CN104016868B - 2,4,6-chloride trinitro--1,3-diphenylethyllene benzene derivatives, preparation and application thereof - Google Patents

2,4,6-chloride trinitro--1,3-diphenylethyllene benzene derivatives, preparation and application thereof Download PDF

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CN104016868B
CN104016868B CN201410133037.1A CN201410133037A CN104016868B CN 104016868 B CN104016868 B CN 104016868B CN 201410133037 A CN201410133037 A CN 201410133037A CN 104016868 B CN104016868 B CN 104016868B
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chlorobenzaldehyde
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CN104016868A (en
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彭新华
徐俊辉
魏建平
李芳美
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Nanjing University of Science and Technology
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Abstract

The invention discloses a kind of 2,4,6-trinitro--1,3-diphenylethyllene benzene derivatives containing chlorine substituent, preparation and application thereof.The chemical structure characteristic of this compounds is: on the middle phenyl ring of 1,3-diphenylethyllene benzene 2,4, and 6 have three nitros, and neighbour on the phenyl ring of both sides, contraposition is connected with chlorine atom, or is connected with chlorine atom at ortho para simultaneously.From nuclear magnetic spectrogram, the coupling constant of toluylene double bond is approximately 16.0Hz, confirms as transconfiguration.This compounds is under catalytic condition, and by Microwave-assisted synthesis, preparation technology is simple, solvent-free, fast, and green safety.Potentially can be used in luminescent device and energetic material field.

Description

2,4,6-chloride trinitro--1,3-diphenylethyllene benzene derivatives, preparation and application thereof
Technical field
The invention belongs to energetic material and organic light emission field, be specifically related to a kind of 2,4,6-trinitro--1,3-diphenylethyllene benzene derivatives containing chlorine substituent, preparation and application thereof.
Background technology
The double bond existed in diphenylethylene compounds structure and the conjugative effect of phenyl ring, make such compound chemistry Nature comparison stablize.Many nitros stilbenes compound is the very important chemical intermediate of one, can be widely used in the field of nonlinear optics and the heat-resisting energetic material of high energy.Such as it can be used for synthesizing new part for nonlinear optical material and the high temperature powder being used as military and civilian.Wherein, performance significant picryl sulfide base ethene (HNS) belongs to the one in many nitros stilbenes compound, it is yellow crystals, and fusing point, up to 317 DEG C, is a kind of high temperature powder, there is good physics, chemical stability, mechanical sensitivity is low, insensitive to static sparking, and radiation resistance is strong, by being first made up of Swede K.G.Shipp the sixties in last century, being widely used in the field such as oilfield exploitation and aerospace.
Document (G.X.Wang, C.H.Shi, X.D.Gong, H.M.Xiao, J.Phys.Chem.A2009,113,1318) performance such as structure, density, detonation parameter of many nitro toluylenes derivative by theoretical research, such material exhibits goes out very strong applicability.Document (Z.G.FengandB.R.Chen, Prop., Explos., Pyrotech., 1991,16,12; Z.G.FengandB.R.Chen, Prop., Explos., Pyrotech.1992,17,237; L.Q.Wang, Y.H.Liu, J.G.Zhang, T.L.Zhang, L.Yang, X.J.Qiao, X.C.HuandJ.Y.Guo, Chin.J.Chem.2007,25,1044) also to report and synthesized the compound of a series of many nitro toluylenes, such compounds property is superior, simultaneously owing to having double bond, whole molecular system has stronger conjugative effect, thus can promote the fusing point of this compounds, i.e. resistance toheat.Chlorine atom in 2,4,6-wherein chloride trinitro--1,3-diphenylethyllene benzene derivatives can be transformed into other functional group (-NH as active function groups 2,-N 3,-NO 2deng) or be connected with other structural unit; Document (A.Kvaran, A.E. , C.Evans, J.K.F.Geirsson, J.Mol.Struct.2000,553,79 – 90) also inquire into relation between the photochemistry of similar structures and structure.So there is extremely important status in the synthesis of the compound building many nitros diphenylethlene class novel under other conjugated system.
Microwave reaction is promoting that the research in organic reaction has become a focus of organic chemistry filed, a large amount of experimental studies shows, organic reaction is carried out by microwave technology, the fast decades of times of the heating means that speed of response is more traditional even thousands of times, and have easy and simple to handle, productive rate is high and the feature such as easy purification of products, safety, therefore, microwave organic reaction development rapidly.Some documents are had to relate in pyrroles's catalysis by synthesizing diphenyl ethylene derivatives under microwave condition.(K.M.Poulsen, T.Reenberg, T. andJ.B.Christensen, Synth.Commun.2004,34,2215; S.SaravananandP.C.Srinivasan, Synth.Commun.2001,31,823) but, many nitro compounds have certain explosivity, directly under microwave-excitation, temperature is wayward, is easy to the decomposition causing compound, has potential danger.
