CN106256829B - A kind of preparation method and applications of benzimidazole and benzo isobioquin group mercury ion fluorescence probe - Google Patents
A kind of preparation method and applications of benzimidazole and benzo isobioquin group mercury ion fluorescence probe Download PDFInfo
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- CN106256829B CN106256829B CN201610537680.XA CN201610537680A CN106256829B CN 106256829 B CN106256829 B CN 106256829B CN 201610537680 A CN201610537680 A CN 201610537680A CN 106256829 B CN106256829 B CN 106256829B
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
Abstract
The invention discloses a kind of preparation method of response type mercury ion fluorescence probe.It is characterized in that a kind of new mercury ion detecting probe based on benzimidazole and the carboxylic acid derivates of benzo isoquinolines 11 prepared by raw material of 1,8 naphthalene anhydrides, 3,4 diaminobenzoic acids, n-butylamine and lawesson reagent.The fluorescence probe has convieniently synthesized, and reaction condition is gentle, it is easy to the advantages of purifying and stable optical performance.The fluorescent probe molecule of the present invention can be in HEPES（pH=7.4）And acetonitrile mixed solution（Volume ratio is 3:7）Medium makes C=S double bonds in fluorescent probe molecule be changed into C=O double bonds by the specific reaction with mercury ion, produces strong blue-green fluorescent（39.6 times of Fluorescence Increasing）, the concentration of its fluorescence intensity and mercury ion has good linear relationship.The high selectivity to mercury ion is shown simultaneously, is not disturbed by other metal cations.The fluorescent probe molecule is well suited for the application in water environment system, all has important actual application value in fields such as biological medicine chemistry, environmental sciences.
Description
Technical field
The present invention relates to environmental analysis, bioanalysis detection technique field, and in particular to a kind of response type mercury ion fluorescent
The application of the preparation method of molecular probe and the fluorescent molecular probe in terms of mercury ion is detected.
Background technology
Mercury has very strong bio-toxicity, has bad shadow to internal system, immune system, nervous system of people etc.
Ring.Absorption of human body mercury by way of there is three kinds, be alimentary canal, respiratory tract and skin respectively.Mercury has cumulative effect in vivo, no
Can be excreted by metabolic process, into human body after directly sink to liver, very big is destroyed to brain, nerve, eyesight.Connect for a long time
Touch and take in mercury and apparent illness occurs, such as serious Nausea and vomiting, stomachache and renal dysfunction pass through Minamata
The limbs of patient are showed, the state of mind is with regard to that can find out the extent of injury of the mercury to human body.According to《People's Republic of China's environment is protected
Defend the doctrine》Regulation, Drinking Water and farmland irrigating water's mercury content must not exceed 0.001mg/L.Mercury produces toxicity in water body
Scope is about 0.01-0.001mg/L, and mercury is much larger than this in water body by the toxicity after accumulation, lives in mercury contaminated
The content of methyl mercury is than high up to ten thousand times in water in the fish body in waters, after being accumulated through food chain by maximum harm or I
The mankind.Mercury it is harmful to crops and without profit, but crops can easily absorb, the content influence crops of mercury in soils
Grow, be directly connected to the yield and quality of crops.Not only the microorganism in soil can not degrade mercury, have even
Can be converted into the compound of more toxic by biomethylation, these things after being enriched with through food chain it is final still
Into the internal of people.It can be seen that, mercury is also to despise with harm to the pollution of soil.Therefore the analysis of heavy metal Hg and detection
Become an important topic for current chemical analysis field.The method of detection mercury ion ion has many kinds at present, wherein
The characteristics of XRF has quick response and high sensitivity, therefore detect mercury ion using fluorescence probe come qualitative and quantitative
Oneself turns into the focus of research（CN201410555700.7, CN201410369075.7, CN201010166304.7,
CN201410768327.3, CN201110122460.8, CN201410207062.X, CN201110421734.3,
CN201210047116.1, CN201310273704.1, CN201210526466.6, CN201410400848.3 etc.）.Probe class
Type is broadly divided into complexing mercury ion fluorescence probe and response type mercury ion fluorescence probe.Wherein because mercury ion is with very strong
Thiophilic property, the response type fluorescence probe based on thiophilic property has high specificity and environmental suitability, can preferably answer
Detection for mercury ion.
The content of the invention
An object of the present invention is to provide a kind of benzimidazole and benzo isobioquin group mercury ion reaction fluorescence probe
And preparation method thereof, be with 1,8- naphthalene anhydrides, 3,4- diaminobenzoic acids, n-butylamine and lawesson reagent be raw material, synthesis to mercury from
Son has high selectivity, the new mercury ion fluorescence probe of specific recognition.
