CN104447363B - Cation type water-soluble post [5] aromatic hydrocarbons and preparation thereof and as receptor application in detection silver ion - Google Patents
Cation type water-soluble post [5] aromatic hydrocarbons and preparation thereof and as receptor application in detection silver ion Download PDFInfo
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Abstract
The present invention designs and has synthesized a kind of cation type water-soluble post [5] aromatic compound, not only having one in its structure has five phenyl ring to constitute post framework, also respectively connect five trimethylamine groups at lower edges, it is a kind of post aromatic hydrocarbons containing multiple recognition sites, and in water, have good dissolubility, such that it is able to pure water mutually in form stable coordination compound by the trimethylamine group of cationic and silver ion complexation.Experiment shows, in the aqueous solution of cation type water-soluble post aromatic hydrocarbons, and only Ag+Addition its ultraviolet absorption peak at 293nm can be made to be remarkably reinforced, and the addition of remaining cation can not make its aqueous solution uv absorption at 293nm change.Therefore, this post aromatic hydrocarbons is to Ag+There is good selectivity ultraviolet identification ability, can be as Ag+Acceptor molecule is at pure water middle detection silver ion mutually.Titration is real to be shown, this post aromatic hydrocarbons is to Ag+Lowest detectable limit can reach 1.25 × 10‑5 M。
Description
Technical field
The present invention relates to a kind of post arene compounds, particularly relate to a kind of cation type water-soluble post [5] aromatic hydrocarbons and
Preparation method；The present invention also relate to this cation type water-soluble post [5] aromatic hydrocarbons as acceptor molecule detection silver ion in
Application, belong to cation detection technical field.
Background technology
The research that Novel macrocyclic host molecule post aromatic hydrocarbons causes World Science man dense after being in the news first in 2008 is emerging
Interest.Itself and the Subjective and Objective bonding action of guest molecule and self assembly behavior all become the focus of research.Meanwhile, as novel master
Body molecule is by becoming the focus of Recent study as the function new with the compound displaying of inorganic nano material.And as a class
The post aromatic hydrocarbons of novel macrocyclic host molecule is compared to calixarenes, and it has more symmetrical column structure, therefore is named " post aromatic hydrocarbons ".
Owing to the derivatization of post aromatic hydrocarbons is relatively easy, therefore its achievement in research is maked rapid progress.
Along with making rapid progress of modern science and technology, the scope of daily use silver and compound thereof increases the most day by day.Silver with
And the Related product of silver is widely used in electronics, plating, sensitive material, chemical engineering industry and scientific research field.Relating to each of silver
The production of each industry of row and application can produce various silver-containing waste water.Compared with other industry, although the wastewater flow rate of generation
Very big, but the character of its waste water to determine it the most serious to the pollution effect of environment.Silver ion in waste water exists
Migration, diffusion in environment will pollute natural water, and human body and hydrobiological health will be produced serious harm.Therefore,
Identification and the detection of silver ion suffer from important application in fields such as environmental science, life sciences and medical science.Detection silver ion
Method a lot, and colorimetry receives much attention due to the reason such as convenient and swift.But, the water solublity of most receptors compound
Difference, ion identification can only be carried out in organic facies, it is impossible to realize pure water mutually in silver ion is identified.
Summary of the invention
It is an object of the invention to provide a kind of cation type water-soluble post [5] aromatic hydrocarbons；
It is a further object of the present invention to provide the preparation method of a kind of cation type water-soluble post [5] aromatic hydrocarbons；
It is a further aim of the invention provide above-mentioned water solublity post [5] aromatic hydrocarbons as silver ion acceptor molecule pure
Aqueous phase detects the application of silver ion.
