CN102911111B - Carbazole benzaldehyde-p-phenylenediamine bi-schiff base and preparation method thereof - Google Patents
Carbazole benzaldehyde-p-phenylenediamine bi-schiff base and preparation method thereof Download PDFInfo
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- CN102911111B CN102911111B CN201210443685.8A CN201210443685A CN102911111B CN 102911111 B CN102911111 B CN 102911111B CN 201210443685 A CN201210443685 A CN 201210443685A CN 102911111 B CN102911111 B CN 102911111B
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- phenyl aldehyde
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- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 239000002262 Schiff base Substances 0.000 title abstract description 5
- IJRLYKKENQLDEK-UHFFFAOYSA-N benzaldehyde benzene-1,4-diamine 9H-carbazole Chemical compound C1(=CC=C(C=C1)N)N.C(C1=CC=CC=C1)=O.C1=CC=CC=2C3=CC=CC=C3NC12 IJRLYKKENQLDEK-UHFFFAOYSA-N 0.000 title abstract 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims abstract description 43
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 239000007850 fluorescent dye Substances 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- -1 carbazole phenyl aldehyde Chemical class 0.000 claims description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 239000000843 powder Substances 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 238000001953 recrystallisation Methods 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 238000000034 method Methods 0.000 abstract description 3
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 abstract description 2
- 238000000746 purification Methods 0.000 abstract description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 abstract 1
- 125000003172 aldehyde group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000006482 condensation reaction Methods 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 239000002585 base Substances 0.000 description 33
- 229910021645 metal ion Inorganic materials 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 229940125904 compound 1 Drugs 0.000 description 9
- 238000011160 research Methods 0.000 description 5
- 238000001291 vacuum drying Methods 0.000 description 5
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- QBKSWRVVCFFDOT-UHFFFAOYSA-N gossypol Chemical compound CC(C)C1=C(O)C(O)=C(C=O)C2=C(O)C(C=3C(O)=C4C(C=O)=C(O)C(O)=C(C4=CC=3C)C(C)C)=C(C)C=C21 QBKSWRVVCFFDOT-UHFFFAOYSA-N 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 150000004753 Schiff bases Chemical class 0.000 description 2
- QHOPXUFELLHKAS-UHFFFAOYSA-N Thespesin Natural products CC(C)c1c(O)c(O)c2C(O)Oc3c(c(C)cc1c23)-c1c2OC(O)c3c(O)c(O)c(C(C)C)c(cc1C)c23 QHOPXUFELLHKAS-UHFFFAOYSA-N 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229930000755 gossypol Natural products 0.000 description 2
- 229950005277 gossypol Drugs 0.000 description 2
- 150000001455 metallic ions Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- QGJXVBICNCIWEL-UHFFFAOYSA-N 9-ethylcarbazole-3-carbaldehyde Chemical compound O=CC1=CC=C2N(CC)C3=CC=CC=C3C2=C1 QGJXVBICNCIWEL-UHFFFAOYSA-N 0.000 description 1
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
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Abstract
本发明涉及一种咔唑苯甲醛缩对苯二胺双席夫碱及其制备方法。以对苯二胺与咔唑、对氟苯甲醛为原料，通过醛基与伯胺的缩合反应，得到了一种具有共轭结构的双席夫碱。该工艺合成成本低，产率高，反应条件温和，产品易于纯化。因为该化合物具有共轭、刚性平面结构，所以表现出了较强的荧光性能，Cu2+对化合物的荧光具有很强的增强作用，可以作为Cu2+荧光探针，应用于荧光探针领域。The invention relates to a carbazole benzaldehyde p-phenylenediamine bis-Schiff base and a preparation method thereof. Using p-phenylenediamine, carbazole, and p-fluorobenzaldehyde as raw materials, a bis-Schiff base with a conjugated structure was obtained through the condensation reaction of aldehyde groups with primary amines. The process has the advantages of low synthesis cost, high yield, mild reaction conditions and easy purification of products. Because the compound has a conjugated and rigid planar structure, it exhibits strong fluorescence properties. Cu 2+ has a strong enhancement effect on the fluorescence of the compound. It can be used as a Cu 2+ fluorescent probe in the field of fluorescent probes .
Description
Technical field:
The present invention relates to two Schiff's base of a kind of carbazole phenyl aldehyde contracting Ursol D and preparation method thereof, this Schiff's base has good fluorescence property, and can complexation of metal ions, can be used as metal-ion fluorescent probe.