Summary of the invention
The object of this invention is to provide 2,4,6-trinitro--1, the 3-diphenylethyllene benzene derivatives that a class contains chlorine substituent, and provide the microwave assisted synthesizing method of this compound, this compound potentially can apply to luminescent device and energetic material field.
Realizing the object of the invention technical scheme is:
A kind of 2,4,6-chloride trinitro--1,3-diphenylethyllene benzene derivatives, is characterized in that its chemical structural formula of this compound is:
Wherein in molecular structure, on the middle phenyl ring of 1,3-diphenylethyllene benzene 2,4,6 have three nitros, and neighbour on the phenyl ring of both sides, contraposition is connected with chlorine atom, namely R 1, R 2, R 3in have one be connected with chlorine atom other for hydrogen, or R 1, R 3be chlorine atom simultaneously, R 2for hydrogen atom.
The preparation method of above-mentioned 2,4,6-trinitro--1, the 3-diphenylethyllene benzene derivatives containing chlorine substituent, is characterized in that comprising following reaction formula and step:
By 2,4,6-trinitro-m-xylene and Chlorobenzaldehyde mixed dissolution in organic solvent, add basic catalyst and carrier, raw material and basic catalyst uniform loading are on carrier, except desolventizing under normal pressure, obtain the solid mixture of load raw material, then this solid mixture is transferred in microwave reactor, react under certain output rating, reaction terminates rear acetone extraction product, then removes acetone and obtain crude product, and crude product obtains target product after recrystallization.Wherein, Chlorobenzaldehyde selects o-chlorobenzaldehyde, m chlorobenzaldehyde, 4-chloro-benzaldehyde and 2,4 dichloro benzene formaldehyde.
Wherein, one or more in N methyl piperazine, morpholine, triethylamine, pyridine, piperidines selected by the alkaline catalysts added.
In reaction, the mol ratio of 2,4,6-trinitro-m-xylenes and Chlorobenzaldehyde is 1:2.1, and the reaction times is 15min.
In reaction, carrier selects silica gel, NaOH, KOH, K 2cO 3in one (NaOH, KOH, K 2cO 3for pressed powder).
In reaction, the output rating of microwave is set to 300-400W.
Organic solvent selects methylene dichloride, and recrystallization solvent selects acetone-ethanol mixed solvent.
The application of above-mentioned 2,4,6-trinitro--1, the 3-diphenylethyllene benzene derivatives containing chlorine substituent, the type compound can be used in optical material field, as nonlinear optical organic, photosensitizers etc. or the important intermediate as energetic material field.
The present invention compared with prior art, its remarkable advantage is: (1) synthesis is containing 2 of chlorine substituent, 4,6-trinitro--1,3-diphenylethyllene benzene derivative, the compound of the type has the structure type of typical D-π-A-π-D system, and (wherein D represents supplied for electronic group, π represents electronic bridge, and be double bond in structure, A represents electron acceptor(EA), i.e. electron-withdrawing group), this kind of structure type is conducive to the transmission of electronics.From ultraviolet-visible light spectrum analysis, this analog derivative absorption bands is wide, and absorbing wavelength, near ultraviolet and visible region, embodies good optical characteristics; (2) synthesize this compounds by traditional method and need long time (reaching 48h), cause loss and the waste of time of the energy like this; And adopt microwave reaction only to need 15min just can reach comparatively ideal productive rate.(3) many nitro-compounds have certain danger, directly synthesize under the condition of microwave-excitation, easily form too high raw material or the product of making of local temperature and decompose.And adopt inexpensive callable silica gel to carry out load, raw material or product dispersion can be made, make whole reaction system safer.(4) need to use benzene or toluene as solvent and azeotropic agent by traditional method, benzene, to bad environmental, does not meet the requirement of Green Chemistry, and adopts novel method of the present invention to synthesize, and avoids using solvent, forms solvent-free system.
Accompanying drawing explanation
Fig. 1 is the hydrogen nuclear magnetic spectrum of product 2,4,6-trinitro--1,3-bis-(4 '-chloro-styrene base) benzene in example 1 of the present invention, and X-coordinate is chemical shift.
