CN106496236A - A kind of colorimetric fluorescence two-channel silver ion transducer molecule and its synthesis and application - Google Patents
A kind of colorimetric fluorescence two-channel silver ion transducer molecule and its synthesis and application Download PDFInfo
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Abstract
Present invention design has synthesized a kind of 2 phenyl 1H imidazoles [4 of sensor molecule for being capable of colorimetric fluorescence Dual channel detection silver ion, 5 b] azophenlyene, the sensor molecule forms dimer with intermolecular hydrogen bonding first, then act on forming Supramolecular self assembly system by π pi accumulations between azophenlyene ring, so as to the solution of causative subject molecule have issued strong fluorescence；And imidazoles is as an identification function site with azophenlyene ring, high selectivity identification silver ion is reached in water-bearing media in the molecule, and identification process is not disturbed by other cationes.Additionally, after silver ion is added at room temperature, the fluorescence intensity of the solution can decrease fast（＜ 3 seconds）, good bore hole recognition effect can be reached.The Ag made using the sensor molecule+Test paper also can conveniently detect the silver ion in environmental system.
Description
Technical field
The present invention relates to a kind of silver ion sensor molecule, more particularly to one kind can the colorimetric fluorescence dual pathways be by silver from
Sensor molecule 2- phenyl -1H- imidazoles [4,5-b] azophenlyene of son；The present invention also relates to the silver ion sensor point
Sub application of the fluorescence than colour discrimination silver ion in aqueous, belongs to the field of chemical synthesis and technical field of anion detection.
Background technology
Along with developing rapidly for science and technology, silver ion and its compound are widely used and bullion, plating, feels
The fields such as luminescent material.And the expansion with silver ion and its use of a compound, the silver ion amount being discharged in environment also gradually increases
Plus, As time goes on, the migration in the environment of silver ion in waste water, diffusion not only pollute natural water, to human body
And hydrobiological health causes very serious harm.Therefore, the identification of silver ion and detection are in environmental science, life sciences
Important meaning is suffered from fields such as medical science.
The method of detection silver ion is a lot, and colorimetric fluorescence method is received much attention due to the reason such as convenient and swift.At present, if
The silver ion sensor of meter and synthesis has had a lot, but as which is strongly professional, high cost and recognition time are long, these
Factor all constrains the large-scale promotion of a lot of sensor molecules and uses.
Content of the invention
It is an object of the invention to provide a kind of silver ion sensor molecule 2- phenyl -1H- imidazoles [4,5-b] azophenlyene；
It is a further object of the present invention to provide the synthetic method of above-mentioned silver ion sensor molecule；
It is a further aim of the invention provide the sensor molecule in aqueous colorimetric fluorescence identifying silver ion should
With.
First, the structure of silver ion sensor and synthesis
The chemical name of the silver ion sensor molecule of the present invention is 2- phenyl -1H- imidazoles [4,5-b] azophenlyene, is labeled as ZH, its
Structural formula is as follows：
The synthesis of silver ion sensor molecule, is that glacial acetic acid is catalyst, 2,3- diaminophenazines and benzene first with DMF as solvent
Aldehyde is with 1:1~1:1.5 mol ratios, in 80 ~ 85 DEG C of 7 ~ 8h of back flow reaction；Reaction terminates rear sucking filtration；The ethanol of gained solid heat is washed
Wash, be vacuum dried, then use DMF-H2O recrystallization, obtain yellow solid, as sensor molecule ZH.
0.4 ~ 0.6 times for benzaldehyde mole of the consumption of catalyst glacial acetic acid.
2nd, the cations recognition experiment of silver ion sensor
1st, fluorescence identifying performance of the silver ion sensor to cation
The DMSO solution (2 × 10 of 0.5 mL sensor molecule ZH is pipetted respectively-4mol·L-1) in a series of 10mL color comparison tubes
In, it is separately added into Fe3+, Hg2+, Ag+, Ca2+, Cu2+, Co2+, Ni2+, Cd2+, Pb2+, Zn2+, Cr3+, Mg2+Perchlorate DMSO
Solution (4 × 10-3mol·L-1) 0.25 mL.Sequentially add 2.5ml pH=7.2 buffer solution（With 4- hydroxyethyl piperazine second
Sulfonic acid and TBAH regulating allocation into pH=7.2 water）, finally with DMSO constant volumes to 5mL, now acceptor density
For 2 × 10-5mol·L-1, the percentage by volume 50% of water in system, cation concn are 10 times of acceptor density, observe each
Response of the receptor to cation.
