CN101550092B - 2-(hydroxybenzeneimino) methylene-4-(4'-nitrobenzophenone)azo-phenol, preparation and applications - Google Patents
2-(hydroxybenzeneimino) methylene-4-(4'-nitrobenzophenone)azo-phenol, preparation and applications Download PDFInfo
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- CN101550092B CN101550092B CN2009100223140A CN200910022314A CN101550092B CN 101550092 B CN101550092 B CN 101550092B CN 2009100223140 A CN2009100223140 A CN 2009100223140A CN 200910022314 A CN200910022314 A CN 200910022314A CN 101550092 B CN101550092 B CN 101550092B
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- hydroxybenzeneimino
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Abstract
The invention provides a compound 2-(hydroxybenzeneimino) methylene-4-(4'- nitrobenzophenone) azo-phenol, which is prepared by the reaction of nitro-salicylaldehyde and aminophenol. The 2-(hydroxybenzeneimino) methylene-4-(4'-nitrobenzophenone) azo-phenol prepared by the invention has remarkable recognition effect to F<-> in acetonitrile solution, when the F<-> is added to the receptor solution, the color of the solution changes from light yellow to purple; when other ions such as negative ions of C1<->, Br<->, I<-> and the like are added, the color of the receptor solution does not change, thereby realizing the selective naked-eye recognition to fluorine ions. The test paper for detecting fluorine ions by qualitative color comparison prepared by the compound can detect the fluorine ions by qualitative color comparison more conveniently, thereby being characterized by simplicity, quick speed, high efficiency, practicality, and the like.
Description
Technical field
The invention belongs to chemosynthesis technical field, relate to a kind of compound based on phenolic hydroxyl group and Schiff alkali---2-(hydroxybenzeneimino base) methylene radical-4-(4 '-nitrophenyl) azo-group phenol; The present invention also relates to the preparation method and the application of its conduct than colour discrimination fluorion acceptor of this compound simultaneously.
Background technology
In recent years, received people's attention with the anionic method of synthesis of receptor colorimetric detection.The colour-change of generation was come the qualitative detection negatively charged ion when this method interacted through utilizing artificial receptors and negatively charged ion, and can also detect anionic content quantitatively through corresponding mensuration.At present, people have developed a large amount of anionic colorimetric identification receptors.Wherein, much receive the stronger negatively charged ion of physical efficiency selectivity ratios colour discrimination alkalescence, recognition site is generally provided by the structural unit that urea or thiourea group, amido or carboxamido-group, guanidine radicals etc. contain the NH hydrogen bond donor, and the signal reporter group is chromophoric group normally.
Among many negatively charged ion; Owing to seeming, the special role of fluorion in numerous disease and environmental science be even more important; For example fluorion can be used on the one hand prevention and the treatment osteoporosis of carious tooth and useful to the mankind; On the other hand, excessive fluorine can cause fluorosis again, but the simple electroneutral acceptor molecule that can discern fluorion is still less.Therefore it is simple to design composite structure, is easy to synthetic and is a focus of Subjective and Objective Anion Recognition research to the anion receptor of specifying the selective colorimetric recognition capability of negatively charged ion.
Summary of the invention
The purpose of this invention is to provide a kind of compound based on phenolic hydroxyl group and Schiff alkali---2-(hydroxybenzeneimino base) methylene radical-4-(4 '-nitrophenyl) azo-group phenol.
Another object of the present invention provides the preparation method of this compound.
A further object of the invention just provides this compound as the application than colour discrimination fluorion acceptor.
The present invention more has a purpose, just provides a kind of this compound of utilizing and becomes the test paper than colour discrimination fluorion.
