CN109970937A - A kind of ionic conjugated poly-schiff base and preparation method thereof - Google Patents

A kind of ionic conjugated poly-schiff base and preparation method thereof Download PDF

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CN109970937A
CN109970937A CN201910301550.XA CN201910301550A CN109970937A CN 109970937 A CN109970937 A CN 109970937A CN 201910301550 A CN201910301550 A CN 201910301550A CN 109970937 A CN109970937 A CN 109970937A
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schiff base
conjugated poly
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宫琳丹
郑文岐
范路安
杜松辉
张博
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Harbin Engineering University
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Abstract

The present invention provides a kind of ionic conjugated poly-schiff base and preparation method thereof, include the following steps: with compound (9,9- bis- (6- bromine hexyl) -2, bis- fluorenes aldehyde of 7-) it is raw material, it in the case where 110 DEG C of anhydrous lithium chlorides are catalyzed and under nitrogen atmosphere, carries out polycondensation reaction with o-phenylenediamine and obtains intermediate polymer；Intermediate polymer is dissolved in THF, and carries out quaternization reaction with trimethylamine aqueous solution and obtains water-soluble ionic-type conjugated poly-schiff base.The C=N double bond structure that main chain of the present invention contains can carry out complexation reaction with ion, side chain contains quaternary ammonium cationic groups, improve the dissolubility of sample, to solve the problems, such as that schiff bases is water-soluble bad, which can realize that the specific detection to aqueous environments copper ion, synthetic method of the present invention are simple, it is easy to industrialized production, the present invention, which prepares ionic conjugated poly-schiff base, can realize quick, sensitive, accurate, economic detection to copper ion in aqueous solution, and selectivity is high, be suitble to trace detection.

