CN106518792A - Cyanide ion fluorescent sensor molecule and synthesis and application thereof - Google Patents
Cyanide ion fluorescent sensor molecule and synthesis and application thereof Download PDFInfo
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- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
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- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
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Abstract
The invention provides a cyanide ion fluorescent sensor molecule, namely, 2,3-dihydroxyphenazine. The cyanide ion fluorescent sensor molecule is synthesized by using water as a solvent and o-phenylenediamine and 2,5-dyhydroxyl-1,4-benzoquinone as substrates through reflux. Experiments show that the fluorescence sensor molecule can specifically identify cyanide ions in pure water in a high sensitive mode; after aqueous solutions of F-, Cl-, Br-, I-, AcO-, H2PO4-, HSO4- and other negative ions are respectively added in a fluorescent sensor molecule aqueous solution, it is found that only the addition of CN- can enhance the fluorescence of the fluorescent sensor molecule aqueous solution, the response speed is very quick (about 10 seconds), and the identification process is not affected by other negative ions. A titration experiment shows that the cyanide ion fluorescence spectrum detection limit of the fluorescent sensor molecule is 5.65* 10<-7> mol/L, and the detection process has very high sensitivity. CN- test paper based on H-1 is prepared and can conveniently and rapidly detect CN- in water.
Description
Technical field
The present invention provides a kind of cryanide ion fluorescent optical sensor molecule 2,3- dihydroxyphenazines and its synthetic method；This
The bright application for further relating to fluorescent optical sensor molecule high sensitivity fluorescence identifying cryanide ion in aqueous, belongs to chemical synthesis neck
Domain and technical field of anion detection.
Background technology
As chemical sensor is had broad application prospects in chemistry, environment or even living things system, in recent years, chemistry
The design synthesis of sensor increasingly causes the concern of people.The existing chemical sensor that can recognize metal ion among these,
There is the chemical sensor that can recognize anion.Fluorescence spectrum has the advantages that in measure easy to operate, quick and sensitivity is high,
The main means of testing having developed in ion identification.
In numerous anion, cyanide has very strong toxicity, and is very easy to be absorbed by the body, can orally,
Respiratory tract or skin enter human body.Cyanide is entered in stomach, under the dissociation of hydrochloric acid in gastric juice, can be hydrolyzed to hydrogen cyanide immediately and be inhaled
Receive.After this kind of material enters blood circulation, the Fe of the cytochrome oxidase in blood3+With CN-With reference to generation cyaniding high ferro is thin
Born of the same parents' chromo-oxidase, loses the ability of transmission electronics, makes breathing chain interruption, cell death by suffocation.As cyanide is in lipoid
Solubility than larger, so central nervous system is first subjected to harm, especially respiratory center is more sensitive.Respiratory failure is
It is the lethal main cause of cyanide acute poisoning.Therefore, CN-Detection life science and environment monitoring etc. field have emphatically
The application wanted.Up to the present, although have already been proposed the method for various detection cyanide ions, but many of which method
The operation of expensive instrument and complexity is needed, the application of these methods is this severely limits.
The content of the invention
It is an object of the invention to provide a kind of simple structure, synthesizes convenient cryanide ion fluorescent optical sensor molecule；
It is a further object of the present invention to provide the synthetic method of above-mentioned cryanide ion fluorescent optical sensor molecule；
It is a further aim of the invention providing above-mentioned cryanide ion fluorescent optical sensor molecule fluorescence identifying cryanide ion in pure water
Application.
First, sensor molecule and its synthesis
The cryanide ion fluorescent optical sensor molecule of the present invention is its chemical name with azophenlyene as fluorophor, with-OH as recognition site
For 2,3- dihydroxyphenazines, H-1 is labeled as.Its structure is as follows：
The synthesis of sensor molecule H-1：It is that, with water as solvent, o-phenylenediamine and 2,5- dihydroxy-Isosorbide-5-Nitrae-benzoquinones are substrate, are carried out
Back flow reaction, precipitation reaction product are filtered, and THF lotions obtain brown solid and are sensor molecule.
