CN108689897A - A kind of preparation method and application of the bigcatkin willow aldehydes schiff base compounds with fluorescent characteristic - Google Patents
A kind of preparation method and application of the bigcatkin willow aldehydes schiff base compounds with fluorescent characteristic Download PDFInfo
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- CN108689897A CN108689897A CN201810669868.9A CN201810669868A CN108689897A CN 108689897 A CN108689897 A CN 108689897A CN 201810669868 A CN201810669868 A CN 201810669868A CN 108689897 A CN108689897 A CN 108689897A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C337/00—Derivatives of thiocarbonic acids containing functional groups covered by groups C07C333/00 or C07C335/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C337/06—Compounds containing any of the groups, e.g. thiosemicarbazides
- C07C337/08—Compounds containing any of the groups, e.g. thiosemicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. thiosemicarbazones
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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Abstract
The preparation method and application of the invention discloses a kind of bigcatkin willow aldehydes schiff base compounds with fluorescent characteristic.Schiff bases I of the present invention issues orange-yellow fluorescence in 365nm purple light light irradiations, product is dissolved in respectively after water and ethyl alcohol uses 365nm purple light light irradiation unstressed configurations again, there is blue-fluorescence after triethanolamine is added, aqueous solution, which is added after sodium sulphate and potassium sulfate, the unstressed configurations phenomenon such as has fluorescent emission phenomenon, and the sodium phosphates such as sodium chloride is added occur.Unstressed configuration under product Schiff base II ultraviolet lamps is dissolved in unstressed configuration after water, but has blue-green fluorescent under 365nm ultraviolet lights after aqueous solution addition triethanolamine;Sodium sulphate or potassium sulfate is added fluorescence generation under 365nm ultraviolet lights.As it can be seen that the schiff bases with photoluminescent property prepared by the method for the present invention has a fluorescence response to sulfate and triethanolamine in aqueous solution, fluorescence is strong under 365nm ultraviolet lights.
Description
Technical field
The preparation method and application of the present invention relates to a kind of bigcatkin willow aldehydes schiff base compounds with fluorescent characteristic.
Background technology
Schiff bases compound has important answer in medicine, catalysis, analytical chemistry, corrosion and photochromic field
With, and aromatic ring class schiff bases has better chemical property, such as fluorescent characteristic, electrochemical catalysis characteristic compared with other type schiff bases
Deng, schiff bases is used for detecting and differentiating the content of metal ion and quantitative analysis metal ion as ligand in analytical chemistry,
And reach the quantitative analysis to certain ions, such as Chinese patent by means such as chromatography, fluorescence analysis, photometric analysis
(CN102584700A, a kind of bigcatkin willow aldehydes schiff bases and its preparation method and application) reports diazanyl naphthalene derivatives combination bigcatkin willow
Fluorescence response of the schiff bases that aldehyde obtains to copper ion.The synthesis of bigcatkin willow aldehyde radical schiff bases with fluorescent characteristic is just gradually applied
In chemical sensor, hot topic is become to the synthesis and performance test of such compound.
Sulfate is widely present in water body and air, and work is played in the generation of metabolism and atmospheric aerosol to plant
With the chemiluminescence detection to it is a research topic explored always.The common method of sulfate radical is measured at present
There are ion chromatography, barium sulfategravimetry, turbidimetry, volumetric method, barium chromate and spectrophotometry etc., the side of fluoroscopic examination sulfate radical
The still rare report of method.The report that Schiff bases fluorescent material is synthesized using salicylide as substrate has repeatedly been applied for a patent, but majority is
Study the fluorescent characteristic of complex, the substance equally to organic matter, as aniline have fluorescence response (CN101619032A, one
Class schiff base compounds and its detection amino benzenes compounds), but such compound structure is complicated, and synthesis difficulty is big.Therefore it looks for
To it is a kind of it is simple in structure, can easy synthesis the schiff base of salicylaldehyde with fluorescence detection function, be the direction studied at present.
Invention content
The present invention is intended to provide a kind of preparation method and application of the bigcatkin willow aldehydes schiff base compounds with fluorescent characteristic.
The above-mentioned purpose of the present invention is achieved by following technical solution:
A kind of preparation method of schiff bases I, reacts preparation with semicarbazides with salicylide in ethanol solution;
Preparation route is as follows:
Preferably, above-mentioned preparation method specifically comprises the following steps:With 1.0mol/L NaOH solutions by 2.12g
(0.019mol) semicarbazide hydrochloride pH is adjusted to 7;10ml absolute ethyl alcohols, 2ml (0.019mol) salicylides are pipetted with pipette and are mixed
It closes;Above-mentioned two solution is mixed in 100ml round-bottomed flasks, electromagnetic agitation, reflux about 3h in 80 DEG C of thermostatical oil domains;Reaction is burnt
Bottle moves into the large beaker equipped with 400ml ice water and product is precipitated, absolute ethyl alcohol washs, filter, product is placed in culture dish, is close
Envelope moves into drying box drying.
Schiff bases I is used to prepare the purposes for the material for having fluorescence response to sulfate radical or triethanolamine class compound.