As a result find, when the DMSO of ZH (when being separately added into above-mentioned cationic solution in aqueous 50%) solution, only Ag+
Addition make the color of solution decorporate immediately, and its strong yellow fluorescence is quenched completely.In its corresponding ultraviolet spectra, Ag+'s
Adding declines absworption peak of the ZH solution at 403nm（Fig. 1）.In its corresponding fluorescence emission spectrum, Ag+Addition make
Emission peak of the ZH solution at 548nm disappears（Fig. 2）.And the addition of remaining cation to the fluorescence spectrum of LT solution without obvious shadow
Ring.Illustrate that sensor molecule in aqueous can single-minded selectivity fluorescence identifying Ag+.
2nd, ZH is to Ag+Titration experiments
ZH is made into 2 × 10 with DMSO-4The bulk solution of mol L, takes the DMSO solution of the ZH of 0.5mL（2.0×10-4mol/L）
In 10mL color comparison tubes, the buffer solution of 2.5mL is added（Adjusted with 4- hydroxyethyl piperazine ethanesulfonic acid and TBAH and matched somebody with somebody
The water of the pH=7.2 being set to）, with DMSO constant volumes to 5mL, now acceptor density is 2 × 10-5mol·L-1, shake up standing.Pipette
The solution of the ZH of 2.5mL（2.0×10-5mol/L）In quartz cell, Ag is gradually added into accumulation sample-adding method+Perchlorate
DMSO solution, surveys its Ultraluminescence spectrum in room temperature（Fig. 3-6）.Being gradually dropped with silver ion in ultra-violet absorption spectrum,
Absworption peak at 403 nm gradually weakens.Being gradually dropped with silver ion in fluorescence spectrum, the emission peak at 548nm is gradually
Disappear, illustrate that sensor ZH can be in DMSO（Aqueous 50%）Sensitive quickly single-minded detection Ag in solution+.ZH is to Ag+Fluorescence
Spectral detection is limited to 2.92 × 10-7M, ultraviolet spectra detection are limited to 7.73 × 10-8M, and process have very high sensitive
Degree.
3rd, interference free performance detection
In order to determine receptor ZH to Ag+Detection results, we have carried out following test again：Take two groups of 10ml color comparison tubes to add respectively
Enter the DMSO solution (2 × 10 of the above-mentioned ZH of 0.5mL-4mol·L-1), then it is separately added into 0.25mLFe3+, Hg2+, Ag+, Ca2+, Cu2 +, Co2+, Ni2+, Cd2+, Pb2+, Zn2+, Cr3+, Mg2+Perchlorate DMSO solution (4 × 10-3mol·L-1), then add successively
Enter 2.5mLpH=7.2 buffer solution（With 4- hydroxyethyl piperazine ethanesulfonic acid and TBAH regulating allocation into pH=7.2
Water）, finally with DMSO constant volumes to 5mL.Add 0.25mLAg in another set again respectively+Perchlorate DMSO solution,
A kind of other ten cationes of 0.25mL are separately added in each color comparison tube（Fe3+, Hg2+, Ca2+, Cu2+, Co2+, Ni2+, Cd2+,
Pb2+, Zn2+, Cr3+, Mg2+）Perchlorate DMSO solution, sequentially add 2.5mLpH=7.2 buffer solution（With 4- hydroxyl second
Base piperazine ethanesulfonic acid and TBAH regulating allocation into pH=7.2 water）, finally with DMSO constant volumes to 5mL.Mixing
Observed after uniform.
Fig. 7,8 are respectively ultraviolet interference free performance and the fluorescence interference free performance that ZH is recognized to silver ion.As a result find, plus
After entering 12 kinds of cationes, ultraviolet absorption peak of the ZH solution at 403nm declines, and fluorescence emission peak is quenched.This and Ag+To ZH's
Impact is consistent（Fig. 1,2）.So as to receptoroid detection Ag is described+Substantially do not disturbed by other cationes.
4th, sensor ZH identifications Ag+Response time
Common sensor molecule colorimetric or fluorescence identifying Ag+Identification process need longer response time, this factor is past
Toward having made promoting the use of for a lot of sensor molecules.Therefore, we have probed into sensor LT to Ag+The time of response.Work as addition
After silver ion, solution colour takes off immediately, and fluorescence is quenched completely, it can be seen that sound of sensor molecule ZH to silver ion
Should can occur between a moment（< 3s）.Therefore sensor molecule ZH has detection speed faster.
5th, sensor ZH identifications Ag+Cyclic reversibility
In recent years, the recyclability of acceptor molecule became the big focus in cations recognition research, and therefore, we have inquired into this
Acceptor molecule is to Ag+The recyclability of identification.It is well known that iodide ion and silver ion have very strong associative ability, be a kind of very
Good Ag+Ion precipitation agent, therefore we select iodide ion as Ag+Chelating agent.Experimental phenomena shows：When in ZH- Ag+Network
Appropriate I is added in fit system-Ion, I-Ion can rapidly by Ag+From on host molecule, solution complexation is got off, and forms AgI and sinks
Form sediment, color of the solution under uviol lamp is recovered, suitable with main body.Corresponding fluorescence spectrum also returns to the water of original host molecule
Flat.When we go to recognize Ag with the solution again+During ion, the fluorescent quenching of the system, and the peak height substantially with acceptor molecule
Unanimously, so it is repeatedly circulated reaching more than four times（Fig. 9）.Therefore, sensor molecule ZH is that one kind is capable of circulation makes
Ag+Fluorescent optical sensor.
6th, sensor ZH is to Ag+Recognition mechanism
For sensor molecule ZH to Ag+Recognition mechanism is probed into, and we are by characterization methods such as nuclear-magnetism titration, high resolution mass spectrums
Verified.Nuclear-magnetism titration spectrogram shows：At 13.45ppm, the signal peak of-NH is disappeared immediately with the addition of silver ion, and
Also gradually weaken at azophenlyene ring hydrogen proton signal peak.High resolution mass spectrum is to main body and the coordination compound as shown by data of ion：
Appearance at 699.02 and the amino of two molecular receptors slough two hydrogen atoms and then and the molecular weight after silver ion is coordinated consistent.
Therefore, we to sensor LT to Ag+Recognition mechanism is inquired into as follows：In the solution of pH=7.2, the imidazoles of two acceptor molecules
In ring there is deprotonation effect in-NH- keys, and after the addition of silver ion destroys intermolecular hydrogen bonding, silver ion and two molecular receptors divide
The nitrogen-atoms coordination of-N- and azophenlyene ring in the imidazole ring of son, destroys the pi-pi accumulation of sensor molecule, with Ag+In conjunction with shape
Into [2ZH+Ag+– 2H+] metal complex（Figure 10）.
3rd, the Ag based on ZH+Ion detection reagent paper
Ag+The making of ion reagent paper：ZH is configured to 2 × 10-4mol·L−1Aqueous solution；The filter paper for processing is cut into circle
Shape template.Filter paper is infiltrated respectively 10 minutes in above-mentioned solution, ZH is fully adsorbed in then take out on filter paper and is dried.The filter
Paper is in yellow fluorescence under fluorescent lamp.
When Deca Ag on filter paper+When, the original yellow fluorescence of filter paper is disappeared, and the Deca of other cationes is to filter paper
Fluorescence do not affect.This distinct fluorescence color comparative illustration ZH is to Ag+There is the fluorescence identifying ability of height.
In sum, design has synthesized 2- phenyl -1H- imidazoles [4,5-b] azophenlyene (ZH) herein, and the sensor molecule is first
Dimer is formed with intermolecular hydrogen bonding, then acts on forming Supramolecular self assembly system by pi-pi accumulation between azophenlyene ring, so as to
The solution of causative subject molecule have issued strong fluorescence；And imidazoles is as an identification function site, in this point with azophenlyene ring
Son reaches high selectivity identification silver ion in water-bearing media, and identification process is not disturbed by other cationes.Additionally, working as
After adding silver ion at room temperature, the fluorescence intensity of the solution can decrease fast（＜ 3 seconds）, good bore hole identification can be reached
Effect, the Ag made using the sensor molecule+Response reagent paper also can conveniently detect the silver ion in environmental system.
Description of the drawings
Fig. 1 is ZH (c=2.0 × 10−5Mol/L the uv absorption spectra of silver ion, in aqueous solution), is added.
