CN103467461A - Preparation of multi-stimulating responsive material containing thienyl maleimide by substitution reaction method - Google Patents
Preparation of multi-stimulating responsive material containing thienyl maleimide by substitution reaction method Download PDFInfo
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Abstract
The invention discloses a method for preparing a multi-stimulating responsive material by a substitution reaction method. The method comprises the following steps: carrying out a reaction on maleimide, a solvent N, N-dimethylformamide and a halogenating reagent to obtain 3, 4-dihalomaleimide; carrying out a reaction on 3, 4-dihalomaleimide, potassium carbonate, acetone and a halide, and extracting, drying and purifying to obtain N-substituent-3, 4-dihalomaleimide; carrying out a reaction on N-substituent-3, 4-dihalomaleimide, a bi(triphenyl phosphine) palladium chloride catalyst, N, N-dimethylformamide and 2-tributyl stannyl thiophene, and extracting, drying, filtering and purifying to obtain the N-substituent-3, 4-bi(2'-thienyl) maleimide multi-stimulating responsive material. The multi-stimulating responsive material is good in thermal stability, simple in synthetic step and high in solid fluorescence quantum efficiency, has piezallochromic, thermochromic and gasochromic properties, and can be used for organic light emitting diodes, organic light emitting field effect transistors, organic solid lasers and fluorescence sensors.
Description
Technical field
The present invention relates to the method for the standby multiple stimulation responsive materials of a kind of substitution reaction legal system, particularly contain multiple stimulation responsive materials of thienyl maleimide and preparation method thereof.
Background technology
In recent years, the organic solid fluorescent material has very large application potential in having photoelectric functional material due to it, has attracted interest (Yang Shuaijun, organic solid fluorescent material progress, 2013 of Many researchers; Anthony, ChemPlusChem, 2012,77,518).Along with going deep into of people research, find that some material can only change intermolecular interaction and saboteur's structure not, realize different responses under can externally stimulating.Wherein, stimuli responsive fluorescence transition material (gas-discoloration, thermochromism and piezochromic material) is for the exploitation of information storage, optical recording and sensor significant (Kishimura, Nat. Mater., 2005,4,546; Hirata, Adv. Mater., 2006,18,2725; Pucci, J. Mater. Chem., 2007,17,783).
The piezallochromy phenomenon refers to that the fluorescence color of material can change along with the variation of ambient pressure. the behavior of piezallochromy can be both on physical structure can be also the change on chemical structure; although be to change the most general method of fluorescent emission by changing molecular structure of chemistry at present; but this method can not obtain high-level efficiency and can repeat the solid fluorescence material (Chung of switching; J. Am. Chem. Soc.; 2009; 131,8163; Davis, Nature, 2009,459,68).The piezallochromy fluorescent material that change on physical structure causes is a kind of in the situation that do not change the chemical structure of ingredient; thereby the stacked structure that stimulates to change molecule by power is realized the intelligent material (Sagara that the fluorescent material glow color changes; Nat. Chem.; 2009; 1,605; Chi, Chem. Soc. Rev., 2012,41,3878), a kind of piezallochromy phenomenon of Harima seminar recent findings, its generation is that the accumulation mode due to molecule is changed (Ooyama, Eur. J. Org. Chem., 2009 that cause in process of lapping to amorphous state by initial crystal habit, 31,5221).High-resolution fluorescence records need to have very large variation on fluorescence intensity; owing on molecular level, piezallochromy mechanism people being lacked to sufficient understanding; up to the present also only have a small amount of several materials to be in the news and there is switchable piezallochromy character (Chung; J. Chem. Soc.; 2009; 131,8163; Luo, Adv. Mater., 2011,23,3261; Luo, Chem. Eur. J., 2011,17,10515).
