CN104961647A - Fluorescent recognition cupper ion (CU2+) sensor molecules and composition and application thereof - Google Patents
Fluorescent recognition cupper ion (CU2+) sensor molecules and composition and application thereof Download PDFInfo
- Publication number
- CN104961647A CN104961647A CN201510362068.9A CN201510362068A CN104961647A CN 104961647 A CN104961647 A CN 104961647A CN 201510362068 A CN201510362068 A CN 201510362068A CN 104961647 A CN104961647 A CN 104961647A
- Authority
- CN
- China
- Prior art keywords
- fluorescence
- sensor molecule
- dmso
- copper ion
- buffer system
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Landscapes
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
The invention discloses fluorescent recognition copper ion (CU2+) sensor molecules and belongs to the field of chemical synthesis and cation detection. DMF as solvent, glacial acetic acid as a catalyst and N,N-diethyl salicylic aldehyde and naphthalene diamine as a substrate are subjected to a reflux reaction and then are subjected to cooling, suction filtration, washing and recrystallization, and then brown yellow crystals are obtained. Experiments show that in a DMSO/H2O HEPES buffer system for the sensor molecules, only CU2+ can be added to quench green fluorescence of the system under an ultraviolet lamp, but other cations cannot quench fluorescence of the system when added; only CU2+ can enable the color of the system to change from yellow to colorless, but other cations cannot enable the color of the system to change when added. Thus, the sensor can be used for quick naked-eye detection of CU2+, the lowest fluorescence detection limit of the sensor can reach 3.37*10-8M, and the other cations have no obvious interference on recognition of CU2+.
Description
Technical field
The present invention relates to a kind of copper ion sensor molecule and synthetic method thereof, particularly relate to a kind of sensor molecule of fluorescence identifying cupric ion; The present invention also relates to the application of this sensor molecule highly selective fluorescence identifying cupric ion simultaneously, belongs to the field of chemical synthesis and cation detection field.
Background technology
In the middle of the indispensable trace element of human body, the 3rd is occupy after the content of copper is positioned at iron and zinc, copper plays vital effect in human body, as the important component that it is blood, liver and brain albumen, be the activeconstituents of important enzyme in human body, it also has important impact to the hemopoietic function of the metabolism of iron and human body.But the content of copper also has strict standard in human body, too much very fewly all to work the mischief to every function of human body.If content is below the normal, can impact the growth of the color of hair, bone and brain, also can affect human central nervous and immunity system simultaneously.Seriously may cause the disease such as cancer of the stomach and esophagus cancer.If but the copper that in human body, enrichment is excessive also can be detrimental to health.As cardiovascular and cerebrovascular diseases, hepatitis, kidney disease, and the nervous system disease that cerebellum motor disorder causes is as graceful gram of syndromes, Wilson's disease etc.Therefore, people pay close attention to more and more and are devoted to that development research is efficient, highly selective detects Cu
2+method, as inductively coupled plasma atomic emission spectrometry, atomic absorption spectrum, electrochemical method etc.But these methods need complicated electrical instrumentation mostly, loaded down with trivial details Sample Preparation Procedure.By contrast, fluorescence technique provides a detection mode easily and efficiently.
The R and D of chemical sensor probe, have received in the application in the fields such as chemical industry, environment, biology and have paid close attention to widely.At present, single chemical sensor has become very welcome detection analysis means due to the advantage of its rapid detection time and low cost.But the report at present about the chemical sensor of cupric ion detection is less.
Summary of the invention
The object of this invention is to provide a kind of fluorescence identifying copper ion sensor molecule;
Another object of the present invention is to provide a kind of synthetic method of this fluorescence identifying copper ion sensor molecule;
The prior object of the present invention is to provide the method for this fluorescence identifying copper ion sensor Molecular Detection cupric ion.
One, fluorescence identifying copper ion sensor molecule
Fluorescence identifying copper ion sensor molecule of the present invention (is labeled as
t), its chemical name is 4-(diethylin) salicylic aldehyde 1,5-diaminonaphthalene bis-Schiff base, and its structural formula is as follows:
。
Two, the synthesis of fluorescence identifying copper ion sensor molecule
Make solvent with DMF, catalyzer made by Glacial acetic acid, and N, N-diethyl salicylic aldehyde and naphthylene diamine are that reaction substrate carries out back flow reaction, and yellow mercury oxide is separated out in cooling, filters, and washing, recrystallization, obtains tan crystals and be sensor molecule
t.Reaction formula is as follows:
The mol ratio of substrate N, N-diethyl salicylic aldehyde and naphthylene diamine is 2:1 ~ 2.5:1, and the consumption of catalyzer Glacial acetic acid is 1.5 ~ 5.0% of hydroxyl m-terephthal aldehyde molar weight; The temperature of back flow reaction is 80 ~ 85 DEG C, and the reaction times is 6 ~ 8h.
