CN102311404A - 2,2'-bis(2-hydroxy-4-sulfonic-1-naphthylamine azoxyl)-5,5'-dimethyl-4,4'-bithiazole and preparation method thereof - Google Patents

2,2'-bis(2-hydroxy-4-sulfonic-1-naphthylamine azoxyl)-5,5'-dimethyl-4,4'-bithiazole and preparation method thereof Download PDF

Info

Publication number
CN102311404A
CN102311404A CN201110292383A CN201110292383A CN102311404A CN 102311404 A CN102311404 A CN 102311404A CN 201110292383 A CN201110292383 A CN 201110292383A CN 201110292383 A CN201110292383 A CN 201110292383A CN 102311404 A CN102311404 A CN 102311404A
Authority
CN
China
Prior art keywords
preparation
dimethyl
thiazole
solution
join
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.)
Granted
Application number
CN201110292383A
Other languages
Chinese (zh)
Other versions
CN102311404B (en
Inventor
王君玲
张殿龙
樊月琴
王科伟
贾治芳
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shanxi Datong University
Original Assignee
Shanxi Datong University
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Shanxi Datong University filed Critical Shanxi Datong University
Priority to CN 201110292383 priority Critical patent/CN102311404B/en
Publication of CN102311404A publication Critical patent/CN102311404A/en
Application granted granted Critical
Publication of CN102311404B publication Critical patent/CN102311404B/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Landscapes

  • Thiazole And Isothizaole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The invention relates to a bis-heterocyclic triazene compound, and specifically relates to a 2,2'-bis(2-hydroxy-4-sulfonic-1-naphthylamine azoxyl)-5,5'-dimethyl-4,4'-bithiazole and a preparation method thereof. The preparation method comprises the following steps of: (1) preparation of 2,5-dibromohexanedione; (2) preparation of 2,2'-diamino-5,5'-dimethyl-4,4'-bithiazole; (3) preparation of 5,5'-dimethyl-4,4'-bithiazole-2,2'- bis-diazonium salt; (4) preparation of an objective product BHSNAADMBT. The technical scheme of the invention connects bithiazole heterocycle and naphthalene ring derivative with fluorescence property together to synthesize a reagent with double functional-analytical groups and large steric hindrance; and the compound of the invention not only has high reaction sensitivity with metal ions, but also has good selectivity. The reagent is a good photometric analysis developer and a novel fluorescence analytical reagent with high sensitivity and good selectivity as well.

Description

2,2 '-two (2-hydroxyls-4-sulfonic group-1-naphthalene ammonia azo-group)-5,5 '-dimethyl--4,4 '-the Lian thiazole and preparation method thereof
Technical field
The present invention relates to a kind of double heterocyclic tri azene compound, be specially 2,2 ＇-two (2-hydroxyl-4-sulfonic group-1-naphthalene ammonia azo-group)-5,5 ＇ -Dimethyl- -4,4 ＇ -Join thiazole and preparation method thereof.
Background technology
Triazene reagent is that the good developer of metals ion photometric analysiss such as silver, cadmium, mercury, nickel, copper (is risen grace river, Jiang Wanquan, Zhu Yurui etc., chemical reagent, 1992,14 (2): 109).Because of it contains-the N=N-NH-functional group, because p-is pi-conjugated ,-NH-has stronger acidity.Under alkaline condition, be prone to and the transition metal ion coordination after the deprotonation, be good coordinating group.That such reagent has is highly sensitive, be prone to advantages such as synthetic, enjoys people to pay close attention to.But selectivity and sensitivity are still waiting to improve, and usually only are used for photometric analysis as developer, seldom are used for the fluoroscopic examination of metals ion as fluorescent reagent.Two triazene reagent contain two-N=N-NH-functional group, have increased the coordination ability of reagent and metals ion, than the general higher (Z.G.Chen of single triazene reagent sensitivity; W.Chen, F.Y.Lei, et al.; Chinese J. Anal.Chem., 2003,31 (10): 1279).Introduce in the molecule and help the stronger heterocycle structure unit of look ability, help improving reagent analytical performance (new developer and in Application in Photometric Analysis. Pan Jiaomai, Li Zaijun, Zhang Qiying, Fang Guozhen, Chemical Industry Press, 2003,165).Application number: 200810054988.4 have put down in writing a kind of two (2-diazoamino benzo thiazole)-biphenyl; This material is a kind of two three nitrogen desaturation compounds of heterocyclic that have; Can be used for the detection of Hg in the fluoroscopic examination of metals ion, particularly alkaline medium (II).Application number: 200810080130.5 be a kind of 4,4 '-two [5,6-two chloro-2-[4-morpholinodithio diazoamino] biphenyl-3,3 '-disulfonic acid, more than two examples be two triazene structures, have comparatively good detection character.But, need further to explore the better compound of structure in order to improve the susceptibility that detects metals ion.
Summary of the invention
The good developer that the present invention is based on two triazenes and be metals ions such as silver, cadmium, mercury, nickel, copper is again the characteristic of highly sensitive, that selectivity is good fluorescent reagent and 2,2 ＇-two (2-hydroxyl-4-sulfonic group-1-naphthalene ammonia azo-group)-5,5 ＇ are provided -Dimethyl--4,4 ＇ joins the preparation and the application of thiazole.
The present invention is realized by following technical scheme, a kind of 2,2 ＇-two (2-hydroxyl-4-sulfonic group-1-naphthalene ammonia azo-group)-5,5 ＇ -Dimethyl--4,4 ＇ -Join thiazole (BHSNAABT), its molecular structural formula:
Figure 2011102923830100002DEST_PATH_IMAGE001
。
A kind of 2,2 ＇-two (2-hydroxyl-4-sulfonic group-1-naphthalene ammonia azo-group)-5,5 ＇ -Dimethyl--4,4 ＇ -Join the preparation method of thiazole, comprise the following steps:
The preparation of (1) 2,5-dibromo hexanedione
In the 250ml there-necked flask of magnetic stirring apparatus tap funnel and reflux is housed, add 3,4-hexanedione and chloroform and glacial acetic acid; Be heated with stirring in the oil bath about 80 ℃, the mixed solution of dropping liquid bromine and chloroform from separating funnel, reaction begins immediately; After bromine dropwises, continue heating till solution becomes orange from red-brown, in ice bath, be cooled to 0 ℃ rapidly; Yellow needle-like deposition is promptly arranged, and suction filtration is used the chloroform recrystallization; Yellow needle-like solid, promptly 1,4-dibromo dimethyl diketone.
(2) 2,2 ＇-diamino--5,5 ＇ -Dimethyl--4,4 ＇ -Join the preparation of thiazole
In the there-necked flask that magnetic stirring apparatus and reflux are housed, add 2,5-dibromo hexanedione, thiocarbamide and ethanol; Reflux is 1.5 hours in oil bath, then reactant is poured in the hot water, drips to weakly alkaline with strong aqua, and the needle-like deposition of taupe is arranged; Suction filtration, thick product, bullion is with 50% ethyl alcohol recrystallization; Get pure article, i.e. 4,4 ＇ -Join thiazole-2,2 ＇-diamines.
(3) 5,5 ＇ -Dimethyl--4,4 ＇ -Join the preparation of thiazole-2,2 ＇-dual nitrogen salt
Take by weighing 2,2 ＇-diamino--5,5 ＇ -Dimethyl--4,4 ＇ -Join thiazole, hydrochloric acid (1+1) dissolving is cooled to 0～5 ℃ with ice-water bath, constantly stirs slowly to drip NaNO down 2Water-soluble solution, stir about 1 hour, it is subsequent use to get diazonium salt solution A.
(4) preparation of title product BHSNAADMBT
Take by weighing 1-amino-2-hydroxyl-4-naphthene sulfonic acid and be dissolved in 10% sodium hydroxide solution, this solution slowly is added drop-wise among the above-mentioned diazonium salt solution A, dropwise, stirred 1 hour, regulate pH5 ~ 6 with 10% NaOH solution, placement is spent the night, suction filtration.The water washing precipitation uses aqueous ethanolic solution (1+1) washing to get the thick product of sorrel for several times for several times again.Thick product is with ETHYLE ACETATE: sherwood oil (1:3) is an eluent, gets pure article through column chromatography for separation.
Results of elemental analyses is: C:46.12%; H:2.91 %; N:15.51%; S:17.71%.By molecular formula C 28H 22N 8O 8S 4Calculated value is C:46.28%; H:3.03 %; N:15.43%; S:17.63%.IR:3500 ~ 3400cm -13050 cm are arranged-absorption peak of OH -1There are the absorption peak of Ar-H, 1610 cm in the place -1The place has
Figure 2011102923830100002DEST_PATH_IMAGE002
Absorption peak, 3200 cm -1There are-the NH-absorption peak 1190 cm at the place -1, 1100 cm -1, 620 cm -1, 520 cm -1The place has-SO 3The H absorption peak, by ultimate analysis and IR spectroscopy check, synthetic product conforms to target molecule.
Technical scheme of the present invention couples together double thiazole heterocycle and the naphthalene nucleus verivate with photoluminescent property through the triazene structure; Synthetic have two functional-analytical groups and than large space sterically hindered reagent; Not only higher sensitivity is arranged, and have selectivity preferably with the metals ion reaction.This reagent is good photometric analysis developer, also is the novel fluorescence analytical reagent highly sensitive, that selectivity is good.
Advantage of the present invention and positively effect:
(1) reagent has the two triazene coordination functional structure unit of linear pattern, and through conjugation triazene structure, after two naphthalene nucleus that will have a fluorescent characteristic connected, conjugated system further increased, thereby fluorescent yield is increased.It is new fluorescent reagent highly sensitive, that selectivity is good.
(2) introducing helps the stronger heterocyclic group double thiazole structure of look ability in the reagent molecule, and analytical performance is superior to general similar reagent.
(3) 2 of naphthalene nucleus introducing hydroxyl auxochromess in the reagent molecule; Help the reagent color development, hydroxyl also is good dentate simultaneously, has strengthened the coordination ability of reagent and Hg (II); 4 of naphthalene nucleus are introduced the wetting ability sulfonic group, help the water color development of reagent.
(4) preparation method of the present invention is simple, and is with low cost, is used in tensio-active agent TritonX-100 and exists down, and the fluoroscopic examination of Hg in the alkaline medium (II) also is the developer of photometric analysis, is used for the photometric analysis of mercury ion.
To detect Hg (II) is example:
In the 25mL volumetric flask, add Hg (II) standardized solution of 5 μ g successively, 3% TritonX-100 2.0mL; 0.2g/L the DMF solution 1.5mL of BHSNAADMBT, the borax of pH 10.2-sodium hydroxide buffer solution 3.0mL is diluted with water to scale; Shaking up, place 5min, is reference with the blank reagent; Place the 485nm place to survey the absorbancy of complex compound, apparent molar absorption coefficient ε=2.5 * 10 with the 1cm cuvette 5Lmol -1Cm -1
         
The different molar absorptivity contrasts of surveying mercury triazene developer of table 1
Triazene developer title Apparent molar absorption coefficient
Equal tribromo-benzene basic weight nitrogen aminoazobenzene 7.7×10 4
O-bromophenyl diazoamino nitrogen benzide 8.9×10 4
To acetylphenyl diazoamino nitrogen benzide 1.1×10 5
4-methyl-2-arsono phenyl diazoamino nitrogen benzide 1.85×10 5
4,4 '-two (the amino azo-groups of 5-sulfonic group-8-hydroxyl-7-quinoline)-3,5,3 ', 5 '-tetrabromodiphenyl ether ? 2.3×10 5
Fluorescent reagent 2,2 ＇-two (2-hydroxyl-4-sulfonic group-1-naphthalene ammonia azo-group)-5,5 ＇ that contain the double heterocyclic tri azene structure -Dimethyl--4,4 ＇ -Join thiazole (BHSNAADMBT) in alkaline medium to Hg 2+Fluoroscopic examination:
Measure 10～20mL trade effluent sample in beaker, add chloroazotic acid 3mL, be heated near doing under stirring. add hydrochloric acid 2mL again, little fire is heated near doing.Add certain water gaging after the cooling, move in the 50mL volumetric flask,, shake up with the water constant volume.Pipette a certain amount of sample solution in the 25mL volumetric flask, measure, the results are shown in Table 2. by this method
Other gets the people and sends out appearance through acetone immersion 50 minutes, and washing is clean, oven dry.Accurately take by weighing and send out appearance about 10.0g, add 50mLHClO 4: HNO 3(1:8) mixed solution, after little fire heating makes abundant reaction, the intensification evaporate to dryness, addend drips H 2SO 4Solution (1:1) is used the water extraction raffinate, changes in the 10mL volumetric flask, and regulating the pH value is 7, and water is diluted to scale, gets a certain amount of diluent determining at every turn.
In the 25mL tube comparison tubes, add the mercurous ionic sample of certain volume successively, 1.3 * 10 -5The BHSNAADMBT ethanolic soln 3.0mL of mol/L; The pH value is borax-sodium hydroxide buffer solution 2.5mL of 9.7; 3% TritonX-100 aqueous solution 2.0mL; The water constant volume is surveyed its fluorescence intensity with Cary Eclipse type spectrophotofluorometer (Co., Ltd in U.S.'s Varian technology) in λ ex/ λ em=382nm/495nm place then.
Mensuration result to the mercury ion in the different samples sees table 2.
 
The detected result (n=5) of Hg in table 2 sample (II)
Figure 2011102923830100002DEST_PATH_IMAGE003
Building-up reactions principle of the present invention:
Figure 2011102923830100002DEST_PATH_IMAGE006
Embodiment
Embodiment 1
2,2 ＇-two (2-hydroxyl-4-sulfonic group-1-naphthalene ammonia azo-group)-5,5 ＇ -Dimethyl--4,4 ＇ -Join thiazole (BHSNAADMBT), its molecular structural formula:
Figure 2011102923830100002DEST_PATH_IMAGE007
2,2 ＇-two (2-hydroxyl-4-sulfonic group-naphthalidine azo-group)-5,5 ＇ -Dimethyl--4,4 ＇ -Join the preparation method of thiazole (BHSNAADMBT), comprise the following steps:
The preparation of (1) 2,5-dibromo hexanedione
In the 250mL there-necked flask of magnetic stirring apparatus tap funnel and reflux is housed; Add 28.5g (0.25mol) 3; 4-hexanedione and 45mL chloroform and 10mL glacial acetic acid; Be heated with stirring in the oil bath about 80 ℃, from separating funnel, dripping the mixed solution of 80g liquid bromine and 30 mL chloroforms lentamente, reaction begins immediately.After bromine dropwises, continue heating till solution becomes orange from red-brown, in ice bath, be cooled to 0 ℃ rapidly, yellow needle-like deposition is promptly arranged, suction filtration is used the chloroform recrystallization, gets yellow needle-like solid, 121 ~ 122 ℃ of mp.
(2) 2,2 ＇-diamino--5,5 ＇ -Dimethyl--4,4 ＇ -Join the preparation of thiazole
In the there-necked flask that magnetic stirring apparatus and reflux are housed, add 27.2g (0.1mol) 2,5-dibromo hexanedione; 15.2g (0.2mol) thiocarbamide and 200mL ethanol; Reflux 1.5h in oil bath pours reactant in the hot water (80-100 ℃) of 500 mL into then, drips to weakly alkaline with strong aqua; The needle-like deposition that taupe is arranged, suction filtration.Thick product, bullion is with 50% ethyl alcohol recrystallization, must pure article, 247 ℃ of fusing points.
(3) 5,5 ＇ -Dimethyl--4,4 ＇ -Join the preparation of thiazole-2,2 ＇-dual nitrogen salt
Take by weighing 9.0g (0.04 mol) 2,2 ＇-diamino--5,5 ＇ -Dimethyl--4,4 ＇ -Join thiazole, add 75mL hydrochloric acid (1+1) dissolving, be cooled to 0～5 ℃, constantly stir slow Dropwise 5 .6g (0.08mol) NaNO down with ice-water bath 2Be dissolved in the solution of 40 mL water, stir about 1h, it is subsequent use to get diazonium salt solution A.
(4) preparation of title product BHSNAADMBT
Take by weighing 1-amino-2-hydroxyl-4-naphthene sulfonic acid 19.2g (0.08 mol) and be dissolved in the sodium hydroxide solution of 120mL 10%, this solution slowly is added drop-wise among the above-mentioned diazonium salt solution A, dropwise; Stir 1h; Regulate pH5 ~ 6 with 10% NaOH solution, placement is spent the night, suction filtration.The water washing precipitation uses aqueous ethanolic solution (1+1 volume ratio) washing to get the thick product of sorrel for several times for several times again.Thick product is with ETHYLE ACETATE: sherwood oil (1:3 volume ratio) is an eluent, gets pure article through column chromatography for separation.