Thermochromism be solid by heat treated after the phenomenon that changes of fluorescence, be generally to be transformed into the Thermodynamically stable state by the thermodynamic instability state.Within 2005, the people such as Mutai have reported that first case is due to the accumulation mode difference, and cause the visibly different phenomenon of solid fluorescence (Mutai, Nature Materials. 2005,4,685), they find that simple terpyridyl has variform, in unsetting and needle-like crystal, fluorescence is very weak, but very strong fluorescence is arranged in tabular crystal, and research shows that needle-like crystal keeps cool to room temperature after 10 min to form tabular crystal under 89 ℃, and fluorescence increases can be by force.After tabular crystal is warmed up to 100 ℃, rapid cool to room temperature, form needle-like crystal, and fluorescence disappears.Within 2009, two kinds of synthetic anilss with trifluoromethyl of Wang Yue seminar have thermal discoloration property (Wang, Adv. Mater., 2009,21,3165).In these two compounds due to amino existence, phenyl ring can rotate freely, make molecule conception can the variation, so they have two to three stable accumulation mode, the fluorescence difference of each accumulation mode, after can and melting by heating between accumulation mode, cooling method transforms mutually.
Gas-discoloration comprises three kinds of patterns, a kind of fluorescence molecule that is the solvent gas molecule promotes is piled up the transformation to steady state by unsteady state, a kind of is that gas molecule is inserted in the lattice of fluorescence molecule, change the accumulation mode of fluorescence molecule, also having a kind of is to change optical property (Zhang, J. Mater. Chem., 2012 of fluorescence molecule by chemical reaction, 22,11427).Wherein, solvent promotes that the pattern changed mutually is topmost gas-discoloration pattern (Heng, Langmuir, 2008,24,2157; Kumar M, Chem.-Eur. J., 2011,17,11102).
The aryl maleimide, owing to can sending strong fluorescence and having high luminous efficiency, has been subject to many concern (Kaletas, J. Phys. Chem. A, 2005,109,6440 of people in recent years; Yeh, Chem. Mater., 2006,18,832).These serial compounds are found in natural goods the earliest, have good biological activity, but owing in laboratory, can easily synthesizing and obtain.Therefore they are widely used in medicine and Organic Light Emitting Diode (OLED) (Nishizuka, Nature, 1984,308,693; Mahboobi, J. Org. Chem., 1999,64,4697; Chow, Synth. Met., 2005,149,59; Chan, Macromolecules, 2006,39,3262).Thiophene is the group that a class has photoelectric activity, because containing lone-pair electron, sulphur atom make it can become a good electron-donating group (to body), therefore at 3 of the maleimide (acceptor) of electron deficiency, No. 4 thienyl group is introduced in position, can in molecule, form strong dipole-dipole interaction, shift (ICT) thereby contribute to form intramolecular charge, thereby the electronic effect of this donor-receiver type structure easily changes under extraneous stimulation and causes the variation of fluorescence.
Summary of the invention
The method that the purpose of this invention is to provide the multiple stimulation responsive materials of the standby thienyl-containing maleimide of a kind of substitution reaction legal system.The thienyl group that is about to have electron donation is incorporated on 3, No. 4 positions of maleimide.Utilize thienyl group to shift and luminous to the intramolecular charge of maleimide base group, this luminosity can change and change along with conformation and the intermolecular hydrogen bonding effect of thienyl group simultaneously, therefore, pass through outside stimulus, as heat, pressure and solvent vapo(u)r change the physical structure of material, thus the conversion of the fluorescence intensity of realization or color.
The multiple stimulation responsive materials of the thienyl-containing maleimide that a kind of substitution reaction legal system is standby has following chemical structure:
R=CH wherein
2c
6h
5, CH
2c
6f
5or C
nh
2n+1(n=1,2,4,6,8,10,12).
The uv-absorption maximum wavelength of multiple stimulation responsive materials in methylene dichloride is 300 ~ 500 nm, and maximum emission wavelength is 500 ~ 700 nm, and quantum yield is 0.1 ~ 0.8.
The concrete preparation method of multiple stimulation responsive materials of the present invention is as follows:
1) 3, the preparation of 4-dihalo-maleimide:
Maleimide is placed in to a reaction under high pressure bottle, adds DMF, then add halide reagent, seal the bottleneck of reaction under high pressure bottle, be heated to 58 ℃, gradually there is faint yellow solid to produce, total coreaction 48 ~ 72 hours, stop adding heat drop and return room temperature, successively uses 5 times of N, the water of dinethylformamide volume and 3 times of N, the methylene dichloride air exhaust filtering of dinethylformamide volume, obtain 3,4-dihalo-maleimide standby.
