CN104370770A - Bromosalicylaldehyde-based bis-schiff base and use thereof - Google Patents
Bromosalicylaldehyde-based bis-schiff base and use thereof Download PDFInfo
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- CN104370770A CN104370770A CN201410519051.5A CN201410519051A CN104370770A CN 104370770 A CN104370770 A CN 104370770A CN 201410519051 A CN201410519051 A CN 201410519051A CN 104370770 A CN104370770 A CN 104370770A
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- Prior art keywords
- bromo
- aldehyde radical
- schiff bases
- bigcatkin willow
- bromosalicylaldehyde
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Abstract
The invention discloses a bromosalicylaldehyde-based bis-schiff base and a use thereof. The bromosalicylaldehyde-based bis-schiff base has a molecular structural formula shown in the following description, can be used in the field of cation recognition and has a Co<2+> selective recognition capability. The bromosalicylaldehyde-based bis-schiff base has obvious bonding identification effects on Co<2+> and has a latent application value in the field of environment monitoring.
Description
Technical field
The present invention relates to a kind of bromo bigcatkin willow aldehyde radical Bis-Schiff Bases and the application in cations recognition field thereof.
Background technology
Cobalt metal has widespread use in magneticsubstance, plating, glass, dyeing, medicine medical treatment etc., has potential meaning to the research of its related direction such as colorimetric sensor and title complex.Therefore, the chemical sensor developing the concentration of cobalt ions that can measure quickly and accurately in environment in actual life has great importance to environment measuring.
Summary of the invention
The object of this invention is to provide a kind of bromo bigcatkin willow aldehyde radical Bis-Schiff Bases and application thereof.
The molecular structural formula of bromo bigcatkin willow aldehyde radical Bis-Schiff Bases of the present invention is:
。
Above-mentioned bromo bigcatkin willow aldehyde radical Bis-Schiff Bases is applied in cations recognition field, to Co
2+there is Selective recognition ability.
Bromo bigcatkin willow aldehyde radical Bis-Schiff Bases of the present invention is to Co
2+there is obvious bonding recognition reaction, in fields such as environmental monitorings, there is potential using value.
Accompanying drawing explanation
Fig. 1 is the schematic arrangement of bromo bigcatkin willow aldehyde radical Bis-Schiff Bases of the present invention.
Fig. 2 is the building-up reactions formula of bromo bigcatkin willow aldehyde radical Bis-Schiff Bases in the embodiment of the present invention.
Fig. 3 is that the obtained bromo bigcatkin willow aldehyde radical Bis-Schiff Bases of the embodiment of the present invention is to cationic response fluorescence spectrum figure.
Embodiment
embodiment:
(1) synthesis of bromo bigcatkin willow aldehyde radical Bis-Schiff Bases
According to following reaction formula synthetic bromide for bigcatkin willow aldehyde radical Bis-Schiff Bases:
。
Concrete steps are:
2 mmoles 3 are added in the there-necked flask of 50 milliliters, the bromo-Benzaldehyde,2-hydroxy of 5-bis-(0.5598 gram) and 20 milliliters of dehydrated alcohols, after dissolving completely, stir, control temperature is at 8 ~ 10 DEG C of low-temp reactions, at the uniform velocity drip the mixing solutions of 1 mmole quadrol and 5 milliliters of dehydrated alcohols again, stirring reaction is continued 1 hour after dripping, leave standstill suction filtration after 0.5 hour and wash twice respectively with dehydrated alcohol and anhydrous diethyl ether, with dehydrated alcohol-anhydrous methanol mixed solvent recrystallization that volume ratio is 3:1, in the vacuum drying oven that the faint yellow powder crystal obtained is placed on 40 DEG C dry 24 hours for subsequent use, be bromo bigcatkin willow aldehyde radical Bis-Schiff Bases.
The performance of the bromo bigcatkin willow aldehyde radical Bis-Schiff Bases that the present embodiment obtains is as follows:
Solubility property: be soluble in methyl-sulphoxide (DMSO), DMF (DMF) organic solvent, be slightly soluble in the common solvents such as ethanol, methyl alcohol, ether.Productive rate: 87%, m.p. 172.0 ~ 173.0 ° of C. MS, m/z:582.67 (M-);
1h NMR (500 MHz, DMSO-d
6) δ 8.58 (s, 2H, HC=N), 7.73 (s, 4H, ArH), 3.99 (s, 2H, OH), 3.36 (s, 4H, CH2), 2.51 (t, J=5 Hz, solvent peaks); IR (KBr, ν/cm-1): 3430,3072,2921,2855,1636 (-C=N), 1597,1445,1363,1288,1214,1161,1036,867,688; Anal.Calcd.for C
16h
12br
4n
2o
2(%): C 32.92, H 2.07, N 4.80; Found:C 32.91, H 2.09, N 4.84.