Claims (3)

1. two tri azene compounds are 2,2 ＇-two (2-hydroxyl-4-sulfonic group-1-naphthalene ammonia azo-group)-5,5 ＇ -Dimethyl--4,4 ＇ -Join thiazole, it is characterized in that molecular structural formula is:
。
2. ＇-two (2-hydroxyl-4-sulfonic group-1-naphthalene ammonia azo-group)-5,5 ＇ -Dimethyl--4,4 ＇ -Join the preparation method of thiazole (BHSNAADMBT), it is characterized in that: comprise the following steps
The preparation of (1) 2,5-dibromo hexanedione
In the 250ml there-necked flask of magnetic stirring apparatus, tap funnel and reflux is housed, add 3,4-hexanedione and chloroform and glacial acetic acid are being heated with stirring in the oil bath about 80 ℃; The mixed solution of dropping liquid bromine and chloroform from separating funnel, reaction begins immediately, after bromine dropwises, continues heating till solution becomes orange from red-brown; Be cooled to 0 ℃ in the ice bath, yellow needle-like deposition is promptly arranged, suction filtration is used the chloroform recrystallization; Yellow needle-like solid, promptly 1,4-dibromo dimethyl diketone;
(2) 2,2 ＇-diamino--5,5 ＇ -Dimethyl--4,4 ＇ -Join the preparation of thiazole
In the there-necked flask that magnetic stirring apparatus and reflux are housed, add 2,5-dibromo hexanedione; Thiocarbamide and ethanol, reflux is 1.5 hours in oil bath, then reactant is poured in the hot water; Drip to weakly alkaline with strong aqua, the needle-like deposition of taupe is arranged, suction filtration;
Thick product, bullion must pure article, i.e. 4,4 ＇ with 50% ethyl alcohol recrystallization -Join thiazole-2,2 ＇-diamines;
(3) 5,5 ＇ -Dimethyl--4,4 ＇ -Join the preparation of thiazole-2,2 ＇-dual nitrogen salt
Take by weighing 2,2 ＇-diamino--5,5 ＇ -Dimethyl--4,4 ＇ -Join thiazole, hydrochloric acid (1+1) dissolving is cooled to 0～5 ℃ with ice-water bath, constantly stirs slowly to drip NaNO down 2Water-soluble solution stirred 1 hour, and it is subsequent use to get diazonium salt solution A;
(4) preparation of title product BHSNAADMBT
Take by weighing 1-amino-2-hydroxyl-4-naphthene sulfonic acid and be dissolved in 10% sodium hydroxide solution, this drips of solution is added among the above-mentioned diazonium salt solution A, dropwise; Stirred 1 hour, and regulated pH5 ~ 6 with 10% NaOH solution, placement is spent the night; Suction filtration, water washing precipitation get the thick product of sorrel with the aqueous ethanolic solution washing for several times more for several times; Thick product is with ETHYLE ACETATE: sherwood oil (1:3) is an eluent, gets pure article through column chromatography for separation.
3. 2,2 ＇ according to claim 1-two (2-hydroxyl-4-sulfonic group-1-naphthalene ammonia azo-group)-5,5 ＇ -Dimethyl--4,4 ＇ -Join thiazole, be applied to detect the concentration of mercury ion in the mercurous sample as developer and fluorescent reagent.
CN 201110292383 2011-10-03 2011-10-03 2,2'-bis(2-hydroxy-4-sulfonic-1-naphthylamine azoxyl)-5,5'-dimethyl-4,4'-bithiazole and preparation method thereof Expired - Fee Related CN102311404B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN 201110292383 CN102311404B (en) 2011-10-03 2011-10-03 2,2'-bis(2-hydroxy-4-sulfonic-1-naphthylamine azoxyl)-5,5'-dimethyl-4,4'-bithiazole and preparation method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN 201110292383 CN102311404B (en) 2011-10-03 2011-10-03 2,2'-bis(2-hydroxy-4-sulfonic-1-naphthylamine azoxyl)-5,5'-dimethyl-4,4'-bithiazole and preparation method thereof