(1) 2-(hydroxybenzeneimino base) methylene radical-4-(4 '-nitrophenyl) azo-group phenol
The chemical structural formula of The compounds of this invention 2-(hydroxybenzeneimino base) methylene radical-4-(4 '-nitrophenyl) azo-group phenol is following:
R=o-OH
b, corresponding compound is 2-(2 '-hydroxybenzeneimino base) methylene radical-4-(4 '-nitrophenyl) azo-group phenol a;
R=m-OH
b, corresponding compound is 2-(3 '-hydroxybenzeneimino base) methylene radical-4-(4 '-nitrophenyl) azo-group phenol b;
R=p-OH
b, corresponding compound is 2-(4 '-hydroxybenzeneimino base) methylene radical-4-(4 '-nitrophenyl) azo-group phenol c.Its corresponding structural formula is following:
(2) preparation of 2-(hydroxybenzeneimino base) methylene radical-4-(4 '-nitrophenyl) azo-group phenol
Method 1: will be dissolved in the absolute ethyl alcohol to nitro azo salicylal; Adding was reacted 2～4 hours down in 60～90 ℃ the amino-phenol of 1～1.2 times of molar weight of nitro azo salicylal, generated red precipitate; Leave standstill, suction filtration; Use N, dinethylformamide-absolute ethyl alcohol mixing solutions recrystallization promptly gets target compound.
N, in dinethylformamide-absolute ethyl alcohol mixing solutions, N, dinethylformamide mixes with 1: 100～1: 150 volume ratio with absolute ethyl alcohol.
Method 2: will place porphyrize in the agate mortar with 1: 1～1: 1.2 mol ratio to nitro azo salicylal and amino-phenol; Add absolute ethyl alcohol and make mixture moistening (the alcoholic acid add-on is: add 1ml ethanol in per 2 gram mixtures); Continue to grind 0.5～1h, generate red solid; When the mixture color no longer changes, dry, use N, dinethylformamide-absolute ethyl alcohol mixing solutions recrystallization promptly gets target compound.
N, in dinethylformamide-absolute ethyl alcohol mixing solutions, N, dinethylformamide mixes with 1: 100～1: 150 volume ratio with absolute ethyl alcohol.
Wherein amino-phenol comprises Ortho-Aminophenol, Metha Amino Phenon, PARA AMINOPHENOL.When adopting Ortho-Aminophenol to be raw material, products therefrom is 2-(2 '-hydroxybenzeneimino base) methylene radical-4-(4 '-nitrophenyl) azo-group phenol a; When adopting Metha Amino Phenon to be raw material, products therefrom is 2-(3 '-hydroxybenzeneimino base) methylene radical-4-(4 '-nitrophenyl) azo-group phenol b; When adopting PARA AMINOPHENOL to be raw material, products therefrom is 2-(4 '-hydroxybenzeneimino base) methylene radical-4-(4 '-nitrophenyl) azo-group phenol c.
That adopts in the aforesaid method can buy from market and get nitro azo salicylal.
Utilize method 1 preparation target compound, productive rate is low relatively, and the reaction times is longer.And employing method 2 preparation target compound productive rates are higher, and the reaction times is short, and at room temperature reacts, and simple synthetic method is prone to row, more meet green synthetic theory.
(3) compound is as the application than colour discrimination fluorion acceptor
1, the Anion Recognition performance of acceptor
Pipette the acetonitrile solution (2 * 10 of 0.5mL acceptor a, b, c respectively
-4MolL
-1) in a series of 10mL tube comparison tubess.Add 0.5mLF respectively
-, Cl
-, Br
-, I
-Acetonitrile solution (the 0.01molL of anionic 4-butyl ammonium
-1), to 5ml, this moment, acceptor density was 2 * 10 with dilution in acetonitrile
-5MolL
-1, anion concentration is 50 times of acceptor density.Leave standstill after mixing, observe each acceptor anionic response.
Experimental result: add F
-The time solution colour by the light yellow purple that becomes, and when adding other ion, the receptor solution color is constant.Therefore, acceptor a, b, c in acetonitrile solution to the selective colorimetric recognition capability of fluorion.
2, ultraviolet-visible (UV-vis) spectrum of acceptor and negatively charged ion effect
Survey the UV-vis spectrum of mixing solutions of acetonitrile solution and the acceptor and the different anions of above-mentioned acceptor respectively, as shown in Figure 1, in UV-vis spectrum, acceptor a has maximum absorption band at the 382nm place, in acceptor a, adds F respectively
-, Cl
-, Br
-, I
-The TBuA salts solution time, have only the adding of fluorion that acceptor is significantly reduced at the absorption peak at 382nm place, the new strong absorption peak of appearance simultaneously at 550nm place, other negatively charged ion does not have obvious influence to the absorption peak of acceptor.Compound acceptor b, c have the similar recognition capability with a to negatively charged ion.