The purpose of the present invention is achieved through the following technical solutions.
A kind of mercury ion fluorescence probe and preparation method thereof, it is characterised in that：
（1）A kind of response type mercury ion fluorescence probe, it is characterized in that with following chemical molecular structural formula：
Fig. 1 molecular structure of compounds
（2）Mercury ion fluorescence probe its preparation method is as follows：
A. the preparation of benzimidazole and benzo isoquinolines -11- carboxylic acids：By 1,8- naphthalic anhydrides and 3,4- diaminourea
Benzene is dissolved in acetum, is heated to reflux 12h；After reaction terminates, room temperature is cooled to, suction filtration is simultaneously washed with acetic acid, dried
Obtain crude product；Crude product is dissolved in 5% sodium hydroxide solution, filters insoluble matter, using concentrated hydrochloric acid adjust pH value 2~3 it
Between, separate out greenish yellow solid, suction filtration, boiling water washing, dry product.
B. the preparation of benzimidazole and benzo isoquinolines -11- acyl chlorides：By benzimidazole and benzo isoquinolines -11-
Carboxylic acid is suspended in dichloromethane, and oxalyl chloride is added in system, and 5h is stirred at room temperature, and produces a large amount of yellow suspension things, solid is taken out
Filter, dichloromethane is washed for several times, dry yellow product.
c. NThe preparation of-butyl-benzene and imidazo benzisoquinoline ketone -11- carboxylic acid amides：By benzimidazole and benzo isoquinoline
Quinoline ketone -11- acyl chlorides is suspended in dichloromethane, and n-butylamine is sequentially added in system, and acid binding agent triethylamine is stirred overnight at room temperature；
After reaction terminates, the NaOH of reaction solution 5% washings, anhydrous Na SO4Dry, absolute ethyl alcohol recrystallizes to obtain yellow product.
D. the preparation of mercury ion fluorescence probe：WillN- butyl-benzene and imidazo benzisoquinoline ketone -11- carboxylic acid amides and labor
Gloomy reagent is dissolved in toluene solvant, and nitrogen protection 12 h of lower backflow, reaction is cooled to room temperature after terminating, concentrated solvent, column chromatography
Isolated mercury ion fluorescence probe.
It is a further object to provide a kind of selectivity is good, sensitivity is high, the inspection of good water solubility and Fluorescence Increasing
Survey the fluorescence probe of mercury ion：In cushioning liquid CH3CN-HEPES (in 0.02 M, pH=7.4) (7/3, v/v), visit by fluorescence
The concentration of pin is 1 μM, and excitation wavelength is 367nm, carries out mercury ion detecting measure.
Advantages of the present invention and effect are：
（1）The present invention obtains high selectivity mercury ion fluorescent molecular probe, with the benzimidazole acene that chemical property is stable
And isoquinolines are fluorescence molecule parent, thiocarboxamide is mercury ion recognition group.
（2）Probe molecule raw material of the present invention is easy to get, and preparation process is simple, the easily controllable synthetic yield of condition compared with
Height, stable optical performance.
（3）The present invention obtains high selectivity mercury ion fluorescent molecular probe, generation that can be with mercury ion by sulphur atom
Specific reaction, makes C=S double bonds in fluorescent probe molecule be changed into C=O double bonds, produces hyperfluorescence（39.6 times of Fluorescence Increasing）.
The probe molecule has sensitivity higher, and water-soluble preferable, strong to mercury ion recognition capability, response speed is very fast.Therefore such
Type probe has actual application value in fields such as biochemistry, environmental sciences.
Brief description of the drawings
Fig. 1 molecular structure of compounds
The synthetic route of Fig. 2 intermediates 1
The synthetic route of Fig. 3 intermediates 2
The synthetic route of Fig. 4 intermediates 3
Fig. 5 compounds A synthetic route
In Fig. 6 Fig. 7, the test of fluorescence probe of the invention is in cushioning liquid CH3CN-HEPES (0.02 M, pH=
7.4) carried out in (7/3, v/v) in system.
Fig. 6 is fluorescence probe of the invention（1uM）Fluorescence emission spectrum change is with dense after various concentrations mercury ion is added
The relation of degree, abscissa is wavelength, and ordinate is fluorescence intensity.
Fig. 7 is fluorescence probe of the invention（1uM）It is separately added into the different metal ions Ni of 10 equivalents2+、Ba2+、Ag+、Cd2 +、Mg2+、Cu2+、Mn2+、Fe3+、Zn2+、Co2+、Al3+、Ca2+、Pb2+、K+、Hg2+Fluorescence spectrum afterwards, abscissa is wavelength, indulges and sits
Mark fluorescence intensity.
