CN106749241B - Four formoxyl diimide derivative of 1,4,5,8- naphthalene and application thereof - Google Patents
Four formoxyl diimide derivative of 1,4,5,8- naphthalene and application thereof Download PDFInfo
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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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- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25D—PROCESSES FOR THE ELECTROLYTIC OR ELECTROPHORETIC PRODUCTION OF COATINGS; ELECTROFORMING; APPARATUS THEREFOR
- C25D3/00—Electroplating: Baths therefor
- C25D3/02—Electroplating: Baths therefor from solutions
- C25D3/38—Electroplating: Baths therefor from solutions of copper
Abstract
The present invention relates to a kind of four formoxyl diimide derivatives of 1,4,5,8- naphthalene and application thereof.The Isosorbide-5-Nitrae, 5,8- naphthalene, four formoxyl diimide derivative are compound shown in formula I, can be used as the application of the smoothing agent of acid copper plating.In formula I, R1And R2It is respectively selected from: hydrogen, C1~C6Alkyl, halogenated C1~C6Group shown in alkyl, group shown in formula II or formula III, and R1And R2In at least one be group shown in group shown in formula II or formula III；M is 1 or 2；X is halogen；Wherein, R3~R8It is respectively and independently selected from: C1~C3Integer a kind of in alkyl, that n is 1~12, the integer that p is 1~6.
Description
Technical field
The present invention relates to a kind of naphthoyl imide compounds and application thereof, specifically, are related to a kind of Isosorbide-5-Nitrae, 5,8- naphthalene tetramethyls
Acyl group diimide derivative and application thereof.
Background technique
Electroplating engineering is to study chemical process and physics mistake conducted in electroplating industry and the production of other related industries
One engineering science of journey common law is one of the key technology of advanced manufacturing technology industrial chain.It is with chemistry, physics
A cross discipline based on, electronics, machinery and mathematics.Since the application of 19th century mid-term electroplating technology, the technology
It is constantly improved and is developed.After 21 century, with the development of electronic technology and need, copper electroplating layer is because of it
Have many advantages, such as good electric conductivity, thermal conductivity and mechanical ductility and is widely used in the fields such as electronics and IT products.Electricity
Coating technology has evolved into important component indispensable in national economic development, and is widely used in machinery, shipbuilding, aviation
Many aspects such as space flight, military project, electronics, nuclear industry, light industry, dairy industry, to improve the corrosion resistance, dicoration and function of product
It can property.For example after the piece surfaces such as automobile door handle, instrument board, trade mark have plated one layer of coat of metal its appearance can become
It obtains more aesthetically pleasing；Hard chrome is plated in cylinder inner wall, the wearability of product can be improved to extend the service life of product；It is fastening
Part surface plates zinc and can greatly improve the corrosion resistance of product after post-processing process appropriate；The plated with gold on sanitaryware
The corrosion resistance of product can be improved in category coating, the service life of extension product can make product appearance get a promotion again.Therefore, it is electroplated
It is closely bound up with daily life, it is small to arrive lighter, spectacle frame, the surface treatment of aircraft, automobile is arrived greatly, we can
The most of product seen all is by electroplating processes.
Since the geomery of electroplating device in industrial production is different, the current density of workpiece surface each point is each in electroplating bath
It is different, it is difficult to obtain thickness distribution if depending merely on the modes such as the convection current for improving plating solution uniformly and meets the copper plating of various functional requirements
Layer.Therefore industrially in order to obtain the uniform copper coating of surface-brightening, excellent physical properties, thickness distribution, common method is
Organic additive is added in electrolytic copper plating solution.
In copper sulfate baths common additive by its effect in the plating solution can be divided mainly into inhibitor, brightener and
Three kinds of leveling agent.In the case that additive is controlled by diffusing step in practical electroplating process, electroplating additive particle is usual
It will appear diffusion, and be adsorbed at the biggish electrode surface protrusion of tension and on the active site of electro-deposition, cause in electricity
The metallic atom adsorbed in pole surface constantly moves to the recess of electrode surface and enters inside metal lattice, to play
The bright levelling effect of additive.The concentration of additive often only has 1/102 to 1/105 times of concentration of metal ions, but this
A little a small amount of additives can bring coating morphology composition and crystal lattice orientation strong influence.Therefore, in order to make plated material
Surface topography and physical property meet the standard and requirement of every profession and trade, electroplating additive plays in acid copper sulfate plating
Very key effect.