3, the ultraviolet titration of acceptor
Pipette the acetonitrile solution (2 * 10 of 2mL acceptor a
-5MolL
-1) in quartz colorimetric utensil, add F gradually with accumulation application of sample method
-The acetonitrile solution (1molL of 4-butyl ammonium
-1), in 25 ℃ of uv absorption spectrums (acetonitrile is made reference) of following the trail of system in the titration process.(see figure 4)
Absorption spectrometry shows: when not adding negatively charged ion, because intramolecular charge shifts, acceptor molecule a has 1 absorption peak at the 382nm place, in the acetonitrile solution of acceptor molecule, add Cl respectively
-, Br
-, I
-During the acetonitrile solution of 4-butyl ammonium, solution colour and absorption spectrum have no significant change, and explain that this type of acceptor molecule is to the not obviously effect of these several kinds of negatively charged ion.And adding object negatively charged ion F
-The time, acceptor molecule a reaches the effect of bore hole identification by the light yellow purple that becomes.In the ultraviolet titration process along with F
-Continuous adding, the absorption peak at 382nm place disappears, and new absorption peak occurred at the 550nm place.Show along with F
-Adding, capture the H on the acceptor phenolic hydroxyl group respectively
a, H
bForm negative oxygen ion, formed and taken off the proton product A and take off the proton product B, thereby the increasing of acceptor molecule electric density causes absorption peak generation red shift, red shift is to the 556nm place.Simultaneously, at the 444nm place tangible isobestic point is arranged.Carry out along with titrating, the isobestic point red shift is to the 462nm place.In this process, do not have the appearance of tangible isobestic point, explain that the object negatively charged ion at first is the hydrogen bond that destroys in the host molecule, acceptor molecule is sloughed two protons step by step and is formed salt negative ion (see figure 4) then.
4,
1The HNMR titration experiments
For illustrate between acceptor molecule and negatively charged ion take off proton-effect this, carried out
1The HNMR titration experiments.With DMSO-d
6Be solvent, we have done the nuclear-magnetism titration of negatively charged ion to acceptor.With a is example, preparation 0.5ml 2.5mmoll
-1The DMSO-d of a
6Solution places the nuclear-magnetism pipe, at first does the hydrogen spectrum of a, then to the DMSO-d that wherein drips tetrabutyl ammonium fluoride with microsyringe
6Solution adopts the accumulation sampling system, makes the object anion concentration be added drop-wise to 12 times one by one from 0.1 times of main body, does the hydrogen spectrum after every dropping once fully shakes up one time.The H of acceptor molecule a
bProton moves to δ 10.31, H owing to receive the chemical shift that influences of conjugated system to High-Field
aProton chemical shifts moves to δ 15.31 to low field.Along with F
-The DMSO-d of 4-butyl ammonium
6Strength of solution is added to 12 times, H from 0.1 multiplication
bThe F that adding of proton peak
-Completely dissolve when being 0.1 times is because H
bForm pentacyclic intramolecular hydrogen bond with N, relative and H
aThe six-ring rigidity strong, easily fracture.Very fast H
aAlso completely dissolve of proton peak.Work as F
-Concentration be increased to 5 times the time, new absorption peak has appearred at 14.88 places.Along with F
-Continuous adding, new absorption peak is gradually to low field displacement, and uprises gradually, works as F
-Concentration be increased to 8 times the time, new absorption peak chemical shift is δ 15.79, final chemical shift is δ 16.12.Explain that acceptor molecule substep under the effect of fluorion sloughs H
b, H
a, generated highly stable bifluoride hydride ion (HF simultaneously
2 -) (see figure 5).
For further illustrate between acceptor molecule and negatively charged ion take off proton-effect this, carried out following experiment: in the solution of acceptor a, add certain density NaOH solution, receptor solution becomes purple, adds HClO again
4, solution reverts to the color of acceptor.Prove that thus proton-effect has taken place to take off acceptor compound really.
