CN106496121A - 5 aromatic hydrocarbons of post/M-phthalic acid, 1,8 naphthalimide coordination compound and its preparation and application - Google Patents
5 aromatic hydrocarbons of post/M-phthalic acid, 1,8 naphthalimide coordination compound and its preparation and application Download PDFInfo
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Abstract
The present invention devises a kind of 5 aromatic hydrocarbons of post/M-phthalic acid 1,8 naphthalimide coordination compounds, it is based on 5 aromatic hydrocarbons of copolymerization post, M-phthalic acid base 1,8 naphthalimides are object, are driving force by self assembly with C H π and electrostatic attraction, by the part M-phthalic acid base 1 with negative charge under alkaline environment, 8 naphthalimide inclusions in the cavity of post aromatic hydrocarbons, so as to complete Subjective and Objective assembling process.After aluminium ion is added in the solution of 5 aromatic hydrocarbons of post/M-phthalic acid, 1,8 naphthalimide coordination compound so that the Fluorescence Increasing of complex solution simultaneously produces yellow fluorescence；Continuously add anion CN‑, there is red shift and simultaneously produce green fluorescence in the fluorescence of complex solution.Therefore, can be as new supermolecule fluorescent optical sensor, for the Al in continuous detecting environment3+And CN‑.
Description
Technical field
The present invention relates to a kind of -1,8 naphthalimide coordination compound of 5 aromatic hydrocarbons of post/M-phthalic acid；The present invention is also related to simultaneously
And 5 aromatic hydrocarbons of post/M-phthalic acid -1, application of the 8 naphthalimide coordination compounds in continuous detecting aluminium ion and cyanide ion, category
In ion detection technical field.
Background technology
It is well known that ion plays an important role in chemistry, biological, medicine, technological process field.Generally, great majority
Biological and environment reaction is carried out all in aqueous systems, therefore, detects that the ion in aqueous solution is very important.Up till now
Till, there are multiple useful strategies or method, such as design water solublity receptor or design master/guest complexes are water miscible sensing
The sensor that device is used to develop effectively can be applied in water.However, these methods be present.Firstly, since
Most organic group is little in water solubility, and it is difficult a kind of water solublity for being simultaneously introduced signal group and binding site
Learn sensor.Secondly, host-guest coordination compound chemical sensor is easily disturbed by other guest ions.Finally, it is often more important that, perhaps
Polyion has higher lanthanum hydrate, blocks the combination between ion and sensor.For example, the lanthanum hydrate of fluorion be-
504KJmol-1.Therefore, new strategy or method are developed, to realize that effectively detection ion remains a challenge in water.
Aluminum is widely used by people as a kind of common metal.But as the reasons such as man memory power forfeiture can be caused
It is confirmed as food contaminant and is controlled by.The species of aluminium composition and beverage in aluminium pot dress beverage, resting period
Length and brand are relevant.Aluminum will seriously threaten sufferer skeleton, brain and nerve under long-term accumulation in renal failure sufferer body
System is all entered via diet regimen in vivo by what major part aluminum absolutely, is therefore directed to Different Package beverage, but content is identical
Beverage carry out detection aluminium content.Because aluminum is difficult to be absorbed and the normal person of general metabolic function by the intestines and stomach, the aluminum absorbed in diet
More than 90% can be by feces, and urine even what perspiration excretes food hygiene relevant unit in native land and clearly do not stipulate
The normal range of the aluminum metal content of food, but aluminum normally cannot excrete and cause aluminum by the renal failure sufferer of renal insufficiency
Poisoning.Therefore, it is intended that thus experiment learns that all kinds of packaged beverage aluminum metal content numbers select beverage packaging to do sufferer according to this
Go out suggestion.As a result show, under identical content thing, aluminium pot dixie cup aluminium content is substantially high than bottled drink, and Folium Camelliae sinensis class beverage
Aluminium content is universal higher.
