CN109810103A - A kind of compound and preparation method and application with aggregation-induced emission effect - Google Patents
A kind of compound and preparation method and application with aggregation-induced emission effect Download PDFInfo
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- 238000001514 detection method Methods 0.000 claims abstract description 38
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- 239000007864 aqueous solution Substances 0.000 claims description 12
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
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- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
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Abstract
The invention discloses a kind of compound with aggregation-induced emission effect and preparation method and application, the structural formula of compound isThe compound not only has aggregation-induced emission effect, but also to CN‑Detection has the wider range of linearity, high sensitivity and good selectivity and other effects.
Description
Technical field
The present invention relates to technical field of fluorescence detection, and in particular to a kind of compound with aggregation-induced emission effect and
Preparation method and application.
Background technique
Here statement only provides background information related to the present invention, without necessarily constituting the prior art.
With the reach of science, the safety of living environment and food causes extensive concern.Cyano anion is right because of its
Human body has greatly to endanger to be had been a great concern with toxicity.Cyano anion mainly with the metal in Cytochrome P450 from
Son effect, causes it to transmit the Disability of electronics in respiratory chain, then damages central nervous system, even result in death.
Nonetheless, cyanide is widely used in many modern industries, such as metallurgy, plating, synthetic fibers, herbicide etc., to water
Very big pollution is caused with natural environment, and cyano anion is made to enter human body by water and food chain.However, world health group
The maximum safe concentration that knitting allows in (WHO) regulation drinking water is 1.9 μM.Therefore, developing low-cost, it is easy, it is highly sensitive and
Highly selective is necessary for detecting the colorimetric of cryanide ion and fluorescence chemical sensor in environment.Base has now been developed
In the CN of number of mechanisms-The colorimetric and fluorescence chemical sensor of detection, such as Intramolecular electron transfer (ICT)[26,27], excitation state
Intermolecular proton transfer (ESIPT) and Photo-induced electron transfer (PET) etc..However, most of be used for CN-The sensing of detection
Material is soluble in organic solvent but not soluble in water, and the CN of quantity mostly-It is present in water, such as industrial wastewater, drinking water and reality
Test discharge water etc..Therefore, exploitation detects CN in aqueous solution-Sensor it is most important.
Sensing material with aggregation inducing effect (AIE) can be used as detects CN in aqueous solution-Good selection.AIE
Bioactive molecule does not issue fluorescence in a solvent, and issues strong fluorescence due to forming aggregation in aqueous solution.However, according to
Known to the present inventor, while there is AIE effect and to CN-The sensing material of good sensing capabilities is seldom.Therefore, it is necessary to
There is provided one kind has AIE effect and detects CN-Sensing material.
Summary of the invention
In order to solve the deficiencies in the prior art, the object of the present invention is to provide a kind of changes with aggregation-induced emission effect
Closing object and preparation method and application, the compound not only has aggregation-induced emission effect, but also to CN-Detection has wider
The range of linearity, high sensitivity and good selectivity and other effects.
To achieve the goals above, the technical solution of the present invention is as follows:
In a first aspect, a kind of compound with aggregation-induced emission effect, structural formula are as follows:
Second aspect, a kind of preparation method of above compound comprising it is following anti-to be that starting material passes through with intermediate 1
Route is answered to prepare:
The present invention provides the synthetic method of the compound, and the yield of the compound is higher, up to 90%.
The third aspect, a kind of detection sensor, above compound is as detection sensing material.It is discovered by experiment that this hair
The compound of bright preparation has aggregation inducing effect, and compound prepared by the present invention can be used as detection sensing material.
A kind of application of fourth aspect, above compound or detection sensor in detection cyano anion.By into one
The experiment of step finds that compound prepared by the present invention is as sensing material to detection CN-With highly sensitive and good selection
Property, thus use compound test CN prepared by the present invention-With preferable effect.
5th aspect, a method of sample to be tested is added to containing the molten of above compound detection cyano anion
In liquid, detected using UV-Vis spectra or fluorescence spectrum.
The invention has the benefit that
The present invention provides a kind of compound of structure novel, D- π-A type sensing material of the compound based on ICT,
Middle dibenzothiophenes is as electron donating group, and barbiturates is as electron-withdrawing group.Naked eye colorimetric and fluorescent sensing material DTB exist
It shows in 99%DMSO aqueous solution to CN-The high sensitivity of detection and good selectivity.Sensing material DTB is to CN-It shows
Fast-response, high anti-jamming capacity, the wider range of linearity and lower detection limit (21.6nM).
Detailed description of the invention
The Figure of description for constituting a part of this disclosure is used to provide further understanding of the disclosure, and the disclosure is shown
Meaning property embodiment and its explanation do not constitute the improper restriction to the disclosure for explaining the disclosure.