Publications (2)

Publication Number Publication Date
CN102311404A true CN102311404A (en) 2012-01-11
CN102311404B CN102311404B (en) 2013-10-30

Family

ID=45425006

Family Applications (1)

Application Number Title Priority Date Filing Date
CN 201110292383 Expired - Fee Related CN102311404B (en) 2011-10-03 2011-10-03 2,2'-bis(2-hydroxy-4-sulfonic-1-naphthylamine azoxyl)-5,5'-dimethyl-4,4'-bithiazole and preparation method thereof

Country Status (1)

Country Link
CN (1) CN102311404B (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103159753A (en) * 2013-01-14 2013-06-19 南京大学 4, 4'-din-butyl-5, 5'-bi (4-pyridyl)-2, 2'-bihiazole and preparation method thereof and fluorescent sensing and biologic application of iron ion
CN103980227A (en) * 2014-05-07 2014-08-13 山西大同大学 2,2'-Bis(2-carboxyl-5-methyl-4-hydroxyphenylazo)-6,6'-bibenzobithiazole, and preparation method and application thereof
CN105753755A (en) * 2016-03-21 2016-07-13 山西大同大学 3, 3'-dimethylthio-4, 4'-bis(2,6-dichloro-4-nitrophenyl diazoamino) biphenyl, preparation method and application
CN109134454A (en) * 2018-09-14 2019-01-04 山西大同大学 A kind of preparation method and application of thiazoles azo-compound

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4918022A (en) * 1989-03-13 1990-04-17 Ohio State University Analysis of bulk asbestos samples
JPH11172131A (en) * 1997-12-12 1999-06-29 Kanto Chem Co Inc Stabilized composition of titanium yellow
CN1715274A (en) * 2005-07-05 2006-01-04 雁北师范学院 Double heterocyclic tri azene compound and its preparing method and use
CN101274920A (en) * 2008-05-16 2008-10-01 山西大同大学 Bis(2-benzothiazolydiazoamino)-biphenyl, preparation and application thereof
CN101440071A (en) * 2008-12-13 2009-05-27 山西大同大学 4,4'-bis[5,6- dichloro-2-benzothiazolylazoamino] biphenyl-3,3'-disulfonic acid, preparation and use thereof

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4918022A (en) * 1989-03-13 1990-04-17 Ohio State University Analysis of bulk asbestos samples
JPH11172131A (en) * 1997-12-12 1999-06-29 Kanto Chem Co Inc Stabilized composition of titanium yellow
CN1715274A (en) * 2005-07-05 2006-01-04 雁北师范学院 Double heterocyclic tri azene compound and its preparing method and use
CN101274920A (en) * 2008-05-16 2008-10-01 山西大同大学 Bis(2-benzothiazolydiazoamino)-biphenyl, preparation and application thereof
CN101440071A (en) * 2008-12-13 2009-05-27 山西大同大学 4,4'-bis[5,6- dichloro-2-benzothiazolylazoamino] biphenyl-3,3'-disulfonic acid, preparation and use thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
王君玲，等: "新显色剂2-磺酸基苯基-1,4-二重氮氨基偶氮苯与Hg的显色反应及其应用", 《分析试验室》, vol. 27, 31 January 2008 (2008-01-31), pages 77 - 79 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103159753A (en) * 2013-01-14 2013-06-19 南京大学 4, 4'-din-butyl-5, 5'-bi (4-pyridyl)-2, 2'-bihiazole and preparation method thereof and fluorescent sensing and biologic application of iron ion
CN103159753B (en) * 2013-01-14 2015-11-25 南京大学 4,4 '-di-n-butyl-5,5 '-two (4-pyridyl)-2,2 '-double thiazole and method for making thereof and to the fluorescence sense of iron ion and biologic applications
CN103980227A (en) * 2014-05-07 2014-08-13 山西大同大学 2,2'-Bis(2-carboxyl-5-methyl-4-hydroxyphenylazo)-6,6'-bibenzobithiazole, and preparation method and application thereof
CN105753755A (en) * 2016-03-21 2016-07-13 山西大同大学 3, 3'-dimethylthio-4, 4'-bis(2,6-dichloro-4-nitrophenyl diazoamino) biphenyl, preparation method and application
CN105753755B (en) * 2016-03-21 2017-10-27 山西大同大学 Double (the 2,6 dichloro-4,4 nitrophenyl diazonium amino) biphenyl of 3,3 ' dimethyl sulphur-based 4,4 ' and preparation method and application
CN109134454A (en) * 2018-09-14 2019-01-04 山西大同大学 A kind of preparation method and application of thiazoles azo-compound
CN109134454B (en) * 2018-09-14 2021-08-27 山西大同大学 Preparation method and application of bithiazole azo compound

