CN104193706B - A kind of based on not alkali and the preparation and detecting the application in mercury ion as acceptor molecule of the bilateral west of 1,5-diaminonaphthalene - Google Patents
A kind of based on not alkali and the preparation and detecting the application in mercury ion as acceptor molecule of the bilateral west of 1,5-diaminonaphthalene Download PDFInfo
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- CN104193706B CN104193706B CN201410181866.7A CN201410181866A CN104193706B CN 104193706 B CN104193706 B CN 104193706B CN 201410181866 A CN201410181866 A CN 201410181866A CN 104193706 B CN104193706 B CN 104193706B
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- diaminonaphthalene
- dmso
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- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 239000003513 alkali Substances 0.000 title claims abstract description 16
- 230000002146 bilateral effect Effects 0.000 title claims abstract description 15
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical group [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 title description 19
- 238000002360 preparation method Methods 0.000 title description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 87
- 238000001514 detection method Methods 0.000 claims description 11
- 238000010521 absorption reaction Methods 0.000 claims description 9
- 125000002091 cationic group Chemical group 0.000 claims description 5
- 230000008859 change Effects 0.000 claims description 5
- 238000002211 ultraviolet spectrum Methods 0.000 claims description 4
- 238000002474 experimental method Methods 0.000 abstract description 6
- 238000004448 titration Methods 0.000 abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 2
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000006501 nitrophenyl group Chemical group 0.000 abstract 1
- 125000006853 reporter group Chemical group 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 150000002500 ions Chemical class 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 150000001768 cations Chemical class 0.000 description 4
- 238000002189 fluorescence spectrum Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000001455 metallic ions Chemical class 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000011896 sensitive detection Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
- G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
- G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
- G01N21/33—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using ultraviolet light
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- 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
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
- G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
- G01N21/78—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator producing a change of colour
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- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
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Abstract
It is a kind of based on the bilateral west of 1,5-diaminonaphthalene not alkali acceptor molecule that the present invention has synthesized a kind of design and synthesis, and being colorimetric signal group with nitrophenyl, take 1,5-diaminonaphthalene as fluorescent signal reporter group, to the west of not alkali C=N be Hg
2+hydrolysis binding site, single selective colorimetric-fluorescence two channels identification Hg in water-bearing media
2+ion.Fluorometric titration experiment shows, Hg
2+the hydrolytic action of this receptor can be promoted thus discharge 1,5-diaminonaphthalene, launching strong blue-fluorescence.This receptor is to Hg
2+lowest detectable limit can reach 3.74 × 10
-9m.In addition, the present invention has prepared the Hg based on this receptor
2+test paper, conveniently can detect the Hg in water-bearing media
2+ion.
Description
Technical field
The invention belongs to cation detection technical field, relate to a kind of acceptor detecting mercury ion, particularly relate to a kind of acceptor molecule based on the bilateral west of 1,5-diaminonaphthalene not alkali, the present invention also relates to based on the mercury ion detecting test paper of this receptor molecule and at colorimetric-fluorescence two channels identification Hg simultaneously
2+application.
Background technology
Mercury is a kind of application heavy metal widely, the electronic products such as luminescent lamp used in everyday, computer, mobile phone, battery all in various degree employ mercurous material.These electronic products be finished discarded after, the final entered environment in the form of an ion of part mercury, causes serious pollution to environment.Mercury ion all has a great impact animals and plants and HUMAN HEALTH, and such as, mercury ion has very strong toxicity to the brain of people, kidney, stomach and neural system.Therefore, mercury ion identification and detect have important application in fields such as environmental science, life science and medical science.The method detecting mercury ion is a lot, and colorimetry or fluorescent method receive much attention due to the reason such as convenient and swift.Current people design and synthesis gone out some can with Hg
2+the compound of response type identification.But the synthesis of most receptors compound is complicated, to Hg
2+sensitivity lower, accurately rapid detection can not go out Hg
2+.Therefore, a kind of highly selective of design and synthesis, highly sensitive detection mercury ion acceptor molecule remain a very large challenge.
Summary of the invention
The object of this invention is to provide a kind of mercury ion acceptor molecule based on the bilateral west of 1,5-diaminonaphthalene not alkali.
Another object of the present invention is to provide a kind of mercury ion detecting test paper based on above-mentioned mercury ion acceptor molecule and is detecting the application in mercury ion.
one, based on the bilateral west of 1,5-diaminonaphthalene not alkali acceptor molecule
The present invention is based on the bilateral west of 1,5-diaminonaphthalene not alkali acceptor molecule, its structural formula is as follows:
。
two, based on the preparation of the bilateral west of 1,5-diaminonaphthalene not alkali acceptor molecule
With dimethyl formamide (DMF) for solvent, 5-(nitrophenyl) furans-2-formaldehyde and 1,5-diaminonaphthalene are substrate, under the effect of Glacial acetic acid, and stirring reaction 4 ~ 6h at 60 ~ 80 DEG C; Reaction terminates rear cooling, suction filtration, obtains yellow solid; Use DMF recrystallization, obtain mercury ion acceptor compound, be designated as L.
