CN104151193B - (methylene imine base-(4-styryl-tribenzylamine)) phenol photosensitizers and synthetic method thereof - Google Patents
(methylene imine base-(4-styryl-tribenzylamine)) phenol photosensitizers and synthetic method thereof Download PDFInfo
- Publication number
- CN104151193B CN104151193B CN201410327507.8A CN201410327507A CN104151193B CN 104151193 B CN104151193 B CN 104151193B CN 201410327507 A CN201410327507 A CN 201410327507A CN 104151193 B CN104151193 B CN 104151193B
- Authority
- CN
- China
- Prior art keywords
- tribenzylamine
- styryl
- photosensitizers
- phenol
- imine base
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Abstract
The invention discloses (methylene imine base-(4-styryl-tribenzylamine)) phenol photosensitizers and synthetic method thereof, belong to organic photosensitive agent field.Its chemical formula is:
photosensitizers of the present invention is tested through ultraviolet-visible spectrometer, and it has good absorption in visible region, and maximum absorption wavelength is positioned at 290nm-400nm, can produce fluorescence response to cadmium ion; Through fluorescence spectrophotometer test, it has good response in visible region to cadmium ion, may be used for identifying cadmium ion, is applied in environment, food, biology and medicine and other fields.
Description
Technical field
The present invention relates to organic photosensitive agent field, especially (methylene imine base-(4-styryl-tribenzylamine)) phenol photosensitizers and synthetic method.
Background technology
At present, vinylbenzene-tribenzylamine class photosensitizers is applied widely in Materials science, biomedicine, chemical engineering, the maximum wavelength of wherein most vinylbenzene-tribenzylamine class photosensitizers or be positioned at below 290nm, or is positioned at more than 400nm; Fluorescence response is produced to cadmium ion simultaneously.Chemical component due to photosensitizers is difficult to regulation and control, cause maximum absorption wavelength be positioned at 290nm-400nm to produce the vinylbenzene-tribenzylamine class photosensitizers of fluorescence response to cadmium ion rare.
Summary of the invention
Goal of the invention of the present invention is: for above-mentioned Problems existing, provides a kind of maximum absorption wavelength to be positioned at the vinylbenzene-tribenzylamine class photosensitizers that can produce fluorescence response to cadmium ion of 290nm-400nm.
(methylene imine base-(4-styryl-tribenzylamine)) the phenol photosensitizers that the present invention relates to, its chemical formula is:
The synthetic method of above-mentioned (methylene imine base-(4-styryl-tribenzylamine)) phenol photosensitizers is as follows:
The concrete steps of synthesis are as follows:
First, 4-amido-styryl-tribenzylamine and 2-hydroxy-benzaldehyde are added in three mouthfuls of vials, 4-amido-styryl-tribenzylamine is 1:1 with the molar weight ratio of 2-hydroxy-benzaldehyde, take ethanol as solvent, its volume is 30-60 times of 2-hydroxy-benzaldehyde, and normal temperature magnetic agitation terminates reaction after 10 hours;
Then, above-mentioned reacted mixture being obtained crude product through vacuum concentration to solid, take hexanaphthene as eluent, is separated, obtains (methylene imine base-(4-styryl-tribenzylamine)) phenol photosensitizers with silica gel chromatographic column.
The present invention is by technique scheme synthesis (methylene imine base-(4-styryl-tribenzylamine)) phenol photosensitizers, and its beneficial effect is:
Synthesis and the separation method of (methylene imine base-(4-styryl-tribenzylamine)) of the present invention phenol photosensitizers are simple, by (methylene imine base-(4-styryl-tribenzylamine)) the phenol photosensitizers prepared by the present invention through ultraviolet-visible spectrometer and the test of fluorescence emission spectrometer, record it, at 290nm-430nm, there is good absorption, fluorescence spectrum illustrates that it has specific emission peak at 450-600nm, after adding cadmium ion, uv-visible absorption spectra and fluorescence emission spectrum all there occurs noticeable change, create new emission peak, illustrate that (methylene imine base-(4-styryl-tribenzylamine)) phenol photosensitizers produces fluorescence response to cadmium ion, environment can be applied in, food, biology and medicine and other fields, for the identification of cadmium ion.