Description

A kind of ionic conjugated poly-schiff base and preparation method thereof
Technical field
The present invention relates to a kind of conjugated poly-schiff base and preparation method thereof more particularly to a kind of ionic conjugated poly-schiff bases And preparation method thereof, belong to field of organic polymer compound.
Background technique
Conjugated polymer is a kind of new functional macromolecule material, has the photoelectricity of metal and inorganic semiconductor material itself Performance is widely applied in fields such as organic display of new generation, novel photovoltaic materials.With common small organic molecule phase Than conjugated polymer has many advantages, such as signal amplification, and photoelectric conversion efficiency is higher, response is sensitive, therefore also serves as sensor material. Schiff bases is a kind of compound containing C=N double bond, is widely used in the fields such as liquid crystal material and absorbing material.Schiff bases C=N double bond in structure can be also used for detection metal ion with metal bonding, small molecule schiff bases.But the dissolubility of schiff bases It is poor, it is limited in the application of water solution system.
The superiority and inferiority etc. of organism physiological function and environment is played metal ion and its important role, with people The industrialized continuous propulsion of class, plurality of heavy metal ion such as: cobalt, lead, chromium, mercury, tin have entered in soil and river, cause Serious environmental pollution.Especially water is the necessity that the mankind live daily, thus we more it is necessary to detect around us Metal ion content in water.So preparation can be dissolved in the fluorescence chemical sensor of water, for detecting Cu2+Have huge Practical value.
Summary of the invention
The purpose of the invention is to provide a kind of ionic conjugated poly-schiff base for detecting copper ion and its preparation Method.
The object of the present invention is achieved like this:
The structural formula of a kind of ionic conjugated poly-schiff base, the ionic conjugated poly-schiff base is as follows:
A kind of preparation method of ionic conjugated poly-schiff base, includes the following steps:
Step 1: with compound (9,9- bis- (6- bromine hexyl) -2,7-, bis- fluorenes aldehyde) be raw material and o-phenylenediamine 100~ Under 120 DEG C of anhydrous lithium chloride catalysis and under nitrogen atmosphere, carries out polycondensation reaction and obtain intermediate polymer；
Step 2: intermediate polymer is dissolved in THF, and is carried out quaternization reaction with trimethylamine aqueous solution and obtained water solubility Ionic conjugated poly-schiff base.
The invention also includes features some in this way:
The step 1 reaction solvent for use is DMF, reaction condition N2Environment, is condensed back by 100~120 DEG C of temperature, Reaction time be 8~for 24 hours；
The molar ratio of (the two fluorenes aldehyde of 9,9- bis- (6- bromine hexyl) -2,7-) and o-phenylenediamine is 1:1~1:3；
The step 2 is in room temperature N224~72h is reacted in environment.
Compared with prior art, the beneficial effects of the present invention are:
The present invention is prepared for a kind of ionic conjugated poly-schiff base of brand new.The C=N double bond structure that main chain contains can Complexation reaction is carried out with ion, side chain contains quaternary ammonium cationic groups, improves the dissolubility of sample, water-soluble to solve schiff bases The bad problem of property, the polymer can realize the specific detection to aqueous environments copper ion；
Synthetic method of the present invention is simple, easy to industrialized production, and the present invention prepares ionic conjugated poly-schiff base and can realize Quick, sensitive, accurate, economic detection to copper ion in aqueous solution, selectivity is high, is suitble to trace detection, the inspection of copper ion Survey is limited to 1.4 × 10-6mol/L。
Detailed description of the invention
Fig. 1 is polymer II1H NMR spectra (DMSO-d6, 20 DEG C, 500MHz)；
Fig. 2 is the infrared spectrogram of polymer II (A is compound I, and B is polymer II)；
Fig. 3 is the 1H NMR spectra (DMSO-d of polymer III6, 20 DEG C, 500MHz)；
Fig. 4 is the infrared spectrogram of polymer III (A is polymer II, and B is polymer III)；
Fig. 5 is fluorescence effect picture of the different metal ions to polymer III；
Fig. 6 is fluorescence effect histogram of the different metal ions to polymer III；
Fig. 7 is that Cu is added in polymer III under different pH2+The fluorescence intensity of front and back；
Fig. 8 is the time Cu to be added to polymer III buffer solution system2+The fluorescence intensity of front and back influences；
Fig. 9 is various concentration Cu2+To the fluorescent effect figure of polymer III；
Figure 10 is the fluorescence intensity and Cu of polymer III2+The linear equation of concentration；
Figure 11 is that other metal ions identify Cu to polymer III2+Interference effect figure.
Specific embodiment
Present invention is further described in detail with specific embodiment with reference to the accompanying drawing.