Three, sensor molecule
trecognition performance
1, sensor molecule
tto Cu
2+ultraviolet identification
Pipette sensor molecule T(c=2.0 × 10 of 0.5mL respectively
-5mol/L) in a series of 10 mL colorimetric cylinders, 0.5ml is added respectively, the Hg of 20 times of equivalents
2+, Ag
+, Ca
2+, Cu
2+, Co
2+, Ni
2+, Cd
2+, Pb
2+, Zn
2+, Cr
3+and Mg
2+etc. cationic solution, use DMSO/H
2o is diluted to 5mL, forms the DMSO/H of sensor molecule
2the HEPES buffer system of O (v/v=9:1).Observe sensor molecule T to various cationic response.Found that to only have Cu
2+add the color from yellow of buffer system become colorless; In corresponding UV spectrum, only has Cu
2+add make the buffer system of sensor molecule in UV spectrum main body maximum go out peak position see Fig. 1 by 418nm violet shift to 386nm(), and all the other cationicly add the DMSO/H that can not make sensor molecule
2there is obvious colour-change in O buffer solution system, sensor molecule can not be made at DMSO/H
2the UV spectrum generation noticeable change of O buffer system.Therefore, sensor molecule can be used as Cu
2+sensor molecule be used for Cu
2+bore hole rapid detection.
2, sensor molecule
tto Cu
2+fluorescence identifying
Pipette sensor molecule T(c=2.0 × 10 of 0.5mL respectively
-5mol/L) in a series of 10 mL colorimetric cylinders, 0.5ml is added respectively, the Fe of 20 times of equivalents
3+, Hg
2+, Ag
+, Ca
2+, Cu
2+, Co
2+, Ni
2+, Cd
2+, Pb
2+, Cu
2+, Cr
3+and Mg
2+etc. cationic solution, use DMSO/H
2o(H
2o is the buffered soln of HEPES) be diluted to 5mL, form the DMSO/H of sensor molecule
2the HEPES buffer system of O (v/v=9:1).Observe sensor molecule T to various cationic response.Found that to only have Cu
2+add and make buffer system green fluorescence quencher under ultraviolet lamp, in corresponding fluorescence spectrum, only have Cu
2+add make the buffer system of sensor molecule 498nm place fluorescence emission peak reduce (λ ex=418nm) (see figure 2).And all the other cationicly add the DMSO/H that can not make sensor molecule
2the quenching of fluorescence of O buffer solution system under ultraviolet lamp, can not make sensor molecule at DMSO/H
2the fluorescence spectrum generation noticeable change of O buffer system.Therefore, sensor molecule can be used as Cu
2+sensor molecule be used for Cu
2+fluorescence rapid detection.
3, sensor molecule T is to Cu
2+the interference--free experiments identified
To the acceptor of ion identification, interference free performance is a very important index.In order to study sensor molecule to Cu
2+the interference free performance identified, we have done following anti-interference test: by the Cu of 20 times of equivalents
2+0.5mL joins sensor molecule (c=2.0 × 10
-5mol/L) DMSO/H
2in the HEPES buffer system of O (v/v=9:1), then by the Hg of equivalent
2+, Ag
+, Ca
2+, Co
2+, Ni
2+, Cd
2+, Pb
2+, Zn
2+, Cr
3+and Mg
2+solution 0.5ml joins in above-mentioned system respectively, find, in the short period of time, solution fluorescence color no longer changes, this with only add Cu
2+time phenomenon identical.Choose 498nm place fluorescence intensity data in fluorescence spectrum and do histogram (see figure 3), can see clearly from Fig. 3, other positively charged ion is to Cu
2+the short period of time that is identified in do not disturb.Therefore, sensor molecule can single selective identification Cu
2+.
4, sensor molecule is to Cu
2+fluorometric titration
For probing into sensor molecule further to Cu
2+recognition mechanism, We conducted fluorescence emission spectrum titration experiments (see Fig. 4,5).Pipette 2.5mL sensor molecule (c=2.0 × 10
5mol/L) DMSO/H
2the HEPES buffer system of O (v/v=9:1), in quartz cell, adds Cu gradually by accumulation application of sample method
2+.Find, along with Cu
2+add, the quencher gradually of the fluorescence emission peak at 498nm place.