Background technology:
Carbazole is an electron rich virtue heterocycle, has good electron conjugated plane, is therefore the first-selected parent nucleus of many fluorescent chemicalses.In addition, carbazole ring is easy to carry out structural modification, and therefore, carbazole and derivative thereof have been furtherd investigate as optical material and Application and Development in addition.
Schiff's base refers to the compound that a class contains C=N group, on N atom, has lone-pair electron, makes Schiff's base become the important organic ligand of a class.If can research and develop a kind of Schiff's base with fluorescence property, due to Schiff's base can with metallic ion coordination, so with the variation due to its space structure of the Schiff's base of metallic ion coordination, its fluorescence property also can change thereupon, therefore just can follow the trail of by the variation of Schiff's base fluorescence property some behavioural characteristic of metal ion.Here it is in recent years, studies hotter metal-ion fluorescent probe.And about the research of this problem, people have made extensive work.For example, have investigator to utilize N-ethyl carbazole-3-formaldehyde and quadrol to synthesize N-ethyl carbazole schiff base compounds for raw material, and studied the impact of each metal ion species on its fluorescence property, result shows Cu
2+its fluorescence of quencher effectively, can be used as and survey Cu
2+fluorescent probe [functional materials, 2011,9 (42): 1588-1590].In addition, numerous investigators have also done large quantity research for other some metal-ion fluorescent probes, such as Zn
2+, Ni
2+, Co
2+etc..
Schiff base metal ion fluorescence probe has a good application prospect because of it, and investigators have done a large amount of research work.But, owing to thering is the shortcomings such as the fluorescence property of shortage, fluorescence Schiff's base of fluorescence Schiff's base of novel texture is bad, restricted to a certain extent the use of Schiff's base fluorescent probe.For these problems, the invention provides the two Schiff's base of a kind of new carbazole phenyl aldehyde contracting Ursol D, this Schiff's base has good fluorescent emission in solution.Through retrieval, this schiff base structure has no relevant report.
Summary of the invention:
The object of the invention is for the deficiencies in the prior art, provide a kind of new carbazole phenyl aldehyde contracting phenylenediamine two Schiff's base, this Schiff's base has good fluorescence performance, can be used as metal-ion fluorescent probe.And this technique has, and cost is low, easy and simple to handle, mild condition, productive rate advantages of higher.
Another object of the present invention is to provide the preparation method of the two Schiff's base of described carbazole phenyl aldehyde contracting Ursol D.
Another object of the present invention is to provide the application of the two Schiff's base of described carbazole phenyl aldehyde contracting Ursol D.
In order to realize such object, in technical scheme of the present invention, adopting carbazole and p-Fluorobenzenecarboxaldehyde is that raw material has been prepared carbazole phenyl aldehyde, utilizing again carbazole phenyl aldehyde and cheap Ursol D is raw material, has obtained the two Schiff's base of a kind of carbazole phenyl aldehyde contracting phenylenediamine.
The present invention is achieved by the following measures:
The two Schiff's base of new carbazole phenyl aldehyde contracting Ursol D that the present invention relates to, its chemical structure is as follows:
The reaction principle of preparation formula of the present invention (I) compound is as follows:
(1) preparation of carbazole phenyl aldehyde
(2) preparation of the two Schiff's base of carbazole phenyl aldehyde contracting phenylenediamine
The method of preparation formula of the present invention (I) compound is as follows:
(1) preparation of carbazole phenyl aldehyde
Carbazole phenyl aldehyde is prepared according to bibliographical information.
(2) preparation of the two Schiff's base of carbazole phenyl aldehyde contracting phenylenediamine
Take a certain amount of carbazole phenyl aldehyde and be dissolved in solvent, start stirring, until carbazole phenyl aldehyde all dissolves, add a certain amount of Ursol D, add appropriate weak acid, temperature control is at 50 ~ 100 DEG C, reaction for some time, has obtained yellow Schiff's base powder, and powder is selected suitable solvent recrystallization, obtained pure Schiff's base, vacuum-drying obtain product.
