CN106543028B - N,N'（2- aminofluorenes）The preparation method of contracting diphenyl-dimethanal schiff bases iron complex - Google Patents
N,N'（2- aminofluorenes）The preparation method of contracting diphenyl-dimethanal schiff bases iron complex Download PDFInfo
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- CN106543028B CN106543028B CN201610940844.3A CN201610940844A CN106543028B CN 106543028 B CN106543028 B CN 106543028B CN 201610940844 A CN201610940844 A CN 201610940844A CN 106543028 B CN106543028 B CN 106543028B
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
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Abstract
The invention discloses a kind of N, N'（2- aminofluorenes）The preparation method of contracting diphenyl-dimethanal schiff bases iron complex.This method is divided into the progress of two steps, and the first step in absolute ethyl alcohol, using acetic acid as catalyst, is heated to reflux certain time using 2- aminofluorenes and diphenyl-dimethanal as raw material, and N, N' is made（2- aminofluorenes）Contracting diphenyl-dimethanal schiff bases；Second step is with N, N'（2- aminofluorenes）Contracting diphenyl-dimethanal schiff bases and ferric trichloride are that raw material is heated to reflux certain time in absolute ethyl alcohol, and N, N' is made（2- aminofluorenes）Contracting diphenyl-dimethanal schiff bases iron complex.The method of the present invention is easy to operate, and obtained N, N'（2- aminofluorenes）Contracting diphenyl-dimethanal schiff bases iron complex has preferable absorbing property, N, N' in 2-18 GHz ranges（2- aminofluorenes）Contracting diphenyl-dimethanal schiff bases and its iron complex proportion of goods damageds reach -2.124 dB and -10.413 dB respectively.
Description
Technical field
The invention belongs to absorbing material technical field, more particularly to a kind of N, N'（2- aminofluorenes）Contracting diphenyl-dimethanal Schiff
The preparation method of alkali iron complex.
Background technology
Stealth technology has highly important status in Military Application, it combines electronic engineering, aerodynamics, material
A variety of application technologies such as a variety of subjects and infrared, laser, engine such as material, reduce target dissipating with respect to radar
Penetrating area, echo-signal is lost as far as possible and reduces the chance etc. being detected is reached to radar invisible purpose key item
Part presently mainly realizes the stealthy of target by using configuration design and Coated With Absorbing Material.Absorbing material has following several
4 kinds of kind,（1）By the difference of wave-absorbing mechanism, it is divided into and inhales wave mode and interference-type.It is mainly that electromagnetic wave is lost in material itself to inhale wave mode
Absorption；Interference-type is equal using the amplitude for carrying out two row back wave of self-priming wave layer surface layer and bottom, opposite in phase condition carries out
Interference is offset.（2）By the difference of material deterioration inside mechanism, it is divided into magnetic loss type, dielectric loss type and resistor-type.Hydroxy iron powder, iron
Oxysome, magnetic metal and its nano material etc. belong to magnetic medium type absorbing material, its mechanism mainly has domain wall resonance, is total to naturally
Shake, magnetic hystersis loss and aftereffect loss etc..With higher tangent magnetic loss angle, there have that wave-sucking performance is strong, absorption band is wide to be excellent
Performance is a kind of absorbing material being most widely used at present；Barium titanate, ferroelectric ceramics etc. belong to dielectric type absorbing material,
It is using relaxation, decaying, electromagnetic wave absorptions such as electronic polarization, molecular polarization, ionic polarization or the interfacial polarizations of dependence medium as machine
Reason；Silicon carbide fibre, graphite etc. belong to resistor-type absorbing material, and the decaying of electromagnetic energy is mainly on resistance.（3）According to material at
Type technique and bearing capacity are divided into coating-type and structural type two major classes.（4）It can be divided into novel wave-absorbing material sooner or later by study period
With traditional absorbing material, iron carbonyl, ferrite, metal iron powder, barium titanate, silicon carbide, conductive fiber, graphite etc. belong to traditional
Absorbing material, they the characteristics of be to inhale that wave frequency band is narrow, density is big etc..Novel wave-absorbing material has conducting polymer, chiral material, receives
The features such as rice material, retinyl Schiff's base etc., they have absorbability strong, and density is small.But either novel absorbing material
Or traditional absorbing material is all difficult to meet shadow body technology demand for development with rapid changepl. never-ending changes and improvements.So continually developing new suction wave
Material sense is great.