Accompanying drawing explanation
(methylene imine base-(4-styryl-tribenzylamine)) phenol in Fig. 1 embodiment 1
1h nmr spectrum (
1h-NMR);
(methylene imine base-(4-styryl-tribenzylamine)) phenol in Fig. 2 embodiment 1 at N, the uv-visible absorption spectra in N '-dimethyl methane amide;
(methylene imine base-(4-styryl-tribenzylamine)) phenol in Fig. 3 embodiment 1 at N, the fluorescence emission spectrum in N '-dimethyl methane amide;
(methylene imine base-(4-styryl-tribenzylamine)) phenol in Fig. 4 embodiment 1, at N, adds the uv-visible absorption spectra after cadmium ion in N '-dimethyl methane amide;
(methylene imine base-(4-styryl-tribenzylamine)) phenol in Fig. 5 embodiment 1, at N, adds the fluorescence emission spectrum after cadmium ion in N '-dimethyl methane amide.
(methylene imine base-(4-styryl-tribenzylamine)) phenol in Fig. 6 embodiment 2
1h nmr spectrum (
1h-NMR);
(methylene imine base-(4-styryl-tribenzylamine)) phenol in Fig. 7 embodiment 3
1h nmr spectrum (
1h-NMR);
Embodiment
Below in conjunction with embodiment and accompanying drawing, the invention will be further described
Embodiment 1
By 4-amido-styryl-tribenzylamine (10mmol, 4.80g) mix in three mouthfuls of vials with 2-hydroxy-benzaldehyde (10mmol, 1.22g, 1.04ml), with 50ml ethanol for solvent, normal temperature magnetic agitation terminates reaction after 10 hours; Vacuum concentration obtains crude product to solid, take hexanaphthene as eluent, is separated obtains pure product with silica gel chromatographic column.Productive rate 55%, fusing point: 223.6-225.5 DEG C.
Its
1h nmr spectrum as shown in Figure 1,
1h-NMR (D
6-DMSO, 500MHz) δ (ppm): 13.269 (s ,-OH, 1H), 9.115 (s, N=CH, 1H), 7.901-7.886 (d, Ar-H, 2H), 7.711-7.651 (m, Ar-H, 4H), 7.305-7.221 (m, Ar-H, 14H), 7.069-7.021 (m, Ar-H, 2H), 6.951 (m, CH=CH, 2H), 3.56 (s, N-CH
2-Ar, 6H).
Reaction equation is as follows:
Compound concentration is 1 × 10
-5moll
-1the N of (methylene imine base-(4-styryl-tribenzylamine)) phenol, the solution of N '-dimethyl methane amide, use ultraviolet-visible spectrometer, the uv-visible absorption spectra of scanning 200nm-600nm, maximum absorption wavelength is 310nm, and its uv-visible absorption spectra as shown in Figure 2.Using fluorescence emission spectrometer, take 310nm as excitation wavelength, and the fluorescence emission spectrum of scanning 300-680nm, maximum emission wavelength is 440nm and 540nm, and its fluorescence emission spectrum as shown in Figure 3.
Compound concentration is 1 × 10
-5moll
-1the N of (methylene imine base-(4-styryl-tribenzylamine)) phenol, the solution of N '-dimethyl methane amide, configuration 0.5moll
-1(CH
3cOO)
2cd3H
2the aqueous solution of O, the N of (methylene imine base-(4-styryl-tribenzylamine)) phenol that the cadmium-ion solution injecting 3 μ l with microsyringe has configured to 3ml, in N '-dimethyl formamide soln, use ultraviolet-visible spectrometer, the uv-visible absorption spectra of scanning 200nm-600nm, maximum absorption wavelength is 315nm, and its uv-visible absorption spectra as shown in Figure 4.Using fluorescence emission spectrometer, take 315nm as excitation wavelength, and the fluorescence emission spectrum of scanning 300-680nm, maximum emission wavelength is 470nm, and emissive porwer strengthens greatly, and its fluorescence emission spectrum as shown in Figure 5.
In fig. 2, uv-absorbing peak value is at wavelength 310nm and 400nm place, and in the diagram, uv-absorbing peak value, at wavelength 315nm and 420nm place, creates new absorption peak after adding cadmium ion, illustrates that photosensitizers of the present invention creates fluorescence response to cadmium ion.
In figure 3, fluorescence emission spectrum maximum emission wavelength is 440nm and 540nm, in the diagram, fluorescence emission spectrum maximum emission wavelength is 470nm, and maximum emission intensity is increased to 650 (a.u.) by 260 (a.u.), emissive porwer strengthens greatly, illustrates that photosensitizers of the present invention creates fluorescence response to cadmium ion.
Embodiment 2
By 4-amido-styryl-tribenzylamine (10mmol, 4.80g) mix in three mouthfuls of vials with 2-hydroxy-benzaldehyde (10mmol, 1.22g, 1.04ml), with 31.2ml ethanol for solvent, normal temperature magnetic agitation terminates reaction after 10 hours; Vacuum concentration obtains crude product to solid, take hexanaphthene as eluent, is separated obtains pure product with silica gel chromatographic column.Productive rate 54%, fusing point: 223.6-225.5 DEG C.