Cyanogen root is as a kind of virose anion, very big with the harm of people to homoiothermic animal, be characterized in toxicity big,
Effect is fast.The effect of Blausure (German) is extremely rapid, very low in cyaniding hydrogen concentration（0.005mg/L）Air in, people only occurs very short
The headache of time, discomfort, arrhythmia；High in cyaniding hydrogen concentration（0.1mg/L）Air in, people will be dead for dead immediately or speed.
When cyanide is intermediate concentration, people just occurred initial symptoms in 2 ~ 3 minutes, in most cases, dead in 1 hour
Die, also having sometimes.Under the chronic effect of cyanide, as tissue supplies hypoxgia, can draw
Play a series of reflections to sexually revise, such as corpuscular hemoglobin metabolic increases, blood glucose rise to improve blood oxygen easily, acceleration energy
The recovery of metabolism, due to internal SCN-Increase, can also thus cause blood pressure drops, and suppress the poly- iodine function of thyroid, disturb iodine
Combination process, hinder the synthesis of thyroxin, and discharge of the iodine by kidney can be increased, reduce the deposit of internal iodine,
So as to cause Hypothyroidism, strengthen with causing anterior pituitary metabolic secreting thyrotropin, cause thyroid group
Knit hypertrophy enlargement.In addition, the generation of cyanide chronic poisoning is also relevant with the whole nutriture of body, such as vitamin B12 deficiency,
The shortage of protein malnutrition, especially sulfur-containing amino acid can make body for CN-The S of removing toxic substances2O3 2-、S2-And SH-Reduce this
The CN that a little factors can make intake internal-Toxicity increases, and causes a series of sings and symptoms of chronic poisonings to occur.
Post aromatic hydrocarbons has shown very outstanding effect in terms of host-guest chemistry as the new macrocycle molecule of a class.Logical
The modification to post aromatic hydrocarbons structure is crossed, many host-guest chemistry systems are developed well.It is well known that 5 aromatic hydrocarbons of copolymerization post is carried
For a good cavity structure, so the guest molecule with suitable construction size can be penetrated in its cavity reaches master
The result of object inclusion.
1,8- naphthalimide material has big π keys conjugated system, with good fluorescence spectral characteristic.Its high fluorescence volume
Sub- efficiency, good luminescent properties make them in bioprobe, novel screen liquid crystal toner, organic electroluminescent light diode etc.
Reverse side has certain application.Therefore, by M-phthalic acid -1,8 naphthalimides pass through π ... in the solution with 5 aromatic hydrocarbons of post
π, hydrogen bond action, are self-assembly of the coordination compound of inclusion, to as new supermolecule sensor, being matched somebody with somebody by interionic competition
The position seriality detection for realizing ion.
Content of the invention
The purpose of the present invention is according to 5 aromatic hydrocarbons of post and M-phthalic acid -1, the property of 8 naphthalimides, there is provided a kind of
- 1,8 naphthalimide coordination compound of 5 aromatic hydrocarbons of post/M-phthalic acid；
It is a further object of the present invention to provide a kind of -1,8 naphthalimide coordination compound of 5 aromatic hydrocarbons of post/M-phthalic acid is in ion
The application that applies in seriality fluoroscopic examination aluminium ion and cyanide ion of detection field.
First, -1,8 naphthalimide coordination compound of 5 aromatic hydrocarbons of post/M-phthalic acid
5 aromatic hydrocarbons of post/M-phthalic acid -1 of the present invention, 8 naphthalimide coordination compounds, based on 5 aromatic hydrocarbons of copolymerization post, isophthalic
1,8 naphthalimide of diformyl is object, with C-H π and electrostatic attraction as driving force, will carry under alkaline environment
Part M-phthalic acid -1 of negative charge, in the cavity of 8 naphthalimide inclusions to post aromatic hydrocarbons, so that complete Subjective and Objective assembling
Process.
The preparation of -1,8 naphthalimide coordination compound of 5 aromatic hydrocarbons of post/M-phthalic acid：It is by 5 aromatic hydrocarbons of post, isophthalic diformazan
Acid -1,8 naphthalimides, NaOH are dissolved in the water, and 1 ~ 3min is stirred at room temperature, and obtain final product 5 aromatic hydrocarbons of post/2- hydroxyl -3- naphthoic acids
Coordination compound aqueous solution.5 aromatic hydrocarbons of post, -1,8 naphthalimide of M-phthalic acid, the mol ratio of NaOH are 1:2:2.