Fig. 2 is ZH and its fluorescence spectrum when adding 10 times of cation（Excitation wavelength：415nm, launch wavelength
548nm）.
Ags of the Fig. 3 for variable concentrations+The ultraviolet spectra of receptor ZH in the presence of (0-16 times).
Ags of the Fig. 4 for variable concentrations+The scatterplot of receptor ZH in the presence of (0-16 times).
Ags of the Fig. 5 for variable concentrations+The fluorescence spectrum of receptor ZH in the presence of (0-14.2 times).
Ags of the Fig. 6 for variable concentrations+The scatterplot of receptor ZH in the presence of (0-14.2 times).
Fig. 7 is the ultraviolet interference free performance that ZH is recognized to silver ion.
Fig. 8 is the fluorescence interference free performance that ZH is recognized to silver ion.
Fig. 9 is the fluorescence reversibility that ZH is recognized to silver ion.
Figure 10 be ZH to silver ion recognition mechanism figure.
Specific embodiment
Below by specific embodiment to the synthesis of silver ion sensor of the present invention, sign and in detection aqueous solution cloudy from
The application of son is described further.
Instrument and reagent
1H NMR use Mercury-400BB type nmr determinations, and TMS is internal standard.IR uses Digilab FTS-3000
FT-IR type infrared spectrometers (KBr tablettings) are determined；Fusing point uses X-4 numerical monitor micro melting point apparatus (the non-school of thermometer
Just) determine；Fluorescence spectrum is using Japan Shimadzu Corporation RF -5301 fluorescence spectrophotometer record.
Cation used is perchlorate, and solvent is（DMSO/H2O(1:1, v/v) HEPES buffer solution (pH=7.2)
(analysis is pure).It is pure that other reagents are commercially available analysis.
First, the synthesis of silver ion fluorescent optical sensor
By 2 mmol 2, in 3- diaminophenazines and 0.75ml benzaldehydes 100 mL round-bottomed flasks of addition, 20 mL DMF are added,
0.3 ~ 0.5ml glacial acetic acid, 80 DEG C ~ 85 DEG C 7 ~ 8h of heating reflux reaction in oil bath is added after question response stops, filtering；By institute
Solid heat washing with alcohol 3 ~ 5 times, in vacuum drying oven after drying, use DMF-H2O recrystallization, obtain brown solid.
Its synthesis type is as follows：
ZH:Yield：80%; m.p. >300℃;1H NMR (DMSO-d 6,600MHz) δ 13.45 (s 1H), 8.52
(s 1H), 8.38-8.37 (d 2H),8.26-8.23 (d 3H),7.89-7.88 (d 2H),7.67-7.66 (d 3H)
.13C NMR (DMSO-d 6,150MHz) δ 159.90, 149.25, 142.25, 142.08, 140.88, 140.86,
140.62, 140.23, 132.22, 130.16, 129.87, 129.86, 129.60, 129.43, 129.23,
128.18, 115.23, 109.87, 106.29; IR (KBr cm-1) v: 3115 (NH), 1693 (C=N); ESI-MS
m/z (M+H)+Calcd for C19H12N4297.1135; Found 297.114.
2nd, the detection of silver ion
1st, fluoroscopic examination
DMSO-H in sensor molecule ZH2O （H2The percentage by volume of O is 45 ~ 50%）In solution, Fe is separately added into3+, Hg2+,
Ag+, Ca2+, Cu2+, Co2+, Ni2+, Cd2+, Pb2+, Zn2+, Cr3+, Mg2+Perchlorate DMSO solution, if sensor molecule is molten
The strong yellow fluorescence of liquid is quenched completely, then that explanation is added is Ag+If the fluorescence of the solution of sensor molecule does not become
Change, then that explanation is added is not Ag+.
2nd, open hole detection
DMSO-H in sensor molecule ZH2O（H2The percentage by volume of O is 45 ~ 50%）In solution, Fe is separately added into3+, Hg2+,
Ag+, Ca2+, Cu2+, Co2+, Ni2+, Cd2+, Pb2+, Zn2+, Cr3+, Mg2+Perchlorate DMSO solution；If sensor molecule is molten
Liquid is changed into pale pink from original yellow, then that explanation is added is Ag+If the color of sensor molecule solution does not become
Change, then that explanation is added is not Ag+.
