CN105541839B - Single tetracarboxylic acid diimide of nitro monoamideization 3,4,9,10 and preparation method thereof - Google Patents
Single tetracarboxylic acid diimide of nitro monoamideization 3,4,9,10 and preparation method thereof Download PDFInfo
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- CN105541839B CN105541839B CN201610081863.5A CN201610081863A CN105541839B CN 105541839 B CN105541839 B CN 105541839B CN 201610081863 A CN201610081863 A CN 201610081863A CN 105541839 B CN105541839 B CN 105541839B
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- tetracarboxylic acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D471/06—Peri-condensed systems
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
- G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
- G01N21/78—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator producing a change of colour
Abstract
The invention discloses a kind of single tetracarboxylic acid diimide of nitro monoamideization 3,4,9,10 and preparation method thereof, comprise the following steps：1) substitute 3,4,9,10 tetracarboxylic acid diimides to be dissolved in anhydrous aprotic solvent mono amino, after adding organic acid binding agent, add acyl chlorides, reacted under the conditions of anhydrous and oxygen-free, obtain intermediate product；2) intermediate product is dissolved in non-polar organic solvent, adds nitric acid, reaction, obtain single tetracarboxylic acid diimide analog derivative of nitro monoamideization 3,4,9,10.The present invention has synthesized single tetracarboxylic acid diimide of nitro monoamideization 3,4,9,10, enriches the structure of the tetracarboxylic acid diimide of monoamidesization 3,4,9,10.The compound can be used for the colorimetric determination of fluorine ion.The reaction condition of the present invention is gentle, and reactions steps are simple, and yield is higher, can reach more than 60%.
Description
Technical field
The present invention relates to single tetracarboxylic acid diimide of nitro monoamideization 3,4,9,10- and preparation method thereof, belonging to has
Machine synthesis technical field.
Background technology
Tetracarboxylic acid diimide (PBI) has excellent physics and chemical property, and its fluorescence quantum yield is high, photo-thermal is stable
Property good and solubility it is good, be the fluorogen of a kind of excellent performance.Moreover, it also has unique photoelectric property and oxygen
Change reducing property, be a kind of generally acknowledged organic material with high value.Organic effect crystal can be applied to
The sciemtifec and technical spheres such as pipe, photochromic material, extinction array, organic solar batteries, light emitting diode, color liquid crystal filter.
And it is a kind of method being connected to various functional groups on tetracarboxylic acid diimide being commonly used to form amide structure.Therefore
Performing the derivatization reaction to monoamides tetracarboxylic acid diimide becomes particularly important, and among these, nitration reaction can change
Change is the conjugated pi system of derivative, is a kind of important derivatization so as to effectively improve the photoelectric properties of this analog derivative
Method.And after connection nitro, using nitro as reaction bridge, other substitution groups can be connected, so as to abundant monoamides
The structure of tetracarboxylic acid diimide, laid the first stone further to study its application.
The content of the invention
It is an object of the invention to provide a kind of single tetracarboxylic acid diimide of nitro monoamideization 3,4,9,10- and its preparation
Method, this method have the advantages that synthesis step is simple, raw material is easy to get and yield is high.
In order to solve the above technical problems, the technical solution adopted by the present invention is：
A kind of tetracarboxylic acid diimide of single nitro monoamideization 3,4,9,10-, its structure are：
The preparation method of single tetracarboxylic acid diimide of nitro monoamideization 3,4,9,10-, comprises the following steps：
1) substitute 3,4,9,10- tetracarboxylic acid diimides to be dissolved in anhydrous aprotic solvent mono amino, add organic
After acid binding agent, acyl chlorides is added, is reacted under the conditions of anhydrous and oxygen-free, obtains intermediate product；
2) intermediate product is dissolved in non-polar organic solvent, adds nitric acid, reaction, obtain single nitro monoamideization 3,4,9,
10- tetracarboxylic acid diimide analog derivatives.