Fig. 1 is DTB in DMSO/H2With f in O mixed solutionwThe ultraviolet spectrogram of variation；
Fig. 2 is DTB in DMSO/H2With f in O mixed solutionwThe fluorescence spectra of variation；
Fig. 3 is DTB and fwCorresponding wavelength and fluorescence intensity curve, wherein dot is wavelength, and five-pointed star is that fluorescence is strong
Degree；
Fig. 4 is for DTB to the selective ultraviolet spectrogram of various anion (2.0 equivalent) in 99%DMSO aqueous solution；
Fig. 5 is for DTB to the selective fluorescence spectra of various anion (2.0 equivalent) in 99%DMSO aqueous solution；
Fig. 6 is that DTB detects CN-The histogram of interference--free experiments；
Fig. 7 is for DTB with various concentration C N in 99%DMSO aqueous solution-Ultraviolet spectra when (0~2.0 equivalent) titrates
Figure；
Fig. 8 is for DTB to the CN of various concentration in 99%DMSO aqueous solution-The fluorescence spectra of detection, illustration are that DTB exists
Fluorescence intensity at 585nm is with CN-The point diagram of concentration variation；
Fig. 9 is DTB to CN-Detection limit linear graph.
Specific embodiment
It is noted that described further below be all exemplary, it is intended to provide further instruction to the disclosure.Unless another
It indicates, all technical and scientific terms used herein has usual with disclosure person of an ordinary skill in the technical field
The identical meanings of understanding.
It should be noted that term used herein above is merely to describe specific embodiment, and be not intended to restricted root
According to the illustrative embodiments of the disclosure.As used herein, unless the context clearly indicates otherwise, otherwise singular
Also it is intended to include plural form, additionally, it should be understood that, when in the present specification using term "comprising" and/or " packet
Include " when, indicate existing characteristics, step, operation, device, component and/or their combination.
The present disclosure proposes a kind of compound with aggregation-induced emission effect and preparation method and applications.The compound
Not only there is aggregation-induced emission effect, but also to CN-Detection has the wider range of linearity, high sensitivity and good selection
Property and other effects.
A kind of exemplary embodiment of the disclosure provides a kind of compound with aggregation-induced emission effect, structure
Formula is as follows:
The another embodiment of the disclosure provides a kind of preparation method of above compound comprising with intermediate 1
It is prepared for starting material by following reaction route:
The present invention provides the synthetic method of the compound, and the yield of the compound is higher, up to 90%.
For barbiturates.
In one or more embodiments of the embodiment, process are as follows: aldol is carried out using intermediate 1 and barbiturates
It can be obtained after condensation reaction.
In the series embodiment, the condition of aldol reaction are as follows: heating reflux reaction in a solvent.Due to barbiturates
Itself has acidity, thus may not need addition acidic catalyst.
In the series embodiment, the molar ratio of intermediate 1 and barbiturates is 1:0.9~1.1.
Since there is no industrialization for intermediate 1, thus present disclose provides a kind of compound conducts by industrialization
Prepared by raw material, synthetic route is as follows:
Wherein, the synthesis process of intermediate 1 can refer to: Wei Xuejian, Zhang Xian, Yao Jinshui " novel two-photon compound 3-
The synthesis and its optical property of (1- vinyl furan) dibenzothiophenes " " synthesis chemistry " the 3rd phase 348- of volume 18 in 2010
Page 351.
For the third of the disclosure embodiment there is provided a kind of detection sensor, above compound senses material as detection
Material.It is discovered by experiment that the compound of disclosure preparation has aggregation-induced emission effect, the compound of disclosure preparation can be with
As detection sensing material.
In one or more embodiments of the embodiment, including dimethyl sulfoxide (DMSO) aqueous solution, compound dissolution
In dimethyl sulfoxide (DMSO) aqueous solution.By experiment aggregation inducing effect of the discovery compound in DMSO aqueous solution compared with
It is good.Wherein, when the percentage of water in DMSO aqueous solution is 99%, the aggregation inducing effect of compound in the solution is best, glimmering
Luminous intensity increases 12.9 times compared in pure DMSO solvent.
The 4th kind of the disclosure embodiment there is provided a kind of above compound or detection sensor detection cyano yin from
Application in son.By further testing discovery, the compound of disclosure preparation is as sensing material to detection CN-With height
Sensitivity and good selectivity, thus using the compound test CN of disclosure preparation-With preferable effect.
Sample to be tested is added embodiment there is provided a kind of method for detecting cyano anion for the 5th kind of the disclosure
To in the solution containing above compound, detected using UV-Vis spectra or fluorescence spectrum.