Then so far from last century the nineties, external major Additive Production quotient (German Atotech, Japan is big and waits)
It is proposed dye-types additives such as " 210 " " Ultra " in the domestic market for general hardware electroplating industry copper facing.And dye-type
The use of electroplating additive will increase the cost of economy and environment, and the plating addition of existing dye-type in water pollution control
Agent there are types few, difficult the defects of preparing (preparation process complicated), easily decomposing and is at high cost.So research and development preparation process is relatively simple
Single, low cost, and environmentally friendly reactive monoazo dyestuffs type electroplating additive is by the concern of this field scientist.
Chinese patent literature CN 105646346A discloses the naphthoyl imide compounds as straight and even dose of acid electroplating,
But its performance still has room for improvement.
Summary of the invention
The present inventor, which designs and synthesized the four formoxyl imidodicarbonic diamide of 1,4,5,8- naphthalene of structure novel a kind of, to spread out
Biology, after tested, the series derivates show the good chemical property for inhibiting copper deposition.
A purpose of the invention is, provides a kind of Isosorbide-5-Nitrae of structure novel, and 5,8- naphthalene, four formoxyl imidodicarbonic diamide is derivative
Object.
The four formoxyl diimide derivative of 1,4,5,8- naphthalene is compound shown in formula I:
In formula I, R1And R2It is respectively selected from: hydrogen (H), C1~C6Alkyl, the C in halogen (F, Cl, Br or I) generation1~C6Alkyl, formula II
Group shown in shown group or formula III, and R1And R2In at least one be group shown in group shown in formula II or formula III；M be 1 or
2；X is halogen (F, Cl, Br or I)；
In formula II and III, R3~R8It is respectively and independently selected from: C1~C3Integer a kind of in alkyl, that n is 1~12, p are 1~6
Integer, curve mark be replace position (similarly hereinafter).
Another object of the present invention is, discloses above-mentioned Isosorbide-5-Nitrae, a kind of use of 5,8- naphthalene, four formoxyl diimide derivative
On the way: i.e. application of the compound shown in formula I as the smoothing agent of acid copper plating (such as using copper sulphate as electroplate liquid).
In addition, the method has main steps that the present invention also provides a kind of method of compound shown in preparation formula I: with
Isosorbide-5-Nitrae, 5,8- naphthalene, four formoxyl dianhydride (compound shown in formula IV) is starting material, firstly, will be shown in formula IV using the prior art
Compound is converted into four formoxyl imidodicarbonic diamide of 1,4,5,8- naphthalene (compound shown in formula V)；Then, change as shown in formula IV or V
Close object and R1aY or R2aY and/or NH2R1bNH2、NH2R2bNH2、H2R1bY、NH2R2bY、YR1bY or YR2bY reaction, obtains intermediate；
Finally, gained intermediate is reacted through " quaternization ", object (compound shown in formula I) is obtained.
Wherein, Y is halogen (F, Cl, Br or I)；R1aAnd R2aIt is respectively selected from: C1~C6Alkyl or halogen (F, Cl, Br or I) generation
C1~C6It is a kind of in alkyl；R1bAnd R2bIt is respectively selected from: a kind of in group shown in III a of group shown in II a of formula or formula；N's and p determines
It is adopted with it is described previously identical.
Detailed description of the invention
Fig. 1 is the cyclic voltammetry curve of compound shown in I A of formula；
Fig. 2 is the cyclic voltammetry curve of compound shown in I B of formula；
Fig. 3 is the cyclic voltammetry curve of compound shown in I C of formula；
Fig. 4 is the cyclic voltammetry curve of compound shown in I D of formula；
Fig. 5 is the cyclic voltammetry curve of compound shown in I E of formula；
Fig. 6 is the cyclic voltammetry curve of compound shown in formula Nap；
Fig. 7 is the cyclic voltammetry curve of compound shown in formula JGB.
Specific embodiment
In a preferred technical solution of the invention, R1And R2It is respectively selected from: H, the C in halogen (F, Cl, Br or I) generation1~C6
Group shown in alkyl, group shown in formula II or formula III, and R1And R2In at least one be base shown in group shown in formula II or formula III
Group；M is 1 or 2；X is halogen (F, Cl, Br or I)；
In formula II and III, R3~R8It is respectively and independently selected from: C1~C3Integer a kind of in alkyl, that n is 1~6, p are 1~3
Integer.