In order to study the assembling process of 1,8 naphthalimide of 5 aromatic hydrocarbons of copolymerization post and M-phthalic acid base, do first glimmering
Light titration experiments.When the water for adding 5 aromatic hydrocarbons of copolymerization post in the NaOH solution containing -1,8 naphthalimide of M-phthalic acid
When in solution, solution produces yellow fluorescence.With the increase of 5 aromatic hydrocarbons of copolymerization post, the fluorescence intensity of solution gradually weakens.Work as addition
5 aromatic hydrocarbons of copolymerization post reach twice equivalent after, with the increase of its addition, the yellow fluorescence of solution no longer becomes substantially
Change, it was demonstrated that have Inclusion property between host and guest, as shown in Figure 1.
Fig. 2 is -1,8 naphthalimide solution of 5 aromatic hydrocarbons of different mol ratio copolymerization post and guest molecule M-phthalic acid
Nuclear-magnetism titration experiments.Wherein, b, c, d, e, f are respectively guest molecule（- 1,8 naphthalimide of M-phthalic acid）Based on concentration
2,1,0.5,0.3,0.25 times of equivalent of 5 aromatic hydrocarbons of body molecule copolymerization post.From figure 2 it can be seen that with guest molecule concentration
Increase, H on guest moleculea-HeMove to High-Field, caused by this is the shielding action institute for having induction due to inclusion guest molecule.?
The close methylene moiety in naphthalene nucleus part for demonstrating guest molecule is penetrated in the cavity of 5 aromatic hydrocarbons of copolymerization post, when mol ratio after
Continue and increase to 1:When 2, these peak values are basically unchanged, and illustrate that Subjective and Objective molecule is 1:2 mol ratio complexation.
Mass spectruies of the Fig. 3 for -1,8 naphthalimide coordination compound of 5 aromatic hydrocarbons of post/M-phthalic acid.Matter composition and division in a proportion is 313.2,
Show that Subjective and Objective molecule is with 1:2 quantitative relation complexation.
2nd, application of -1,8 naphthalimide coordination compound of 5 aromatic hydrocarbons of post/M-phthalic acid in ion detection
1st, -1,8 naphthalimide of 5 aromatic hydrocarbons of post/M-phthalic acid is to aluminum ions fluorescence response
5 aromatic hydrocarbons of post/M-phthalic acid -1,8 naphthalimide coordination compounds are dissolved in water, concentration are configured to for 1 × 10- 5The aqueous solution of mol/L.0.5mL is pipetted respectively in a series of 10 mL color comparison tubes, and 50 times of equivalents are separately added in color comparison tube
Fe3+, Hg2+, Ag+, Ca2+, Cu2+, Co2+, Ni2+, Cd2+, Pb2+, Al3+, Zn2+, Cr3+, Mg2+, Tb3+, La3+Plasma, determines
The fluorescence intensity change of solution.It was found that only Al3+Addition make the Fluorescence Increasing of solution, open complex fluorescent.Such as Fig. 4 institutes
Show.Illustrate that -1,8 naphthalimide coordination compound of 5 aromatic hydrocarbons of post/M-phthalic acid can be to Al3+Carry out narrow spectrum fluorescence identifying.
Therefore, the coordination compound can be used for the detection that realization body molecule implements spectroscopy to aluminium ion.