3rd, detection paper
The making of Silver detection reagent paper：ZH is configured to 2 × 10-4mol·L−1Aqueous solution；The filter paper for processing is cut into
Circular shuttering.Filter paper is infiltrated respectively 10 minutes in above-mentioned solution, ZH is fully adsorbed in then take out on filter paper and is dried.Should
Filter paper is in yellow fluorescence under fluorescent lamp.
Silver detection：Deca Fe on reagent paper3+, Hg2+, Ag+, Ca2+, Cu2+, Co2+, Ni2+, Cd2+, Pb2+, Zn2+, Cr3 +, Mg2+Perchlorate DMSO solution, if the original yellow fluorescence of reagent paper disappears and color fade, Deca be described be silver-colored from
Son；If the fluorescence of Test paper and color are without changing, what Deca was described is not silver ion.
Claims (10)
1. a kind of colorimetric fluorescence two-channel silver ion transducer molecule, its structure are as follows：
.
2. the synthesis of colorimetric fluorescence two-channel silver ion transducer molecule as claimed in claim 1, with DMF as solvent, glacial acetic acid
For catalyst, 2,3- diaminophenazines carry out back flow reaction with benzaldehyde for substrate；Reaction terminates rear sucking filtration, gained solid heat
Washing with alcohol, vacuum drying, DMF-H2O recrystallization, obtain yellow solid and are silver ion sensor molecule.
3. the synthesis of colorimetric fluorescence two-channel silver ion transducer molecule as claimed in claim 2, it is characterised in that：2,3- diaminos
Base azophenlyene is 1 with the mol ratio of benzaldehyde:1~1:1.5；The temperature of the back flow reaction is 80 ~ 85 DEG C, and reflux time is 7
~8h.
4. the synthesis of colorimetric fluorescence two-channel silver ion transducer molecule as claimed in claim 2, it is characterised in that：Glacial acetic acid
0.4 ~ 0.6 times for benzaldehyde mole of consumption.
5. application of the colorimetric fluorescence two-channel silver ion transducer molecule as claimed in claim 1 in fluorescence identifying silver ion,
It is characterized in that：DMSO-H in sensor molecule2In O solution, Fe is separately added into3+, Hg2+, Ag+, Ca2+, Cu2+, Co2+, Ni2 +, Cd2+, Pb2+, Zn2+, Cr3+, Mg2+Perchlorate DMSO solution, if the strong yellow fluorescence of sensor molecule solution is quenched completely
Go out, then that explanation is added is Ag+If the fluorescence of the solution of sensor molecule does not change, that addition is described is not Ag+.
6. application of the colorimetric fluorescence two-channel silver ion transducer molecule as claimed in claim 1 in fluorescence identifying silver ion,
It is characterized in that：The DMSO-H2In O solution, H2The percentage by volume of O is 45 ~ 50%.
7. application of the colorimetric fluorescence two-channel silver ion transducer molecule as claimed in claim 1 in ultraviolet identification silver ion,
It is characterized in that：DMSO-H in sensor molecule2In O solution, Fe is separately added into3+, Hg2+, Ag+, Ca2+, Cu2+, Co2+, Ni2 +, Cd2+, Pb2+, Zn2+, Cr3+, Mg2+Perchlorate DMSO solution；If sensor molecule solution is changed into light from original yellow
Pink colour, then that explanation is added is Ag+If the color of sensor molecule solution does not change, that addition is described is not Ag+.
8. application of the colorimetric fluorescence two-channel silver ion transducer molecule as claimed in claim 7 in ultraviolet identification silver ion,
It is characterized in that：The DMSO-H2In O solution, H2The percentage by volume of O is 45 ~ 50%.
9. a kind of Silver detection examination for being loaded with colorimetric fluorescence two-channel silver ion transducer molecule as claimed in claim 1
Paper.
10. the application of Silver detection reagent paper as claimed in claim 9 silver ion in detection aqueous solution, it is characterised in that：?
Deca Fe on Silver detection reagent paper3+, Hg2+, Ag+, Ca2+, Cu2+, Co2+, Ni2+, Cd2+, Pb2+, Zn2+, Cr3+, Mg2+High chlorine
The DMSO solution of hydrochlorate, if the original yellow fluorescence of reagent paper disappears and color fade, what Deca was described is silver ion；If detection examination
, without changing, what Deca was described is not silver ion for the fluorescence of paper and color.
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