Preferably, in step 1), the aprotic solvent is dichloromethane, ethyl acetate, toluene, tetrahydrofuran, ether
Or benzene.
If using proton solvent, such as methanol, ethanol etc., solvent can react with acyl chlorides under the reaction conditions,
Because the amount of solvent is far more than raw material, yield can be substantially reduced, even zero.
Preferably, in step 1), organic acid binding agent is triethylamine, pyridine, quinoline or ethylenediamine, preferably pyridine.
As long as the organic basic material for being dissolved in common organic solvents may be used to test substantially.
Adding the effect of organic acid binding agent is：During reaction, a small amount of acidic materials can be produced, add organic tie up
Sour agent in time can neutralize these acidic materials so that the reaction direction as much as possible to generation product is carried out, and improves production
Rate.
Preferably, in step 1), acyl chlorides is added dropwise.
It is added dropwise that acyl chlorides is rapid as far as possible, is uniformly diffused into solvent in order that enabling, raising yield.
It is further preferred that the acyl chlorides is chloroacetic chloride, chloracetyl chloride or 1- furans acyl chlorides.
Preferably, in step 1), the temperature of reaction is 25-70 DEG C, and the time of reaction is 0.5-5h, preferably 1-3h, is entered
One step is preferably 1.5-2h.So that reaction can be carried out fully, reaction effect is optimal.
Preferably, 40-70 DEG C of the temperature of reaction.
Preferably, in step 1), mono amino substitutes 3,4,9,10- tetracarboxylic acid diimides, acyl chlorides and organic acid binding agent
Mol ratio be 1:1-3:1-3.
Preferably, in step 2), the non-polar organic solvent is dichloromethane, ethyl acetate or toluene.
Preferably, in step 2), the nitric acid is fuming nitric aicd.Fuming nitric aicd is the nitric acid that mass fraction is 86-98%,
Due to strong volatility, constantly thering is gas outwards to be escaped from solution, therefore claim fuming nitric aicd.
It is further preferred that in step 2), the mol ratio of the nitric acid and intermediate product is 10-100:1.
Preferably, after the completion of step 2) reaction, with unsaturated carbonate aqueous salt solu-tion, to be produced until there is no gas.
Purpose using unsaturated carbonate aqueous salt solu-tion is exactly to remove fuming nitric aicd.
It is further preferred that described unsaturated carbonate saline solution is Na2CO3Or K2CO3。
The above-mentioned tetracarboxylic acid diimide of single nitro monoamideization 3,4,9,10- answering in fluorine ion colorimetric determination
With.
Substitute 3,4,9,10- tetracarboxylic acid diimides to be dissolved in anhydrous aprotic solvent mono amino, add appropriate
Organic acid binding agent, is then added dropwise acyl chlorides, is reacted 0.5~5 hour in normal temperature to range of circulating flow, TLC tracking reactions, reaction
Terminate post processing, intermediate product is obtained through chromatogram column separating purification.This product is dissolved in non-polar organic solvent, adds nitre
Acid, react, TLC tracking reactions, terminate to reaction, with unsaturated carbonate aqueous salt solu-tion, directly under ice-water bath to normal temperature condition
To be produced to there is no gas, the tetrabasic carboxylic acid of final product list nitro monoamideization 3,4,9,10- is obtained through chromatogram column separating purification
Imidodicarbonic diamide analog derivative.
Synthetic route：
Wherein, R is arbitrarily containing hetero atom or without heteroatomic aliphatic group or aromatic radical.
Beneficial effects of the present invention are：
(1) present invention has synthesized single tetracarboxylic acid diimide of nitro monoamideization 3,4,9,10-, enriches monoamides
The structure of 3,4,9,10- tetracarboxylic acid diimides.
(2) the tetracarboxylic acid diimide compound of single nitro monoamideization 3,4,9,10- that the present invention synthesizes can be used for fluorine
The colorimetric determination of ion.
(3) reaction condition of the invention is gentle, and reactions steps are simple, and yield is higher, can reach more than 60%.
Brief description of the drawings
Fig. 1 is the nucleus magnetic hydrogen spectrum of product A in embodiments of the invention 1；
Fig. 2 is the mass spectrum of the product A in the embodiment of the present invention 1；
Fig. 3 is the UV-vis uv-vis spectras of product A in embodiments of the invention 1；
Fig. 4 is the nucleus magnetic hydrogen spectrum of product B in embodiments of the invention 2；
Fig. 5 is the mass spectrum of product B in embodiments of the invention 2；
Fig. 6 is the UV-vis uv-vis spectras of product B in embodiments of the invention 2；
Fig. 7 is the nucleus magnetic hydrogen spectrum of products C in embodiments of the invention 3；
Fig. 8 is the mass spectrum of products C in embodiments of the invention 3；
Fig. 9 is the UV-vis uv-vis spectras of products C in embodiments of the invention 3；
The UV-vis uv-vis spectras titration figure that Figure 10 is the product A in embodiments of the invention 1；
The UV-vis uv-vis spectras titration figure that Figure 11 is the product B in embodiments of the invention 2；
Figure 12 is the UV-vis uv-vis spectras titration figure of the products C in embodiments of the invention 3.
Embodiment
Further illustrated with reference to embodiment.
Mono amino in following examples substitute 3,4,9,10- tetracarboxylic acid diimides by tetracarboxylic dianhydride with
Publication about Document methods described synthesizes.Tetracarboxylic dianhydride and organic acyl chlorides be by market buy obtain, such as Tianjin Skien this life
Change Science and Technology Ltd..
Document is Yefeng Wang, Liang Zhang, Guanjun Zhang, Yue Wu, Shengying Wu,
Jianjun Yu,Limin Wang A new colorimetric and fluorescent bifunctional probe
for Cu2+and F-ions based on perylene bisimide derivatives Tetrahedron Letters
55(2014)3218–3222
Embodiment 1
Substitute 3,4,9,10- tetracarboxylic acid diimides to be dissolved in new steaming tetrahydrofuran 300 milligrams of mono aminos, add
0.2 milliliter of pyridine, 0.5 milliliter of chloroacetic chloride is then added, reacted 2 hours under reflux conditions, TLC tracking reactions, reaction terminates
Afterwards, reaction solution is poured into 50 milliliters of water, extracted 3 times, every time 30 milliliters with dichloromethane.Merge organic phase, after removing solvent
Obtain crude product.Crude product carries out silica gel column chromatography, and leacheate is dichloromethane：Ethyl acetate=20:1.Obtain intermediate product
195 milligrams, yield is about 65%.This product is dissolved in dichloromethane, adds 0.5 milliliter of fuming nitric aicd, under normal temperature condition, TLC
Track to reaction to terminate, to be produced until there is no gas, liquid separation with unsaturated carbonate aqueous salt solu-tion three times, collect organic phase,
Remove solvent and obtain crude product.Crude product carries out silica gel column chromatography, and leacheate is dichloromethane：Ethyl acetate=50:1.Produced
Thing A185 milligrams, yield are about 95%.The gross production rate of two steps is about 61%.
As shown in figure 1, hydrogen spectrum is divided into three parts：Chemical shift from 1 to 3, on A acid amides group (refer to 3,4,9,
Two cyclic amides connected on 10) hydrogen on alkyl chain；4 to 6 be the hydrogen on the carbon that acid amides group is joined directly together with nitrogen；7 to 9
Between share seven groups of peaks, wherein 7.27 be CDCl3Solvent peak, be followed successively by the singlet of 2,9 from right to left, 5,6,11,12
The doublet of position, gulf position connect the singlet of NH on acid amides.
As shown in Fig. 2 mass spectrum is with ESI ion guns, is drawn under negative ion mode, obtain molecular ion peak 655.2197.