O-phenylenediamine is 1 with the mol ratio of 2,5- dihydroxy -1,4- benzoquinones:1.2~1:1.3；The temperature of back flow reaction is 95
~ 100 DEG C, reflux time is 6 ~ 8 hours.
2nd, sensor molecule is to Anion Recognition performance study
1st, cryanide ion recognition performance is studied
The DMSO solution of 2 μ L sensor molecules H-1 is pipetted respectively（5×10-2 mol·L-1）4.5 are equipped with a series of 10 mL
mLH2In the colorimetric cylinder of O, F is separately added into-, Cl-, Br-, I-, AcO-, H2PO- 4, HSO- 4, ClO- 4, CN-、SCN-The aqueous solution（1×
10-2mol·L-1）0.5ml.Now acceptor density is 2 × 10-5mol·L-1, 50 times for acceptor density of anion concentration.Observation
Response of sensor molecule H-1 to each anion.
As a result find, as the H in H-1 using DMSO as solubilizer2The aqueous solution of above-mentioned anion is separately added in O solution
When, only CN-Addition make the fluorescence color of the solution of H-1 be changed into yellow from dark orange.In its corresponding fluorescence spectrum, CN-
Addition emission peak of sensor molecule H-1 at 548nm is strengthened and slight blue shift is occurred（Fig. 1）, and remaining the moon from
The addition of son is had no significant effect to the color of the solution of sensor molecule H-1 and fluorescence spectrum.Illustrate sensor molecule with
Hs of the DMSO as solubilizer2Can single-minded selective fluorescence identifying CN in O solution-。
2nd, to CN-Titration experiments
Take the DMSO solution of 2 μ L sensor molecules H-1（5×10-2 mol·L-1）5mL H are housed in a series of 10 mL2O's
In colorimetric cylinder, now acceptor density is 2 × 10-5mol·L-1.Pipette the above-mentioned solution of 2.5mL H-1（2.0×10-5mol/L）
In quartz cell, CN is gradually added into accumulation sample-adding method-Water solution, survey its fluorescence spectrum in 25 DEG C（Fig. 2）.In fluorescence light
With CN in spectrum-The solution of water be gradually added into, the emission peak at 548nm is gradually increasing, and illustrates that sensor H-1 can be with
DMSO is used as solubilizer sensitive quick single-minded detection CN in aqueous-.Fluorescence spectrum detections of the H-1 to cryanide ion is limited to
5.65 × 10-7Mol/L, detection process have very high sensitivity.
3rd, interference free performance detection
In order to determine acceptor H-1 to CN-Detection results, tested as follows：Take two groups of 10ml colorimetric cylinders and add 2 in a group
The DMSO solution of μ L H-1（5×10-2 mol·L-1）, then it is separately added into 0.5 mL F-, Cl-, Br-, I-, AcO-, H2PO- 4,
HSO- 4, ClO- 4, SCN-The aqueous solution（1×10-2 mol·L-1）, then use H2O is diluted to 5 mL scales.In another set
It is initially charged the DMSO solution of 2 μ L H-1（5×10-2 mol·L-1）, then add 0.5 mL CN respectively-, in each colorimetric cylinder again
In be separately added into other anion of 0.5 mL（F-, Cl-, Br-, I-, AcO-, H2PO- 4, HSO- 4, ClO- 4, SCN-）The aqueous solution, so
After use H2O is diluted to 5 mL scales.Observed after being well mixed.
As a result find, add F-, Cl-, Br-, I-, AcO-, H2PO- 4, HSO- 4, ClO- 4, SCN-Afterwards, H-1+CN-Fluorescent emission
Peak is not changed substantially.This and CN-Impact to H-1 is consistent（Fig. 1,2）.So as to illustrate H-1 to detecting CN-Substantially
Do not disturbed by other cations（Fig. 3,4）.
4th, sensor H-1 identifications CN-Response time
Common fluorescent optical sensor molecule needs longer reaction time, this factor often to constrain the identification process of ion
Many sensor molecules are promoted the use of.Therefore, the time of its response has been probed on the basis of identification sensitivity height again.（Figure
5）.From figure 5 it can be seen that in CN-Add subsequent 10 seconds or so of H-1, substantially completely, fluorescence intensity is substantially completely beaten for reaction
Open and no longer change.Therefore sensor molecule H-1 has detection speed faster.
5th, fluorescence invertibity
In recent years, the recyclability of acceptor molecule became the big focus in Anion Recognition research, therefore, we have inquired into this
Acceptor molecule is to CN-The recyclability of identification.Experimental phenomena shows：When in L-1-CN-Appropriate HClO is added in complex system4,
Color of the solution under bore hole and uviol lamp is recovered, suitable with main body L-1.Corresponding ultraviolet and fluorescence spectrum is also returned to originally
The level of host molecule.When we go to recognize CN with the solution again-During ion, the fluorescence of the system is opened, and substantially with biography
The peak height of sensor molecule is consistent.So it is repeatedly circulated reaching more than 4 times (Fig. 6).Therefore, this receptor molecule L -1 is
A kind of CN that can be recycled-And HClO4Ion colorimetric fluorescent optical sensor.
6th, sensor H-1 is to CN-Recognition mechanism
For sensor molecule H-1 to CN-Recognition mechanism is probed into, and we characterize hand by nuclear-magnetism titration, high resolution mass spectrum etc.
Duan Jinhang checking.Nuclear-magnetism titration spectrogram shows：The signal peak of-the OH at 10.94 ppm disappears immediately with the addition of cryanide ion
Lose, and azophenlyene ring hydrogen proton signal peak is significantly moved to High-Field.Therefore, we to sensor H-1 to CN-Cognitron
Reason is inquired into as follows：As addition CN-When, the Hydrogen Proton of two-OH of sensor H-1 is sloughed.High resolution mass spectrum is to main body and ion
Complex as shown by data：Appearance at 257.00 sloughs the molecular weight that two Hydrogen Protons add two sodium ions again with sensor H-1
Unanimously（Fig. 7）.
In sum, present invention design has synthesized a kind of cryanide ion fluorescent optical sensor molecule H-1.Azophenlyene conduct in the molecule
The stable system of one rigid structure, the solution of causative subject molecule have issued strong fluorescence.After the molecule is combined with cryanide ion
Cause solution colour to be changed into glassy yellow and fluorescence generation opening from dark orange under uviol lamp, be presented as in spectrum change
“OFF-ON”.Cryanide ion in the sensor molecule detection environment capable of circulation of this " OFF-ON " type.
3rd, the value of cryanide ion Test paper and compare and apply
Cryanide ion efficiently in detection environmental system, is tried using the cryanide ion detection that the sensor molecule is fabricated to for convenience
Paper.
The making of Test paper：By the H-1 being configured to 0.1 mol L-1 H2The solution of O（DMSO can be used as solubilising
Agent）, move in two colorimetric cylinders.Clip after filter paper drying Jing processing is about into 4cm, the filter paper of wide about 1cm two, difference
Infiltration 10 minutes in two above-mentioned colorimetric cylinders makes H-1 be carried on filter paper respectively, then takes out and dry.Inspection filter paper is existed
Under fluorescent lamp, the filter paper for being loaded with H-1 is in orange fluorescence.
Detection cryanide ion；When cryanide ion is added dropwise on the filter paper for be loaded with H-1, the original orange fluorescence of filter paper is changed into yellow
Color fluorescence, and the dropwise addition of other anion is not affected on the fluorescence of filter paper.This strikingly color contrast also illustrate that the biography
Sensor molecule has the fluorescence identifying ability of height to cryanide ion.
Description of the drawings
Fig. 1 is H-1 (c=2.0 × 10-5Mol/L the aqueous solution)（With DMSO as solubilizer, DMSO:H2O=1:99.96）
The middle fluorescence spectra for adding anion.
Fig. 2 is H-1 (c=2.0 × 10-5Mol/L the aqueous solution)（With DMSO as solubilizer, DMSO:H2O=1:99.96）
In and fluorescence spectra when adding 50 times of anion（Excitation wavelength：415 nm, 568 nm of launch wavelength）.
CNs of the Fig. 3 for variable concentrations-There is the fluorescence spectrum of lower sensor H-1 in (0.00 ~ 10.16 times).
CNs of the Fig. 4 for variable concentrations- There is the scatter diagram of lower sensor H-1 in (0.00 ~ 10.16 times).
Fig. 5 is H-1（2×10-5mol/L）Add CN-Fluorescence intensity in 550 nm of launch wavelength and time is right afterwards
Should be related to.
Fig. 6 is the fluorescence invertibity that H-1 is recognized to cryanide ion.
Fig. 7 is H-1 to CN-Recognition mechanism figure.
Specific embodiment
Below by specific embodiment to the synthesis of inventive sensor molecule, sign and relay fluorescence identifying cyanogen from
The application of son is described further.
Instrument：1H NMR use Mercury-400BB type nmr determinations, and TMS is internal standard.IR uses Digilab
FTS-3000 FT-IR type infrared spectrometers (KBr compressing tablets) is determined；Fusing point is using X-4 numerical monitor micro melting point apparatus (temperature
Degree meter is not corrected) determine；Fluorescence spectrum is using Japan Shimadzu Corporation RF -5301 XRFs record.
Reagent：Anion used（F-, Cl-, Br-, I-, AcO-, H2PO- 4, HSO- 4, ClO- 4）It is 4-butyl ammonium,
CN-, SCN-Ion is sodium salt, and solvent is H2O (analysis is pure).It is pure that other reagents are commercially available analysis.
The synthesis of embodiment one, sensor molecule H-1 and sign
0.5 ~ 0.6 mol o-phenylenediamines are taken, 0.6 ~ 0.72 mol 2,5- dihydroxy-Isosorbide-5-Nitrae-benzoquinones is added to 100 ~ 120 ml
Stir and uniform in water, be heated to 95 DEG C, back flow reaction 7 hours；Stop stirred overnight after heating, precipitation is filtered, on a small quantity
THF lotions obtain brown solid and are sensor molecule H-1.85 % of yield.
H-1: m. p.: 248~250 ℃. 1H NMR (DMSO-d 6) δ = 7.28 (s, 2H, H-C=C-OH),
7.72 (dd, Jortho = 6.5 Hz, Jmeta = 3.5 Hz, 2H, H-C=C-H), 8.05 (dd, Jortho = 6.5
Hz, Jmeta = 3.5 Hz, 2H, H-C=C-H), 10.94 (br s, 2H, OH); 13C NMR (DMSO-d 6) δ =
106.5 (C=C-OH), 127.8 (C=CH), 128.2 (C=CH), 139.9 (C=C-N), 141.5 (C=N), 154.6
(C-OH). ESI-MS m/z: (M-H)- Calcd. for C12H8N2O2 211.0804; Found 211.0243。
Its synthetic route is as follows：
Embodiment two, sensor molecule H-1 fluorescence identifying cryanide ion
DMSO solution (the 0.05 mol L of 2 μ L sensor molecules H-1 are pipetted respectively-1) in a series of 10 mL colorimetric cylinders,
It is separately added into F-, Cl-, Br-, I-, AcO-, H2PO- 4, HSO- 4, ClO- 4, CN-And SCN-The aqueous solution（1×10-2mol·L-1）；If
The solution colour of sensor molecule H-1 is changed into glassy yellow from dark orange under uviol lamp, and fluorescence occurs to strengthen, then explanation adds
That what is entered is CN-If the fluorescence of the solution of sensor molecule H-1 does not change, that illustrate addition is not CN-。
The application of embodiment three, cryanide ion Test paper
1st, the making of Test paper
Sensor molecule H-1 is configured to into 0.1 mol L−1DMSO-H2O（With DMSO as solubilizer, DMSO:H2O=1:
99.96v/v）Solution.Clip after filter paper drying Jing processing is about into 4cm, the filter paper of wide about 1cm is infiltrated above-mentioned molten
10 minutes in liquid, H-1 is made to be carried on filter paper, taking-up is dried.Filter paper will be examined under fluorescent lamp, the filter paper of H-1 will be loaded with
In yellow fluorescence.