Its
1h nmr spectrum as shown in Figure 6,
1h-NMR (D
6-DMSO, 500MHz) δ (ppm): 13.269 (s ,-OH, 1H), 9.115 (s, N=CH, 1H), 7.901-7.886 (d, Ar-H, 2H), 7.711-7.651 (m, Ar-H, 4H), 7.305-7.221 (m, Ar-H, 14H), 7.069-7.021 (m, Ar-H, 2H), 6.951 (m, CH=CH, 2H), 3.56 (s, N-CH
2-Ar, 6H).
Embodiment 3
By 4-amido-styryl-tribenzylamine (10mmol, 4.80g) mix in three mouthfuls of vials with 2-hydroxy-benzaldehyde (10mmol, 1.22g, 1.04ml), with 62.4ml ethanol for solvent, normal temperature magnetic agitation terminates reaction after 10 hours; Vacuum concentration obtains crude product to solid, take hexanaphthene as eluent, is separated obtains pure product with silica gel chromatographic column.Productive rate 57%, fusing point: 223.6-225.5 DEG C.
Its
1h nmr spectrum as shown in Figure 7,
1h-NMR (D
6-DMSO, 500MHz) δ (ppm): 13.269 (s ,-OH, 1H), 9.115 (s, N=CH, 1H), 7.901-7.886 (d, Ar-H, 2H), 7.711-7.651 (m, Ar-H, 4H), 7.305-7.221 (m, Ar-H, 14H), 7.069-7.021 (m, Ar-H, 2H), 6.951 (m, CH=CH, 2H), 3.56 (s, N-CH
2-Ar, 6H).
Above-described embodiment and test result explanation, the present invention passes through molecular designing, synthesize (methylene imine base-(4-styryl-tribenzylamine)) phenol photosensitizers, its maximum absorption wavelength is positioned at 290nm-400nm, and fluorescence response can be produced to cadmium ion, study this kind of photosensitizers, can cadmium ion be identified, use it for environment, food, biology and medicine and other fields.
Claims (3)
1. (methylene imine base-(4-styryl-tribenzylamine)) phenol photosensitizers, is characterized in that its chemical formula is:
2. the synthetic method of (methylene imine base-(4-styryl-tribenzylamine)) phenol photosensitizers as claimed in claim 1, is characterized in that the method step is as follows:
First, 4-amido-styryl-tribenzylamine and 2-hydroxy-benzaldehyde are added in three mouthfuls of vials, 4-amido-styryl-tribenzylamine is 1:1 with the molar weight ratio of 2-hydroxy-benzaldehyde, take ethanol as solvent, its volume is 30-60 times of 2-hydroxy-benzaldehyde, and normal temperature magnetic agitation terminates reaction after 10 hours;
Then, above-mentioned reacted mixture being obtained crude product through vacuum concentration to solid, take hexanaphthene as eluent, is separated, obtains (methylene imine base-(4-styryl-tribenzylamine)) phenol photosensitizers with silica gel chromatographic column.
3. the purposes of (methylene imine base-(4-styryl-tribenzylamine)) phenol photosensitizers as claimed in claim 1, is characterized in that: use it for identification cadmium ion.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410327507.8A CN104151193B (en) | 2014-07-10 | 2014-07-10 | (methylene imine base-(4-styryl-tribenzylamine)) phenol photosensitizers and synthetic method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410327507.8A CN104151193B (en) | 2014-07-10 | 2014-07-10 | (methylene imine base-(4-styryl-tribenzylamine)) phenol photosensitizers and synthetic method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104151193A CN104151193A (en) | 2014-11-19 |
| CN104151193B true CN104151193B (en) | 2016-01-20 |
Family
ID=51876857
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410327507.8A Expired - Fee Related CN104151193B (en) | 2014-07-10 | 2014-07-10 | (methylene imine base-(4-styryl-tribenzylamine)) phenol photosensitizers and synthetic method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104151193B (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1266884A1 (en) * | 2000-03-22 | 2002-12-18 | BF Research Institute, Inc. | Image diagnosis probe based on substituted azobenzene or analogue thereof for disease attributable to amyloid accumulation and composition for image diagnosis containing the same |
| CN101602819A (en) * | 2009-07-13 | 2009-12-16 | 重庆大学 | Contain the synthetic and application of the visible light photosensitizer with conjugated structure schiff base type of adjacent hydroxyl |
| JP2014115433A (en) * | 2012-12-10 | 2014-06-26 | Sharp Corp | Manufacturing method of photoreceptor, photoreceptor, and image forming apparatus including photoreceptor |
-
2014
- 2014-07-10 CN CN201410327507.8A patent/CN104151193B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1266884A1 (en) * | 2000-03-22 | 2002-12-18 | BF Research Institute, Inc. | Image diagnosis probe based on substituted azobenzene or analogue thereof for disease attributable to amyloid accumulation and composition for image diagnosis containing the same |
