Fig. 4 is P1 solid state powders phase-state change figure after green light pre-irradiation in Application Example 1.
Fig. 5 be in Application Example 1 P1 solid state powders under green light irradiation the temperature that is captured by infrared camera with irradiation
The variation of time.
Fig. 6 is that P1 solid state powders and blank glass the plate temperature under green light irradiation change over time in Application Example 1
Curve.
Fig. 7 is the P1 solid state powders cyclic curve that temperature changes with irradiation time under green light irradiation in Application Example 1.
Fig. 8 is the stress-strain diagram that P1 bonds measured by two aluminium flakes in Application Example 2.
Fig. 9 is the schematic diagram that two aluminium flakes that P1 is bonded in Application Example 2 lift 11.15kg weights.
Figure 10 is that green light irradiates adhesive melts in Application Example 2, loses bonding effect.
Specific implementation mode
With reference to specific embodiment to a kind of azo inducing realization solid-liquid transformation based on photo-thermal of the present invention
Benzene derivative and its preparation method and application is described further, but protection scope of the present invention is not limited to this.
Prepare embodiment 1：
1. two mouthfuls of reaction tubes are added in 3.68g (20mmol) gallicins and 9.365g (62.0mmol) bromo pentane silane
In, add the K of 5.52g (40.0mmol)2CO3, the TBAB of catalyst equivalent (20 mg), then be added 100ml acetone solvents,
After being stirred evenly under nitrogen atmosphere 48h is reacted at 70 DEG C；Acetone solvent is rotated and is removed to room temperature by postcooling that the reaction was complete,
It is extracted with dichloromethane and water, concentrates organic phase, then silicagel column purifies, and obtained product is denoted as a1-COOCH3；
1H NMR(400MHz,CDCl3) δ 7.28 (s, 2H), 4.04 (dt, J=10.4,5.2Hz, 6H), 3.90 (s, 3H),
1.81 (ddd, J=19.5,13.9,6.9Hz, 6H), 1.44 (ddt, J=35.4,14.5,7.3Hz, 12H), 0.94 (td, J=
7.1,3.3Hz,9H)；
2. by 2.96g (7.5mmol) a1-COOCH3It is added in reaction tube with 815mg (15mmol) potassium hydroxide, then adds
Enter 50ml alcohol solvents, reacts 4h at 80 DEG C after being stirred evenly under nitrogen atmosphere；Postcooling that the reaction was complete is to room temperature, dilute salt
Acid adjusts product pH to 1, filters and is rinsed solid product to neutrality with deionized water, and obtained product is denoted as a1-COOH,
Yield 96.5%；
1H NMR (400MHz, CDCl3) δ 7.36 (s, 2H), 4.07 (dd, J=14.4,6.8Hz, 6H), 1.91-1.75
(m, 6H), 1.53-1.37 (m, 12H), 0.96 (dd, J=11.3,7.1Hz, 9H)；
3. 113mg (0.5mmol) azobenzene derivative COOH-AZO and 572mg (2 mmol) bis-naphthol is added two mouthfuls
In reaction tube, 110mg (0.7mmol) EDC and 20 mg (0.16mmol) DMAP is added, 20ml dichloromethane is then added will
All reactants dissolve, and react 48h at room temperature after being stirred evenly under nitrogen atmosphere；Poured into after the reaction was complete in beaker plus water and
Dichloro extracts organic phase, and revolving removes dichloromethane, and silicagel column purification, irrigation is dichloromethane, and obtained product is denoted as a1-
OH；
1H NMR (400MHz, CDCl3) δ 8.14 (d, J=8.9Hz, 1H), 8.02 (d, J=8.2Hz, 1H), 7.95-
7.87 (m, 2H), 7.85-7.69 (m, 6H), 7.63-7.47 (m, 5H), 7.43-7.28 (m, 4H), 7.25 (d, J=4.6Hz,
1H),7.22–7.13(m,1H)；
4. 50mg (0.13mmol) a1-COOH and 50mg (0.1mmol) a1-OH is added in two mouthfuls of reaction tubes, add
Then 25mg (0.12mmol) EDC and 10mg (0.008mmol) DMAP is added 15ml dichloromethane and dissolves all reactants,