1,5-diaminonaphthalene (1,5-DAN) control in the scope of 1:2.0 ~ 1:3.0 with the mol ratio of 5-(nitrophenyl) furans-2-formaldehyde, the consumption of catalyzer Glacial acetic acid controls 20 ~ 50% of reaction substrate integral molar quantity time, and the productive rate of acceptor molecule can reach more than 75%.
three, the cations recognition experiment of acceptor molecule
1, the cations recognition performance study of acceptor molecule
Pipette the DMSO solution (2 × 10 of 0.5 mL acceptor molecule respectively
-4molL
-1) in a series of 10 mL colorimetric cylinders, then three distilled water pipetting 1.0mL are respectively in the above-mentioned colorimetric cylinder adding acceptor, then add Fe respectively
3+, Fe
2+, Hg
2+, Ag
+, Ca
2+, Cu
2+, Co
2+, Ni
2+, Cd
2+, Pb
2+, Zn
2+, Cr
3+, Mg
2+, Na
+, K
+dMSO solution (0.004 molL
-1) 0.5 mL.Be diluted to 5mL with DMSO, now acceptor density is 2 × 10
-5molL
-1, cation concn is 20 times of acceptor density.Mix rear placement about 15 minutes, observe acceptor to the response of each negatively charged ion.Find, at the DMSO/H of acceptor molecule
2in O (4:1, V/V) system, when adding above-mentioned cationic DMSO solution respectively, only has Hg
2+add, the DMSO/H of acceptor can be made
2o system is become colorless by yellow; In corresponding UV spectrum, Hg
2+add, the DMSO/H of acceptor can be made
2the absorption peak of O system at 451nm place disappears, and the absorption peak at 351nm place strengthens (Fig. 1).And all the other cationicly add acceptor DMSO/H
2color and the UV spectrum of O system have no significant effect.In its corresponding fluorescence emission spectrum, when adding Hg
2+afterwards, take 381nm as the DMSO/H of excitation wavelength, acceptor molecule
2o system launches very strong blue-fluorescence (Fig. 2) at 446nm place.
2, the titration experiments of acceptor
Pipette 2 mL acceptor molecules
'sdMSO/H
2o (4:1; V/V) solution (2.0 × 10
-5mol/L) in quartz cell, Hg is added gradually by accumulation application of sample method
2+the solution of DMSO, survey its fluorescence emission spectrum (Fig. 3) in 25 DEG C.Along with Hg
2+add gradually, be that excitation wavelength strengthens gradually at the emission peak at 446nm place with 381nm.
3, interference free performance detects
In order to measure acceptor molecule to Hg
2+detection results, we have carried out again following test: get two groups of 10mL colorimetric cylinders, add the DMSO/H of 0.5mL acceptor respectively
2o (4:1; V/V) solution, then add the various cationic DMSO solution (4 × 10 of 0.5mL respectively
-3molL
-1), and wherein one group add three distilled water of 1.0mL after be diluted to 5mL scale with DMSO; Hg is added respectively in other one group
2+, then add three distillations of 1.0mL, be then diluted to 5mL scale with DMSO.Above-mentioned solution is mixed rear placement to observe after 15 minutes, and survey its uv-visible absorption spectra and fluorescence spectrum in 25 DEG C.
Anti-interference as can be seen from ultraviolet, acceptor is adding Hg
2+add other positively charged ion wherein more afterwards, do not have a greater change in the absorption at 415nm place.In fluorescence interference--free experiments, acceptor adds Hg
2+after adding other positively charged ion wherein more afterwards, do not have a greater change in the emissive porwer at 446nm place.Therefore, illustrate that acceptor is to Hg
2+detection substantially cationicly to affect by other.
Fig. 4 is Receptor recognition Hg
2+the anti-interference absorption histogram of ultraviolet.Fig. 4 illustrates and adds Hg
2+, the absorption peak of acceptor at 415nm place disappears, then add other 14 kinds of positively charged ions again after, acceptor appoints disappearance at the absorption peak at 415nm place, this and Hg
2+consistent on the impact of acceptor.Fig. 5 is Receptor recognition Hg
2+the anti-interference spectrum histogram of fluorescence.Fluorogram display acceptor is adding Hg
2+launch very strong fluorescence afterwards at 446nm place, then add other 14 kinds of positively charged ions more wherein, acceptor is appointed so can launch very strong fluorescence at 446nm place.Thus illustrate that this receptoroid detects Hg
2+substantially not by other cationic interference.