2nd, the application of Test paper
F is added dropwise on the filter paper for be loaded with H-1-, Cl-, Br-, I-, AcO-, H2PO- 4, HSO- 4, ClO- 4, CN-And SCN-It is water-soluble
Liquid, if the dark orange fluorescence of filter paper is changed into glassy yellow and fluorescence, that illustrate dropwise addition is CN-；If the dark orange fluorescence of filter paper
Do not change, then that explanation is added dropwise is not CN-。
Claims (9)
1. a kind of cryanide ion fluorescent optical sensor molecule, its structure are as follows：
。
2. the synthetic method of cryanide ion fluorescent optical sensor molecule as claimed in claim 1, is the o-phenylenediamine and 2 with water as solvent,
5- dihydroxy-Isosorbide-5-Nitrae-benzoquinones is substrate, carries out back flow reaction, and precipitation reaction product is filtered, and THF lotions obtain brown solid and are
Sensor molecule.
3. the synthetic method of cryanide ion fluorescent optical sensor molecule as claimed in claim 1, it is characterised in that：O-phenylenediamine and 2,5-
The mol ratio of dihydroxy -1,4- benzoquinones is 1:1.2~1:1.3.
4. the synthetic method of cryanide ion fluorescent optical sensor molecule as claimed in claim 1, it is characterised in that：The temperature of back flow reaction
For 95 ~ 100 DEG C, reflux time is 6 ~ 8 hours.
5. cryanide ion fluorescent optical sensor molecule as claimed in claim 1 recognizes the application in cryanide ion in pure water, and its feature exists
In：In the aqueous solution of cryanide ion fluorescent optical sensor molecule, anion F is separately added into-, Cl-, Br-, I-, AcO-, H2PO- 4, HSO- 4,
ClO- 4, CN-、SCN-The aqueous solution；If the Fluorescence Increasing of sensor molecule solution, and under uviol lamp fluorescence color by dark
Orange is changed into yellow, then that explanation is added is CN-；If the fluorescence of sensor molecule solution does not change, illustrate to add
Be not CN-。
6. cryanide ion fluorescent optical sensor molecule as claimed in claim 1 recognizes the application in cryanide ion in pure water, and its feature exists
In：In the aqueous solution of the cryanide ion fluorescent optical sensor molecule, the concentration of sensor molecule is 5.65 × 10−7 mol/L~2×
10-5mol·L-1。
7. the application in cryanide ion fluorescent optical sensor molecule pure water as claimed in claim 1 in identification cryanide ion, it is characterised in that：
Anion F-, Cl-, Br-, I-, AcO-, H2PO- 4, HSO- 4, ClO- 4, CN-、SCN-The aqueous solution in, the concentration of anion is 1 ×
10-2mol·L-1。
8. a kind of cryanide ion Test paper for being loaded with cryanide ion fluorescent optical sensor molecule as claimed in claim 1.
9. the cryanide ion Test paper for being loaded with cryanide ion fluorescent optical sensor molecule as claimed in claim 8 is used for fluorescence identifying cyanogen
Ion, it is characterised in that：F is added dropwise on cryanide ion Test paper-, Cl-, Br-, I-, AcO-, H2PO- 4, HSO- 4, ClO- 4, CN-、
SCN-The aqueous solution, if the color of filter paper fluorescence is changed into yellow from dark orange, illustrate be added dropwise be CN-；If the fluorescence of filter paper does not have
Change, then that explanation is added dropwise is not CN-。
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