The application selects 2- aminofluorenes and diphenyl-dimethanal synthesis of conjugate Bis-Schiff Bases and its iron complex, and it is new to obtain structure
Grain husk, electric conductivity are good, the excellent New Type Radar absorbing material of absorbing property.The synthesis and its iron cooperation of such conjugation schiff bases
The research of physical performance will have certain meaning, especially such conjugation to the development in conductive material field, radar-wave absorbing field
Schiff base metal salt complex has potential application in suction wave field.
Invention content
The object of the present invention is to provide a kind of N, N'（2- aminofluorenes）The preparation of contracting diphenyl-dimethanal schiff bases iron complex
Method.
The specific steps are：
(1) 1 mL diphenyl-dimethanals are dissolved in 3 mL absolute ethyl alcohols, diphenyl-dimethanal ethanol solution is made.
(2) 0.8 mmol is weighed（0.3000 g）The absolute ethyl alcohol of 2- aminofluorenes and 3 mL is added to three mouthfuls of burnings of 50 mL
In bottle, three-necked flask is fixed on magnetic stirring apparatus, uniform stirring, and instills 0.25mL acetic acid into three-necked flask and be catalyzed
Diphenyl-dimethanal ethanol solution made from step (1) is then slowly dropped into three by agent under nitrogen atmosphere protection by constant pressure funnel
In mouth flask, after flowing back and stir 6 hours in 60 DEG C of oil bath pans, there is tan precipitate generation, the Temperature fall after reaction stops
To room temperature, filtering, precipitation is recrystallized with absolute ethyl alcohol, dry, and yellow powder, as N, N' is made（2- aminofluorenes）Contracting biphenyl two
Formaldehyde schiff bases.
(3) it is 1 in molar ratio:3 weigh N, N' made from step (2)（2- aminofluorenes）Contracting diphenyl-dimethanal schiff bases and
FeCl3, FeCl3It is dissolved in 3 mL absolute ethyl alcohols, FeCl is made3Ethanol solution, N, N'（2- aminofluorenes）Contracting diphenyl-dimethanal
Schiff bases and 20 mL absolute ethyl alcohols are added in three-necked flask, be then added dropwise into three-necked flask with constant pressure funnel made from
FeCl3Ethanol solution, simultaneously magnetic agitation 8 hours of flowing back at 80 DEG C, there is green matter generation, three times with washes of absolute alcohol,
By responseless FeCl3It removes, is dried through 80 DEG C of vacuum drying ovens, obtain N, N'（2- aminofluorenes）Contracting diphenyl-dimethanal Schiff
Alkali iron complex.
The method of the present invention is easy to operate, and obtained N, N'（2- aminofluorenes）Contracting diphenyl-dimethanal schiff bases iron complex
With preferable absorbing property, N, N' in 2-18 GHz ranges（2- aminofluorenes）Contracting diphenyl-dimethanal schiff bases and its iron cooperation
The object proportion of goods damageds reach -2.124 dB and -10.413 dB respectively.
Description of the drawings
Fig. 1 is the N, N' of the present invention（2- aminofluorenes）The structural formula of contracting diphenyl-dimethanal schiff bases.
Fig. 2 is N obtained, N' in the embodiment of the present invention（2- aminofluorenes）The infrared spectrum of contracting diphenyl-dimethanal schiff bases.
Fig. 3 is N obtained, N' in the embodiment of the present invention（2- aminofluorenes）Contracting diphenyl-dimethanal schiff bases iron complex it is red
External spectrum.
Fig. 4 is N obtained, N' in the embodiment of the present invention（2- aminofluorenes）The reflection loss of contracting diphenyl-dimethanal schiff bases is bent
Line.