Further preferred embodiment is: R1And R2It is respectively selected from: the C in H, F generation6Alkyl, III institute of group shown in formula II or formula
Show group, and R1And R2In at least one be group shown in group shown in formula II or formula III；M is 1 or 2；X is Br or I；
In formula II and III, R3~R8It is methyl, the integer that n is 1~6, p is 1 or 2.
Further preferred embodiment is again: R1And R2It is respectively selected from following groups a kind of:
Below by embodiment, the present invention is further elaborated, it is therefore intended that is best understood from the contents of the present invention, is lifted
Example do not limit the scope of the invention.
Embodiment 1
The preparation of four formoxyl imidodicarbonic diamide of 1,4,5,8- naphthalene (compound shown in formula V):
By Isosorbide-5-Nitrae, 5,8- naphthalene, four formoxyl dianhydride (2g, 7.5mmol) and ammonium acetate (11.5g, 150mmol) are dissolved in acetic acid
(40mL), heating stirring back flow reaction 1h.Reaction solution is cooled to room temperature, decompression filters and with acetic acid (50mL) and ether
(100mL) washing filter cake obtains yellow solid (compound shown in formula V), yield 95%.
Embodiment 2
The preparation of compound shown in I A of formula:
By compound shown in formula IV (2.14g, 8mmol), 80mL deionized water, N, N- dimethyl -1,3- diaminopropanes
(2.82g, 32mmol) mixing is placed in a reaction flask, and is heated to 80 DEG C, is stirred to react 15h.Stop reaction, be cooled to room temperature, uses
Methylene chloride (20mL) extracts 5 times, collects organic phase, and dry with anhydrous sodium sulfate.Product is concentrated and through silica gel column layer point
From (methylene chloride: triethylamine be 40:1 (v/v)), chromatography obtain product again with ethyl alcohol recrystallization obtain yellow solid (in
Mesosome A), yield 85%.
Take intermediate A (0.434g, 1mmol) to be dissolved in 20mL acetonitrile, then into reaction system be added iodomethane (2.28g,
16mmol), 18h is stirred at room temperature.Reaction solution is depressurized and is filtered, acquired filter cake obtains yellow solid after being washed with acetonitrile (20mL)
(compound shown in I A of formula), yield 90%.
Intermediate A:1H NMR(400MHz,CDCl3): δ 8.75 (s, 4H), 4.26 (t, J=7.6Hz, 4H), 2.44 (t, J
=7.2Hz, 4H), 2.24 (s, 12H), 1.92 (m, 4H)；13C NMR(100MHz,CDCl3):162.8,130.9,126.7,
126.6,57.2,45.4,39.4,25.9；HRMS (TOF-ESI): m/z:calcd for C24H29N4O4: 437.5159；
Found:437.5157.
Compound shown in I A of formula:1H NMR (400MHz, DMSO): δ 8.73 (s, 4H), 4.16 (t, J=7.6Hz, 4H),
3.48(m,4H),3.05(s,18H),2.17(m,4H)；13C NMR(100MHz,DMSO):162.9,130.5,126.4,
126.2,63.2,52.2,37.4,21.6；HRMS (TOF-ESI): m/z:calcd for C13H34N2O2: 233.1285；
Found:233.1287.
Embodiment 3
The preparation of compound shown in I B of formula:
By compound shown in formula V (0.532g, 2mmol), Isosorbide-5-Nitrae-dibromobutane (0.322g, 1.5mmol), potassium carbonate
(0.552g, 2mmol), the potassium iodide of catalytic amount are dissolved in the n,N-Dimethylformamide of 40mL (DMF), are heated to 60 DEG C, stir
Mix reaction 20h.Reaction solution is poured into 200mL water, a large amount of solids are precipitated, decompression filters and obtains filter cake, is rinsed with water (50mL)
Clean filter cake dries to obtain gray solid (intermediate B), yield 80%.
By intermediate B (0.4g, 1mmol), trimethy-lammonium chloride (0.96g, 10mmol), sodium bicarbonate (0.84g,
It 10mmol) is dissolved in 30mL acetonitrile, is heated to 80 DEG C, is stirred to react 12h.It is cooled to room temperature to reaction solution, it is molten to rotate acetonitrile
Agent obtains yellow solid (compound shown in I B of formula), yield 85% with methanol/recrystallized from acetonitrile.