In sum, compound of the present invention is to F
-Tangible recognition effect is arranged, when adding F
-The time, such acceptor molecule is by the faint yellow purple that becomes, thereby realized F
-Open hole detection.
(4) than the preparation and the application of colour discrimination fluorion test paper
1, than the preparation of colour discrimination fluorion test paper
To in zero(ppm) water, soak, to place concentration be 1.5 * 10 to air dried filter paper
-3～2.5 * 10
-3MolL
-1Soaked in the acetonitrile solution of acceptor compound 1～2 minute, taking-up is dried and is promptly got than colour discrimination fluorion test paper.
2, than the application of colour discrimination fluorion test paper
On than colour discrimination fluorion test paper, drip F
-(0.01molL
-1), find that filter paper shows lavender.On an other test paper, drip F
-(0.1molL
-1), this test paper deepens purple, and visible this method can realize the detection to the different concns fluorion, has easy, efficient, practical characteristic.
Description of drawings
Fig. 1 is that acceptor a is in acetonitrile solution (2 * 10
-5MolL
-1) UV-vis spectrogram when interacting with various negatively charged ion
Fig. 2 is that acceptor b is in acetonitrile solution (2 * 10
-5MolL
-1) UV-vis spectrogram when interacting with various negatively charged ion
Fig. 3 is that acceptor c is in acetonitrile solution (2 * 10
-5MolL
-1) UV-vis spectrogram when interacting with various negatively charged ion
Fig. 4 is F in the acetonitrile
-The absorption spectrum of acceptor a (R=0.992 Ks=5.0 * 10 when existing
5)
Fig. 5 is DMSO-d
6Middle acceptor molecule a is at F
-When existing
1H NMR spectrum
Embodiment
The preparation of embodiment 1, compound a
Take by weighing 1mmol nitro azo salicylal is placed the 100ml round-bottomed flask, add the 25ml absolute ethyl alcohol and make solvent, in 60～90 ℃ of oil baths, heat; Backflow adds 1mmol Ortho-Aminophenol (Metha Amino Phenon, PARA AMINOPHENOL) reaction 2～4 hours then until whole dissolvings, has red precipitate to generate; Leave standstill, suction filtration; DMF-EtOH (N, dinethylformamide and absolute ethyl alcohol are with the mixing solutions of 1: 150 volume ratio formation) recrystallization promptly gets target compound a.Productive rate: 74%.
A: red solid, m.p.294-296 ℃;
1H NMR (DMSO-d
6, 400MHz) δ 15.34 (s, 1H, O-H) .10.24 (s, H, O-H), 9.27 (s, 1H, N=C-H); IR (KBr, cm
-1) v:3436 (O-H), 1616 (C=N), 1332 (N=N); Anal.Calcd.for C
17H
14N
4O
9(%): C, 60.71; H, 3.60; N, 16.66; Found (%): C, 63.60; H, 5.41; N, 13.50.
The preparation of embodiment 2 compound b
Take by weighing 1mmol nitro azo salicylal is placed the 100ml round-bottomed flask, add the 25ml absolute ethyl alcohol and make solvent, in 60～90 ℃ of oil baths, heat; Backflow adds 1mmol then and asks amino-phenol reaction 2～4 hours until whole dissolvings, has red precipitate to generate; Leave standstill, suction filtration; DMF-EtOH (N, dinethylformamide and absolute ethyl alcohol are with the mixing solutions of 1: 150 volume ratio formation) recrystallization promptly gets target compound b.Productive rate: 61%.
B: red solid, m.p.297-299 ℃;
1H NMR (DMSO-d
6, 400MHz) δ 14.64 (s, 1H, O-H) .9.81 (s, 1H, O-H), 9.14 (s, 1H, N=C-H), IR (KBr, cm
-1) v:3444 (O-H), 1612 (C=N), 1342 (N=N); Anal.Calcd.for C
17H
14N
4O
9(%): C, 60.61; H, 3.10; N, 16.46; Found (%): C, 63.50; H, 5.32; N, 13.40.
