CN104557645A - Dibromosalicylaldehyde thiourea derivative and application thereof - Google Patents
Dibromosalicylaldehyde thiourea derivative and application thereof Download PDFInfo
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- CN104557645A CN104557645A CN201410825816.8A CN201410825816A CN104557645A CN 104557645 A CN104557645 A CN 104557645A CN 201410825816 A CN201410825816 A CN 201410825816A CN 104557645 A CN104557645 A CN 104557645A
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- dibromosalicylaldehyde
- thiourea derivative
- application
- thiourea
- derivative
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Abstract
The invention discloses a dibromosalicylaldehyde thiourea derivative and application thereof. The molecular structure of the dibromosalicylaldehyde thiourea derivative is shown in the Specification; the dibromosalicylaldehyde thiourea derivative is applied to the field of cation recognition, and has selectivity recognizability for Ti<4+>. The dibromosalicylaldehyde thiourea derivative has a potential application value in the fields of environmental monitoring and the like.
Description
Technical field
The present invention relates to a kind of Dibromosalicylaldehyde 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 Dibromosalicylaldehyde thiourea derivative and application thereof.
The molecular structural formula of Dibromosalicylaldehyde thiourea derivative of the present invention is:
。
Above-mentioned Dibromosalicylaldehyde 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 Dibromosalicylaldehyde thiourea derivative of the present invention.
Fig. 2 is the building-up reactions formula of Dibromosalicylaldehyde thiourea derivative in the embodiment of the present invention.
Fig. 3 is the fluorescence spectrum figure that Dibromosalicylaldehyde thiourea derivative that the embodiment of the present invention obtains responds positively charged ion.
Embodiment
Embodiment:
(1) synthesis of Dibromosalicylaldehyde thiourea derivative
According to following reaction formula synthesis Dibromosalicylaldehyde 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 1.2165 grams of intermediates (5 mmole) and be placed in 200 milliliters of there-necked flasks also by 80 milliliters of dehydrated alcohol heating for dissolving, water bath with thermostatic control is heated to 65 DEG C, separately take 1.3995 gram 3, the bromo-Benzaldehyde,2-hydroxy of 5-bis-(5 mmole) is also dissolved in 25 milliliters of dehydrated alcohols, the latter is slowly instilled the former at 65 DEG C by control temperature, a large amount of brown color precipitations 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 4:1, Dibromosalicylaldehyde thiourea derivative is obtained after drying.Productive rate: 76.8%.mp: 173~175 oC, MS-ESI：m/z 503.6 (MH
-)；Calcd. Mr：505.22；
1H NMR (500 MHz, DMSO-d
6) δ 14.39 (s, 1H, OH), 9.90 (s, 1H, NH), 9.51 (s, 1H, NH), 8.92 (s, 1H, HC=N), 7.92 (dd, J1 = 20.7 Hz, J2 = 20.4 Hz, 2H, ArH), 7.47 (d, J = 13.4 Hz, 4H, ArH), 7.35~7.41 (m, 2H, ArH ), 7.31 (t, J = 12.95 Hz, 2H, ArH), 7.13 (t, J = 12.2 Hz, 1H, ArH) ; IR(KBr，ν/cm
-1): 3343, 3143, 3062, 2945, 1611(-C=N), 1591, 1521, 1446, 1348, 1291, 1261, 1231, 1200, 1157, 1104, 1026, 973, 943, 866, 827, 755, 739, 695, 633；Anal.Calcd.for C
20H
15SN
3OBr
2(%): C 47.55, H 2.99, N 8.32, S 6.35; found: C 47.32, H 3.12, N 8.24, S 6.20。
(2) application of Dibromosalicylaldehyde thiourea derivative that obtains of the present embodiment
Cations recognition: the Dibromosalicylaldehyde 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 Dibromosalicylaldehyde 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 Dibromosalicylaldehyde 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 Dibromosalicylaldehyde 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 Dibromosalicylaldehyde thiourea derivative; Dibromosalicylaldehyde thiourea derivative and Ti are described
4+show obvious bonding recognition reaction.Therefore Dibromosalicylaldehyde 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. a Dibromosalicylaldehyde thiourea derivative, is characterized in that the molecular structural formula of this Dibromosalicylaldehyde thiourea derivative is:
。
2. the application of Dibromosalicylaldehyde thiourea derivative according to claim 1, is characterized in that described Dibromosalicylaldehyde thiourea derivative is applied to Ti
4+carry out Selective recognition.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410825816.8A CN104557645A (en) | 2014-12-28 | 2014-12-28 | Dibromosalicylaldehyde thiourea derivative and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410825816.8A CN104557645A (en) | 2014-12-28 | 2014-12-28 | Dibromosalicylaldehyde thiourea derivative and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN104557645A true CN104557645A (en) | 2015-04-29 |
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ID=53074824
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105675557A (en) * | 2016-01-07 | 2016-06-15 | 济南大学 | New method for detecting content of thiourea based on benzyne fluorescent reagent |
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 |
| CN103130695A (en) * | 2013-03-24 | 2013-06-05 | 桂林理工大学 | Thiourea schiff base derivative and application thereof |
| CN103159655A (en) * | 2013-03-28 | 2013-06-19 | 桂林理工大学 | Salicylic aldehyde thiourea derivative and application thereof |
-
2014
- 2014-12-28 CN CN201410825816.8A patent/CN104557645A/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 |
| CN103130695A (en) * | 2013-03-24 | 2013-06-05 | 桂林理工大学 | Thiourea schiff base derivative and application thereof |
| CN103159655A (en) * | 2013-03-28 | 2013-06-19 | 桂林理工大学 | Salicylic aldehyde thiourea derivative and application thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105675557A (en) * | 2016-01-07 | 2016-06-15 | 济南大学 | New method for detecting content of thiourea based on benzyne fluorescent reagent |
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Application publication date: 20150429 |