Present invention design has synthesized one kind containing fluorenyl ionic conjugated poly-schiff base, and the polymer is glimmering as metal ion Optical sensor is for detecting Cu2+。
The object of the invention can be achieved through the following technical solutions:
One kind containing fluorenyl ionic conjugated poly-schiff base, and the polymer formulae is as follows:
A kind of synthetic method of above-mentioned polymer, reaction route are as follows:
Specific synthesis step is as follows:
Step 1: be raw material and o-phenylenediamine 100 with compound I (9,9- bis- (6- bromine hexyl) -2,7-, bis- fluorenes aldehyde)~ Under 120 DEG C of anhydrous lithium chloride catalysis and under nitrogen atmosphere, carries out polycondensation reaction and obtain polymer II.
Step 2: polymer II is dissolved in THF, and quaternization reaction is carried out with trimethylamine aqueous solution and obtains water-soluble poly Close object III.
In the above method, it is DMF that the first step, which reacts solvent for use, and catalyst is anhydrous LiCl, reaction condition N2Environment, 100~120 DEG C of temperature, be condensed back, the reaction time be 8~for 24 hours.
In the above method, in first step reaction, the molar ratio of compound I and o-phenylenediamine is 1:1~1:3.
In the above method, second step reaction need to be in room temperature N224~72h is reacted in environment.
Every step product all passes through nuclear magnetic resonance spectrometer (NMR) and fourier transform infrared spectroscopy instrument (FT-IR) is tied Structure characterization.
Ionic conjugated polymer of the present invention containing fluorenyl and phenyl ring can be used as underwater gold category ion fluorescence biography Sensor is for detecting Cu2+。
Ionic conjugated polymer of the present invention containing fluorenyl and phenyl ring, due to introducing long alkyl on main chain Chain, then quaternized processing is carried out to it, make the polymer that there is good water solubility.The polymer has good fluorescence simultaneously Characteristic and optical activity can be applied to Cu in water2+Detection, there is high sensitivity, easy to operate, it is excellent that detection limit is low etc. Point.
Embodiment 1
(1) preparation of polymer II
0.11g compound I is added in the reaction flask of 100ml, by 0.065g, (dialdehyde and diamines molar ratio are adjacent for 1:3) Phenylenediamine, polymer solvent DMF, catalyst are anhydrous LiCl, reaction condition N2Environment, is condensed back by 100 DEG C of temperature, when Between 12h.After room temperature to be restored, the liquid that reaction was completed is slowly dropped in the ice water of 500ml and is precipitated, there is the analysis of yellow floccule Out, it is centrifuged, it is dry, it washs repeatedly for several times up to the amido peak disappearance in polymer nuclear magnetic spectrogram, is dried in vacuo 12h at 40 DEG C Obtain yellow powder 0.086g, yield 58.3%.
1H NMR (500MHz, DMSO, TMS, 20 DEG C, ppm): δ=8.31-7.90 (m, Ph-H, 6H), 7.73-7.04 (t ,-CH=N, 1H, Ph-H, 2H), 3.46-3.28 (t ,-CH2-Br,4H),2.86-2.58(m,-CH2-(CH2)5-Br,4H), 2.21-1.77(m,-CH2(CH2)4-Br),1.56-1.18(m,-CH2-(CH2)2-Br,4H),1.13-0.81(m,-CH2- (CH2)3-Br,4H),0.64-0.33(m,-CH2-(CH2)5-Br,4H)。
As shown in Figure 2, polymer II is compared with compound I, 3386cm-1The stretching vibration peak at place phenyl ring hydrogen (Ph-H), 2924cm-1And 742cm-1Alkyl (the CH at place2-CH2) vibration peak still exists, while 2732cm-1And 1694cm-1The aldehyde at place Base peak (H-C=O) has disappeared, finally, polymer is in 1604cm-1There is new vibration peak in place, usual imido grpup (C=N) Infrared absorption peak appears in 1600~1670cm-1Between, the structure of conjugated polymer II can determine that peak is imido grpup at this Infrared absorption peak.
Above-mentioned data prove that polymer II is successfully prepared.
(2) synthesis (polymer III) containing fluorenyl ionic conjugated polymer
40mg polymer II is put into the reaction flask of 100ml, is dissolved in the THF of 20ml, 25ml front three aqueous amine is added Solution, in room temperature N2It is reacted for 24 hours in environment.Liquid after reaction is transferred in eggplant type bottle, vacuum rotary steam to powdered, The product is put into vacuum oven, drying for 24 hours, obtains yellow powder polymer III in 30 DEG C of environment.Yield is 87.4%.
1H NMR (500MHz, DMSO, TMS, 20 DEG C, ppm): δ=8.58-7.92 (m, Ph-H, 6H), 7.69-6.98 (t, CH=N, 1H, Ph-H, 2H), 3.93-3.25 (s ,-N-CH3,18H),3.24-3.16(m,-CH2-Br,4H),2.98-2.81 (m,-CH2-CH2-Br,4H),2.21-2.01(m,-CH2-(CH2)4-Br,4H),1.49-0.49(m,-(CH2)2-(CH2)2- Br,-CH2-(CH2)5-Br,12H)。
Fig. 4 it is found that polymer III compared with polymer II, 3436cm-1The stretching vibration peak at place phenyl ring hydrogen (Ph-H), 2938cm-1And 742cm-1Alkyl vibration peak (the CH at place2-CH2) and 1631cm-1Imido grpup (C=N) vibration peak at place is still deposited , while polymer polymerizing object III is in 1099cm-1There is new vibration peak in place, the infrared suction of (C-N) in usual tertiary amine groups It receives summit and appears in 1360~1020cm-1Between, the structure of conjugated polymer III can determine that peak is the red of tertiary amine groups at this Outer absorption peak.