(2) application of bromo bigcatkin willow aldehyde radical Bis-Schiff Bases that obtains of the present embodiment
Cations recognition: the bromo bigcatkin willow aldehyde radical Bis-Schiff Bases that the present embodiment is obtained is dissolved in DMF (DMF) solvent, makes its concentration be 1 × 10
-5molL
-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
-5molL
-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 bromo bigcatkin willow aldehyde radical Bis-Schiff Bases 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 that bromo bigcatkin willow aldehyde radical Bis-Schiff Bases is to cationic response fluorescence spectrum figure.
From the experimental result of Fig. 3, in 19 kinds of positively charged ions of test, only has Co
2+show with bromo bigcatkin willow aldehyde radical Bis-Schiff Bases and significantly respond effect; As shown in Figure 3, when adding Co
2+after, its fluorescence intensity there occurs significantly and weakens Quenching, reduces 14 times than the fluorescence intensity of simple bromo bigcatkin willow aldehyde radical Bis-Schiff Bases; Bromo bigcatkin willow aldehyde radical Bis-Schiff Bases and Co are described
2+show obvious bonding recognition reaction.Therefore bromo bigcatkin willow aldehyde radical Bis-Schiff Bases can as a kind of highly selective Co
2+fluorescent probe, has potential using value in fields such as environmental monitorings.
Claims (2)
1. a bromo bigcatkin willow aldehyde radical Bis-Schiff Bases, is characterized in that the molecular structural formula of this bromo bigcatkin willow aldehyde radical Bis-Schiff Bases is:
。
2. the application of bromo bigcatkin willow aldehyde radical Bis-Schiff Bases according to claim 1, is characterized in that described bromo bigcatkin willow aldehyde radical Bis-Schiff Bases is applied to Co
2+carry out Selective recognition.
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|---|---|---|---|
| CN201410519051.5A CN104370770A (en) | 2014-10-06 | 2014-10-06 | Bromosalicylaldehyde-based bis-schiff base and use thereof |
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|---|---|---|---|
| CN201410519051.5A CN104370770A (en) | 2014-10-06 | 2014-10-06 | Bromosalicylaldehyde-based bis-schiff base and use thereof |
Publications (1)
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|---|---|
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106632290A (en) * | 2016-11-16 | 2017-05-10 | 淮阴师范学院 | Benzoate compound and synthesis method and application thereof |
| CN106928090A (en) * | 2017-03-29 | 2017-07-07 | 齐鲁工业大学 | Two（4 methoxybenzylidenes）The preparation and use of the diamines of propane 1,3 |
| CN106946735A (en) * | 2017-03-29 | 2017-07-14 | 齐鲁工业大学 | Two（4 methoxybenzylidenes）The preparation and use of the diamines of dodecane 1,12 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102786533A (en) * | 2011-05-18 | 2012-11-21 | 苏州大学 | Helicene analogs and preparation method thereof |
-
2014
- 2014-10-06 CN CN201410519051.5A patent/CN104370770A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102786533A (en) * | 2011-05-18 | 2012-11-21 | 苏州大学 | Helicene analogs and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| S.B.CHAVAN等: "Synthesis of New Bis-Schiff bases via environmentally benign grindstone technique", 《DER PHARMA CHEMICA》, vol. 2, no. 6, 31 December 2010 (2010-12-31), pages 139 - 143 * |
| ZHENGLIANG LU等: "Syntheses, Crystal Structures, and Magnetic Characterization of Five New Dimeric Manganese(III) Tetradentate Schiff Base Complexes Exhibiting Single-Molecule-Magnet Behavior", 《INORGANIC CHEMISTRY》, vol. 45, no. 9, 31 December 2006 (2006-12-31), pages 3538 - 3548 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106632290A (en) * | 2016-11-16 | 2017-05-10 | 淮阴师范学院 | Benzoate compound and synthesis method and application thereof |
| CN106632290B (en) * | 2016-11-16 | 2019-09-27 | 淮阴师范学院 | A kind of benzoate compounds and its synthetic method and application |
| CN106928090A (en) * | 2017-03-29 | 2017-07-07 | 齐鲁工业大学 | Two（4 methoxybenzylidenes）The preparation and use of the diamines of propane 1,3 |
| CN106946735A (en) * | 2017-03-29 | 2017-07-14 | 齐鲁工业大学 | Two（4 methoxybenzylidenes）The preparation and use of the diamines of dodecane 1,12 |
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Application publication date: 20150225 |