Embodiment
Embodiment 1：The synthesis of intermediate 1
The synthetic route of Fig. 2 intermediates 1
0.99g 1 is weighed, 8- naphthalic anhydrides and 0.76g 3,4- diaminobenzoic acid are suspended in 50mL acetic acid, nitrogen
The lower backflow 10h of protection.Room temperature is cooled to after question response is complete, the grass green compound of generation is through depressurizing suction filtration and being washed with acetic acid
For several times, it is placed in the sodium hydroxide solution that 100 mL 5% are dried and be dissolved in air.Insoluble matter in solution is filtered, in filter
Go out in liquid to add concentrated hydrochloric acid regulation pH value has a solid generation between 2~3, in solution, suction filtration and washed with boiling water for several times it is yellow
Green body 1.1g (intermediate 1), yield 63%.Nucleus n-ness spectrum is characterized as below：1H NMR (400 MHz, DMSO) δ 8.77
(s, 1H), 8.47 (dd, J = 15.1, 7.6 Hz, 4H), 8.35 (dd, J = 7.8, 5.0Hz, 4H), 8.22
(dd, J = 17.6, 8.8Hz, 4 H), 8.14 (s, 1H), 7.92 (d, J = 8.4 Hz, 2H), 7.85-7.65
(m, 5H).
The synthesis of intermediate 2
The synthetic route of Fig. 3 intermediates 2
Weigh intermediate 1 (1.0g, 3.2mmol) to be suspended in 40 mL dichloromethane, add 8mL oxalyl chlorides and instill 3-4
DMF is dripped as catalyst, 5h is stirred at room temperature, and is produced a large amount of yellow suspension things, is washed for several times by solid suction filtration and with dichloromethane,
Yellow crude 1.02g is obtained, it is not purified to be directly used in next step.
The synthesis of intermediate 3
The synthetic route of Fig. 4 intermediates 3
Weigh 0.66 g（2mmol) intermediate 2 is suspended in 20mL dichloromethane, sequentially adds 0.83mL (8mmol) three
Ethamine and 0.3mL (3mmol) n-butylamine, triethylamine are stirred overnight at room temperature as acid binding agent.Washed three times, then used with 5% NaOH
Water washing once, finally uses NaSO4Dry, be spin-dried for obtaining yellow solid, recrystallized with absolute ethyl alcohol, obtain pure yellow solid
0.71g（Intermediate 3), yield 97.2%.1H NMR (400 MHz, DMSO) δ 8.93 (s, H), 8.73 (d, J = 4
Hz, 2H), 8.53 (d, J = 8 Hz, 1H), 8.38-8.45 (m, 2H), 7.89-7.92 (m, 3H), 2.52
(t, J = 4 Hz, 2H), 1.54-1.61 (m, 2H), 1.34-1.43 (m, 2H), 0.95 (t, J = 6 Hz,
3H). 13C NMR (100 MHz, CDCl3) δ 167.35, 160.53, 150.95, 145.84, 135.57,
135.48, 132.76, 132.35, 132.17, 132.13, 132.00, 131.91, 131.81, 131.42,
127.60, 127.45, 127.35, 127.06, 126.95, 126.88, 125.59, 124.31, 122.72,
120.13, 119.89, 118.55, 115.67, 113.89, 40.03, 31.86, 20.16, 13.87 HRMS-ESI
(m/z) [M+H]+Calculated value 370.1556, measured value 370.1535.
Compound A synthesis
Fig. 5 compounds A synthetic route
Weigh intermediate 3 (0.36g, 1mmol), lawesson reagent（0.44g, 1.1mmol）50mL circles are placed in 10mL toluene
In the flask of bottom, the lower backflow 12h of nitrogen protection.Reaction is cooled to room temperature after terminating, and concentrates, column chromatography (V Dichloromethane:V Acetone=10:1) divide
From 0.23g target products, yield 60%.1H NMR (400 MHz, DMSO) δ 9.42 (s, 1H), 8.72 (d, J =
8.0 Hz, 1H), 8.53 (s, 1H), 8.44-8.52 (m, 3H), 8.02-8.08 (m, 4H), 7.82-7.93
(m, 4H), 7.49-7.65 (m, 6H), 3.93-3.97 (m, 4H), 1.87-1.93 (m, 4H), 1.53-1.64
(m, 4H), 1.09 (q, J = 8.0 Hz, 6H),. 13C NMR (100 MHz, CDCl3) δ 198.38, 160.17,
150.53, 148.03, 145.97, 145.23, 138.79, 135.58, 135.43, 134.79, 133.27,
131.89, 131.63, 131.44, 128.71, 127.86, 127.30, 127.12, 127.04, 126.69,
126.50, 126.14, 123.21, 120.20, 119.33, 119.26, 115.20, 112.69, 46.82, 30.31,
20.46, 13.93.5, 115.67, 113.89, 40.03, 31.86, 20.16, 13.87. HRMS-ESI (m/z) [M
+H]+Calculated value 386.1327, measured value 386.1312.