Fig. 5 is N obtained, N' in the embodiment of the present invention（2- aminofluorenes）Contracting diphenyl-dimethanal schiff bases iron complex it is anti-
Penetrate damage curve.
Specific implementation mode
With reference to specific embodiment, the present invention is furture elucidated, but embodiment is not intended to limit protection scope of the present invention.
Embodiment：
(1) 1 mL diphenyl-dimethanals are dissolved in 3 mL absolute ethyl alcohols, diphenyl-dimethanal ethanol solution is made.
(2) 0.8 mmol is weighed（0.3000 g）The absolute ethyl alcohol of 2- aminofluorenes and 3 mL is added to three mouthfuls of burnings of 50 mL
In bottle, three-necked flask is fixed on magnetic stirring apparatus, uniform stirring, and instills 0.25mL acetic acid into three-necked flask and be catalyzed
Diphenyl-dimethanal ethanol solution made from step (1) is then slowly dropped into three by agent under nitrogen atmosphere protection by constant pressure funnel
In mouth flask, after flowing back and stir 6 hours in 60 DEG C of oil bath pans, there is tan precipitate generation, the Temperature fall after reaction stops
To room temperature, filtering, precipitation is recrystallized with absolute ethyl alcohol, dry, and yellow powder is made, and is confirmed through infrared spectrum, mass spectrum, as N,
N'（2- aminofluorenes）Contracting diphenyl-dimethanal schiff bases（Yield 90%, 301-312 DEG C of fusing point）, structural formula is：
。
(3) it is 1 in molar ratio:3 weigh N, N' made from step (2)（2- aminofluorenes）Contracting diphenyl-dimethanal schiff bases and
FeCl3, FeCl3It is dissolved in 3 mL absolute ethyl alcohols, FeCl is made3Ethanol solution, N, N'（2- aminofluorenes）Contracting diphenyl-dimethanal
Schiff bases and 20 mL absolute ethyl alcohols are added in three-necked flask, be then added dropwise into three-necked flask with constant pressure funnel made from
FeCl3Ethanol solution, simultaneously magnetic agitation 8 hours of flowing back at 80 DEG C, there is green matter generation, three times with washes of absolute alcohol,
By responseless FeCl3It removes, is dried through 80 DEG C of vacuum drying ovens, obtain N, N'（2- aminofluorenes）Contracting diphenyl-dimethanal Schiff
Alkali iron complex places it in spare in drier.
Using the U.S.（Hewlett-Packard）Agilent company N5230C type vector network analyzers, in 2-18 gigahertz frequency ranges,
Electromagnetic parameter is carried out to schiff bases made from the present embodiment and its iron complex（ε`,ε``,μ`,μ``）Test.
According to transmission line theory, reflection loss of the single layer microwave absorbing coating in electromagnetic wave vertical incidence（RL）It can be by following
Formula be calculated：
RL(dB)=20lg|(Z in-Z 0)/(Z in+Z 0)|。
In formula, ZinIt is the input impedance of microwave absorbing coating, Z0It is the wave impedance of free space, μrAnd εrRespectively microwave absorbing coating
Complex permeability and complex dielectric permittivity, d be material thickness, f is the frequency of incident electromagnetic wave, and c is the light velocity.RL values be equal to-
10 dB mean 90% microwave absorbability, so the dB of RL≤- 10 are usually regarded as a material if appropriate for as electromagnetic wave
One important evidence of absorbent.By surveyed electromagnetic parameters and the microwave absorbing coating of thickness 2.5-5.0 mm is obtained according to formula
Reflection loss curve in 2-18 GHz ranges, as a result sees figures 3 and 4.From figure it is found that in 2-18 GHz ranges N, N'（2-
Aminofluorene）Contracting diphenyl-dimethanal schiff bases and its iron complex proportion of goods damageds reach -2.124 dB and -10.413 dB respectively.