In above-mentioned reactant, Ma Lai Xian Ya An ︰ Luization Shi Ji ︰ DMF is 4 mmol ︰ 8～16mmol ︰ 2～3ml;
Described halide reagent is selected from thionyl chloride or bromine.
2) N-substituting group-3, the preparation of 4-dihalo-maleimide:
Get prepared by step 1) 3,4-dihalo-maleimide is placed in round-bottomed flask, adds salt of wormwood and acetone, stirring at room 30 minutes, solution colour is progressively deepened, then adds halides, at room temperature continues to stir 24 hours, stopped reaction, the mixed solution that adds the saturated aqueous common salt by the ethyl acetate of 3 times of acetone volumes and 3 times of acetone volumes to form is extracted, and uses dried over mgso, adopts column chromatography purification, obtain N-substituting group-3,4-dihalo-maleimide is standby.
Wherein 3,4-dihalo-maleimide: Tan Suan Jia ︰ Bing Tong ︰ halides is 1 mmol ︰ 1 ~ 3 mmol ︰ 4～5ml ︰ 1 ~ 3 mmol;
Described halides is selected from CH
3i, C
6h
5cH
2br, C
6f
5cH
2br or C
nh
2n+1br (n=2,4,6,8,10,12);
3) N-substituting group-3, the preparation of 4-bis-(2 '-thienyl) maleimide:
By step 2) the N-substituting group-3 for preparing, 4-dihalo-maleimide and bi triphenyl phosphorus palladium chloride catalyzer are put into the twoport flask, vacuumize, pour into nitrogen, after triplicate is taken out filling, inject 2-tributyl stannyl thiophene and anhydrous N with syringe, dinethylformamide, after being warming up to 100 ℃, reaction is 12 hours, to be cooledly after room temperature, add by 5 times of N, the methylene dichloride of dinethylformamide volume and 5 times of N, the mixed solution that the saturated potassium fluoride aqueous solution of dinethylformamide volume forms, repeatedly extract 5 times, the organic layer that merges each extraction, use anhydrous magnesium sulfate drying, filter, through column chromatography purification, obtain N-substituting group-3, 4-bis-(2 '-thienyl) maleimide, it is multiple stimulation responsive materials of the present invention.
N-substituting group-3 wherein, 4-dihalo-horse carrys out the inferior amine ︰ of acyl bi triphenyl phosphorus dichloride palladium catalyst ︰ N, and N-bis-methyl first acyl amine ︰ 2-tributyl stannyl thiophene are 2 mmol ︰ 0.005 ~ 0.05 mmol ︰ 10 ml ︰ 4 ~ 12 mmol.
Described substituting group refers to CH
2c
6h
5, CH
2c
6f
5or C
nh
2n+1(n=1,2,4,6,8,10,12).
Multiple stimulation responsive materials prepared by the present invention, the uv-absorption maximum wavelength in methylene dichloride is 300 ~ 500 nm, and maximum emission wavelength is 500 ~ 700 nm, and quantum yield is 0.1 ~ 0.8.
Multiple stimulation responsive materials of the present invention has that Heat stability is good, synthesis step are simple, solid state fluorescence quantum yield advantages of higher, and has the character such as piezallochromy, thermochromism and gas-discoloration.The fluorescent optical sensor that it can be used for Organic Light Emitting Diode, organic light-emitting field effect transistor, organic solid laser apparatus and various outside stimuluss are responded, such as pressure, temperature, solvent vapo(u)r etc.
The accompanying drawing explanation
Fig. 1 is the chemical structural formula of the multiple stimulation responsive materials of thienyl-containing maleimide of the present invention.
Fig. 2 is the N-PFBBR-3 of the embodiment of the present invention 1 preparation, 4-bis-(2 '-thienyl) maleimide multiple stimulation responsive materials chemical structural formula.
Fig. 3 is the N-PFBBR-3 of the embodiment of the present invention 1 preparation, the response under the fluorescent emission wavelength of 4-bis-(2 '-thienyl) maleimide externally stimulates.