One, cation type water-soluble post aromatic hydrocarbons
Cation type water-soluble post aromatic hydrocarbons (being designated as P) of the present invention, not only having one in its structure has five phenyl ring groups
Become post framework, also respectively connected five trimethylamine groups at lower edges, be a kind of post aromatic hydrocarbons containing multiple recognition sites, and
And in water, have good dissolubility, such that it is able to pure water mutually in by the trimethylamine group of cationic and silver ion complexation
Form stable coordination compound and identify silver ion.Its structural formula is as follows:
。
Two, the preparation of cation type water-soluble post aromatic hydrocarbons
The preparation method of subject cationic type water solublity post [5] aromatic hydrocarbons, comprises the following steps that:
(1) synthesis of Isosorbide-5-Nitrae-two (4-bromine butoxy) benzene (compound 1): with acetone as solvent, potassium carbonate and potassium iodide are
Catalyst, under nitrogen protection, makes hydroquinone and Isosorbide-5-Nitrae-dibromobutane back flow reaction 48 ~ 72h；Precipitate with cold water, filter, water
Washing, chromatography is pure, obtains white powdery solids, to obtain final product.
The mol ratio of hydroquinone and 1,4-dibromobutane is 1:5 ~ 1:10.Hydroquinone is 1 with the mol ratio of potassium carbonate:
2~1:8；Hydroquinone is 1:2 ~ 1:4 with the mol ratio of potassium iodide.
The synthesis of (2) two (4-bromine butoxy) post [5] aromatic hydrocarbons (compounds 2): with 1,2-dichloroethanes is solvent, borontrifluoride
Borate ether is catalyst, makes Isosorbide-5-Nitrae-two (4-bromine butoxy) benzene and paraformaldehyde that reaction 1 ~ 3h is stirred at room temperature, obtains green
Mixture；Rotation is evaporated off solvent, and solid uses column chromatography, and obtains white powdery solids and is compound two (4-bromine fourth oxygen
Base) post [5] aromatic hydrocarbons.
1,4-bis-(4-bromine butoxy) benzene is 1:2 ~ 1:5 with the mol ratio of paraformaldehyde；1,4-bis-(4-bromine butoxy) benzene
It is 1:1 ~ 1:4 with the mol ratio of boron trifluoride diethyl etherate.
(3) synthesis of cation type water-soluble post [5] aromatic hydrocarbons (compound P): by two (4-bromine butoxy) post [5] aromatic hydrocarbons with
Trimethylamine joins in etoh solvent, and reflux 12 ~ 36h；Rotation is evaporated off ethanol, gained solid deionized water dissolving, filters, rotation
Aqueous solvent is evaporated off, obtains water white solid, be cation type water-soluble post aromatic hydrocarbons.
Compound two (4-bromine butoxy) post [5] aromatic hydrocarbons is 1:15 ~ 1:30 with the mol ratio of trimethylamine.
Above-mentioned reaction equation is as follows:
。
Three, cations recognition is tested
1, to cations recognition performance study
Pipette the aqueous solution (2 × 10 of 0.5 mL cation type water-soluble post aromatic hydrocarbons P respectively-4 mol·L-1) in a series of
In 10 mL color comparison tubes, it is then respectively adding Fe3+、Fe2+、Hg2+、Ag+、Ca2+、Cu2+、Co2+、Ni2+、Cd2+、Pb2+、Zn2+、Cr3 +、Mg2+、Na+、K+Aqueous solution (0.004 mol L-1) 0.5 mL.Be diluted with water to 5mL, now the concentration of post aromatic hydrocarbons be 2 ×
10-5mol·L-1, cation concn is 20 times of post density of aromatic hydrocarbon.Place about 10 minutes after mix homogeneously, observe post [5] virtue
The hydrocarbon response to each cation.
Find, in the aqueous solution of cation type water-soluble post aromatic hydrocarbons, after being separately added into the aqueous solution of above-mentioned cation,
In corresponding ultraviolet spectra, only Ag+Addition the aqueous solution of post aromatic hydrocarbons absworption peak at 293nm can be made to strengthen (see figure 1),
And remaining cation add coupled columns aromatic hydrocarbons aqueous solution at 293nm ultraviolet spectra without significant change.Therefore, post aromatic hydrocarbons is to Ag+There is good selectivity ultraviolet identification ability, can be as Ag+Acceptor molecule is at pure water middle detection silver ion mutually.