5, sensor molecule
tto Cu
2+the mensuration of fluorescence lowest detectable limit
According to 3s
b/ S method calculates
tto Cu
2+the minimum detectability of fluorescence spectrum can reach 3.37 × 10
-8m.(see figure 6).Therefore this sensor molecule Cu
2+detection there is higher sensitivity.
Great many of experiments shows, in sensor molecule
t'sdMSO/H
2in O buffer system, H
2the percent by volume of O is 5 ~ 15% time, and sensor molecule is at DMSO/H
2the fluorescence identifying performance to cupric ion can be realized in O buffer system.
6, sensor molecule
trecognition mechanism probe into
From the working curve of Fig. 5, sensor molecule main body
twith Cu
2+coordination ratio be 1:2, according to pertinent literature, we infer may be Cu
2+with acceptor
tupper-OH ,-CH=N-, and the H in solution
2o molecule defines coordinate bond all with it, causes acceptor
tmolecule in original conjugated system be destroyed.Infrared spectrum also proves its Cu very well
2+with the coordination prototropy effect of acceptor T.Therefore, we are to sensor molecule
tto Cu
2+recognition mechanism inquire into as follows: Cu
2+with sensor molecule
ton O, N impurity there is coordination, then there is ICT process, its conjugated system changed, causes host fluorescence quencher.Sensor molecule
tto Cu
2+the following reaction formula of recognition mechanism:
。
Accompanying drawing explanation
Fig. 1 is in main body T (c=2.0 × 10
5mol/L) DMSO/H
2in the HEPES buffer system of O (v/v=9:1), add different positively charged ion Hg
2+, Ag
+ca
2+, Cu
2+, Co
2+, Ni
2+, Cd
2+, Pb
2+, Zn
2+, Cr
3+and Mg
2+(c=4.0 × 10
3mol/L) ultraviolet spectrogram;
Fig. 2 is in main body T (c=2.0 × 10
5mol/L) DMSO/H
2in the HEPES buffer system of O (v/v=9:1), add different positively charged ion Hg
2+, Ag
+ca
2+, Cu
2+, Co
2+, Ni
2+, Cd
2+, Pb
2+, Zn
2+, Cr
3+and Mg
2+(c=4.0 × 10
3mol/L) fluorescence spectrum figure;
Fig. 3 is main body
t(c=2.0 × 10
5mol/L) to Cu
2+(c=4.0 × 10
3mol/L) the anti-interference figure identified is (black: T adds other each cationic fluorescence intensity, grey: to add Cu
2+after add each cationic fluorescence intensity again).
Fig. 4 is in main body
t(c=2.0 × 10
5mol/L) DMSO/H
2in the HEPES buffer system of O (v/v=9:1), accumulation adds Cu
2+fluorometric titration figure;
Fig. 5 is in main body
t(c=2.0 × 10
5mol/L) DMSO/H
2in the HEPES buffer system of O (v/v=9:1), accumulation adds Cu
2+time fluorescence emission spectrogram at 498 nm places.
Fig. 6 is for being 418nm, DMSO/H in excitation wavelength
2in the HEPES buffer system of O (v/v=9:1), Cu
2+between add-on 0 ~ 4.0 times of equivalent, at 498nm place solution fluorescence intensity linear fit spectrogram.
Embodiment
Below by specific embodiment to structure, the synthesis of sensor molecule of the present invention and be described in detail the fluorescence identifying method of cupric ion, the Synthesis and applications of Test paper.