Fig. 2 is the hydrogen nuclear magnetic spectrum of product 2,4,6-trinitro--1,3-bis-(2 '-chloro-styrene base) benzene in example 2 of the present invention, and X-coordinate is chemical shift.
Fig. 3 is the hydrogen nuclear magnetic spectrum of product 2,4,6-trinitro--1,3-bis-(2 ', 4 '-dichlorostyrene base) benzene in the embodiment of the present invention 3, and X-coordinate is chemical shift.
Fig. 4 is the relation curve of product 2,4,6-trinitro--1,3-bis-(4 '-chloro-styrene base) benzene absorbancy and wavelength in trichloromethane in the embodiment of the present invention 6.
Embodiment
Below in conjunction with drawings and Examples, the present invention is described in further detail.
Embodiment 1:
2,4,6-trinitro--1,3-bis-(4 '-chloro-styrene base) benzene (R 1, R 2for hydrogen atom, R 3for chlorine atom) Microwave synthesize:
By 2,4,6-trinitro-m-xylene 0.48g (2.0mmol) and 4-chloro-benzaldehyde 0.59g(4.2mmol) mixed dissolution is in 20mL methylene dichloride, drip piperidines 0.08g (0.9mmol) and carrier silica gel (3.0g), raw material and basic catalyst uniform loading are on carrier, except desolventizing under normal pressure, obtain the solid mixture of load raw material, after mixing, the solid transfer obtained uncoveredly is placed in microwave reactor to Pyrex reaction flask, and under 300W power, microwave took out after 15 minutes.Reaction terminates rear acetone extraction product, then removes acetone and obtain crude product, finally uses the mixed solvent recrystallization of acetone and ethanol.Obtain target compound (0.75g), productive rate 77%.
Yellow crystals, fusing point: 158-160 DEG C, IR (ν, cm -1): 3094,1634,1588,1543,1490,1333,972; 1hNMR (500MHz, CDCl 3), δ 8.76(s, 1H), 7.43-7.37 (m, 8H), 7.17 (d, J=16.60Hz, 2H), 6.84 (d, J=16.60Hz, 2H), 1.56 (s, H 2o); (as shown in Figure 1)
13cNMR (126MHz, CDCl3), δ 145.70,136.68,135.02,132.31,129.89,128.26,127.68,127.35,120.78,115.34. mass spectral molecular ion peak be: 485.029
Concrete reaction equation is as follows:
Embodiment 2:
2,4,6-trinitro--1,3-bis-(2 '-chloro-styrene base) benzene (R 2, R 3for hydrogen atom, R 1for chlorine atom) Microwave synthesize:
By 2,4,6-trinitro-m-xylene 0.48g (2.0mmol) and o-chlorobenzaldehyde 0.59g(4.2mmol) mixed dissolution is in 20mL methylene dichloride, drip piperidines 0.08g (0.9mmol) and carrier NaOH(3.0g), raw material and basic catalyst uniform loading are on carrier, except desolventizing under normal pressure, obtain the solid mixture of load raw material, after mixing, the solid transfer obtained uncoveredly is placed in microwave reactor to Pyrex reaction flask, and under 300W power, microwave took out after 15 minutes.Reaction terminates rear acetone extraction product, then removes acetone and obtain crude product, finally uses the mixed solvent recrystallization of acetone and ethanol.Obtain target compound (0.88g), productive rate 85.7%.
Yellow solid, fusing point: 167-168 DEG C, IR (ν, cm -1): 3098,1631,1602,1547,1473,1402,1347,979; 1hNMR (500MHz, CDCl 3), δ 8.82 (s, 1H), 7.66 – 7.64 (m, 2H); 7.42 – 7.40 (m, 2H), 7.33 – 7.32 (m, 4H), 7.29 (d; J=16.60Hz, 2H), 7.20 (d, J=16.60Hz, 2H); (as shown in Figure 2)
13cNMR (126MHz, CDCl 3), 151.01,145.83,134.10,133.32,132.25,130.22,129.83,129.03,126.40,126.27,120.80,117.58. mass spectral molecular ion peak is: 485.118
Concrete reaction equation is as follows:
Embodiment 3:
2,4,6-trinitro--1,3-bis-(2 ', 4 '-dichlorostyrene base) benzene (R 1, R 3for chlorine, R 2for hydrogen atom) Microwave synthesize:
By 2,4,6-trinitro-m-xylene 0.48g (2.0mmol) and 2,4-dichlorobenzaldehyde (0.70g, 4.2mmol) mixed dissolution is in 20mL methylene dichloride, drip morpholine and carrier salt of wormwood (3.0g), raw material and basic catalyst uniform loading are on carrier, except desolventizing under normal pressure, obtain the solid mixture of load raw material, after mixing, the solid transfer obtained uncoveredly is placed in microwave reactor to Pyrex reaction flask, and under 300W power, microwave took out after 15 minutes.Reaction terminates rear acetone extraction product, then removes acetone and obtain crude product, finally uses the mixed solvent recrystallization of acetone and ethanol.Obtain target compound (0.90g), productive rate 81.1%.