The preparation of embodiment 3, compound c
Take by weighing 1mmol nitro azo salicylal is placed the 100ml round-bottomed flask, add the 25ml absolute ethyl alcohol and make solvent, in 60～90 ℃ of oil baths, heat; Backflow adds 1mmol PARA AMINOPHENOL reaction 2～4 hours then until whole dissolvings, has red precipitate to generate; Leave standstill, suction filtration; DMF-EtOH (N, dinethylformamide and absolute ethyl alcohol are with the mixing solutions of 1: 150 volume ratio formation) recrystallization promptly gets target compound c.Productive rate: 54%.
C: sorrel solid, m.p.＞300 ℃;
1H NMR (DMSO-d
6, 400MHz) δ 14.27 (s, 1H, O-H) .9.76 (s, 1H, O-H), 9.14 (s, 1H, N=C-H), IR (KBr, cm
-1) v:3445 (O-H), 1615 (C=N), 1332 (N=N); Anal.Calcd.for C
17H
14N
4O
9(%): C, 60.41; H, 3.40; N, 16.76; Found (%): C, 63.60; H, 5.23; N, 13.10.
The preparation of embodiment 4, compound a
Take by weighing 1mmol to nitro azo salicylal in agate mortar, with its porphyrize, splash into several (about 0.1ml) absolute ethyl alcohols after; Add the 1mmol Ortho-Aminophenol, have red solid a to produce (generate b, the reaction of c is relatively slow) at once; Continue to grind, very fast mixture becomes redness by yellow.Continue to grind about 0.5～1h,, when powder is also no longer moist, explain that reaction finishes basically, oven dry when color no longer changes.DMF-EtOH (N, dinethylformamide and absolute ethyl alcohol are with the mixing solutions of 1: 150 volume ratio formation) recrystallization promptly gets target compound a, productive rate: 86%.
A: red solid; M.p.294-296 ℃;
1H NMR (DMSO-d
6, 400MHz) δ 15.34 (s, 1H, O-H) .10.24 (s, H, O-H), 9.27 (s, 1H, N=C-H); IR (KBr, cm
-1) v:3436 (O-H), 1616 (C=N), 1332 (N=N); Anal.Calcd.for C
17H
14N
4O
9(%): C, 60.71; H, 3.60; N, 16.66; Found (%): C, 63.60; H, 5.41; N, 13.50.
The preparation of embodiment 5, compound b
Take by weighing 1mmol to nitro azo salicylal in agate mortar, with its porphyrize, splash into several (about 0.1ml) absolute ethyl alcohols after, add the 1mmol Metha Amino Phenon, have red solid b to produce, continue to grind, mixture gradually becomes red by yellow.Continue to grind about 0.5～1h,, when powder is also no longer moist, explain that reaction finishes basically, oven dry when color no longer changes.DMF-EtOH (N, dinethylformamide and absolute ethyl alcohol are with the mixing solutions of 1: 150 volume ratio formation) recrystallization promptly gets target compound b, productive rate: 78%.
B: red solid, m.p.297-299 ℃;
1H NMR (DMSO-d
6, 400MHz) δ 14.64 (s, 1H, O-H) .9.81 (s, 1H, O-H), 9.14 (s, 1H, N=C-H), IR (KBr, cm
-1) v:3444 (O-H), 1612 (C=N), 1342 (N=N); Anal.Calcd.for C
17H
14N
4O
9(%): C, 60.61; H, 3.10; N, 16.46; Found (%): C, 63.50; H, 5.32; N, 13.40.
The preparation of embodiment 6, compound c
Take by weighing 1mmol to nitro azo salicylal in agate mortar, with its porphyrize, splash into several (about 0.1m1) absolute ethyl alcohols after, add the 1mmol PARA AMINOPHENOL, have red solid c to produce, continue to grind, mixture gradually becomes red by yellow.Continue to grind about 0.5～1h,, when powder is also no longer moist, explain that reaction finishes basically, oven dry when color no longer changes.DMF-EtOH (N, dinethylformamide and absolute ethyl alcohol are with the mixing solutions of 1: 150 volume ratio formation) recrystallization promptly gets target compound c, productive rate: 64%.