1, the synthesis and characterization of sensor molecule
In the round-bottomed flask of 250mL, add naphthylene diamine 0.237g(1.5mmol), N, N-diethyl salicylic aldehyde 0.770g(4.0 mmol), the catalysis of 1mL (0.017mmol) Glacial acetic acid, 30mL N, N-dimethyl imide (DMF) makees solvent, return stirring 8h at 85 DEG C, there is yellow mercury oxide to separate out, by thick product DMF recrystallization, obtain tan crystals, be sensor molecule T, productive rate: 83% (m.p. > 300 DEG C).Its structural characterization is as follows:
1H NMR (DMSO–
d 6, 400 MHz) ?/ppm1.16 (t 12H,-CH
3), 3.41 (m 8H,-CH
2-), 8.78 (s 1H, N CH),6.38-8.05 (m 12H, ArH),. IR (KBr) ν: 1624 cm
-1(-HC=N-), 3448 cm
-1(N-H). ESI-MS calcd for [C
18H
16N
6O+H
+]
+509.654. Found 509.26。
2, the preparation of Test paper
Filter paper is cut into the square of 8 cm × 8 cm, uses 0.5 molL
-1dilute hydrochloric acid soak 1 hour.With distilled water wash repeatedly after, limit suction strainer limit distilled water wash on a buchner funnel, till filtrate is neutrality.Washed filter paper, except anhydrating, is placed in vacuum drying oven dry by suction strainer.Sensor molecule is mixed with 0.002 molL
-1dMSO/H
2o (v:v=9:1), the buffered soln of pH=7.2, then the filter paper buffered soln of process is fully infiltrated, taking-up is dried.Be cut into the test strip of 0.5 cm × 4 cm, for subsequent use.This test strip is irradiated under ultraviolet lamp, finds in green fluorescence.
3, the detection of cupric ion
By Hg
2+, Ag
+, Ca
2+, Cu
2+, Co
2+, Ni
2+, Cd
2+, Pb
2+, Zn
2+, Cr
3+and Mg
2+be added drop-wise to respectively on Test paper etc. cationic DMSO solution, if test paper does not have fluorescence under ultra violet lamp, that dropping is described is Cu
2+; If test paper green fluorescence considerable change does not occur, then what dropping was described is other positively charged ion.
Claims (10)
1. a fluorescence identifying copper ion sensor molecule, its structural formula is as follows:
。
2. the synthetic method of fluorescence identifying copper ion sensor molecule as claimed in claim 1, be solvent with DMF, catalyzer made by Glacial acetic acid, and N, N-diethyl salicylic aldehyde and naphthylene diamine are that substrate carries out back flow reaction; Yellow mercury oxide is separated out in cooling, suction filtration, and washing, recrystallization, obtains tan crystals.
3. the synthetic method of fluorescence identifying copper ion sensor molecule as claimed in claim 2, is characterized in that: the mol ratio of N, N-diethyl salicylic aldehyde and naphthylene diamine is 2:1 ~ 2.5:1; The consumption of catalyzer Glacial acetic acid is 1.5 ~ 5.0% of N, N-diethyl salicylic aldehyde molar weight.
4. the synthetic method of fluorescence identifying copper ion sensor molecule as claimed in claim 2, is characterized in that: the temperature of back flow reaction is 80 ~ 85 DEG C, and the reaction times is 6 ~ 8h.
5. as claimed in claim 1 fluorescence identifying copper ion sensor molecule at DMSO/H
2the application of cupric ion is identified in the HEPES buffer system of O.
6. as claimed in claim 5 fluorescence identifying copper ion sensor molecule at DMSO/H
2identify the application of cupric ion in the HEPES buffer system of O, it is characterized in that: at DMSO/H
2in the HEPES buffer system of O, add Hg respectively
2+, Ag
+, Ca
2+, Cu
2+, Co
2+, Ni
2+, Cd
2+, Pb
2+, Zn
2+, Cr
3+and Mg
2+dMSO solution time, only have Cu
2+add system color from yellow can be made to become colorless, and add remaining cationic system color and do not change.
7. as claimed in claim 5 fluorescence identifying copper ion sensor molecule at DMSO/H
2identify the application of cupric ion in the HEPES buffer system of O, it is characterized in that: at DMSO/H
2in the HEPES buffer system of O, add Hg respectively
2+, Ag
+, Ca
2+, Cu
2+, Co
2+, Ni
2+, Cd
2+, Pb
2+, Zn
2+, Cr
3+and Mg
2+dMSO solution time, only have Cu
2+add and can make body
Tie up to the green fluorescence quencher under ultraviolet lamp, and all the other cationic adding can not make its quenching of fluorescence.
8. as described in claim 5 ~ 7 fluorescence identifying copper ion sensor molecule at DMSO/H
2identify the application of cupric ion in the HEPES buffer system of O, it is characterized in that: DMSO/H
2in the HEPES buffer system of O, H
2the percent by volume of O is 10 ~ 15%.
9. a load has the Test paper of fluorescence identifying copper ion sensor molecule as claimed in claim 1.