Concrete steps are as follows:
1) take carbazole phenyl aldehyde and be dissolved in solvent, the mol ratio of carbazole phenyl aldehyde and solvent is 1:10 ~ 1:100;
2) take Ursol D and be dissolved in the solution described in step 1), the mol ratio of Ursol D and carbazole phenyl aldehyde is 1:2 ~ 1:8;
3) measuring a certain amount of weak acid and add step 2) in described solution, the consumption of weak acid is 1 ~ 8d;
4) start stirring and start reaction, isothermal reaction 2 ~ 12h at 50 ~ 75 DEG C, has obtained yellow Schiff's base powder, and powder is selected suitable solvent recrystallization, obtains sterling.
Preferably, solvent is methyl alcohol, ethanol or acetone.
Preferably, weak acid is formic acid or acetic acid.
Preferably, recrystallization solvent used is ethanol, chloroform or methylene dichloride.
The present invention reacts carbazole phenyl aldehyde with cheap Ursol D, obtained a kind of new compound, and after tested, these compounds all have good fluorescent emission, and can be used as Cu
2+fluorescent probe (the results are shown in accompanying drawing).
Compound of the present invention, can be used as fluorescent probe and is applied to probe field.
Embodiment:
Technical scheme for a better understanding of the present invention, below is described in further detail by specific embodiment.
Embodiment 1:
Taking carbazole phenyl aldehyde 0.54g (0.002mol) is dissolved in 30ml methyl alcohol, start stirring, until carbazole phenyl aldehyde all dissolves, add Ursol D 0.1g (0.001mol), add 1d formic acid, temperature control is at 60 DEG C, and reaction 2h, has obtained yellow Schiff's base powder, powder is selected Gossypol recrystallized from chloroform, obtained pure Schiff's base, vacuum-drying obtain compound 1, productive rate: 70%.
P1 (reactant: carbazole phenyl aldehyde, Ursol D)
H
1?NMR(400MHz,d-DMSO)?:δ8.66(s,1H),8.17(t,J=10.0,4H),7.74(d,J=4.0,2H),7.52(d,J=8.0,2H),7.45(t,J=8.0,2H),7.39(s,2H),7.32(t,J=8.0,2H)；
Ultimate analysis: C
44h
30n
4: %C85.97 (85.98); %H4.92 (4.91); In 9.10 (9.11) brackets, it is measured value;
MS(ESP)m/z:614.30(M)。
Embodiment 2:
Take carbazole phenyl aldehyde 1.08g (0.004mol) and be dissolved in 50ml ethanol, start stirring, until carbazole phenyl aldehyde all dissolves, add Ursol D 0.1g (0.001mol), add 5d glacial acetic acid, temperature control, at 75 DEG C, reacts 6h, obtain yellow Schiff's base powder, powder is selected Gossypol recrystallized from chloroform, has obtained pure Schiff's base, and vacuum-drying obtain compound 1, productive rate: 67%, compound structure characterization data is shown in embodiment 1.
Embodiment 3:
Take carbazole phenyl aldehyde 2.16g (0.008mol) and be dissolved in 80ml acetone, start stirring, until carbazole phenyl aldehyde all dissolves, add Ursol D 0.1g (0.001mol), add 8d formic acid, temperature control, at 50 DEG C, reacts 8h, obtain yellow Schiff's base powder, powder is selected methylene dichloride recrystallization, has obtained pure Schiff's base, and vacuum-drying obtain compound 1, productive rate: 53%, compound structure characterization data is shown in embodiment 1.
Embodiment 4:
Take carbazole phenyl aldehyde 1.08g (0.004mol) and be dissolved in 100ml methyl alcohol, start stirring, until carbazole phenyl aldehyde all dissolves, add Ursol D 0.1g (0.001mol), add 3d glacial acetic acid, temperature control, at 65 DEG C, reacts 12h, obtain yellow Schiff's base powder, powder is selected ethyl alcohol recrystallization, has obtained pure Schiff's base, and vacuum-drying obtain compound 1, productive rate: 50%, compound structure characterization data is shown in embodiment 1.
Experimental example:
1. the fluorescence property of compound 1 research
Embodiment 1 sample of the purification process of learning from else's experience, with DMSO dissolving, is mixed with 1.0x10
-5the sample solution of mol/ml.
Utilize the ultraviolet-visible pectrophotometer ultra-violet absorption spectrum of working sample respectively, find its uv-absorption maximum wavelength, and then using this as fluorescence exciting wavelength, utilize the fluorescence spectrum (the results are shown in accompanying drawing 1) of fluorescent spectrophotometer assay compound.
Result of study shows: compound has good fluorescent emission.
2. the impact of metal ion on its fluorescence property
Preparation 1.0x10
-5mol/ml's contains Cu (NO
3)
2, Fe (NO
3)
2, Zn (NO
3)
2, Ni (NO
3)
2dMSO solution, get respectively the above-mentioned 1.0x10 having prepared
-5the DMSO solution of the compound 1 of mol/ml, makes it mix with 1:1 with metal ion solution, the fluorescence spectrum of test mixing solution.(the results are shown in accompanying drawing 2 ~ 3)
Result of study shows: Cu
2+, Fe
2+, Zn
2+, Ni
2+all the fluorescence intensity of compound is had to certain increase effect, but Cu
2+the effect of increase the most obvious, can conclude thus, compound 1 can be used as Cu
2+fluorescent probe.
Brief description of the drawings:
The fluorogram of accompanying drawing 1-compound 1 in DMSO.
The fluorogram of accompanying drawing 2-compound 1 and each metal ion solution mixture.
Claims (3)
1. the two Schiff's base of carbazole phenyl aldehyde contracting Ursol D, is characterized in that: its structural formula is as follows:
2. the application of compound as claimed in claim 1, is characterized in that: be applied to fluorescent probe field.
3. a preparation method for the two Schiff's base of carbazole phenyl aldehyde contracting Ursol D claimed in claim 1, is characterized in that: its preparation method is as follows:
1) take carbazole phenyl aldehyde and be dissolved in solvent, the mol ratio of carbazole phenyl aldehyde and solvent is 1:10～1:100;
2) take Ursol D and be dissolved in the solution described in step 1), the mol ratio of Ursol D and carbazole phenyl aldehyde is 1:2～1:8;
3) measuring a certain amount of weak acid and add step 2) in described solution, the consumption of weak acid is 1～8;
4) start stirring and start reaction, isothermal reaction 2～12h at 50～75 DEG C, has obtained yellow Schiff's base powder, and recrystallization, obtains sterling;
Described solvent is methyl alcohol, ethanol or acetone;
Described weak acid is formic acid or acetic acid;
Described recrystallization solvent is ethanol, chloroform or methylene dichloride.
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| CN104130192B (en) * | 2014-07-30 | 2017-05-24 | 齐鲁工业大学 | Imidazolyl-benzaldehyde p-phenylenediamine bis-Schiff base and preparation method thereof |
| CN104119286B (en) * | 2014-07-30 | 2017-06-20 | 淄博职业学院 | A kind of triazole benzaldehyde-p-phenylenediamine bi-schiff base and preparation method thereof |
| CN105622586A (en) * | 2016-03-14 | 2016-06-01 | 济南正骐生物科技有限公司 | Melamine carbazole formaldehyde Schiff base and preparation method thereof |
| CN105669656A (en) * | 2016-03-14 | 2016-06-15 | 济南正骐生物科技有限公司 | Melamine carbazole benzaldehyde bis-schiff base and preparation method thereof |
| CN105712980A (en) * | 2016-03-14 | 2016-06-29 | 济南正骐生物科技有限公司 | Melamine and shrinkage carbazole benzaldehyde single schiff base and preparation method thereof |
| CN105541809A (en) * | 2016-03-14 | 2016-05-04 | 济南正骐生物科技有限公司 | Melamine condensed carbazole benzaldehyde tris-Schiff base and preparation method thereof |
| CN105585560A (en) * | 2016-03-14 | 2016-05-18 | 济南正骐生物科技有限公司 | Melamine shrinkage carbazole formaldehyde single Schiff base and preparation method thereof |
| CN105646460A (en) * | 2016-03-21 | 2016-06-08 | 济南正骐生物科技有限公司 | Melamine condensed carbazole formaldehyde bis-schiff base and preparation method thereof |
| CN113549004B (en) * | 2021-06-28 | 2023-09-08 | 淮阴师范学院 | 1-pyrene formaldehyde condensed 3-amino-9-ethyl carbazole Schiff base compound as well as preparation method and application thereof |
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| CN101100465A (en) * | 2007-06-12 | 2008-01-09 | 山东大学 | Cationic carbazole compounds and their application as two-photon nucleic acid fluorescent probes |
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