| CN101602819A (en) * | 2009-07-13 | 2009-12-16 | 重庆大学 | Contain the synthetic and application of the visible light photosensitizer with conjugated structure schiff base type of adjacent hydroxyl |
| JP2014115433A (en) * | 2012-12-10 | 2014-06-26 | Sharp Corp | Manufacturing method of photoreceptor, photoreceptor, and image forming apparatus including photoreceptor |
Non-Patent Citations (1)
| Title |
|---|
| Intramolecular Proton Transfer of New Diphenylethylene Derivatives Bearing Imino Group: A Combination of Experimental and Theoretical Investigation;Gao Fang等;《Chin. J. Chem.》;20101231;第28卷;第1057-1068页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104151193A (en) | 2014-11-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Aricó et al. | Template‐Directed Synthesis of Multiply Mechanically Interlocked Molecules Under Thermodynamic Control | |
| Sakai et al. | Effective 2, 6-substitution of piperidine nitroxyl radical by carbonyl compound | |
| CN103409135B (en) | Rhodamine fluorescent molecular probe using quinoline derivative as identification group and synthesis method thereof | |
| CN105462576A (en) | Near infrared BODIPY fluorescence dye and preparation method thereof | |
| CN102911111B (en) | Carbazole benzaldehyde-p-phenylenediamine bi-schiff base and preparation method thereof | |
| Yang et al. | An efficiently colorimetric and fluorescent probe of fluoride, acetate and phosphate ions based on a novel trinuclear Eu-complex | |
| CN107814808B (en) | A kind of near-infrared response type two-photon fluorescence probe and its preparation method and application | |
| Baranov et al. | A synthetic approach to GFP chromophore analogs from 3-azidocinnamates. Role of methyl rotors in chromophore photophysics | |
| Sun et al. | A novel colorimetric and fluorometric probe for the detection of CN− with high selectivity in aqueous media | |
| Montagnon et al. | Chemoselective photooxygenations of furans bearing unprotected amines: their use in alkaloid synthesis | |
| CN103342698A (en) | Dual-fluorophore ratio fluorescence molecular probe for non-fluorescence resonance energy transfer and preparation method thereof | |
| Lei et al. | Cucurbit [8] uril-mediated photodimerization of alkyl 2-naphthoate in aqueous solution | |
| Chen et al. | A turn-on Schiff-base fluorescence sensor for Fe3+ ion | |
| CN104479671A (en) | Rhodamin B double-sulfur fluorescence probe for detecting aqueous mediums and intracellular mercury ions, preparation and application thereof | |
| CN104151193B (en) | (methylene imine base-(4-styryl-tribenzylamine)) phenol photosensitizers and synthetic method thereof | |
| Feng et al. | Fluorogenic and chromogenic detection of biologically important fluoride anion with schiff-bases containing 4-amino-1, 8-naphthalimide unit | |
| Wu et al. | Revealing a nucleophilic addition reaction between aza-BODIPY and cyanide anion | |
| Zubenko et al. | Laser flash photolysis and CIDNP studies of steric effects on coupling rate constants of imidazolidine nitroxide with carbon-centered radicals, methyl isobutyrate-2-yl and tert-butyl propionate-2-yl | |
| Zhu et al. | A cis tetraphenylethene-based Zn complex as probe for selective detection of triphosphate | |
| Habibi‐Khorassani et al. | Dynamic 1H NMR study around the carbon–carbon single bond and partial carbon–carbon double bond in the two particular phosphorus ylides and in an enaminoester | |
| D'Vries et al. | 1D lanthanide coordination polymers based on lanthanides and 4′-hydroxi-4-biphenylcarboxylic acid: Synthesis, structures and luminescence properties | |
| Akbaş et al. | Bis (2-furanylmethyl) monospiro (N/N) cyclotriphosphazenes: synthesis, structural characterization, antiproliferative, and antimigratory activity studies | |
| Wang et al. | Synthesis and characteristics of novel fluorescence dyes based on chromeno [4, 3, 2-de][1, 6] naphthyridine framework | |
| Leung et al. | The stability of imine-containing dynamic [2] rotaxanes to hydrolysis | |
| Bogie et al. | Metal-selective coordination and enhanced fluorescence of a self-assembling ligand scaffold |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20160120 Termination date: 20190710 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |