CN104592075A - Dichlorosalicylaldehyde thiourea derivative and application thereof - Google Patents
Dichlorosalicylaldehyde thiourea derivative and application thereof Download PDFInfo
- Publication number
- CN104592075A CN104592075A CN201410825815.3A CN201410825815A CN104592075A CN 104592075 A CN104592075 A CN 104592075A CN 201410825815 A CN201410825815 A CN 201410825815A CN 104592075 A CN104592075 A CN 104592075A
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- CN
- China
- Prior art keywords
- thiourea derivative
- salicylaldehyde
- dichloro
- dichlorosalicylaldehyde
- application
- Prior art date
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- 0 CC(CNc1c(*=*[C@@](C(C(Cl)=C2)O)C=C2Cl)cccc1)=CNc1ccccc1 Chemical compound CC(CNc1c(*=*[C@@](C(C(Cl)=C2)O)C=C2Cl)cccc1)=CNc1ccccc1 0.000 description 2
- VBJFIGDTDPTFRZ-UHFFFAOYSA-N CCOc1cc(NC(Nc(cccc2)c2N)=S)ccc1 Chemical compound CCOc1cc(NC(Nc(cccc2)c2N)=S)ccc1 VBJFIGDTDPTFRZ-UHFFFAOYSA-N 0.000 description 1
- OYKSTJSVNQYCRE-UHFFFAOYSA-N COc(c(Cl)c1)c(C=O)cc1Cl Chemical compound COc(c(Cl)c1)c(C=O)cc1Cl OYKSTJSVNQYCRE-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-O Nc(cccc1)c1[NH3+] Chemical compound Nc(cccc1)c1[NH3+] GEYOCULIXLDCMW-UHFFFAOYSA-O 0.000 description 1
- QKFJKGMPGYROCL-UHFFFAOYSA-N S=C=Nc1ccccc1 Chemical compound S=C=Nc1ccccc1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 1
Abstract
The invention discloses a dichlorosalicylaldehyde thiourea derivative and application thereof. The molecular structural formula of the dichlorosalicylaldehyde thiourea derivative is as shown in the description. The dichlorosalicylaldehyde thiourea derivative disclosed by the invention is applied to the field of positive ion identification, has selective identification capacity on Ti<4+> and has potential application value in the fields of environmental monitoring and the like.
Description
Technical field
The present invention relates to a kind of dichloro-salicylaldehyde's thiourea derivative and the application in cations recognition thereof.
Background technology
Titanium is a kind of rare metal, is widely used in space flight, military project, medical science, automobile, agricultural-food, the field such as jewelry and mobile phone, is described as " contemporary metal " and " strategy metal ", is to improve the indispensable grand strategy goods and materials of defence equipment level.Property that titanium has " one's own thing ", in human body, can resist the corrosion of secretory product and nontoxic, all adapt to any method for disinfection.Titanium is widely distributed in human body, can stimulate phagocytic cell, and immunizing power is strengthened.Therefore, utilizing chemical sensor to titanium ion rapid detection in the environment, is also highly significant.
Summary of the invention
The object of this invention is to provide a kind of dichloro-salicylaldehyde's thiourea derivative and application thereof.
The molecular structural formula of dichloro-salicylaldehyde's thiourea derivative of the present invention is:
。
Above-mentioned dichloro-salicylaldehyde's thiourea derivative is applied in cations recognition field, to Ti
4+there is Selective recognition ability.In fields such as environmental monitorings, there is potential using value.
Accompanying drawing explanation
Fig. 1 is the schematic arrangement of dichloro-salicylaldehyde's thiourea derivative of the present invention.
Fig. 2 is the building-up reactions formula of dichloro-salicylaldehyde's thiourea derivative in the embodiment of the present invention.
Fig. 3 is the fluorescence spectrum figure that dichloro-salicylaldehyde's thiourea derivative that the embodiment of the present invention obtains responds positively charged ion.
Embodiment
Embodiment:
(1) synthesis of dichloro-salicylaldehyde's thiourea derivative
According to following reaction formula synthesis dichloro-salicylaldehyde thiourea derivative:
Concrete steps are:
Use thiocarbanil and O-Phenylene Diamine are 1:1 according to mol ratio, and at 20 DEG C, reaction generates white solid, i.e. intermediate N (2-is amino) phenyl-N-phenylthiourea, and suction filtration also uses washing with alcohol three times, for subsequent use after vacuum-drying; Get 0.7299 gram of intermediate (3 mmole) and be placed in 200 milliliters of there-necked flasks also with 60 milliliters of dissolve with ethanol, water bath with thermostatic control is heated to 60 DEG C, separately take 0.573 gram 3, the chloro-Benzaldehyde,2-hydroxy of 5-bis-(3 mmole) is also dissolved in 25 milliliters of dehydrated alcohols, control temperature is at 60 DEG C, the latter is slowly instilled the former, a large amount of brown precipitates is there is after 0.5 hour, continue reaction 3 hours, suction filtration after standing for some time, and with absolute ethanol washing three times, be placed in vacuum drying oven dry crude product.With the dichloromethane-ethanol mixed solvent recrystallization that volume ratio is 5:1, after drying, obtain dichloro-salicylaldehyde's thiourea derivative.Productive rate: 71.8%.MS-ESI:m/z 413.8 (MH
-); Calcd. Mr:416.32;
1h NMR (500 MHz, DMSO-d
6) δ 14.24 (s, 1H, ArOH), 9.94 (s; 1H, NH), 9.56 (s, 1H; NH), 8.95 (s, 1H, HC=N); 7.77 (s, 2H, ArH), 7.52 ~ 7.30 (m; 8H, ArH), 7.14 (t, J=15 Hz; 1H, ArH), 3.36,2.51 (s, solvent peaks); IR (KBr, ν/cm
-1): 3347,3177,3047,2925,1612 (-C=N), 1592,1521,1496,1472,1454,1347,1289,1258,1230,1199,1176,1105,1039,1027,962,897,879,853,751,739,694,645; Anal.Calcd.for C
20h
15sN
3oCl
2(%): C 57.70, H 3.63, N 10.09, S 7.70; Found:C 57.58, H 3.75, N 10.01, S 7.56.