Embodiment 2
In cushioning liquid CH3(in 0.02 M, pH=7.4) (7/3, v/v), the concentration of fluorescence probe is 1 μ to CN-HEPES
M, excitation wavelength is 367nm.
In cushioning liquid, excited with 367nm light, fluorescent probe molecule at 400-700nm unstressed configuration emission peak when to
Hg is added dropwise in solution2+(0-13equiv), system generates strong fluorescence emission peak at 400-700nm, and with Hg2+Concentration
Increase, fluorescence intensity is strengthening always, until Hg2+When concentration is the 12equiv of concentration and probe concentration, fluorescence intensity no longer strengthens（Such as
Fig. 6）, it is obvious that such Fluorescence Increasing is due to Hg2+Reacted with the S atom in probe, generate HgS, C=S double bonds of probe
It is changed into C=O double bonds.
Embodiment 3
1 μM of fluorescence probe solution is configured, 10equiv different metal ions Ni is then separately added into solution2+、Ba2 +、Ag+、Cd2+、Mg2+、Cu2+、Mn2+、Fe3+、Zn2+、Co2+、Al3+、Ca2+、Pb2+、K+, determine in the presence of each metal ion, it is glimmering
The fluorescence emission spectrum of light probe molecule；
The fluorescence spectroscopic titration of probe molecule is tested with reference to mercury ion, the present invention is sentenced by competing metal ion experiment
Determine selectivity of the probe to mercury ion, 10equiv different metal ions Ni is separately added into the solution2+、Ba2+、Ag+、Cd2+、
Mg2+、Cu2+、Mn2+、Fe3+、Zn2+、Co2+、Al3+、Ca2+、Pb2+、K+Afterwards, fluorescence spectrum does not have significant change, in similarity condition
Under, add Hg2+（After 10equiv), fluorescent emission intensity is remarkably reinforced, and is shown by the monitoring to fluorescent emission intensity：This hair
It is bright to be very suitable for as mercury ion fluorescence probe（Fig. 7）.
Claims (3)
1. a kind of mercury ion fluorescence probe, it is characterized in that with following chemical molecular structural formula：
。
2. mercury ion fluorescence probe according to claim 1, its preparation method is as follows：
（1）The preparation of benzimidazole and benzo isoquinolines -11- carboxylic acids：1,8- naphthalic anhydrides and 3,4- diaminobenzenes is molten
In acetum, 12h is heated to reflux；After reaction terminates, room temperature is cooled to, suction filtration is simultaneously washed with acetic acid, slightly dry
Product；Crude product is dissolved in 5% sodium hydroxide solution, filters insoluble matter, adjusts pH value between 2~3 using concentrated hydrochloric acid, analysis
Go out greenish yellow solid, suction filtration, boiling water washing, dry product；
（2）The preparation of benzimidazole and benzo isoquinolines -11- acyl chlorides：By benzimidazole and benzo isoquinolines -11- carboxylic acids
It is suspended in dichloromethane, oxalyl chloride is added in system, 5h is stirred at room temperature, a large amount of yellow suspension things is produced, by solid suction filtration, two
Chloromethanes is washed for several times, dry yellow product；
（3）NThe preparation of-butyl-benzene and imidazo benzisoquinoline ketone -11- carboxylic acid amides：By benzimidazole and benzisoquinoline
Ketone -11- acyl chlorides is suspended in dichloromethane, and n-butylamine is sequentially added in system, and acid binding agent triethylamine is stirred overnight at room temperature；Instead
After should terminating, reaction solution 5%NaOH washings, anhydrous Na SO4Dry, absolute ethyl alcohol recrystallizes to obtain yellow product；
（4）The preparation of mercury ion fluorescence probe：WillN- butyl-benzene and imidazo benzisoquinoline ketone -11- carboxylic acid amides and Lawson's examination
Agent is dissolved in toluene solvant, and nitrogen protection 12 h of lower backflow, reaction is cooled to room temperature after terminating, concentrated solvent, column chromatography for separation
Obtain mercury ion fluorescence probe molecule.
3. the application of mercury ion fluorescence probe according to claim 1, it is characterised in that：Mercury ion fluorescence probe is in water ring
The quick detection of mercury ion in the system of border.
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