A kind of preparation method of schiff bases II is prepared with salicylide and thiosemicarbazides reaction;
Preparation route is as follows:
Preferably, above-mentioned preparation method specifically comprises the following steps:10mL absolute ethyl alcohols and 2mL salicylides are mixed in
In 100mL round-bottomed flasks, 1.73g thiosemicarbazides is added, the electromagnetic agitation back flow reaction 3 hours in 80 DEG C of thermostatical oil domain pots;3
As a child stopped that yellow liquid is obtained by the reaction afterwards, round-bottomed flask is moved into cold water, product is precipitated, is filtered, then absolute ethyl alcohol
Washing, it is dry.
Schiff bases II is used to prepare the purposes for the material for having fluorescence response to sulfate radical or triethanolamine class compound.
Advantageous effect:
Schiff bases with photoluminescent property prepared by the method for the present invention in aqueous solution has sulfate and triethanolamine
Fluorescence response, fluorescence is strong under 365nm ultraviolet lights.
Description of the drawings
Fig. 1 is the fluorescence emission spectrum that triethanolamine is added in schiff bases I aqueous solutions;
Fig. 2 is the fluorescence emission spectrum that sodium sulphate is added in schiff bases I aqueous solutions;
Fig. 3 is the fluorescence emission spectrum that potassium sulfate is added in schiff bases I aqueous solutions;
Fig. 4 is the fluorescence emission spectrum that sodium sulphate is added in schiff bases II aqueous solutions;
Fig. 5 is the fluorescence emission spectrum that potassium sulfate is added in schiff bases II aqueous solutions;
Fig. 6 is the fluorescence emission spectrum that triethanolamine is added in schiff bases II aqueous solutions.
Specific implementation mode
It is specific with reference to the accompanying drawings and examples to introduce essentiality content of the present invention, but the guarantor of the present invention is not limited with this
Protect range.
The synthesis of 1 schiff bases I
2.12g (0.019mol) semicarbazide hydrochlorides pH is adjusted to 7 with 1.0mol/L NaOH solutions;It is pipetted with pipette
10ml absolute ethyl alcohols, 2ml (0.019mol) salicylides simultaneously mix;Above-mentioned two solution is mixed in 100ml round-bottomed flasks, at 80 DEG C
Electromagnetic agitation, reflux about 3h in thermostatical oil domain.Reaction flask is moved into, product, nothing are precipitated in the large beaker equipped with 400ml ice water
Water-ethanol washing, suction filtration, product are placed in culture dish, seal, move into drying box, obtain white powdery solids product 3.20g, manage
By yield 3.40g, yield 94.1%.1H NMR(CDCl3, 500MHz), δ:10.18 (s, 1H, OH), 9.96 (s, 1H ,-NH-),
8.14 (s, 1H ,-CH=N-), 7.75 (m, 1H, Ar), 7.15 (m, 1H, Ar), 6.82 (d, 2H, Ar), 6.40 (s, 2H ,-NH2).
Infrared spectrum:3490(NH2Stretching vibration), 2920-3270 (stretching vibration of hydroxyl stretching vibration and phenyl ring), 1600-1700
(- C=O stretching vibrations), 1260 (stretching vibrations of benzene-C-O- keys), 700 (bending vibrations of-C-H- keys on phenyl ring).
It is reacted in ethanol solution with semicarbazides with salicylide first, obtains schiff bases I, it is true to carry out instrumental characterizing to product
Determine structure, which is white solid, issues orange-yellow fluorescence in 365nm purple light light irradiations, product is dissolved in water and ethyl alcohol respectively
It uses 365nm purple light light irradiation unstressed configurations again afterwards, has blue-fluorescence (such as Fig. 1), aqueous solution that sodium sulphate is added after triethanolamine is added
And have fluorescent emission phenomenon after potassium sulfate, such as Fig. 2 and Fig. 3, and the sodium phosphates such as sodium chloride are added etc. unstressed configurations phenomenon occur.
The synthesis of 2 schiff bases II
10mL absolute ethyl alcohols and 2mL salicylides are mixed in 100mL round-bottomed flasks, 1.73g thiosemicarbazides is added,
Electromagnetic agitation back flow reaction 3 hours in 80 DEG C of thermostatical oil domain pots.3 as a child stopped that yellow liquid is obtained by the reaction afterwards, and round bottom is burnt
Bottle moves into cold water, and product is precipitated, and filters, and then absolute ethyl alcohol washs, and is dried to obtain yellow powder solid product.
1H NMR (CDCl3,500MHz), δ:11.38 (s, 1H, OH), 9.88 (s, 1H ,-NH-), 8.37 (s, 1H ,-CH=
N-), 8.05 (d, 1H, Ar), 7.95 (s, 2H ,-NH2), 7.20 (m, 1H, Ar), 6.82 (m, 2H, Ar).
Product Schiff base II is yellow solid product, unstressed configuration under ultraviolet lamp, is dissolved in unstressed configuration after water, but aqueous solution is added
There is blue-green fluorescent such as Fig. 4 after triethanolamine under 365nm ultraviolet lights;Sodium sulphate or potassium sulfate is added in 365nm ultraviolet lights
Under there is fluorescence to generate such as Fig. 5 and Fig. 6.