Intermediate B:1H NMR(400MHz,CDCl3): δ 11.52 (s, 1H), 8.69 (s, 4H), 3.75 (t, J=7.6Hz,
2H), 3.56 (t, J=7.2Hz, 2H), 1.92 (m, 2H), 1.75 (m, 2H)；13C NMR(100MHz,CDCl3):160.8,
138.9,133.7,122.6,47.2,39.4,28.4,27.9；HRMS (TOF-ESI): m/z:calcd for C18H14BrN2O4:
401.0131；Found:401.0128.
Compound shown in I B of formula:1H NMR(400MHz,DMSO):δ11.43(s,1H),8.62(s,4H),3.56(s,
9H), 3.22 (t, J=7.6Hz, 2H), 3.14 (t, J=7.2Hz, 2H), 1.71 (m, 2H), 1.56 (m, 2H)；13C NMR
(100MHz,DMSO):160.8,138.9,133.7,122.6,54.8,47.2,39.4,28.4,27.9；HRMS (TOF-ESI):
M/z:calcd for C21H22N3O4: 380.1605；Found:380.1601.
Embodiment 4
The preparation of compound shown in I C of formula:
Compound shown in formula IV (2g, 7.5mmol) and 6- bromine hexylamine (2.88g, 16mmol) are dissolved in the N, N- bis- of 40mL
In methylformamide (DMF), 50 DEG C of reaction 4h are heated to, are again heated to 120 DEG C of reaction 12h.Reaction solution is cooled to room temperature, is revolved
Solvent is evaporated, obtains brown crude product, then (methylene chloride/acetone is 10/1- methylene chloride/acetone (2% first with chromatography
Alcohol) it is 10/3) to obtain light yellow solid (intermediate C), (3.77g, 85%).
By intermediate C (0.59g, 1mmol), trimethy-lammonium chloride (0.96g, 10mmol), sodium bicarbonate (0.84g,
It 10mmol) is dissolved in 30mL acetonitrile, is heated to 80 DEG C, is stirred to react 12h.It is cooled to room temperature to reaction solution, it is molten to rotate acetonitrile
Agent obtains yellow solid 0.467g (compound shown in I C of formula), yield 85% with methanol/recrystallized from acetonitrile.
Intermediate C:1H NMR(400MHz,CDCl3): δ 8.71 (s, 4H), 4.16 (t, J=7.6Hz, 4H), 2.61 (t, J
=7.2Hz, 4H), 1.82 (m, 4H), 1.62 (m, 4H), 1.36 (m, 8H)；13C NMR(100MHz,CDCl3):162.8,
130.9,126.7,126.6,57.2,45.4,43.8,39.4,36.8,25.9；HRMS (TOF-ESI): m/z:calcd for
C26H29Br2N4O4: 593.0468；Found:593.0464.
Compound shown in I C of formula:1H NMR (400MHz, DMSO): δ 8.62 (s, 4H), 4.16 (t, J=7.6Hz, 4H),
3.48 (t, J=7.2Hz, 4H), 3.05 (s, 18H), 1.71 (m, 8H), 1.45 (m, 8H)；13C NMR(100MHz,DMSO):
162.4,130.3,126.1,125.8,63.2,52.2,48.9,45.6,42.3,37.4,21.6；HRMS (TOF-ESI): m/z:
calcd for C16H23N2O2: 275.1754；Found:275.1756.
Embodiment 5
The preparation of compound shown in I D of formula:
By compound shown in formula V (0.532g, 2mmol), compound a (0.825g, 3mmol), potassium carbonate (0.828g,
1.5mmol), the potassium iodide of catalytic amount is dissolved in the n,N-Dimethylformamide (DMF) of 30mL, is heated to 120 DEG C, is stirred to react
20h.Reaction solution is poured into 200mL water, a large amount of solids are precipitated, decompression filters, and gained filter cake rinses filter cake with water (50mL), dries
It does to obtain gray solid, obtains light yellow solid (intermediate through silicagel column column chromatography for separation (methylene chloride/acetone=10/3 (v/v))
D) (0.921g, 75%).
It takes intermediate D (0.656g, 1mmol), trimethy-lammonium chloride (0.96g, 10mmol), sodium bicarbonate (0.84g,
It 10mmol) is dissolved in 30mL acetonitrile, is heated to 80 DEG C, is stirred to react 12h.It is cooled to room temperature to reaction solution, it is molten to rotate acetonitrile
Agent obtains yellow solid 0.544 (compound shown in I D of formula), yield 85% with methanol/recrystallized from acetonitrile.
Intermediate D:1H NMR(400MHz,CDCl3): δ 8.78 (s, 4H), 4.16 (t, J=7.6Hz, 4H), 3.89 (t, J
=7.2Hz, 4H), 3.51 (t, J=7.2Hz, 4H), 3.31 (t, J=7.6Hz, 4H), 3.15 (m, 8H)；13C NMR(100MHz,
CDCl3):163.4,130.6,125.9,124.6,67.2,65.4,58.8,39.4,36.8,25.9；HRMS (TOF-ESI): m/
Z:calcd for C26H29Br2N4O8: 657.0265；Found:657.0264.
Compound shown in I D of formula:1H NMR (400MHz, DMSO): δ 8.75 (s, 4H), 4.14 (t, J=7.6Hz, 4H),
3.84 (t, J=7.2Hz, 4H), 3.48 (t, J=7.2Hz, 4H), 3.26 (t, J=7.6Hz, 4H), 3.15 (m, 8H) 3.05 (s,
18H)；13C NMR(100MHz,DMSO):163.3,130.4,125.8,124.4,67.2,65.4,58.8,46.8,39.4,
36.8,25.9；HRMS (TOF-ESI): m/z:calcd for C13H23N2O4: 307.1652；Found:307.1649.
Embodiment 6
The preparation of compound shown in I E of formula:
By compound shown in formula V (0.532g, 2mmol), 1,1,2,2- tetrahydro perfluoro-hexyl iodide (0.935g,
2.5mmol), potassium carbonate (1.656g, 3mmol), the potassium iodide of catalytic amount are dissolved in the n,N-Dimethylformamide of 30mL (DMF)
In, 100 DEG C are heated to, 8h is stirred to react.Reaction solution is poured into 200mL water after being cooled to room temperature, a large amount of solids are precipitated, is depressurized
It filters, acquired filter cake rinses filter cake well with water (50mL), recrystallized with ethanol as solvent to filter cake, dry greyish white
Color solid (intermediate E a) (0.512g, 50%).
By intermediate E a (0.512g, 1mmol), Isosorbide-5-Nitrae-dibromobutane (0.322g, 1.5mmol), potassium carbonate (0.552g,
2mmol), the potassium iodide of catalytic amount is dissolved in the n,N-Dimethylformamide (DMF) of 30mL, is heated to 100 DEG C, is stirred to react
8h.Reaction solution is poured into 200mL water after being cooled to room temperature, a large amount of solids are precipitated, decompression filters, acquired filter cake water
(50mL) rinses filter cake well, then carries out chromatography (methylene chloride/methanol=50/1 (v/v)) to filter cake and dry white solid
Body (intermediate E b) (0.485g, 75%).
By intermediate E b (0.323g, 0.5mmol), trimethy-lammonium chloride (0.96g, 10mmol), sodium bicarbonate (0.84g,
It 10mmol) is dissolved in 30mL acetonitrile, is heated to 80 DEG C, is stirred to react 12h.It is cooled to room temperature to reaction solution, it is molten to rotate acetonitrile
Agent obtains yellow solid (compound shown in I E of formula) (0.266g, 85%) with methanol/recrystallized from acetonitrile.
Intermediate E a:1H NMR(400MHz,CDCl3): δ 11.27 (s, 1H), 8.63 (s, 4H), 3.79 (t, J=7.6Hz,
2H),1.98(m,2H)；13C NMR(100MHz,CDCl3):159.1,138.6,135.8,124.6,124.0,121.3,
120.6,118.5,117.2,109.5,28.9,24.7；19F NMR(400MHz,CDCl3):δ-80.9(m,3F),-114.7(m,
2F),-124.3(m,2F),-126.0(m,2F)；HRMS (TOF-ESI): m/z:calcd for C20H10F9N2O4:
513.0491；Found:513.0489.