48h is reacted at room temperature after being stirred evenly under nitrogen atmosphere；It is poured into after the reaction was complete in beaker and adds water and dichloro extraction organic phase,
Revolving removes dichloromethane, and silicagel column purification, irrigation is dichloromethane solution, and obtained final product has bond properties
Azobenzene derivatives are denoted as P1；
1H NMR (400MHz, CDCl3) δ 8.04-7.96 (m, 2H), 7.96-7.84 (m, 4H), 7.74 (d, J=
9.2Hz, 4H), 7.60 (dd, J=8.9,1.9Hz, 2H), 7.55-7.48 (m, 3H), 7.48-7.40 (m, 3H), 7.39-7.29
(m, 3H), 6.84 (s, 2H), 3.93 (t, J=6.6 Hz, 2H), 3.76-3.63 (m, 4H), 1.77-1.66 (m, 6H), 1.39
(tdd, J=14.0,9.8,6.1Hz, 12H), 0.91 (dt, J=10.8,7.1Hz, 9H)；
The structural formula of the azobenzene derivative COOH-AZO, bis-naphthol and gallicin is：
From left to right it is followed successively by COOH-AZO, bis-naphthol and gallicin.
Application Example 1：
(1) P1 solid state powders have green light the absorption of specificity, take 5mg P1 to measure its absorption spectrum, it was demonstrated that in green Region
It is implicitly present in absorption (Fig. 3).
(2) solid state powder P1 is taken to be placed in pan paper on piece, with 175mW cm-2The green light of power irradiates powder, powder temperature
It gradually rises, the gradually fusing (Fig. 4) after reaching fusing point.
(3) 175mW cm are used-2The green light of power irradiates powder, and infrared camera captures in its 6 minutes temperature with irradiation time
The data of heating, as shown in Figure 5.
(4) sample P 1 and blank glass plate are respectively in 175mW cm-2It is irradiated under the green light of power, temperature becomes with light application time
The curve of change is as shown in fig. 6, illustrate sample P 1 truly has extraordinary photo-thermal effect.
(5) 1 solid state powder of the sample P cyclic curve (Fig. 7) that temperature changes with irradiation time under green light irradiation.
Application Example 2：
(1) 5mg azobenzene derivatives P1 is taken to be placed on aluminium flake, acted on green light makes it melt or directly heat above
Fusing, then covers another aluminium flake on liquid, and cooling at room temperature until P1 becomes solid-state again, two aluminium flakes are close
Be bonded in one piece, Fig. 8 is the stress-strain diagram for testing adhesive strength.
(2) 5mg azobenzene derivatives P1 is taken to be placed on aluminium flake, acted on green light makes it melt or directly heat above
Fusing, then covers another aluminium flake on liquid, and cooling at room temperature until P1 becomes solid-state again, two aluminium flakes are close
Be bonded in one piece, and can be used for lifting the weight (Fig. 9) that quality is 2200,000 times of P1 itself.
(3) within 5 minutes, 175mW cm-2Green light irradiation is bonded in 5mg P1 samples one piece of two sheet glass
It separates (Figure 10).
Claims (7)
1. a kind of inducing the azobenzene derivatives for realizing solid-liquid transformation based on photo-thermal, which is characterized in that its molecular structural formula is as follows：
Wherein, R1=-OCnH2n+1, n=1,2,3 ... 18；R2=-CnH2n+1, n=1,2,3 ... 18 ,-I ,-Br ,-Cl ,-NO2Or-
NH2In any one.
2. a kind of preparation method inducing the azobenzene derivatives for realizing solid-liquid transformation based on photo-thermal, which is characterized in that using double
With carboxyl azobenzene, gallic acid-derivate, final product is obtained by two step esterifications respectively for two hydroxyls of naphthols.