(2) application of dichloro-salicylaldehyde's thiourea derivative that obtains of the present embodiment
Cations recognition: dichloro-salicylaldehyde's thiourea derivative that the present embodiment is obtained is dissolved in DMF (DMF) solvent, makes its concentration be 1 × 10
-4molL
-1; Metal-salt (vitriol or muriate) being dissolved in volume ratio is in the DMF-distilled water mixed solvent of 4:1, makes its concentration be 1 × 10
-4molL
-1.Altogether select 19 metal ion species, comprised alkalimetal ion: Na
+, K
+, alkaline-earth metal ions: Mg
2+, Ca
2+, Ba
2+, transition metal ion: Ti
4+, Cr
3+,mn
2+, Fe
2+, Fe
3+, Co
2+, Ni
2+, Cu
2+, Zn
2+, Cd
2+, Hg
2+, rare earth ion: Ce
4+, and other metal ion: Al
3+, Pb
2+.
By the DMF solution of above-mentioned obtained dichloro-salicylaldehyde's thiourea derivative and metal salt solution by volume 2:1 be mixed with mixed solution system, and be placed in dark surrounds 24 hours, after question response system reaches balance, the fluorescence emission spectrum carrying out each individual system measures.Fig. 3 is the fluorescence spectrum figure that dichloro-salicylaldehyde's thiourea derivative responds positively charged ion.
From the experimental result of Fig. 3, in 19 kinds of positively charged ions of test, only has Ti
4+show with dichloro-salicylaldehyde's thiourea derivative and significantly respond effect; As shown in Figure 3, when adding Ti
4+after, its fluorescence intensity there occurs significantly and weakens Quenching, reduces 12 ~ 14 times than the fluorescence intensity of simple dichloro-salicylaldehyde's thiourea derivative; Dichloro-salicylaldehyde's thiourea derivative and Ti are described
4+show obvious bonding recognition reaction.Therefore dichloro-salicylaldehyde's thiourea derivative can as a kind of highly selective Ti
4+fluorescent probe, has potential using value in fields such as environmental monitorings.
Claims (2)
1. dichloro-salicylaldehyde's thiourea derivative, is characterized in that the molecular structural formula of this dichloro-salicylaldehyde's thiourea derivative is:
。
2. the application of dichloro-salicylaldehyde's thiourea derivative according to claim 1, is characterized in that described dichloro-salicylaldehyde's thiourea derivative is applied to Ti
4+carry out Selective recognition.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410825815.3A CN104592075A (en) | 2014-12-28 | 2014-12-28 | Dichlorosalicylaldehyde thiourea derivative and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410825815.3A CN104592075A (en) | 2014-12-28 | 2014-12-28 | Dichlorosalicylaldehyde thiourea derivative and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN104592075A true CN104592075A (en) | 2015-05-06 |
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ID=53118182
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|---|---|---|---|
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2702821A (en) * | 1952-01-28 | 1955-02-22 | Ciba Pharm Prod Inc | Di-phenyl-thioureas |
| CN1089257A (en) * | 1993-01-01 | 1994-07-13 | 山道士有限公司 | N-phenylthiourea derivatives and pharmaceutical use thereof |
| CN103159655A (en) * | 2013-03-28 | 2013-06-19 | 桂林理工大学 | Salicylic aldehyde thiourea derivative and application thereof |
| CN103819376A (en) * | 2014-02-20 | 2014-05-28 | 桂林理工大学 | Dichloro salicylaldehyde thiourea derivative and application thereof |
-
2014
- 2014-12-28 CN CN201410825815.3A patent/CN104592075A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2702821A (en) * | 1952-01-28 | 1955-02-22 | Ciba Pharm Prod Inc | Di-phenyl-thioureas |
| CN1089257A (en) * | 1993-01-01 | 1994-07-13 | 山道士有限公司 | N-phenylthiourea derivatives and pharmaceutical use thereof |
| CN103159655A (en) * | 2013-03-28 | 2013-06-19 | 桂林理工大学 | Salicylic aldehyde thiourea derivative and application thereof |
| CN103819376A (en) * | 2014-02-20 | 2014-05-28 | 桂林理工大学 | Dichloro salicylaldehyde thiourea derivative and application thereof |
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Application publication date: 20150506 |