As shown in figure 3, UV-vis uv-vis spectras are to use amount of substance concentration as 10-5mol·L-1Dichloromethane solution
Test, a length of 550.00nm of maximum absorption wave, photon absorbing intensity 0.208.
Embodiment 2
Substitute 3,4,9,10- tetracarboxylic acid diimides to be dissolved in dichloromethane 300 milligrams of mono aminos, add 0.3 milli
Triethylamine is risen, then adds 0.5 milliliter of chloracetyl chloride, is reacted 1.5 hours under reflux conditions, TLC tracking reactions, reaction terminates
Afterwards, reaction solution is poured into 50 milliliters of water, extracted 3 times, every time 30 milliliters with dichloromethane.Merge organic phase, remove solvent, obtain
To crude product.Crude product carries out silica gel column chromatography, and leacheate is dichloromethane：Ethyl acetate=20:1.Obtain intermediate product 207
Milligram, yield is about 69%.This product is dissolved in dichloromethane, adds 0.5 milliliter of fuming nitric aicd, under normal temperature condition, TLC with
Track to reaction terminates, and, to be produced until there is no gas, liquid separation with unsaturated carbonate aqueous salt solu-tion three times, collects organic phase, removes
Solvent is gone to obtain crude product.Crude product carries out silica gel column chromatography, and leacheate is dichloromethane：Ethyl acetate=50:1.Obtain product
B186 milligrams, yield are about 95%.The gross production rate of two steps is about 65%.
As shown in figure 4, hydrogen spectrum is divided into three parts：Chemical shift from 1 to 3, on A acid amides group (refer to 3,4,9,
Two cyclic amides connected on 10) hydrogen on alkyl chain；4 to 6 be the hydrogen on the carbon that acid amides group is joined directly together with nitrogen；7 to 9
Between share seven groups of peaks, wherein 7.27 be CDCl3Solvent peak, be followed successively by the singlet of 2 from right to left, 5,6,11,12
Doublet, the singlet of 9, gulf position connection acid amides on NH singlet.
As shown in figure 5, mass spectrum is with ESI ion guns, is drawn under negative ion mode, obtain molecular ion peak 689.1796.
As shown in fig. 6, UV-vis uv-vis spectras are to use amount of substance concentration as 10-5mol·L-1Dichloromethane solution
Test, a length of 544.00nm of maximum absorption wave, photon absorbing intensity 0.223.
Embodiment 3
Substitute 3,4,9,10- tetracarboxylic acid diimides to be dissolved in ethyl acetate 300 milligrams of mono aminos, add 0.2 milli
Pyridine is risen, then adds 0.5 milliliter of 1- furans acyl chlorides, is reacted 2 hours under reflux conditions, TLC tracking reactions, reaction terminates
Afterwards, reaction solution is poured into 50 milliliters of water, extracted 3 times, every time 30 milliliters with dichloromethane.Merge organic phase, remove solvent, obtain
To crude product.Crude product carries out silica gel column chromatography, and leacheate is dichloromethane：Ethyl acetate=20:1.Obtain intermediate product 200
Milligram, yield is about 67%.This product is dissolved in dichloromethane, adds 0.5 milliliter of fuming nitric aicd, under normal temperature condition, TLC with
Track to reaction terminates, and, to be produced until there is no gas, liquid separation with unsaturated carbonate aqueous salt solu-tion three times, collects organic phase, removes
Solvent is gone to obtain crude product.Crude product carries out silica gel column chromatography, and leacheate is dichloromethane：Ethyl acetate=50:1.Obtain product
C183 milligrams, yield are about 91%.The gross production rate of two steps is about 62%.
As shown in fig. 7, hydrogen spectrum is divided into three parts：Chemical shift from 1 to 3, on A acid amides group (refer to 3,4,9,
Two cyclic amides connected on 10) hydrogen on alkyl chain；4 to 6 be the hydrogen on the carbon that acid amides group is joined directly together with nitrogen；7 to 9
Between share ten groups of peaks, wherein 7.27 be CDCl3Solvent peak, three groups of peaks being followed successively by from right to left on furans, the substance of 2
Peak, 5,6,11 doublet, the singlet of 9, the doublet of 12, gulf position connect the singlet of NH on acid amides.