Also Published As

Publication number Publication date
CN102311404B (en) 2013-10-30

Similar Documents

Publication Publication Date Title
CN105733564B (en) A kind of Ratiometric fluorescent probe sensitive Mitochondrially targeted pH and its preparation method and application
CN102311404B (en) 2,2'-bis(2-hydroxy-4-sulfonic-1-naphthylamine azoxyl)-5,5'-dimethyl-4,4'-bithiazole and preparation method thereof
CN101440071B (en) 4,4'-bis[5,6- dichloro-2-benzothiazolylazoamino] biphenyl-3,3'-disulfonic acid, preparation and use thereof
CN105924449B (en) One kind detection mercury ion response type fluoresceins fluorescence probe preparation and application
CN104370927B (en) A kind of Schiff bases fluorescent probe compounds and preparation thereof
CN103265539A (en) Fluorescent probe: benzothiazole-terpyridine compound used for distinguishing and detecting zinc ions and cadmium ions, preparation method and application method thereof
CN104830315A (en) Bivalent copper ion fluorescent probe and preparation method and application thereof
CN112724040B (en) Cationic fluorescent probe based on tetraphenylethylene structure
Jiang et al. A nopinone based multi-functional probe for colorimetric detection of Cu 2+ and ratiometric detection of Ag+
CN112920081B (en) Fluorescent probe for selectively identifying hypochlorous acid and preparation method and application thereof
CN107118127A (en) Amino-acid schiff base and its synthetic method and application
CN104962278A (en) Palladium ion fluorescent probe, and preparation method and applications thereof
CN102532017B (en) 3,3'-diethoxy-4,4'-di(8-hydroxy-5-quinoline ammonia azo)azobenzene and preparation method and application thereof
CN114315691B (en) Asymmetric squaraine colorimetric probe for identifying copper ions and application thereof
CN112409292A (en) Multifunctional fluorescent probe, preparation method and application
CN109575003A (en) A kind of cumarin Cu of pyridine triazole modification2+The preparation method of fluorescence probe
CN101602724A (en) 4,4 '-two (the amino azo-groups of 5-sulfonic group-8-hydroxyl-7-quinoline)-3,5,3 ', 5 '-tetrabromodiphenyl ether
He et al. Colorimetric and fluorescent probe for highly selective and sensitive recognition of Cu2+ and Fe3+ based on asymmetric squaraine dye
CN102358722B (en) Method for preparing 3,3'-dihydroxy-4,4'-di(1,1'-dinaphthylamine azo group) azobenzene and application thereof
CN109879883B (en) Double-fluorophore zinc ion fluorescent probe compound and preparation method and application thereof
CN114478319B (en) Synthesis method of dicyanoisophorone derivative and application of dicyanoisophorone derivative in detection of mercury ions
CN103980227B (en) Two (2-carboxyl-5-methyl-4-hydroxybenzene azo)-6, the 6`-biphenyl of 2,2`-double thiazole and its preparation method and application
CN102584857B (en) 2,6-bis-(1,1'-naphthalene amino azo)benzo(1,2-d;4,5-d') dithiazole, and preparation method and application thereof
Enbanathan et al. An AIE dynamic a highly selective and expeditious benzothiazole-pyrazine based colorimetric chemosensor for Ni2+ and fluorogenic chemosensor for Cu2+ and Al3+ detection
CN108863945A (en) A kind of phenanthro- imidazoles Fe3+Probe and its preparation and application

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20131030

Termination date: 20141003

EXPY Termination of patent right or utility model