In one or more embodiments of the embodiment, when being detected using fluorescence spectrum, Detection wavelength be 580~
590nm.When Detection wavelength is under the range, CCN -When increasing to 30 μM from 0, fluorescence (FL) intensity is significantly reduced.And detection limit
For 21.6nM, linear concentration range is 0~30 μM.
In order to enable those skilled in the art can clearly understand the technical solution of the disclosure, below with reference to tool
The technical solution of the disclosure is described in detail in the embodiment of body.
Embodiment
The preparation of compound
The preparation route of compound is as follows:
Wherein, the synthesis process of intermediate 1 refers to Wei Xuejian, Zhang Xian, Yao Jinshui " novel two-photon compound 3- (1- second
Alkenyl furans) dibenzothiophenes synthesis and its optical property " the 348-351 pages of the phase of " synthesis chemistry " 2010 volume 18 the 3rd.
Using dibenzothiophenes as raw material, using TiCl4The Friedel-Crafts reaction of promotion obtains 3- formoxyl dibenzothiophenes (1)；It will
The mixing in the dehydrated alcohol (10mL) steamed again of intermediate 1 (0.3g, 1.42mmol) and barbiturates (0.18g, 1.42mmol)
And return stirring 5 hours, it is then that mixture is cooling and filter, it obtains final compound (hereinafter referred to as DTB), is washed with ethyl alcohol
It washs, is dried in vacuo, obtains faint yellow solid (0.41g, yield 90%).1H NMR:(400MHz,DMSO–d6) δ=11.44 (s,
1H), 11.31 (s, 1H), 9.18 (s, 1H), 8.51 (s, 1H), 8.37-8.42 (m, 2H), 8.16 (d, J=8.0Hz, 1H),
8.09-8.12(m,1H),7.57-7.59(m,2H)；FT–IR:(KBr,cm–1) ν=3252 (N-H), 3014 (C-H), 1722 (C
=O), 1663 (C=C)；HRMS(ESI):m/z[M+H]+Calculated value: C17H11N2O3S:323.0490, measured value: 323.0484.
Aggregation inducing effect (AIE) performance study, cyanogen root anion (CN are carried out respectively to the DTB of preparation-) detection, knot
Fruit difference is as follows:
The AIE effect of DTB
The AIE effect of DTB is studied by ultraviolet spectra and fluorescence spectrum.As shown in Figure 1, between 290nm and 330nm
Absorption peak is classified as the π-π of barbiturates and dibenzothiophenes*Electron transition.In addition, DTB molecule shown at 395nm it is bright
Aobvious absorption peak, this is attributable to the Intramolecular electron transfer (ICT) from dibenzothiophenes to barbiturates.
Compound DTB is in pure DMSO solvent and in DMSO/H2Fluorescence spectrum in O mixture is as shown in Fig. 2, due to water
It is poor solvent, therefore the content of increase water can promote the aggregation of DTB in DMSO solvent, to enhance fluorescence intensity.Cause
This, by increasing percentage of the water in the mixed solution of DMSO and water, (volume ratio of water and DMSO, is denoted as fw) prepare DTB
Micelle-like Nano-structure of Two.Fig. 3 is depicted in different fwThe fluorescence intensity of lower DTB and the variation tendency of wavelength.
As shown in Fig. 2, DTB is in pure DMSO solvent (CDTB=30 μM) in fluorescence intensity it is very weak, and DTB powder issue it is strong glimmering
Light, these are the result shows that DTB has strong AIE effect.In addition, fluorescence intensity (f of the DTB in pure DMSO solventw=0%)
It is very weak.Work as fwWhen less than 80%, the fluorescence intensity of DTB is reduced with the increase of water content.However, working as fwIncrease to 90%
When fluorescence intensity start to increase.In addition, fluorescence intensity is in fwReach maximum value when=99%, with the fluorescence in pure DMSO solvent
Intensity (fw=0%) it compares and increases 12.9 times.These data prove that compound DTB has AIE effect.
From figure 3, it can be seen that working as fwWhen increasing to 99% from 0%, the emission peak of DTB from 501.4nm red shift to
581.8nm.When DTB molecule is assembled under high-moisture, emission peak red shift is attributable to the formation of pi-pi bond.Work as fwIt is no more than
When 80%, water content increase causes the polarity of mixed solvent to increase, Intramolecular electron transfer enhancing, thus with fwIncrease it is glimmering
Light dies down.Work as fwReach 90%, DTB molecule to start to assemble, generates nano particle.Due to the aggregation inducing effect of DTB, keep its glimmering
Light significantly increases.