Intermediate E b:1H NMR(400MHz,CDCl3): δ 8.62 (s, 4H), 3.72 (t, J=7.6Hz, 2H), 3.52 (t, J
=7.2Hz, 2H), 3.14 (t, J=7.6Hz, 2H), 1.82-1.89 (m, 4H), 1.56 (m, 2H)；13C NMR(100MHz,
CDCl3):159.1,138.6,135.8,124.6,124.0,121.3,120.6,118.5,117.2,109.5,69.3,67.9,
50.5,46.7,29.1,24.7；19F NMR(400MHz,CDCl3):δ-80.9(m,3F),-114.6(m,2F),-124.4(m,
2F),-126.0(m,2F)；HRMS (TOF-ESI): m/z:calcd for C24H17BrF9N2O4:647.0222；Found:
647.0223.
Compound shown in I E of formula:1H NMR (400MHz, DMSO): δ 8.61 (s, 4H), 3.72 (t, J=7.6Hz, 2H),
3.47(s,9H),3.14-3.18(m,4H),2.13(m,2H),1.58-1.61(m,4H)；13C NMR(100MHz,DMSO):
159.1,138.6,135.8,124.6,124.0,121.3,120.6,118.5,117.2,109.5,69.3,67.9,54.8,
50.5,46.7,29.1,24.7；19F NMR(400MHz,DMSO):δ-80.9(m,3F),-114.6(m,2F),-124.4(m,
2F),-126.0(m,2F)；HRMS (TOF-ESI): m/z:calcd for C27H25F9N3O4: 626.1696；Found:
626.1698。
Embodiment 7
Prepare a CuSO containing 50g/L4·5H2O and 250g/L H2SO4Copper-bath, with Pt rotating disk electrode (r.d.e) work
For working electrode, platinum stick is used as to electrode and Ag/AgCl as reference electrode, under conditions of revolving speed is 2000 revs/min, in solution
It is 2.5g/L by above-described embodiment prepare compound IA~IE that 0.02mL, concentration is added dropwise in (100mL) every time, does cyclic voltammetric
Curve test, gained cyclic voltammetry curve are shown in Fig. 1~5.The additive amount of additive is bigger when cyclic voltammetry, obtained oxidation
Peak area is smaller, corresponding to be that inhibiting effect is stronger, and when peak area ratio is less than 0.5, the EOT end of test.
Comparative example
With the smoothing agent of existing commercial acid copper plating: " it is green to be good for that " (compound shown in formula b is abbreviated as " JGB ")
Naphthoyl imide compounds (the chemical combination shown in formula c that can be used as the smoothing agent of acid copper plating is reported with CN 105646346A
Object is abbreviated as " Nap ") test of embodiment 7 is repeated, test loop volt-ampere curve is shown in Fig. 6~7, and titration results are shown in Table 1..
Table 1
Titration results (being shown in Table 1) are to have investigated the amount of the consumed additive when peak area ratio is 0.8, compound addition
Amount is fewer, shows that the inhibiting effect of compound is stronger.In other words, the planarization effects of gained coating are also got in the plating process
It is good.
By table 1. it is found that Isosorbide-5-Nitrae provided by the present invention, the plating of 5,8- naphthalene, four formoxyl diimide derivative inhibit effect
Fruit is superior to JGB and Nap (especially compound shown in Formulas I A, IC and ID), is expected to be developed as a kind of plating haveing excellent performance
Smoothing agent.
Claims (10)
1. a kind of Isosorbide-5-Nitrae, 5,8- naphthalene, four formoxyl diimide derivative are compound shown in Formulas I:
In Formulas I, R1And R2It is respectively selected from: hydrogen, C1~C6Alkyl, halogenated C1~C6Shown in alkyl, group shown in Formula II or formula III
Group, and R1And R2In at least one be group shown in group shown in Formula II or formula III；M is 1 or 2；X is halogen；
Wherein, R3~R8It is respectively and independently selected from: C1~C3Integer a kind of in alkyl, that n is 1~12, the integer that p is 1~6；
But do not include following compounds:
2. Isosorbide-5-Nitrae as described in claim 1,5,8- naphthalene, four formoxyl diimide derivative, which is characterized in that wherein, n 1
~6 integer, the integer that p is 1~3.