Above-mentioned data prove that polymer III is successfully prepared.
Embodiment 2
Detection application of the polymer III to copper ion
As shown in figure 5, selecting concentration for 2 × 10-5The polymer III aqueous solution of mol/L, and configure metal ion and polymerization Object III mixed solution is several, and the molar ratio of metal ion and polymer III are 50:1, and mixed solution places 2h after preparing；With 340nm excitation, tests the fluorescence spectrum of various mixed solutions, and compare with polymer III blank sample fluorescence spectrum respectively, sees Examine their influences to polymer III fluorescence spectrum.The best launch wavelength of polymer III blank sample is as seen from Figure 5 382nm, for common metal ion, such as Ca2+、Fe2+、Mn2+、Co2+、Ni2+、Cu2+、Zn2+、Cr3+、Hg2+Deng.Experiment shows When Ca is added into polymer III aqueous solution2+、Fe2+When, fluorescence intensity of the polymer III at 405nm is almost without generation Variation；When Mn is added into system2+、Co2+、Ni2+、Zn2+、Cr3+、Hg2+When, fluorescence intensity hair of the polymer III at 405nm A degree of quenching is given birth to, but it is weaker to quench effect；But Cu2+Addition so that the fluorescence emission spectrum of polymer III is sent out Apparent quenching is given birth to.As seen from Figure 6, Ca2+、Fe2+Addition, the change of polymer III fluorescence spectrum will not be caused substantially； Mn2+、Ni2+、Co2+、Zn2+、Cr3+、Hg2+Also it can make fluorescent quenching, changing intensity is only original 1/7~1/4 to differ；Work as addition Cu2+When, the generation of polymer III fluorescence intensity sharply declines, and fluorescence intensity is about original 1/5, produces quenching substantially.More than The result shows that polymer III is to Cu2+There is high degree of specificity response, is extremely suitable for Cu in detection aqueous solution2+。
As shown in fig. 7, we test Cu under different ph values2+To the fluorescence effect of polymer III.Adding Enter 50 times of polymer III molar ratio Cu2+Afterwards, in acid condition, with the raising of pH, Cu2+Quenching effect become better and better, Until being kept approximately constant after pH=6.It can illustrate above, within the scope of near-neutral pH, polymer III is insensitive to pH , since most of physiology and natural environment are all near pH=7, so polymer III can be used as Cu2+Effective identifier.
As shown in figure 8, the fluorescence spectrum of polymer III aqueous solution blank sample is highly stable, the passage of time is hardly followed And change, illustrate that the conjugated structure of polymer III is sufficiently stable in buffer solution medium, and 50 times of polymer are being added After III molar ratio copper ion, in preceding 6min, the fluorescence intensity of system constantly declines over time, It touches the bottom when 8min, the fluorescence intensity of subsequent system is held essentially constant.
As shown in figure 9, the concentration of polymer III remains 2 × 10-5Mol/L, by constantly change be added after Cu2+It is dense Degree carries out concentration titrations to polymer III.Cu2+0,1,2,4,10,20 and 50 are followed successively by with the concentration ratio of polymer III.From Fig. 9 can be seen that when metal ion is not added, fluorescence intensity of the polymer III at 405nm is 115, when 1 times of equivalent of addition Cu2+When, polymer fluorescent intensity sharply has dropped 1/3, continues growing Cu2+Content, under the fluorescence intensity of polymer continues Drop, but decrease speed obviously slows down, and works as Cu2+When concentration reaches 50 times of equivalents, polymer fluorescent intensity reaches minimum, about former 1/5 come；These phenomenons show the addition of copper ion, and strong interaction has occurred with polymer, keeps polymer fluorescent strong Degree sharply declines.
As shown in Figure 10, according to the optimum reacting time for testing the polymer III and copper ion that measure above, 2 will be contained ×10-5Mol/L polymer III and various concentration copper ion (0~1 × 10-5Mol/L mixing PBS buffer solution) is at room temperature After ultrasonic 8min, its fluorescence intensity change at 405nm is measured.It is drawn according to the fluorescence intensity at copper ion concentration and 405nm Working curve processed.The result shows that Cu2+In fluorescence intensity and mixed system at polymer III system maximum emission wavelength 405nm Copper ion concentration is 0.1~1 × 10-5It is in good linear relationship, equation of linear regression I=-2.16C+ within the scope of mol/L 108.747, (CDL=3Sb/m) is defined according to IUPAC, calculates Cu2+Detection in polymer III aqueous solution is limited to 1.4 × 10-6mol/L。
As shown in figure 11, the Cu of 20 equivalents is added in polymer III solution2+Afterwards, fluorescence intensity of the observation at 405nm Changing value tests other metal ions to identifying Cu in polymer III water with this2+The influence of performance.As shown in Figure 11, exist Ca2+、Fe2+、Co2+、Mn2+、Ni2+、Zn2+、Hg2+And Cr3+Cu is added in the presence of plasma2+, fluorescence at 405nm Intensity value and only addition Cu2+Equally, its fluorescence intensity is made to drop to 1/5 or so of polymer III blank sample.

Claims (6)

1. a kind of ionic conjugated poly-schiff base, characterized in that the structural formula of the ionic conjugated poly-schiff base is as follows:
2. a kind of preparation method of ionic conjugated poly-schiff base, characterized in that include the following steps:
Step 1: being raw material and o-phenylenediamine at 100~120 DEG C with compound (9,9- bis- (6- bromine hexyl) -2,7-, bis- fluorenes aldehyde) Under anhydrous lithium chloride catalysis and under nitrogen atmosphere, carries out polycondensation reaction and obtain intermediate polymer；
Step 2: intermediate polymer is dissolved in THF, and is carried out quaternization reaction with trimethylamine aqueous solution and obtained water soluble ion Type conjugated poly-schiff base.
3. the preparation method of ionic conjugated poly-schiff base according to claim 2, characterized in that the step 1 reaction Solvent for use is DMF, reaction condition N2Environment, 100~120 DEG C of temperature, be condensed back, the reaction time be 8~for 24 hours.
4. the preparation method of ionic conjugated poly-schiff base according to claim 2 or 3, characterized in that described (9,9- bis- Two fluorenes aldehyde of (6- bromine hexyl) -2,7-) it with the molar ratio of o-phenylenediamine is 1:1~1:3.
5. the preparation method of ionic conjugated poly-schiff base according to claim 2 or 3, characterized in that the step 2 In room temperature N224~72h is reacted in environment.
6. the preparation method of ionic conjugated poly-schiff base according to claim 4, characterized in that the step 2 is in room Warm N224~72h is reacted in environment.
CN201910301550.XA 2019-04-16 2019-04-16 A kind of ionic conjugated poly-schiff base and preparation method thereof Pending CN109970937A (en)

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106967205A (en) * 2017-03-17 2017-07-21 暨南大学 The preparation method and applications of Schiff base polymer are conjugated with excellent photocatalysis hydrogen production performance

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106967205A (en) * 2017-03-17 2017-07-21 暨南大学 The preparation method and applications of Schiff base polymer are conjugated with excellent photocatalysis hydrogen production performance

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* Cited by examiner, † Cited by third party
Title
徐志超: ""新型芴基共轭聚合物的合成及其金属离子识别性能研究"", 《中国优秀硕士学位论文全文数据库 工程科技I辑》 *

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Application publication date: 20190705