Selectivity and anti-interference of the DTB to anion
By a series of anion (F-, Cl-, Br-, I-, NO3 -, AcO-, HCO3 -, CO3 2-, SO4 2-, HSO4 -And CN-Deng) respectively
It is added in the solution containing DTB (1mM), and tests its ultraviolet spectra and fluorescence spectrum.Even if Fig. 4,5 display 10 equivalents of addition
Other Common Anions (remove CN-Outside), the ultraviolet spectra of DTB and fluorescence spectrum (λex=400nm, λem=582nm) it is also not bright
Aobvious variation.There are CN-In the case where, maximum absorption band of the DTB at 395nm reduces, and occurs new suction at 285nm
Peak is received, and the intensity of fluorescence emission peak of the DTB at 582nm significantly reduces.This spectrum change shows the chemical structure of DTB
Changed, because of CN-Intramolecular electron transfer is blocked with the nucleophilic addition of DTB, to affect its light
Spectral property.
In order to further illustrate DTB as detection CN-Highly selective fluorescent optical sensor feasibility.As shown in fig. 6,
The various anion that 2.0 equivalents are added in 99%DMSO aqueous solution carry out interference--free experiments to sensor DTB.The result shows that often
The anion seen detects CN to DTB-It has little effect, DTB can be used as CN-The fluorescent optical sensor of detection, and have excellent
Selective and good anti-interference.
DTB is to CN-The research of detection
Various concentration CN is added in DTB in 99%DMSO aqueous solution-Ultraviolet spectra change as shown in fig. 7, with CN-'s
Concentration increases to 2.0 equivalents from 0, and absorption peak of the DTB at 280nm, 315nm, 395nm is gradually reduced.This change procedure table
Bright DTB and CN-Between nucleophilic addition occurs, the conjugated system of DTB is by CN-It destroys, and shows DTB and CN-Between reaction
Produce new compound.
CN of the DTB in 99%DMSO aqueous solution to various concentration is further studied by fluorescent spectrometry-Detection
Energy.As shown in figure 8, with CN-Concentration (0~2.0 equivalent) increases, since the Intramolecular electron transfer (ICT) of DTB is blocked,
Fluorescence emission peak at 582nm gradually decreases.Illustration in Fig. 8 is fluorescence intensity of the DTB at 582nm as CN-(0~
2.0 equivalents) concentration functional arrangement.As can be seen that working as CCN -When increasing to 30 μM from 0, fluorescence intensity is significantly reduced.Work as CCN -It is greater than
At 30 μM, fluorescence intensity is kept approximately constant, and shows CN-It is saturated in the solution, the stoichiometric number that addition reaction occurs with DTB is 1:
1.As shown in figure 9, sensor DTB is to CN-Detection limit (DL) be 21.6nM, linear concentration range be 0~30 μM, far below drink
With CN in water-Permission content.
The foregoing is merely preferred embodiment of the present disclosure, are not limited to the disclosure, for the skill of this field
For art personnel, the disclosure can have various modifications and variations.It is all within the spirit and principle of the disclosure, it is made any to repair
Change, equivalent replacement, improvement etc., should be included within the protection scope of the disclosure.
Claims (10)
1. a kind of compound with aggregation-induced emission effect, characterized in that structural formula is as follows:
2. a kind of preparation method of compound described in claim 1, characterized in that including logical for starting material with intermediate 1
Cross following reaction route preparation:
3. preparation method as claimed in claim 2, characterized in that its process are as follows: carry out hydroxyl using intermediate 1 and barbiturates
It can be obtained after aldehyde condensation reaction.
4. preparation method as claimed in claim 3, characterized in that the condition of aldol reaction are as follows: heat back in a solvent
Stream reaction.
5. the molar ratio of preparation method as claimed in claim 3, intermediate 1 and barbiturates is 1:0.9~1.1.
6. a kind of detection sensor, characterized in that compound described in claim 1 is as detection sensing material.
7. detection sensor as claimed in claim 6, it is characterized in that including dimethyl sulphoxide aqueous solution, compound is dissolved in two
In methyl sulfoxide aqueous solution.
8. detection sensor described in a kind of compound described in claim 1 or claim 6 or 7 is in detection cyano anion
In application.
9. a kind of method for detecting cyano anion, characterized in that being added sample to be tested to containing described in claim 1ization
In the solution for closing object, detected using UV-Vis spectra or fluorescence spectrum.
10. method as claimed in claim 9, characterized in that using fluorescence spectrum detection when, Detection wavelength be 580~
590nm。
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110746404A (en) * | 2019-10-28 | 2020-02-04 | 齐鲁工业大学 | 9-alkylated carbazole compound and preparation method and application thereof |
| CN110818646A (en) * | 2019-11-18 | 2020-02-21 | 温州医科大学 | Aggregation-induced emission-based small-molecule fluorescent probe and preparation method and application thereof |
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