3. Isosorbide-5-Nitrae as claimed in claim 2,5,8- naphthalene, four formoxyl diimide derivative, which is characterized in that wherein, R1And R2
It is respectively selected from: hydrogen, the C of fluoro6Group shown in alkyl, group shown in Formula II or formula III, and R1And R2In at least one be Formula II
Group shown in shown group or formula III；M is 1 or 2；X is Br or I.
4. Isosorbide-5-Nitrae as claimed in claim 3,5,8- naphthalene, four formoxyl diimide derivative, which is characterized in that wherein, R1And R2
It is respectively selected from following groups a kind of:
5. Isosorbide-5-Nitrae as claimed in claim 4,5,8- naphthalene, four formoxyl diimide derivative, which is characterized in that the Isosorbide-5-Nitrae,
Four formoxyl diimide derivative of 5,8- naphthalene is a kind of in following compounds:
6. a kind of application of smoothing agent of four formoxyl diimide derivative of 1,4,5,8- naphthalene as acid copper plating；
Wherein, the Isosorbide-5-Nitrae, 5,8- naphthalene, four formoxyl diimide derivative are compound shown in Formulas I:
In Formulas I, R1And R2It is respectively selected from: hydrogen, C1~C6Alkyl, halogenated C1~C6Shown in alkyl, group shown in Formula II or formula III
Group, and R1And R2In at least one be group shown in group shown in Formula II or formula III；M is 1 or 2；X is halogen；
Wherein, R3~R8It is respectively and independently selected from: C1~C3Integer a kind of in alkyl, that n is 1~12, the integer that p is 1~6.
7. application as claimed in claim 6, which is characterized in that wherein, the integer that n is 1~6, the integer that p is 1~3.
8. application as claimed in claim 6, which is characterized in that wherein, R1And R2It is respectively selected from: hydrogen, the C of fluoro6Alkyl, formula
Group shown in group shown in II or formula III, and R1And R2In at least one be group shown in group shown in Formula II or formula III；M is 1
Or 2；X is Br or I.
9. application as claimed in claim 8, which is characterized in that wherein, R1And R2It is respectively selected from following groups a kind of:
10. the application as described in any one of claim 6~9, which is characterized in that the electricity of acid copper plating used in it
Plating solution is copper sulphate.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1502917A1 (en) * | 2003-07-28 | 2005-02-02 | Clariant International Ltd. | Use of mono- and dicationic naphthalene-based imide dyes in optical layers for optical data recording |
| CN105646346A (en) * | 2015-12-25 | 2016-06-08 | 华东理工大学 | Naphthalimide quaternary ammonium compound with novel structure and application thereof |
-
2016
- 2016-12-28 CN CN201611232060.1A patent/CN106749241B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1502917A1 (en) * | 2003-07-28 | 2005-02-02 | Clariant International Ltd. | Use of mono- and dicationic naphthalene-based imide dyes in optical layers for optical data recording |
| CN105646346A (en) * | 2015-12-25 | 2016-06-08 | 华东理工大学 | Naphthalimide quaternary ammonium compound with novel structure and application thereof |
Non-Patent Citations (5)
| Title |
|---|
| A dual-responsive supra-amphiphile based on a water-soluble pillar[7]arene and a naphthalene diimide-containing guest;Li Shao et al.;《Chem. Commun.》;20150320;第51卷;第7215-7218页 |
| Dynamic Combinatorial Donor-Acceptor Catenanes in Water: Access to Unconventional and Unexpected Structures;Ho Yu Au-Yeung et al.;《J. Org. Chem.》;20110208;第76卷;第1257–1268页 |
| Hydrolysis of aliphatic naphthalene diimides:effect of charge placement in the side chains;Michelle B. Kim et al.;《J. Phys. Org. Chem.》;20080529;第21卷;第731-737页 |
| Molecular Binding Behaviors of Pyromellitic and Naphthalene Diimide Derivatives by Tetrasulfonated 1,5-Dinaphtho-(3n+8)- crown-n (n = 8, 10) in Aqueous Solution;Ling Chen et al.;《J. Org. Chem.》;20130502;第78卷;第5357？5363页 |
| Tri-, tetra- and heptacyclic perylene analogues as new potential antineoplastic agents based on DNA telomerase inhibition;Claudia Sissi et al.;《Bioorg. Med. Chem》;20061010;第15卷;第555-562页 |
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