Yellow solid, fusing point: 166-167 DEG C, IR (ν, cm -1): 3095,1633,1545,1383,1339,976; 1hNMR (500MHz, CDCl 3), δ 8.81(s, 1H), 7.56 (d, J=2.00Hz, 2H), 7.50(d, J=8.40Hz, 2H), 7.32-7.30(dd, J 1=2.00Hz, J 2=8.40Hz, 2H), 7.19(d, J=16.55Hz, 2H), 6.77(d, J=16.55Hz, 2H) and, 1.56 (s, H 2o); (as shown in Figure 3)
13CNMR(126MHz,CDCl 3),δ150.74,145.80,135.30,133.69,133.10,132.40,129.98,129.66,128.11,125.46,120.94,116.71.
Mass spectral molecular ion peak is: 554.947
Concrete reaction equation is as follows:
Embodiment 4:
2,4,6-trinitro--1,3-bis-(3 '-dichlorostyrene base) benzene (R 1, R 3for hydrogen, R 2for chlorine atom) Microwave synthesize:
By 2,4,6-trinitro-m-xylene 0.48g (2.0mmol) and m chlorobenzaldehyde (0.59g, 4.2mmol) mixed dissolution, in 20mL methylene dichloride, drip piperidinyl-1 0 and carrier NaOH(3.0g), raw material and basic catalyst uniform loading are on carrier, except desolventizing under normal pressure, obtain the solid mixture of load raw material, after mixing, the solid transfer obtained uncoveredly is placed in microwave reactor to Pyrex reaction flask, and under 300W power, microwave took out after 15 minutes.Reaction terminates rear acetone extraction product, then removes acetone and obtain crude product, finally uses the mixed solvent recrystallization of acetone and ethanol.Obtain target compound (0.89g), productive rate 86.1%.
Yellow solid, fusing point: 142-143 DEG C, IR (ν, cm -1): 3093,1628,1535,1373,1329,966.
Concrete reaction equation is as follows:
Embodiment 5:
By 1x10 -52,4,6-trinitro--1,3-bis-(the 4 '-chloro-styrene base) benzene (R of mol/L 1, R 2for hydrogen atom, R 3for chlorine) be dissolved in trichloromethane, measure its ultraviolet-visible absorption spectroscopy.(as shown in Figure 4), upper as can be seen from figure, this material has obvious absorption peak near 340nm, and absorption region is wider, has good optical property.
Embodiment 6:
By 2,4,6-trinitro-m-xylene 0.48g (2.0mmol) and o-chlorobenzaldehyde 0.59g(4.2mmol) mixed dissolution is in 20mL methylene dichloride, drip N methyl piperazine (10) and carrier NaOH(3.0g), raw material and basic catalyst uniform loading are on carrier, except desolventizing under normal pressure, obtain the solid mixture of load raw material, after mixing, the solid transfer obtained uncoveredly is placed in microwave reactor to Pyrex reaction flask, and under 300W power, microwave took out after 15 minutes.Reaction terminates rear acetone extraction product, then removes acetone and obtain crude product, finally uses the mixed solvent recrystallization of acetone and ethanol.Obtain target compound (0.80g), productive rate 81.7%.
Embodiment 7:
By 2,4,6-trinitro-m-xylene 0.48g (2.0mmol) and 4-chloro-benzaldehyde 0.59g(4.2mmol) mixed dissolution is in 20mL methylene dichloride, drip piperidines 0.08g (0.9mmol) and carrier KOH(3.0g), raw material and basic catalyst uniform loading are on carrier, except desolventizing under normal pressure, obtain the solid mixture of load raw material, after mixing, the solid transfer obtained uncoveredly is placed in microwave reactor to Pyrex reaction flask, and under 300W power, microwave took out after 15 minutes.Reaction terminates rear acetone extraction product, then removes acetone and obtain crude product, finally uses the mixed solvent recrystallization of acetone and ethanol.Obtain target compound (0.70g), productive rate 73%.