3, acceptor is to Hg
2+the mensuration of lowest detectable limit
25 DEG C, utilize fluorescence spectrum, at acceptor (2 × 10
-4molL
-1) to Hg
2+ion (0.004 molL
-1) titration experiments in, according to added Hg
2+the volume of ion and the design sketch of titration, can obtain this receptor to Hg
2+the lowest detectable limit of ion reaches 3.74 × 10
-9mL
-1.
4, acceptor is to Hg
2+ion identification Analysis on Mechanism
This receptor is at DMSO/H
2to Hg in O system
2+selective fluorescence identifying ability.This receptor does not almost have fluorescence, when adding mercury ion in receptor solution, mercury ion makes the imine linkage hydrolytic cleavage of acceptor, discharge reaction raw materials 1,5-DAN and NPF, cause acceptor molecule to produce very strong fluorescence emission peak, thus realize mercury ion fluorescent identification, and this recognition process is not by the interference of other coexistent metallic ions.
Great many of experiments shows, the DMSO/H of acceptor molecule
2in O, as DMSO and H in system
2the volume ratio of O is at 3:1 ~ 5:1, and the concentration of acceptor molecule adjusts in the scope of 5 ~ 30 μMs, and acceptor molecule is to Hg
2+there is the selectivity fluorescence identifying ability of becoming reconciled.
four, Hg
2+
the factures and applicationsh of ion test paper
By the filter paper that the cleans up DMSO/H at acceptor molecule
2o (4:1; V/V) in system, (0.01 ~ 0.5mol/L) soaks 10 ~ 20 minutes, then takes out and dries, be cut into the test strip of 1 cm × 4cm, be Hg
2+ion detection test paper.
Above-mentioned test paper drips 14 kinds of cationic solutions, by fluorescent lamp, finds, only add Hg
2+, the fluorescence of test paper becomes blueness from black, and other cationicly adds, and the fluorescence color of test paper does not change.
Accompanying drawing explanation
Fig. 1 is the DMSO/H of acceptor molecule
2o (4:1; V/V) ultraviolet spectrogram after various positively charged ion is added in system.
Fig. 2 is the DMSO/H of acceptor molecule
2o (4:1; V/V) the fluorescent emission spectrogram after various positively charged ion is added in system.
Fig. 3 is that acceptor molecule is to Hg
2+fluorometric titration lab diagram.
Fig. 4 is Receptor recognition Hg
2+the anti-interference absorption histogram of ultraviolet.
Fig. 5 is Receptor recognition Hg
2+the anti-interference spectrum histogram of fluorescence.
Embodiment
Be described further to the preparation of acceptor molecule of the present invention, mercury ion detecting test paper and in the application detecting mercury ion in water below by specific embodiment.
1, the preparation of acceptor molecule: add DMF(30mL in 50mL reaction flask), 5-(nitrophenyl) furans-2-formaldehyde (0.868g, 4 mmol), 1,5-diaminonaphthalene (0.237g, 1.5mmol), Glacial acetic acid (1.0mL, 0.017mol), at 80 DEG C of stirring reaction 6h, suction filtration after cooling, obtain yellow solid, use DMF recrystallization, obtain acceptor molecule product, be designated as L.
Productive rate 75%.m.p. >300℃；
1H NMR (DMSO-d
6, 400MHz): δ 8.64 (2H, s, N=CH), 8.38 (4H, d, ArH), 8.27 (1H, d, ArH), 8.16 (4H, d, ArH), 7.36 (1H, d, ArH). IR: (KBr, cm
-1) v: 1598 (CH＝N), 1508 (C=C), 1330 (C=C). Anal. calcd for C
32H
20N
4O
6: C 69.06, H 3.62, N 10.07, O 17.25; found C 69.04, H 3.60, N 10.10, O 17.26. ESI-MS calcd for C
32H
20N
4O
6+H 557.4, found 557.4。
In above-mentioned building-up reactions, the synthetic method reference literature of 5-(nitrophenyl) furans-2-formaldehyde (Wang J X, Chen J C, Li Z J. Chinese. Sci. Bull. 1966,58,419].
2, Hg
2+the making of Test paper: by the filter paper that the cleans up DMSO/H at above-mentioned acceptor molecule
2o (4:1; V/V) soak about 10 minutes in system, taking-up is dried, and is then cut into the test strip of 1 cm × 4cm, is Hg
2+test paper.