2nd, -1,8 naphthalimide coordination compound of 5 aromatic hydrocarbons of post/M-phthalic acid is to aluminum ions titration experiments
It is 1 × 10 in concentration-5The host molecule of mol/L（- 1,8 naphthalimide coordination compound of 5 aromatic hydrocarbons of post/M-phthalic acid）
Aluminium ion is added in aqueous solution（There is very weak fluorescence emission peak when not adding）, with guest molecule（Aluminium ion）The increasing of concentration
Plus, the fluorescence intensity of bulk solution gradually strengthens, as shown in Figure 5.This change is worn due to the guest molecule of short of electricity subsystem
Enter in the cavity of 5 aromatic hydrocarbons of copolymerization post of electron rich system and electron transfer occurs, so as to cause host molecule fluorescence to be opened, equally
Also demonstrate that -1,8 naphthalimide part inclusion of M-phthalic acid has been arrived in the cavity of 5 aromatic hydrocarbons of copolymerization post.
Titration experiments show, 5 aromatic hydrocarbons of post/M-phthalic acid -1, and 8 naphthalimide coordination compounds are to aluminum ions test limit
For 4.13 × 10-8mol/L.
3rd, -1,8 naphthalimide coordination compound of 5 aromatic hydrocarbons of post/M-phthalic acid+fluorescence response of the aluminium ion to cyanide ion
In above-mentioned addition Al3+Bulk solution in, be separately added into CN-, Cl-, Br-, I-, Ac-, H2PO4 -, HSO4 -, ClO4 -, SCN-
Etc. anion, the fluorescence intensity change of solution is observed under uviol lamp.It was found that only CN-Addition, the fluorescence of bulk solution sends out
Raw red shift, shows as green fluorescence, as shown in Figure 6.Therefore, host molecule+aluminium ion again can be with fluorescence identifying CN-.
In sum, based on 5 aromatic hydrocarbons of copolymerization post, 1,8 naphthalimide of M-phthalic acid base is object to the present invention,
It is that driving force passes through self assembly with C-H π and electrostatic attraction, by the part isophthalic diformazan with negative charge under alkaline environment
1,8 naphthalimide inclusion of acidic group in the cavity of post aromatic hydrocarbons, so as to complete Subjective and Objective assembling process.In 5 aromatic hydrocarbons of post/isophthalic
Dioctyl phthalate -1, after adding aluminium ion in the solution of 8 naphthalimide coordination compounds so that the Fluorescence Increasing of complex solution is simultaneously
Yellow fluorescence is produced, and anion CN is added in aluminum ions solution is added-, the fluorescence generation red shift of complex solution is simultaneously
Produce green fluorescence.Therefore, can be as new supermolecule fluorescent optical sensor, for the Al in continuous detecting environment3+And CN-.
Description of the drawings
Fig. 1 is tested for the fluorescence titration of -1,8 naphthalimide coordination compound of 5 aromatic hydrocarbons of post/M-phthalic acid.
Concentration nuclear-magnetism figures of the Fig. 2 for -1,8 naphthalimide coordination compound of 5 aromatic hydrocarbons of post/M-phthalic acid.
Mass spectruies of the Fig. 3 for -1,8 naphthalimide coordination compound of 5 aromatic hydrocarbons of post/M-phthalic acid.
Fig. 4 be -1,8 naphthalimide coordination compound of 5 aromatic hydrocarbons of post/M-phthalic acid to the aluminum ions response diagram of metal.
Fig. 5 is -1,8 naphthalimide coordination compound of 5 aromatic hydrocarbons of post/M-phthalic acid titration figure aluminum ions to metal.
Fig. 6 adds glimmering to the identification of cyanogen root after aluminium ion for -1,8 naphthalimide coordination compound of 5 aromatic hydrocarbons of post/M-phthalic acid
Light figure.
Fig. 7 adds the titration after aluminium ion to cyanogen root for -1,8 naphthalimide coordination compound of 5 aromatic hydrocarbons of post/M-phthalic acid
Figure.
Specific embodiment
Below by specific embodiment to -1,8 naphthalimide coordination compound of 5 aromatic hydrocarbons of post/M-phthalic acid of the present invention
Prepare and detection Al3+And CN-Method be described further.