C: sorrel solid, m.p.＞300 ℃;
1H NMR (DMSO-d
6, 400MHz) δ 14.27 (s, 1H, O-H) .9.76 (s, 1H, O-H), 9.14 (s, 1H, N=C-H), IR (KBr, cm
-1) v:3445 (O-H), 1615 (C=N), 1332 (N=N); Anal.Calcd.for C
17H
14N
4O
9(%): C, 60.41; H, 3.40; N, 16.76; Found (%): C, 63.60; H, 5.23; N, 13.10.
The preparation of the qualitative detection test paper of embodiment 7, acceptor a
Dry after in zero(ppm) water, soaking filter paper for several times.It is 2 * 10 that acceptor a is configured to concentration
-3MolL
-1Acetonitrile solution, then the filter paper for preparing is immersed in the solution.Take out to dry after 2 minutes and get final product.
The preparation of the qualitative detection test paper of embodiment 8, acceptor b
Dry after in zero(ppm) water, soaking filter paper for several times.It is 2 * 10 that acceptor b is configured to concentration
-3MolL
-1Acetonitrile solution, then the filter paper for preparing is immersed in the solution.Take out to dry after 2 minutes and get final product.
The preparation of the qualitative detection test paper of embodiment 9, acceptor c
Dry after in zero(ppm) water, soaking filter paper for several times.It is 2 * 10 that acceptor c is configured to concentration
-3MolL
-1Acetonitrile solution, then the filter paper for preparing is immersed in the solution.Take out to dry after 2 minutes and get final product.
Embodiment 10, utilize the qualitative detection detection paper fluorion of acceptor a, b, c
On the filter paper that soaked acceptor a, b, c, drip F respectively
-(0.01molL
-1), find that filter paper shows lavender.A, b test paper all show lavender, and it is light blue that the c test paper shows.
On the filter paper that soaked acceptor a, b, c, drip F respectively
-(0.1molL
-1), find that filter paper shows lavender.A, b, c test paper all show grape, and the c test paper shows mazarine.
Claims (2)
1. compound 2-(hydroxybenzeneimino base) methylene radical-4-(4 '-nitrophenyl) azo-group phenol is as the application than colour discrimination fluorion acceptor;
The chemical structural formula of said compound 2-(hydroxybenzeneimino base) methylene radical-4-(4 '-nitrophenyl) azo-group phenol is following:
R=o-OH
b, corresponding compound is 2-(2 '-hydroxybenzeneimino base) methylene radical-4-(4 '-nitrophenyl) azo-group phenol a;
R=m-OH
b, corresponding compound is 2-(3 '-hydroxybenzeneimino base) methylene radical-4-(4 '-nitrophenyl) azo-group phenol b;
R=p-OH
b, corresponding compound is 2-(4 '-hydroxybenzeneimino base) methylene radical-4-(4 '-nitrophenyl) azo-group phenol c.
2. compound 2-(hydroxybenzeneimino base) methylene radical-4-(4 '-nitrophenyl) azo-group phenol is characterized in that: adopt following method to be prepared into than colour discrimination fluorion test paper as than the application of colour discrimination fluorion acceptor according to claim 1: will in zero(ppm) water, soak, to place concentration be 1.5 * 10 to air dried filter paper
-3～2.5 * 10
-3MolL
-1Soaked in the acetonitrile solution of acceptor compound 1～2 minute, taking-up is dried and is promptly got than colour discrimination fluorion test paper.
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| CN103743737B (en) * | 2014-01-17 | 2018-07-13 | 陕西理工学院 | A method of F- is detected based on aluminum-eriochrome cyanine R color development systems |
| CN110372534B (en) * | 2019-08-07 | 2022-09-30 | 莆田学院 | 4-nitrobenzene azo vanillin and preparation method and application thereof |
| CN110981748B (en) * | 2019-12-13 | 2021-05-04 | 菏泽学院 | Enhanced azo Salen Schiff base fluorescent probe, synthesis and application thereof |
| CN111103249A (en) * | 2019-12-30 | 2020-05-05 | 南阳师范学院 | Bis-thiourea anion recognition receptor and preparation method thereof |
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