3, Hg
2+detection: at the Hg of above-mentioned preparation
2+test paper drips Fe
3+, Fe
2+, Hg
2+, Ag
+, Ca
2+, Cu
2+, Co
2+, Ni
2+, Cd
2+, Pb
2+, Zn
2+, Cr
3+, Mg
2+, Na
+, K
+dMSO solution (0.004 molL
-1).By fluorescent lamp, if the fluorescence of test paper becomes blueness from black, then that add is Hg
2+if the fluorescence color of test paper does not change, then what add is other positively charged ion.
Claims (5)
1. one kind based on the bilateral west of 1,5-diaminonaphthalene not alkali as acceptor molecule detection Hg
2+in application, it is characterized in that: at the DMSO/H of acceptor molecule
2in O system, only has Hg
2+add, the DMSO/H of acceptor molecule can be made
2o system is become colorless by yellow, and all the other cationic DMSO/H added acceptor molecule
2o system color is without impact;
The described structural formula based on the bilateral west of 1,5-diaminonaphthalene not alkali is as follows:
。
2. as claimed in claim 1 based on the bilateral west of 1,5-diaminonaphthalene not alkali as acceptor molecule detection Hg
2+in application, it is characterized in that: at the DMSO/H of acceptor molecule
2in O system, only has Hg
2+add and can make acceptor molecule DMSO/H
2the absorption peak of UV spectrum at 451nm place of O system disappears, and the absorption peak at 351nm place strengthens; And all the other cationicly add acceptor molecule DMSO/H
2the UV spectrum of O system is without impact.
3. as claimed in claim 1 based on the bilateral west of 1,5-diaminonaphthalene not alkali as acceptor molecule detection Hg
2+in application, it is characterized in that: at the DMSO/H of acceptor molecule
2in O system, only has Hg
2+add and can make acceptor molecule DMSO/H
2o system launches very strong blue-fluorescence at 446nm place.
4. as claimed in claim 1 based on the bilateral west of 1,5-diaminonaphthalene not alkali as acceptor molecule detection Hg
2+in application, it is characterized in that: be prepared into the Hg based on the bilateral west of 1,5-diaminonaphthalene not alkali
2+test paper.
5. as claimed in claim 4 based on the bilateral west of 1,5-diaminonaphthalene not alkali as acceptor molecule detection Hg
2+in application, it is characterized in that: at Hg
2+test paper drips Fe
3+, Fe
2+, Hg
2+, Ag
+, Ca
2+, Cu
2+, Co
2+, Ni
2+, Cd
2+, Pb
2+, Zn
2+, Cr
3+, Mg
2+, Na
+, K
+dMSO solution, by fluorescent lamp, if the fluorescence of test paper becomes blueness from black, then that add is Hg
2+if the fluorescence color of test paper does not change, then what add is other positively charged ion.
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| CN105044061A (en) * | 2015-07-25 | 2015-11-11 | 渤海大学 | High-selectivity method for detecting p-phenylenediamine in aqueous solution |
| US11028194B1 (en) | 2016-02-23 | 2021-06-08 | Jalapeno Holdings, LLC | Bis-Schiff base compositions and formulations |
| US11572351B1 (en) | 2016-02-23 | 2023-02-07 | Systima Technologies, Inc. | Bis-Schiff base compositions and formulations |
| US10501578B1 (en) * | 2016-02-23 | 2019-12-10 | Jalapeno Holdings, LLC | Bis-Schiff base compositions and formulations |
| CN109239026B (en) * | 2018-01-23 | 2021-04-06 | 齐齐哈尔大学 | Amide group-containing fluorescent probe for Hg2+And methods of use |
| US11440851B1 (en) | 2018-02-14 | 2022-09-13 | Systima Technologies, Inc. | Method of making carbon matrix composite from high temperature polymer matrix fiber-reinforced composites |
| US10662329B1 (en) | 2018-06-26 | 2020-05-26 | Jalapeno Holdings, LLC | Bis-Schiff-base thermosetting elastomers |
| 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 |
| US12006411B1 (en) | 2020-08-19 | 2024-06-11 | Systima Technologies, Inc. | Method of making carbonized composites |
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| CN102942541A (en) * | 2012-12-04 | 2013-02-27 | 西北师范大学 | Receptor compound as well as synthesis and application of receptor compound in colorimetric detection of fluorine ions |
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| CN102942541A (en) * | 2012-12-04 | 2013-02-27 | 西北师范大学 | Receptor compound as well as synthesis and application of receptor compound in colorimetric detection of fluorine ions |
Non-Patent Citations (1)
| Title |
|---|
| Amal Kumar Mandal et.al.《Recognition of Hg2þ Ion through Restricted Imine Isomerization: Crystallographic Evidence and Imaging in Live Cells》.《ORGANIC LETTERS》.2012,第14卷(第12期),2980-2983. * |
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