As shown in figure 8, mass spectrum is with ESI ion guns, is drawn under negative ion mode, obtain molecular ion peak 707.2122.
As shown in figure 9, UV-vis uv-vis spectras are to use amount of substance concentration as 10-5mol·L-1Dichloromethane solution
Test, a length of 554.00nm of maximum absorption wave, photon absorbing intensity 0.230.
Identification with fluorine ion uses UV-vis uv-vis spectra titration amount of substance concentration as 10-5mol·L-1Two
Chloromethanes solution testing, the source of fluorine ion is using tetrabutyl amine fluoride.The amount of addition as shown in Figure 10 to Figure 12, wherein
Each M represents that the concentration for adding tetrabutyl amine fluoride is 10-5mol·L-1(Figure 10-12 is respectively A, and B, C UV-vis are ultraviolet
Visible spectrum titrates) it can be seen that A in 6M, B is in 3M, and C is in 5M, i.e.,：The concentration of fluorine ion is respectively A, B, the 6,3,5 of C concentration
Times when, reach saturation.
Above-mentioned although the embodiment of the present invention is described with reference to accompanying drawing, not to invention protection domain
Limitation, one of ordinary skill in the art should be understood that on the basis of technical scheme those skilled in the art are not required to
Pay various modifications that creative work can make or deformation is still within the scope of the present invention.
Claims (8)
- A kind of 1. synthetic method of the tetracarboxylic acid diimide of single nitro monoamideization 3,4,9,10-, it is characterised in that：Including such as Lower step：1) 3,4,9,10- tetracarboxylic acid diimides are substituted to be dissolved in anhydrous aprotic solvent mono amino, addition is organic to tie up acid After agent, acyl chlorides is added, is reacted under the conditions of anhydrous and oxygen-free, obtains intermediate product；Acyl chlorides is added dropwise；The acyl chlorides is chloroacetic chloride, chloracetyl chloride or 1- furans acyl chlorides；The temperature of reaction is 25-70 DEG C, and the time of reaction is 0.5-5h；Mono amino substitutes the mol ratio of 3,4,9,10- tetracarboxylic acid diimides, acyl chlorides and organic acid binding agent to be 1:1-3:1-3；2) intermediate product is dissolved in non-polar organic solvent, adds nitric acid, reaction, obtain single nitro monoamideization 3,4,9,10- Tetracarboxylic acid diimide analog derivative；The non-polar organic solvent is dichloromethane, ethyl acetate or toluene；The nitric acid is fuming nitric aicd；The mol ratio of the nitric acid and intermediate product is 10-100:1；The tetracarboxylic acid diimide of single nitro monoamideization 3,4,9,10- being prepared, its structure are：R is arbitrarily containing hetero atom or without heteroatomic aliphatic group or aromatic radical.
- 2. synthetic method according to claim 1, it is characterised in that：In step 1), the aprotic solvent is dichloromethane Alkane, ethyl acetate, toluene, tetrahydrofuran, ether or benzene.
- 3. synthetic method according to claim 1, it is characterised in that：In step 1), organic acid binding agent be triethylamine, Pyridine, quinoline or ethylenediamine.
- 4. synthetic method according to claim 3, it is characterised in that：Organic acid binding agent is pyridine.
- 5. synthetic method according to claim 1, it is characterised in that：In step 1), the time of reaction is 1-3h.
- 6. synthetic method according to claim 5, it is characterised in that：In step 1), the time of reaction is 1.5-2h.
- 7. synthetic method according to claim 1, it is characterised in that：After the completion of step 2) reaction, with unsaturated carbonate salt solution Solution washs, and to be produced until there is no gas.
- 8. synthetic method according to claim 7, it is characterised in that：Described unsaturated carbonate saline solution is Na2CO3Or K2CO3。
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