Embodiment
In Fig. 1, R=CH
2c
6h
5, CH
2c
6f
5or C
nh
2n+1(n=1,2,4,6,8,10,12).
In Fig. 3, N-PFBBR-3, the variation of 4-bis-(2 '-thienyl) maleimide maximum emission wavelength under the stimulation of pressure and acetone steam.As can be seen from the figure, N-PFBBR-3,4-bis-(2 '-thienyl) maleimide has shown that under pressure and acetone steam condition good piezallochromy and vapour cause color changeable effect, and can be repeatedly.
Following embodiment further illustrates of the present invention, rather than limits the scope of the invention.
Embodiment 1
1) 3, the preparation of 4-dibromo-maleimide:
The maleimide of 3.88 g (40 mmol) is placed in to a reaction under high pressure bottle, the DMF that adds 20 ml, then add the bromine (93 mmol) of 4.77 ml, seal the bottleneck of reaction under high pressure bottle, be heated to 58 ℃, gradually have faint yellow solid to produce, while reacting 48 hours, stop adding heat drop and return room temperature, successively, with water and the 60 ml methylene dichloride air exhaust filterings of 100 ml, obtain 3,4-dibromo-maleimide;
2) N-PFBBR-3, the preparation of 4-dibromo-maleimide:
Get 3 of 1.27 g, 4-dibromo-maleimide (5 mmol) is placed in round-bottomed flask, add the salt of wormwood (5 mmol) of 0.69 g and the acetone of 20ml, stirring at room 30 minutes, solution colour is progressively deepened, the PFBBR bromine of 1.31 g that add again (5 mmol), at room temperature continue to stir 24 hours, stopped reaction, the mixed solution that adds the saturated aqueous common salt by the ethyl acetate of 60ml and 60ml to form is extracted, and uses dried over mgso, adopts column chromatography purification, obtain N-PFBBR-3, the 4-dibromo-maleimide;
3) N-PFBBR-3, the preparation of 4-bis-(2 '-thienyl) maleimide:
N-PFBBR-3 by 0.86 g, the bi triphenyl phosphorus palladium chloride catalyzer (0.01 mmol) of 4-dibromo-maleimide (2 mmol) and 7.02 mg is put into the twoport flask of 25 ml, vacuumize, pour into nitrogen, after triplicate is taken out filling, inject the 2-tributyl stannyl thiophene (4 mmol) of 1.27 ml and the N of 10 ml with syringe, dinethylformamide, be warming up to 100 ℃, react 12 hours, the mixed solution that adds after cooling the saturated potassium fluoride aqueous solution by the methylene dichloride of 50 ml and 50ml to form, repeatedly extract 5 times, the organic layer that merges each extraction, use anhydrous magnesium sulfate drying, filter, through column chromatography purification, can obtain N-PFBBR-3, 4-bis-(2 '-thienyl) maleimide multiple stimulation responsive materials.Its structural formula as shown in Figure 2.
N-PFBBR-3 prepared by the present embodiment, the uv-absorption maximum wavelength of 4-bis-(2 '-thienyl) maleimide multiple stimulation responsive materials in methylene dichloride is 450 nm, and maximum emission wavelength is 590 nm, and quantum yield is 0.52.
By the N-PFBBR-3 of the present invention's preparation, the variation of 4-bis-(2 '-thienyl) maleimide maximum emission wavelength under pressure and acetone steam stimulation, as shown in Figure 3.As can be seen from the figure, N-PFBBR-3,4-bis-(2 '-thienyl) maleimide has shown the gentle color changeable effect that causes of good piezallochromy under pressure and solvent vapo(u)r, and can be repeatedly.