First, the preparation of -1,8 naphthalimide coordination compound of 5 aromatic hydrocarbons of post/M-phthalic acid
1st, the synthesis of -1,8 naphthalimide of M-phthalic acid
With DMF as solvent, 1,8- naphthalene dicarboxylic anhydride and 5- amino isophthalic acids are with 1:1 mol ratio back flow reaction 48h, decompression rotation
Solvent evaporated DMF.By cantilevered out thing absolute ethanol washing three times, then vacuum rotary steam is processed, and product is M-phthalic acid -1,8 naphthalenes
Dicarboximide, yield 80%.1H NMR (600 MHz, d2o) δ 8.52 (s, 1H), 8.39 – 8.32 (m, 2H),
7.84 (s, 1H), 7.79 (d,J= 8.0 Hz, 1H), 4.64 (s, 449H).
Synthesis type is：
2nd, the synthesis of 5 aromatic hydrocarbons of copolymerization post
The synthesis of intermediate 1：By hydroquinone（2.2 g, 20.0 mmol）、K2CO3（13.8 g, 100mmol）、KI （0.83
G, 5mmol）, 1,4 dibromobutanes（17.28 g, 80mmol）And acetone（300mL）It is added in 500mL round-bottomed flasks, stirring is anti-
Answer 3 days（72h）, solid separate out, obtain intermediate 1.Yield is 80%.1H NMR (400MHz, CDCl3)δ(ppm): δ
6.81 (s, 4H), 3.94 (dd,J= 10.0, 5.8 Hz, 4H), 3.48 (t,J= 6.6 Hz, 2H), 3.26
(t,J= 6.8 Hz, 2H), 2.09-1.85 (m, 8H).
The synthesis of intermediate 2：By intermediate 1（3.8 g, 10.0mmol）It is added in 80mL1,2 dichloroethanes and dissolves；
Again by paraformaldehyde（0.686 g, 20.0mmol）, boron trifluoride diethyl etherate（0.686g, 20.0mmol）It is added in solution, in room
Lower stirring reaction 20min of temperature.Reaction after terminating is poured solution in distilled water into, with distilled water wash three times, plus Na2SO4Dry,
Filter, with silica gel mixed sample, organic faciess pillar layer separation（Petroleum ether/dichloromethane=1:1 v/v）, obtain white solid intermediate
2, yield position 40%.1H NMR (400 MHz, CDCl3) δ(ppm): 6.82 (s, 10H), 3.94 (s, 20H), 3.75
(s, 10H), 3.45 (s, 10H), 3.25 (s, 10H), 2.00 (d,J= 47.7 Hz, 41H).
The synthesis of 5 aromatic hydrocarbons of copolymerization post：By intermediate 2（1.00g, 0.51mmol）, trimethylamine（33 % in ethanol,
6.89 mL, 25.5mmol）Add in the ethanol solution of 50ml, back flow reaction 12h, then revolving removes ethanol, by the product for being revolved
Thing adds the distilled water of 20ml, adds acetonitrile and continues to rotate till having white solid to produce.Product is 5 virtue of copolymerization post
Hydrocarbon P, yield 90%.1H NMR (400 MHz, D2O) δ (ppm): 6.73 (s, 10H), 3.79 (s, 31H), 3.09
(s, 21H), 2.90 (s, 93H), 1.54 (s, 41H)..
The synthesis type of 5 aromatic hydrocarbons of copolymerization post is as follows：
.
3rd, the preparation of coordination compound
By 5 aromatic hydrocarbons of post（P5）, -1,8 naphthalimide of M-phthalic acid, NaOH is with 1:2:2 mol ratio is completely dissolved in water
In, 5 aromatic hydrocarbons of post/M-phthalic acid -1,8 naphthalimide coordination compound aqueous solutions is obtained final product, concentration is 5 × 10-5mol/L.
2nd, -1,8 naphthalimide coordination compound continuous fluorescence of 5 aromatic hydrocarbons of post/M-phthalic acid identification Al3+And CN-
In 5 aromatic hydrocarbons of post/M-phthalic acid -1 of above-mentioned preparation, the aqueous solution of 8 naphthalimide coordination compounds, it is separately added into
Fe3+, Hg2+, Ag+, Ca2+, Cu2+, Co2+, Ni2+, Cd2+, Pb2+, Al3+, Zn2+, Cr3+, Mg2+, Tb3+, La3+Solution, if solution
Yellow fluorescence is sent, then that added is Al3+；Otherwise added is other cationic solutions.