10. load has the application of the Test paper of fluorescence identifying copper ion sensor molecule as claimed in claim 9, it is characterized in that: by Hg
2+, Ag
+, Ca
2+, Cu
2+, Co
2+, Ni
2+, Cd
2+, Pb
2+, Zn
2+, Cr
3+and Mg
2+dMSO solution be added drop-wise on Test paper respectively, if test paper does not produce fluorescence, then illustrate drip be Cu
2+solution; If test paper is still in green fluorescence under ultraviolet lamp, then what dropping was described is other positively charged ion.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510362068.9A CN104961647A (en) | 2015-06-26 | 2015-06-26 | Fluorescent recognition cupper ion (CU2+) sensor molecules and composition and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510362068.9A CN104961647A (en) | 2015-06-26 | 2015-06-26 | Fluorescent recognition cupper ion (CU2+) sensor molecules and composition and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN104961647A true CN104961647A (en) | 2015-10-07 |
Family
ID=54215774
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510362068.9A Pending CN104961647A (en) | 2015-06-26 | 2015-06-26 | Fluorescent recognition cupper ion (CU2+) sensor molecules and composition and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104961647A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105669708A (en) * | 2016-01-18 | 2016-06-15 | 新乡医学院 | Coumarin schiff-base copper ion complex-based fluorescent probe for thiol as well as preparation method and application thereof |
| CN108299288A (en) * | 2018-01-30 | 2018-07-20 | 阜阳师范学院 | A kind of copper ion fluorescent optical sensor molecule and preparation method and the application in detecting copper ion |
| CN108586382A (en) * | 2018-04-08 | 2018-09-28 | 山西大学 | A kind of schiff base compound and its preparation and the application in copper ion detection |
| CN110565440A (en) * | 2019-09-06 | 2019-12-13 | 陕西科技大学 | salicylaldehyde Schiff base/graphene oxide modified paper-based material and preparation method and application thereof |
| CN111812069A (en) * | 2020-06-30 | 2020-10-23 | 上海应用技术大学 | Method for rapidly detecting zinc ions in traditional Chinese medicine on site |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101532982A (en) * | 2009-04-11 | 2009-09-16 | 桂林工学院 | Preparation method of an ion selective electrode capable of measuring copper (II) in waste water |
| JP2013053012A (en) * | 2011-08-31 | 2013-03-21 | National Institute Of Advanced Industrial Science & Technology | Organic molecule (schiff base molecule)-including fibrous alumina self-supporting membrane and method of manufacturing the same, and detection method/recovery method for transition metal ion in water with this composite membrane |
| CN103320118A (en) * | 2013-05-08 | 2013-09-25 | 济南大学 | Schiff base cooper ion fluorescence probe and preparation method thereof |
| CN104311450A (en) * | 2014-09-23 | 2015-01-28 | 西北师范大学 | Bis-schiff base sensor capable of circulation monitoring of copper ions, synthesis and applications thereof |
-
2015
- 2015-06-26 CN CN201510362068.9A patent/CN104961647A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101532982A (en) * | 2009-04-11 | 2009-09-16 | 桂林工学院 | Preparation method of an ion selective electrode capable of measuring copper (II) in waste water |
| JP2013053012A (en) * | 2011-08-31 | 2013-03-21 | National Institute Of Advanced Industrial Science & Technology | Organic molecule (schiff base molecule)-including fibrous alumina self-supporting membrane and method of manufacturing the same, and detection method/recovery method for transition metal ion in water with this composite membrane |
| CN103320118A (en) * | 2013-05-08 | 2013-09-25 | 济南大学 | Schiff base cooper ion fluorescence probe and preparation method thereof |
| CN104311450A (en) * | 2014-09-23 | 2015-01-28 | 西北师范大学 | Bis-schiff base sensor capable of circulation monitoring of copper ions, synthesis and applications thereof |
Non-Patent Citations (3)
| Title |
|---|
| CHEMICAL ABSTRACT SERVICE: "RN: 904279-77-2", 《CA网络版STN REGISTRY数据库》 * |
| MALUTAN TH.等: "A Fluorescence Emission, FT-IR and UV-VIS Absorption Study of the Some Uranium (VI) Schiff Bases Complexes", 《JOURNAL OF FLUORESCENCE》 * |
| 王晓婷等: "以N,N-二乙基水杨醛希夫碱为底物的连续识别传感器", 《全国第十七届大环化学暨第九届超分子化学学术研讨会论文摘要集》 * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105669708A (en) * | 2016-01-18 | 2016-06-15 | 新乡医学院 | Coumarin schiff-base copper ion complex-based fluorescent probe for thiol as well as preparation method and application thereof |