Embodiment 2:
1) 3, the preparation of 4-dibromo-maleimide:
The maleimide of 3.88 g (40 mmol) is placed in to a reaction under high pressure bottle, the DMF that adds 20 ml, then add the thionyl chloride (90 mmol) of 6.39 ml, seal the bottleneck of reaction under high pressure bottle, be heated to 58 ℃, gradually have faint yellow solid to produce, while reacting 72 hours, stop adding heat drop and return room temperature, successively, with the water of 100ml and the methylene dichloride air exhaust filtering of 60ml, obtain 3,4-dibromo-maleimide;
2) N-benzyl-3, the preparation of 4-dibromo-maleimide:
Get 3 of 1.27 g, 4-dibromo-maleimide (5 mmol) is placed in round-bottomed flask, add the salt of wormwood (7.5 mmol) of 1.04 g and the acetone of 20ml, stirring at room 30 minutes, solution colour is progressively deepened, the bromotoluene of 0.59 ml added again (5 mmol), at room temperature continue to stir 24 hours, stopped reaction, the mixed solution that adds the saturated aqueous common salt by the ethyl acetate of 60ml and 60ml to form is extracted, and uses dried over mgso, adopts column chromatography purification, obtain N-benzyl-3, the 4-dibromo-maleimide;
3) N-benzyl-3, the preparation of 4-bis-(2 '-thienyl) maleimide:
N-benzyl-3 by 0.69 g, the bi triphenyl phosphorus palladium chloride catalyzer (0.03 mmol) of 4-dibromo-maleimide (2 mmol) and 21.06 mg is put into the twoport flask of 25 ml, vacuumize, pour into nitrogen, after triplicate is taken out filling, inject the 2-tributyl stannyl thiophene (12 mmol) of 3.81 ml and the anhydrous N of 10 ml with syringe, dinethylformamide, be warming up to 100 ℃, react 12 hours, the mixed solution that adds after cooling the saturated potassium fluoride aqueous solution by the methylene dichloride of 50ml and 50ml to form extracts 5 times repeatedly, the organic layer that merges each extraction, use anhydrous magnesium sulfate drying, filter, through column chromatography purification, can obtain N-benzyl-3, 4-bis-(2 '-thienyl) maleimide multiple stimulation responsive materials.Its uv-absorption maximum wavelength in methylene dichloride is 448 nm, and maximum emission wavelength is 585 nm, and quantum yield is 0.58.
Embodiment 3:
1) 3, the preparation of 4-dibromo-maleimide:
The maleimide of 3.88 g (40 mmol) is placed in to a reaction under high pressure bottle, the DMF that adds 25 ml, then add the bromine (85 mmol) of 4.36 ml, seal the bottleneck of reaction under high pressure bottle, be heated to 58 ℃, gradually have faint yellow solid to produce, while reacting 72 hours, stop adding heat drop and return room temperature, add the water of 125ml and the methylene dichloride air exhaust filtering of 75ml, obtain 3,4-dibromo-maleimide;
2) N-methyl-3, the preparation of 4-dibromo-maleimide:
Get 3 of 1.27 g, 4-dibromo-maleimide (5 mmol) is placed in round-bottomed flask, add the salt of wormwood (10 mmol) of 1.31 g and the acetone of 25ml, stirring at room 30 minutes, solution colour is progressively deepened, the methyl iodide of 0.44 ml added again (7 mmol), at room temperature continue to stir 24 hours, stopped reaction, the mixed solution that adds the saturated aqueous common salt by the ethyl acetate of 75ml and 75ml to form is extracted, and uses dried over mgso, adopts column chromatography purification, obtain N-methyl-3, the 4-dibromo-maleimide;
3) N-methyl-3, the preparation of 4-bis-(2 '-thienyl) maleimide:
N-methyl-3 by 0.54 g, the bi triphenyl phosphorus palladium chloride catalyzer (0.07 mmol) of 4-dibromo-maleimide (2 mmol) and 49.14 mg is put into the twoport flask of 25 ml, vacuumize, pour into nitrogen, after triplicate is taken out filling, inject the 2-tributyl stannyl thiophene (9 mmol) of 2.86 ml and the anhydrous N of 10 ml with syringe, dinethylformamide, be warming up to 100 ℃, react 12 hours, the mixed solution that adds after cooling the saturated potassium fluoride aqueous solution by the methylene dichloride of 50ml and 50ml to form, repeatedly extract 5 times, the organic layer that merges each extraction, use anhydrous magnesium sulfate drying, filter, through column chromatography purification, can obtain N-methyl-3, 4-bis-(2 '-thienyl) maleimide multiple stimulation responsive materials.Its uv-absorption maximum wavelength in methylene dichloride is 450 nm, and maximum emission wavelength is 595 nm, and quantum yield is 0.78.