2, titration experiments
Pipette the aqueous solution (2.0 × 10 of 2 mL acceptor molecule P-5Mol/L) in quartz cell, by accumulation sample-adding method gradually
Add Ag+ The solution of water, survey its ultra-violet absorption spectrum (see figure 2)s in 25 DEG C.Along with Ag+Be gradually added into, receptor can be made
Aqueous solution absworption peak at 293nm strengthens, and occurs in that new absorption band at 325 ~ 450nm.
3, interference free performance detection
In order to measure acceptor molecule P to Ag+Detection results, we have carried out again following test: take two groups of 10mL colorimetrics
Pipe, is separately added into aqueous solution and the aqueous solution (4 × 10 of the various cation of 0.5mL of 0.5mL receptor-3mol·L-1).Wherein one
Group is diluted with water to 5mL scale；Another set adds as various in 0.5mL Ag respectively+The aqueous solution (4 × 10 of ion-3mol·L-1), then it is diluted with water to 5mL scale.Its ultraviolet-ray visible absorbing light is surveyed after placing 10 minutes after above-mentioned solution mix homogeneously
Spectrum.
Anti-interference it can be seen that receptor is adding Ag from ultraviolet+It is added thereto to other cation the most again, at 293nm
The absorption at place does not has a greater change.Fig. 3 is Receptor recognition Ag+Ultraviolet anti-interference absorption block diagram.Illustrate to add Ag2+, receptor
Absworption peak at 293nm strengthens, then add other 14 kinds of cationes after, receptor absworption peak at 293nm is the most not
Become, this and Ag+Impact on receptor is consistent.Therefore, illustrate receptor in ultra-violet absorption spectrum to Ag+Detection the most not
Affected by other cation.
4, receptor is to Ag+The mensuration of lowest detectable limit
25 DEG C, utilize ultraviolet spectra, at receptor (2 × 10-4mol·L-1) to Ag+Ion (0.05 mol L-1) titration
In experiment, we are according to the Ag added+The volume of ion and the design sketch of titration, i.e. can get this receptor to Ag+Ion is
Low detection limit reaches 1.25 × 10-5 M·L-1。
Great many of experiments shows, in the aqueous solution of acceptor molecule, the concentration of acceptor molecule is adjusted in the range of 5 μMs ~ 30 μMs
Whole, acceptor molecule is to Ag+There is the selectivity ultraviolet identification ability become reconciled.
Accompanying drawing explanation
Fig. 1 is the uv absorption block diagram after adding various cation in the aqueous solution of acceptor molecule.
Fig. 2 is that acceptor molecule is to Ag+Ultraviolet titration experiments figure.
Fig. 3 is Receptor recognition Ag+The anti-interference block diagram of uv absorption.
Fig. 1, in 3, A is P and the uv absorption of each metal ion species, A0Uv absorption and each metal ion species for P
Self-absorption.
Detailed description of the invention
Below by specific embodiment to the synthesis of the application acceptor compound and at detection Ag+Application work detailed
Explanation.