| CN105669708B (en) * | 2016-01-18 | 2019-06-21 | 新乡医学院 | One kind is based on cumarin schiff bases copper ion complex mercaptan fluorescence probe and its preparation method and application |
| CN108299288A (en) * | 2018-01-30 | 2018-07-20 | 阜阳师范学院 | A kind of copper ion fluorescent optical sensor molecule and preparation method and the application in detecting copper ion |
| CN108586382A (en) * | 2018-04-08 | 2018-09-28 | 山西大学 | A kind of schiff base compound and its preparation and the application in copper ion detection |
| CN108586382B (en) * | 2018-04-08 | 2021-09-28 | 山西大学 | Schiff base compound, preparation thereof and application thereof in copper ion detection |
| CN110565440A (en) * | 2019-09-06 | 2019-12-13 | 陕西科技大学 | salicylaldehyde Schiff base/graphene oxide modified paper-based material and preparation method and application thereof |
| CN111812069A (en) * | 2020-06-30 | 2020-10-23 | 上海应用技术大学 | Method for rapidly detecting zinc ions in traditional Chinese medicine on site |
| CN111812069B (en) * | 2020-06-30 | 2023-04-28 | 上海应用技术大学 | Method for rapidly detecting zinc ions in traditional Chinese medicine on site |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104961647A (en) | Fluorescent recognition cupper ion (CU2+) sensor molecules and composition and application thereof | |
| Hu et al. | Fe3+-selective fluorescent probe based on rhodamine B and its application in bioimaging | |
| Kumar et al. | A coumarin–chalcone hybrid used as a selective and sensitive colorimetric and turn-on fluorometric sensor for Cd 2+ detection | |
| Alamry et al. | A highly selective ratiometric fluorescent pH probe based on a PAMAM wavelength-shifting bichromophoric system | |
| Bhatti et al. | New water soluble p-sulphonatocalix [4] arene chemosensor appended with rhodamine for selective detection of Hg2+ ion | |
| Liu et al. | A novel pyrene-based fluorescent probe for Al3+ detection | |
| Dong et al. | A new naphthopyran-based chemodosimeter with aggregation-induced emission: Selective dual-channel detection of cyanide ion in aqueous medium and test strips | |
| Yuan et al. | New switch on fluorescent probe with AIE characteristics for selective and reversible detection of mercury ion in aqueous solution | |
| Qin et al. | β-Hydroxy-α-naphthaldehyde [2-(quinolin-8′-yloxy) acetyl] hydrazone as an efficient fluorescent chemosensor for Mg2+ | |
| Fang et al. | A highly sensitive fluorescent probe with different responses to Cu2+ and Zn2+ | |
| Kaur et al. | Dansyl-anthracene dyads for ratiometric fluorescence recognition of Cu 2+ | |
| CN103992292A (en) | Schiff base sensor molecule, its synthesis, and its application in fluorescent colorimetric detection of CN<-> in water | |
| CN104311450A (en) | Bis-schiff base sensor capable of circulation monitoring of copper ions, synthesis and applications thereof | |
| CN102879369B (en) | Application of 2,2'-biphenyl imidazole serving as acceptor molecule in CN- detection and recognition | |
| CN102816086A (en) | Salicylidenehydrazine receptor compound, preparation method and application thereof | |
| CN104910043B (en) | Fluorescence colorimetric detection CN‑Sensor molecule and its synthesis and application | |
| Li et al. | A terpyridyl-rhodamine hybrid fluorescent probe for discriminative sensing of Hg (II) and Cu (II) in water and applications for molecular logic gate and cell imaging | |
| CN105968098B (en) | A kind of quinoline substituted containing carbazole, benzimidazole and its preparation method and application | |
| CN105693552B (en) | A kind of cyanide ion sensor molecule and its preparation and the application in detection cyanide ion | |
| Chen et al. | α-Cyanostilbene-based sensor with “AIE and ESIPT” features emitting long-wavelength intense red-fluorescence for highly selective and sensitive detection of Cu2+ | |
| CN113861067B (en) | But dynamic detection aquatic Fe 3+ Al and Al 3+ Molecular probe and application thereof | |
| KR101041040B1 (en) | Pyrene derivatives having CuII ion selectivity, method for preparing therefor, detecting method using the same | |
| Zhao et al. | Deprotonation and chelation synergically triggered near infrared fluorescence for selective detection of Hg (II) | |
| CN108558859A (en) | A kind of preparation and application of the long wave mode Hg2+ fluorescence probes of visualization based on chromene | |
| CN113214108B (en) | Fluorescent probe for detecting cyanide ions and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20151007 |