Claims (6)
1. the multiple stimulation responsive materials of the standby thienyl-containing maleimide of a substitution reaction legal system, its chemical structural formula is as follows:
Wherein: R=CH
2c
6h
5, CH
2c
6f
5or C
nh
2n+1(n=1,2,4,6,8,10,12).
2. the preparation method of the multiple stimulation responsive materials of the standby thienyl-containing maleimide of a substitution reaction legal system is characterized in that the preparation method is as follows:
1) 3, the preparation of 4-dihalo-maleimide:
Maleimide is placed in to a reaction under high pressure bottle, adds DMF, then add halide reagent, seal the bottleneck of reaction under high pressure bottle, be heated to 58 ℃, gradually there is faint yellow solid to produce, react 48 ~ 72 hours, stop adding heat drop and return room temperature, successively use 5 times of N, the water of dinethylformamide volume and 3 times of N, the methylene dichloride air exhaust filtering of dinethylformamide volume, obtain 3,4-dihalo-maleimide standby;
2) N-substituting group-3, the preparation of 4-dihalo-maleimide:
Get prepared by step 1) 3,4-dihalo-maleimide is placed in round-bottomed flask, adds salt of wormwood and acetone, stirring at room 30 minutes, solution colour is progressively deepened, then adds halides, at room temperature continues to stir 24 hours, stopped reaction, the mixed solution that adds the saturated aqueous common salt by the ethyl acetate of 3 times of acetone volumes and 3 times of acetone volumes to form is extracted, and uses dried over mgso, adopts column chromatography purification, obtain N-substituting group-3,4-dihalo-maleimide is standby;
3) N-substituting group-3, the preparation of 4-bis-(2 '-thienyl) maleimide
By step 2) the N-substituting group-3 for preparing, 4-dihalo-maleimide and bi triphenyl phosphorus palladium chloride catalyzer are put into the twoport flask, vacuumize, pour into nitrogen, after triplicate is taken out filling, inject 2-tributyl stannyl thiophene and anhydrous N with syringe, dinethylformamide, after being warming up to 100 ℃, reaction is 12 hours, to be cooledly after room temperature, add by 5 times of N, the methylene dichloride of dinethylformamide volume and 5 times of N, the mixed solution that the saturated potassium fluoride aqueous solution of dinethylformamide volume forms, repeatedly extract 5 times, merge organic layer, use anhydrous magnesium sulfate drying, filter, through column chromatography purification, obtain N-substituting group-3, 4-bis-(2 '-thienyl) maleimide.
3. a kind of substitution reaction legal system according to claim 2 is for the preparation method of the multiple stimulation responsive materials of thienyl-containing maleimide, it is characterized in that maleimide in step 1): halide reagent: DMF is 4 mmol:8～16mmol:2～3ml.
4. the preparation method of the multiple stimulation responsive materials of the standby thienyl-containing maleimide of a kind of substitution reaction legal system according to claim 2, is characterized in that described halide reagent is selected from thionyl chloride or bromine.
5. a kind of substitution reaction legal system according to claim 2 is for the preparation method of the multiple stimulation responsive materials of thienyl-containing maleimide, it is characterized in that step 2) in 3,4-dihalo-maleimide: salt of wormwood: acetone: halides is 1 mmol:1 ~ 3 mmol:4～5ml:1 ~ 3 mmol.
6. the preparation method of the multiple stimulation responsive materials of the standby thienyl-containing maleimide of a kind of substitution reaction legal system according to claim 2, is characterized in that described halides is selected from CH
3i, C
6h
5cH
2br, C
6f
5cH
2br or C
nh
2n+1br (n=2,4,6,8,10,12).
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| CN101812097A (en) * | 2010-04-17 | 2010-08-25 | 中国海洋大学 | Indole carbazole and bisindole maleimide alkaloid and its production and application |
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| CN109503814A (en) * | 2018-11-05 | 2019-03-22 | 福建师范大学 | One kind having photoactive electricity storage polymer and preparation method thereof |
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Application publication date: 20131225 |