Embodiment 8:
By 2,4,6-trinitro-m-xylene 0.48g (2.0mmol) and 4-chloro-benzaldehyde 0.59g(4.2mmol) mixed dissolution is in 20mL methylene dichloride, drip triethylamine 10 and carrier KOH(3.0g), raw material and basic catalyst uniform loading, on carrier, remove desolventizing under normal pressure, obtain the solid mixture of load raw material, after mixing, the solid transfer obtained uncoveredly is placed in microwave reactor to Pyrex reaction flask, and under 300W power, microwave took out after 15 minutes.Reaction terminates rear acetone extraction product, then removes acetone and obtain crude product, finally uses the mixed solvent recrystallization of acetone and ethanol.Obtain target compound (0.73g), productive rate 75%.
Embodiment 9:
By 2,4,6-trinitro-m-xylene 0.48g (2.0mmol) and o-chlorobenzaldehyde 0.59g(4.2mmol) mixed dissolution is in 20mL methylene dichloride, drip triethylamine 10 and carrier KOH(3.0g), raw material and basic catalyst uniform loading, on carrier, remove desolventizing under normal pressure, obtain the solid mixture of load raw material, after mixing, the solid transfer obtained uncoveredly is placed in microwave reactor to Pyrex reaction flask, and under 400W power, microwave took out after 15 minutes.Reaction terminates rear acetone extraction product, then removes acetone and obtain crude product, finally uses the mixed solvent recrystallization of acetone and ethanol.Obtain target compound (0.68g), productive rate 66%.
Comparative example 1
This compounds adopts traditional Aldol-type condensation reaction to synthesize 2 usually, 4,6-trinitro--1,3-diphenylethyllene benzene derivative is with 2,4,6-trinitro-m-xylene and various substituted benzaldehyde are raw material, with benzene as solvent, organic base catalytic, reaction is prepared for 48 hours at a reflux temperature.(see Org.Prep.Proced.Int.1995,27,475) but there is following shortcoming in this reaction conditions: (1) this reaction yield is low; (2) make solvent with benzene in reaction process, and benzene is poisonous, carcinogenic, environment is unfriendly; (3) the long reaction times.
2,4,6-chloride trinitro--1,3-diphenylethyllene benzene derivatives, the chemical structure of general formula of its compound is as follows:
Wherein in molecular structure, on the middle phenyl ring of 1,3-diphenylethyllene benzene 2,4,6 have three nitros, and neighbour on the phenyl ring of both sides, contraposition is connected with chlorine atom, namely R 1, R 2, R 3in have one be connected with chlorine atom other for hydrogen, or R 1, R 3be chlorine atom, other is hydrogen atom simultaneously.The type compound can be used in optical material field, as nonlinear optical organic, and photosensitizers etc. or the important intermediate as energetic material field.

Claims (5)

1. the preparation method of chloride 2,4,6-trinitro--1,3-diphenylethyllene benzene derivatives, is characterized in that comprising the following steps:
By 2,4,6-trinitro-m-xylene and Chlorobenzaldehyde mixed dissolution in organic solvent, add basic catalyst and carrier, raw material and basic catalyst uniform loading are on carrier, except desolventizing under normal pressure, obtain the solid mixture of load raw material, then this solid mixture is transferred in microwave reactor, react under certain output rating, reaction terminates rear acetone extraction product, then removes acetone and obtain crude product, and crude product obtains target product after recrystallization; Wherein, one or more in N methyl piperazine, morpholine, triethylamine, pyridine, piperidines selected by alkaline catalysts, and carrier selects silica gel, NaOH, KOH, K 2cO 3in one; Chlorobenzaldehyde selects o-chlorobenzaldehyde, m chlorobenzaldehyde, 4-chloro-benzaldehyde and 2,4 dichloro benzene formaldehyde.
2. preparation method according to claim 1, is characterized in that: the mol ratio of 2,4,6-trinitro-m-xylene and Chlorobenzaldehyde is 1:2.1, and the reaction times is 15min.
3. preparation method according to claim 1, is characterized in that: the output rating of microwave is set to 300-400W.
4. preparation method according to claim 1, is characterized in that: organic solvent selects methylene dichloride, recrystallization solvent selects acetone-ethanol mixed solvent.
5. the application of 2,4,6-chloride trinitro--1,3-diphenylethyllene benzene derivatives as claimed in claim 1, is characterized in that this compounds is in luminescent device.
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