Al is added in the aqueous solution of -1,8 naphthalimide coordination compound of 5 aromatic hydrocarbons of post/M-phthalic acid of above-mentioned preparation3 +, solution sends yellow fluorescence；CN is separately added into again in solution-, Cl-, Br-, I-, Ac-, H2PO4 -, HSO4 -, ClO4 -, SCN-,
Observe under 365nm uviol lamps.If solution is changed into green fluorescence from yellow fluorescence, show addition is containing CN-Solution, otherwise
Added is other anion solutions.
Claims (7)
1. 5 aromatic hydrocarbons of post/M-phthalic acid -1,8 naphthalimide coordination compounds, it is characterised in that：Object M-phthalic acid -1,8
Naphthalimide part penetrates into the coordination compound for reaching inclusion and being formed in the cavity of 5 aromatic hydrocarbons of main column.
2. 5 aromatic hydrocarbons of post/M-phthalic acid -1 as claimed in claim 1, the preparation method of 8 naphthalimide coordination compounds, its are special
Levy and be：5 aromatic hydrocarbons of post, M-phthalic acid -1,8 naphthalimides, NaOH are completely dissolved in water, obtain final product 5 aromatic hydrocarbons of post/
- 1,8 naphthalimide coordination compound aqueous solution of phthalic acid.
3. 5 aromatic hydrocarbons of post/M-phthalic acid -1 as claimed in claim 2, the preparation method of 8 naphthalimide coordination compounds, its are special
Levy and be：5 aromatic hydrocarbons of post, -1,8 naphthalimide of M-phthalic acid, NaOH are with 1:2:2 mol ratio coordinates.
4. -1,8 naphthalimide complex fluorescent of 5 aromatic hydrocarbons of post/M-phthalic acid as claimed in claim 1 recognizes Al3+Should
With.
5. -1,8 naphthalimide complex fluorescent of 5 aromatic hydrocarbons of post/M-phthalic acid as claimed in claim 4 recognizes Al3+Should
With, it is characterised in that：In 5 aromatic hydrocarbons of post/M-phthalic acid -1, the aqueous solution of 8 naphthalimide coordination compounds, it is separately added into
Fe3+, Hg2+, Ag+, Ca2+, Cu2+, Co2+, Ni2+, Cd2+, Pb2+, Al3+, Zn2+, Cr3+, Mg2+, Tb3+, La3+Solution, if solution
Yellow fluorescence is sent, then that added is Al3+；Otherwise added is other cationic solutions.
6. -1,8 naphthalimide coordination compound continuous fluorescence of 5 aromatic hydrocarbons of post/M-phthalic acid as claimed in claim 1 recognizes Al3+
And CN-Application.
7. -1,8 naphthalimide coordination compound continuous fluorescence of 5 aromatic hydrocarbons of post/M-phthalic acid as claimed in claim 6 recognizes Al3+
And CN-Application, it is characterised in that：Add in the aqueous solution of -1,8 naphthalimide coordination compound of 5 aromatic hydrocarbons of post/M-phthalic acid
Enter Al3+, solution sends yellow fluorescence；CN is separately added into again in solution-, Cl-, Br-, I-, Ac-, H2PO4 -, HSO4 -, ClO4 -,
SCN-, under uviol lamp, if the color from yellow fluorescence of solution is changed into green fluorescence, that added is CN-, otherwise added is
Other anion solutions.
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Cited By (14)
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| CN110954515A (en) * | 2019-12-03 | 2020-04-03 | 山西大学 | 1, 8-naphthalimide derivative and application thereof |
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| CN110954515A (en) * | 2019-12-03 | 2020-04-03 | 山西大学 | 1, 8-naphthalimide derivative and application thereof |
| CN110954515B (en) * | 2019-12-03 | 2020-11-10 | 山西大学 | 1, 8-naphthalimide derivative and application thereof |
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