1, the synthesis of acceptor compound cation type water-soluble post aromatic hydrocarbons:
(1) compound 1(1,4-bis-(4-bromine butoxy) benzene) synthesis: by hydroquinone (2.2 g, 20.0 mmol) and
Isosorbide-5-Nitrae-dibromobutane (17.28 g, 80.0 mmol), potassium carbonate (13.8 g, 100 mmol) also potassium iodide (0.83 g,
5mmol) join the lower backflow of nitrogen protection in the acetone soln of 200mL 72 hours.Then reactant liquor is poured into 300mL cold water
In, there is white precipitate to generate, filter, and rinse with water, obtain white solid.Isolated and purified (the second of gained solid flash column
Acetoacetic ester/petroleum ether, 1:30, v:v) obtain white powdery solids (6.5 g, 86 %).m.p. 86 °C.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). 13C NMR (100
MHz, CDCl3) δ: 153.08, 115.42, 67.37, 33.45, 30.22 , 29.49, 27.99. HRESIMS:
m/z calcd for [M+H]+ C14H20Br2O2, 381.12; found 380.988。
(2) compound 2(bis-(4-bromine butoxy) post [5] aromatic hydrocarbons) synthesis: by compound 1 (3.8 g, 10.0 mmol)
It is dissolved in the 1,2-dichloroethanes of 150mL；Add paraformaldehyde (0.686 g, 20.0 mmol) mix homogeneously, then to mixing
Solution adds boron trifluoride diethyl etherate (1.42 g, 10.0 mmol), 3h is stirred at room temperature, obtain the mixture of green.Rotation steams
Removing solvent, it is solid that gained solid rapid column chromatography isolated and purified (ethyl acetate/petroleum ether, 1:20 v:v) obtains white powder
Body (1.57 g, 40 %).m.p. 124-126 °C.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). 13C NMR (100 MHz, CDCl3) δ (ppm): 149.79, 128.33, 114.77,
67.58, 67.44, 33.74, 31.12, 30.27 and 29.70. HRESIMS: m/z calcd for [M + 6H]+
C75H100Br10O10, m/z 1965.92 ; found 1966.9。
(3) synthesis of target compound P: by compound 2 (1.00 g, 0.51 mmol) and trimethylamine (6.89 mL,
25.5 mmol) join in 50mL ethanol, backflow is overnight；Rotation is evaporated off solvent, and it is water-soluble that gained solid adds 20mL deionization
Solve, be filtrated to get the aqueous solution of clarification.After rotation is evaporated off solvent, obtain water white solid (1.28 g, 95 %).m.p.
218-220 °C. 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). 13C NMR (100 MHz, D2O) δ (ppm):
152.86, 132.00, 71.48, 68.79, 28.49 and 22.18. HRESIMS: m/z of C85H150Br10N10O10
772.3, 557.75, 433.97 and 349.70, 288.47 corresponding to [M-3Br]3+, [M-4Br
]4+, [M-5Br+Na+]5+, [M-6Br+Na+]6+ and [M-7Br+Na+]7+。
2、Ag+Detection
Pipette the aqueous solution (2 × 10 of 0.5 mL cation type water-soluble post [5] aromatic hydrocarbons P respectively-4 mol·L-1) in one be
In row 10 mL color comparison tube, it is then respectively adding Fe3+、Fe2+、Hg2+、Ag+、Ca2+、Cu2+、Co2+、Ni2+、Cd2+、Pb2+、Zn2+、
Cr3+、Mg2+、Na+、K+Aqueous solution (0.004 mol L-1) 0.5 mL.Being diluted with water to 5mL, now the concentration of post aromatic hydrocarbons is 2
×10-5mol·L-1, cation concn is 20 times of post [5] density of aromatic hydrocarbon.Place about 10 minutes after mix homogeneously, observe post
The aromatic hydrocarbons response to each cation.Detection post [5] aromatic hydrocarbons aqueous solution ultraviolet spectra of ultraviolet light at 293nm.If post aromatic hydrocarbons is molten
The absworption peak of liquid ultraviolet light at 293nm strengthens, then that add is Ag+If, post aromatic hydrocarbons aqueous solution ultraviolet spectra at 293nm
Without significant change, then that explanation adds is not Ag+。
Claims (10)
1. cation type water-soluble post [5] aromatic hydrocarbons, its structural formula is as follows:
。
2. the preparation method of cation type water-soluble post [5] aromatic hydrocarbons as claimed in claim 1, comprises the following steps that:
(1) synthesis of Isosorbide-5-Nitrae-two (4-bromine butoxy) benzene: with acetone as solvent, potassium carbonate and potassium iodide are catalyst, nitrogen is protected
Protect down, make hydroquinone and Isosorbide-5-Nitrae-dibromobutane back flow reaction 48 ~ 72h；Precipitate with cold water, filter, washing, chromatography is pure,
Obtain white powdery solids, to obtain final product；
The synthesis of (2) two (4-bromine butoxy) post [5] aromatic hydrocarbons: with 1,2-dichloroethanes is solvent, boron trifluoride diethyl etherate is catalysis
Agent, makes Isosorbide-5-Nitrae-two (4-bromine butoxy) benzene and paraformaldehyde that reaction 1 ~ 3h is stirred at room temperature, obtains the mixture of green；Rotation is evaporated off
Go solvent, solid to use column chromatography, obtain white powdery solids and be compound two (4-bromine butoxy) post [5] aromatic hydrocarbons；
(3) synthesis of cation type water-soluble post [5] aromatic hydrocarbons: two (4-bromine butoxy) post [5] aromatic hydrocarbons is joined with trimethylamine
In etoh solvent, reflux 12 ~ 36h；Rotation is evaporated off ethanol, gained solid deionized water dissolving, filters, and rotation is evaporated off solvent
Water, obtains water white solid, is cation type water-soluble post aromatic hydrocarbons.
3. the preparation method of cation type water-soluble post aromatic hydrocarbons as claimed in claim 2, it is characterised in that: in step (1), to benzene
The mol ratio of diphenol and 1,4-dibromobutane is 1:5 ~ 1:10.
4. the preparation method of cation type water-soluble post aromatic hydrocarbons as claimed in claim 2, it is characterised in that: in step (1), to benzene
Diphenol is 1:2 ~ 1:8 with the mol ratio of potassium carbonate.
5. the preparation method of cation type water-soluble post aromatic hydrocarbons as claimed in claim 2, it is characterised in that: in step (1), to benzene
Diphenol is 1:2 ~ 1:4 with the mol ratio of potassium iodide.
6. the preparation method of cation type water-soluble post aromatic hydrocarbons as claimed in claim 2, it is characterised in that: in step (2), Isosorbide-5-Nitrae-
Two (4-bromine butoxy) benzene is 1:2 ~ 1:5 with the mol ratio of paraformaldehyde.
7. the preparation method of cation type water-soluble post aromatic hydrocarbons as claimed in claim 2, it is characterised in that: in step (2), Isosorbide-5-Nitrae-
Two (4-bromine butoxy) benzene is 1:1 ~ 1:4 with the mol ratio of boron trifluoride diethyl etherate.
8. the preparation method of cation type water-soluble post aromatic hydrocarbons as claimed in claim 2, it is characterised in that: in step (3), two
(4-bromine butoxy) post [5] aromatic hydrocarbons is 1:15 ~ 1:30 with the mol ratio of trimethylamine.
9. cation type water-soluble post [5] aromatic hydrocarbons is detecting Ag as acceptor molecule as claimed in claim 1+In application.
10. cation type water-soluble post aromatic hydrocarbons is detecting Ag as acceptor molecule as claimed in claim 1+In application, its feature
It is: only Ag+Addition cation type water-soluble post [5] aromatic hydrocarbons aqueous solution ultraviolet absorption peak at 293nm can be made obvious
Strengthen, and the addition of remaining cation can not make cation type water-soluble post [5] aromatic hydrocarbons aqueous solution uv absorption at 293nm
Change.
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| CN100439325C (en) * | 2005-12-13 | 2008-12-03 | 北京师范大学 | Calixarene-ethanolamine derivative, its production and use as metal-ion fluorescent identification agent |
| CN104101577B (en) * | 2014-08-05 | 2017-07-14 | 贵州大学 | A kind of method that ratio absorption spectrophotometry determines Ag+ or F |
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