Absorbing property is carried out to the conjugation schiff base compounds and its Fe complexs of synthesis using vector network analyzer
Studies have shown that in 2-18 GHz ranges, conjugation schiff base compounds with after metal salt coordination, inhale wave electromagnetic property relative to
Conjugation schiff base compounds are itself improved, and the reflection loss of complex is obviously higher than schiff base ligand itself to be obtained
It is more, demonstrate importance of the conjugated system flatness in terms of the requirement of absorbing material.
Claims (1)
1. a kind of N, N'-（2- aminofluorenes）The preparation method of contracting diphenyl-dimethanal schiff bases iron complex, it is characterised in that specific
Step is：
(1) 1 mL diphenyl-dimethanals are dissolved in 3 mL absolute ethyl alcohols, diphenyl-dimethanal ethanol solution is made；
(2) absolute ethyl alcohol for weighing 0.8 mmol 2- aminofluorenes and 3 mL, is added in the three-necked flask of 50 mL, and three mouthfuls are burnt
Bottle is fixed on magnetic stirring apparatus, uniform stirring, and is instilled 0.25mL acetic acid into three-necked flask and made catalyst, then by step
(1) diphenyl-dimethanal ethanol solution made from is slowly dropped by constant pressure funnel in three-necked flask under nitrogen atmosphere protection, 60
It flows back in DEG C oil bath pan and after stirring 6 hours, has tan precipitate generation, be naturally cooling to room temperature after reaction stops, filtering,
Precipitation is recrystallized with absolute ethyl alcohol, dry, and yellow powder, as N, N' is made（2- aminofluorenes）Contracting diphenyl-dimethanal schiff bases；
(3) it is 1 in molar ratio:3 weigh N, N' made from step (2)（2- aminofluorenes）Contracting diphenyl-dimethanal schiff bases and FeCl3,
FeCl3It is dissolved in 3 mL absolute ethyl alcohols, FeCl is made3Ethanol solution, N, N'（2- aminofluorenes）Contracting diphenyl-dimethanal schiff bases
It is added in three-necked flask with 20 mL absolute ethyl alcohols, FeCl obtained is then added dropwise into three-necked flask with constant pressure funnel3Ethyl alcohol
Solution, simultaneously magnetic agitation 8 hours of flowing back at 80 DEG C, there is green matter generation, three times with washes of absolute alcohol, will be without anti-
The FeCl answered3It removes, is dried through 80 DEG C of vacuum drying ovens, obtain N, N'（2- aminofluorenes）Contracting diphenyl-dimethanal schiff bases iron coordinates
Object.
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| CN110552008A (en) * | 2019-09-19 | 2019-12-10 | 桂林理工大学 | Preparation method and application of 2, 6-pyridine dimethyl acetal 2-aminofluorene Schiff base corrosion inhibitor |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1656059A (en) * | 2002-05-20 | 2005-08-17 | 日本化药株式会社 | Diimonium salt mixtures, aminium salts mixtures and use thereof |
| CN1878747A (en) * | 2003-11-10 | 2006-12-13 | 日本化药株式会社 | Diimonium salt compound and use thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1656059A (en) * | 2002-05-20 | 2005-08-17 | 日本化药株式会社 | Diimonium salt mixtures, aminium salts mixtures and use thereof |
| CN1878747A (en) * | 2003-11-10 | 2006-12-13 | 日本化药株式会社 | Diimonium salt compound and use thereof |
Non-Patent Citations (2)
| Title |
|---|
| 不同结构席夫碱及其铁盐的合成与红外隐身性能研究;胡映雪 等;《材料开发与应用》;20160229;第31卷(第1期);第55-60页 * |
| 长链共轭聚席夫碱及其盐的合成与性能研究;刘辉林;《中国优秀硕士学位论文全文数据库 工程科技I辑》;20130115;第B014-241页 * |
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Application publication date: 20170329 Assignee: Guilin Yuanjing Electronic Technology Co.,Ltd. Assignor: GUILIN University OF TECHNOLOGY Contract record no.: X2022450000249 Denomination of invention: N. Preparation of N '(2-aminofluorene) biphenyl dialdehyde Schiff base iron complexes Granted publication date: 20181106 License type: Common License Record date: 20221207 |