The measurement of 3 sample Ultraluminescence spectrum
Three kinds of schiff bases are configured to the solution of 50um/L concentration, Cary Eclipse Fluorescence Spectrometer test its
Fluorescent emission under 363nm ultraviolet lights.
The effect of above-described embodiment is specifically to introduce the essentiality content of the present invention, but those skilled in the art should know
Protection scope of the present invention should not be confined to the specific embodiment by road.
Claims (6)
1. a kind of preparation method of schiff bases I, it is characterised in that:Preparation is reacted in ethanol solution with semicarbazides with salicylide;
Preparation route is as follows:
2. preparation method according to claim 1, which is characterized in that specifically comprise the following steps:Use 1.0mol/LNaOH
2.12g (0.019mol) semicarbazide hydrochlorides pH is adjusted to 7 by solution;10ml absolute ethyl alcohols, 2ml (0.019mol) are pipetted with pipette
Salicylide simultaneously mixes;Above-mentioned two solution is mixed in 100ml round-bottomed flasks, in 80 DEG C of thermostatical oil domains electromagnetic agitation, reflux about
3h;Reaction flask is moved into the large beaker equipped with 400ml ice water, product is precipitated, absolute ethyl alcohol washs, filter, product is placed in training
It supports in ware, sealing, move into drying box drying.
3. schiff bases I is used to prepare the purposes for the material for having fluorescence response to sulfate radical or triethanolamine class compound.
4. a kind of preparation method of schiff bases II, it is characterised in that:It is prepared with salicylide and thiosemicarbazides reaction;
Preparation route is as follows:
5. preparation method according to claim 4, which is characterized in that specifically comprise the following steps:By 10mL absolute ethyl alcohols
It is mixed in 100mL round-bottomed flasks with 2mL salicylides, adds 1.73g thiosemicarbazides, electromagnetism stirs in 80 DEG C of thermostatical oil domain pots
Mix back flow reaction 3 hours;3 as a child stopped that yellow liquid is obtained by the reaction afterwards, and round-bottomed flask is moved into cold water, product is precipitated,
It filters, then absolute ethyl alcohol washs, dry.
6. schiff bases II is used to prepare the purposes for the material for having fluorescence response to sulfate radical or triethanolamine class compound.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109824918A (en) * | 2019-03-06 | 2019-05-31 | 南京林业大学 | A kind of nano-cellulose-salicylaldehyde salicyloylhydrazone-polyvinyl alcohol hydrogel fluorescence probe and its preparation method and application |
| CN112023945A (en) * | 2020-09-01 | 2020-12-04 | 广州大学 | Preparation method of mesoporous carbon-based electrocatalyst |
| CN112117469A (en) * | 2020-09-10 | 2020-12-22 | 广州大学 | Foamed nickel electrocatalyst and preparation method thereof |
| CN113651741A (en) * | 2021-07-06 | 2021-11-16 | 许昌学院 | Thiourea Schiff base, preparation method thereof and Zn serving as same2+、Al3+Application of fluorescent probe |
| CN115974728A (en) * | 2022-12-29 | 2023-04-18 | 陕西科技大学 | Synthesis of phenyl semicarbazone and identification of hexavalent chromium ions by phenyl semicarbazone |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107337950A (en) * | 2017-07-21 | 2017-11-10 | 南京信息工程大学 | Fluorescent paint and preparation method thereof made of bigcatkin willow aldehydes schiff bases |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107337950A (en) * | 2017-07-21 | 2017-11-10 | 南京信息工程大学 | Fluorescent paint and preparation method thereof made of bigcatkin willow aldehydes schiff bases |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109824918A (en) * | 2019-03-06 | 2019-05-31 | 南京林业大学 | A kind of nano-cellulose-salicylaldehyde salicyloylhydrazone-polyvinyl alcohol hydrogel fluorescence probe and its preparation method and application |
| CN109824918B (en) * | 2019-03-06 | 2021-06-01 | 南京林业大学 | Nano-cellulose-salicylaldehyde thiosemicarbazone-polyvinyl alcohol hydrogel fluorescent probe and preparation method and application thereof |
| CN112023945A (en) * | 2020-09-01 | 2020-12-04 | 广州大学 | Preparation method of mesoporous carbon-based electrocatalyst |
| CN112023945B (en) * | 2020-09-01 | 2022-07-05 | 广州大学 | Preparation method of mesoporous carbon-based electrocatalyst |
| CN112117469A (en) * | 2020-09-10 | 2020-12-22 | 广州大学 | Foamed nickel electrocatalyst and preparation method thereof |
| CN113651741A (en) * | 2021-07-06 | 2021-11-16 | 许昌学院 | Thiourea Schiff base, preparation method thereof and Zn serving as same2+、Al3+Application of fluorescent probe |
| CN115974728A (en) * | 2022-12-29 | 2023-04-18 | 陕西科技大学 | Synthesis of phenyl semicarbazone and identification of hexavalent chromium ions by phenyl semicarbazone |
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