3. the preparation method according to claim 2 that the azobenzene derivatives for realizing solid-liquid transformation are induced based on photo-thermal,
It is characterized in that, including step in detail below:
1) gallicins and bromo pentane silane are with 1:The molar ratio of 3-4 is added in two mouthfuls of reaction tubes, adds K2CO3, K2CO3With
The molar ratio of gallicin is 1:Then 2-4, the TBAB of catalyst equivalent are added acetone solvent, are stirred under nitrogen atmosphere
After uniformly 48h-72h is reacted at 70 DEG C -90 DEG C；Postcooling that the reaction was complete rotates acetone solvent to room temperature, uses dichloromethane
Alkane and water extraction, concentrate organic phase, and then silicagel column purifies, and obtained product is denoted as a1-COOCH3；
2) is by the product a1-COOCH of step 1)3With potassium hydroxide in molar ratio 1:1-2 is added in reaction tube, and ethyl alcohol is then added
Solvent reacts 4h-6h after stirring evenly under nitrogen atmosphere at 70 DEG C -90 DEG C；Postcooling that the reaction was complete is to room temperature, dilute hydrochloric acid tune
Product pH to 1 is saved, filter and is rinsed solid product to neutrality with deionized water, obtained product is denoted as a1-COOH；
3) by azobenzene derivative COOH-AZO and bis-naphthol with 1:The molar ratio of 4-6 is added in two mouthfuls of reaction tubes, adds
The molar ratio of EDC and DMAP, EDC and azobenzene derivative COOH-AZO are 1:Then 1-2, the DMAP of catalyst equivalent add
Enter dichloromethane and reacts -48h for 24 hours at room temperature after being stirred evenly under all reactants dissolving, nitrogen atmosphere；The reaction was complete
After pour into beaker plus water and dichloro extraction organic phase, revolving remove dichloromethane, silicagel column purification, obtained product is denoted as
a1-OH；
4) by the product a1-COOH of step 2) and the product a1-OH of step 3) with 1:Two mouthfuls of reaction tubes are added in the molar ratio of 1-2
In, add EDC and DMAP, the molar ratio of EDC and a1-COOH are 1:1-2, the DMAP of catalyst equivalent, is then added dichloro
Methane is dissolved up to all reactants, reacts -48h for 24 hours at room temperature after being stirred evenly under nitrogen atmosphere；It is poured into after the reaction was complete
In beaker plus water and dichloro extract organic phase, and revolving removes dichloromethane, and silicagel column purification obtains described real based on photo-thermal induction
The azobenzene derivatives of existing solid-liquid transformation.
4. the preparation method according to claim 3 that the azobenzene derivatives for realizing solid-liquid transformation are induced based on photo-thermal,
It is characterized in that, described induced based on photo-thermal realizes that the molecular structural formula of the azobenzene derivatives of solid-liquid transformation is as follows：
5. the preparation method according to claim 4 that the azobenzene derivatives for realizing solid-liquid transformation are induced based on photo-thermal,
Be characterized in that, the structural formula of the azobenzene derivative COOH-AZO, bis-naphthol and gallicin from left to right according to
It is secondary to be：
6. described in claim 1 induced based on photo-thermal is realized that the azobenzene derivatives of solid-liquid transformation are used as with reversible
Photoswitch adhesive.
7. according to claim 6 realize that the azobenzene of solid-liquid transformation spreads out by described in claim 1 induced based on photo-thermal
Biology is used as having reversible photoswitch adhesive, which is characterized in that solid-state and the photoswitch adhesive for possessing bond properties
Under the irradiation of green light, the luminous energy of absorption can be changed into heat, the raising of temperature leads to azobenzene derivatives fuse itself and nothing
Bond properties；It places after temperature drops under fusing point at room temperature, the azobenzene derivatives of liquid are deposited in the form of solid again
, and possess bond properties.
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| CN114133925A (en) * | 2021-11-26 | 2022-03-04 | 北京京东方技术开发有限公司 | Quantum dot film layer, display device and preparation method of quantum dot film layer |
| CN114133925B (en) * | 2021-11-26 | 2024-02-02 | 北京京东方技术开发有限公司 | Quantum dot film, display device and preparation method of quantum dot film |
| CN114133547A (en) * | 2022-01-17 | 2022-03-04 | 江南大学 | Light-operated bonding-debonding underwater hyperbranched adhesive and preparation method and application thereof |
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