CN105949207A - Preparation method of Meso-tetra(3,4-dihydroxy phenyl) zinc porphyrin - Google Patents
Preparation method of Meso-tetra(3,4-dihydroxy phenyl) zinc porphyrin Download PDFInfo
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- CN105949207A CN105949207A CN201610327684.5A CN201610327684A CN105949207A CN 105949207 A CN105949207 A CN 105949207A CN 201610327684 A CN201610327684 A CN 201610327684A CN 105949207 A CN105949207 A CN 105949207A
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- C07—ORGANIC CHEMISTRY
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
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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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- C—CHEMISTRY; METALLURGY
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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Abstract
The invention discloses a preparation method of Meso-tetra(3,4-dihydroxy phenyl) zinc porphyrin and belongs to the technical field of chemical synthesis and detection. The preparation method of Meso-tetra(3,4-dihydroxy phenyl) zinc porphyrin adopts raw materials in proportion as follows: 1.5 g of 3,4-dihydroxy benzaldehyde, 1.3 mL of pyrrole, 80 mL of nitrobenzene, 7.5 mL of isobutyric acid, 0.40 g of zinc acetate, 35 mL of tetrahydrofuran and 5-10 mL of methanol. The preparation method is simple, and the yield of Meso-tetra(3,4-dihydroxy phenyl) zinc porphyrin is high.
Description
Technical field
The invention belongs to chemosynthesis and detection technique field, particularly to a kind of Meso-tetra-(3,4-dihydroxy
Phenyl) preparation method of zinc porphyrin.
Background technology
First, the synthesis about Meso-tetra-(3,4-dihydroxy phenyl) zinc porphyrin occurred the most in the literature,
Belong to new material.
Secondly, the invention provides a kind of effective synthesis Meso-tetra-(3,4-dihydroxy phenyl) porphin
The method of quinoline zinc, and it is aided with a series of characterization method to its inspection checking.
Summary of the invention
It is an object of the invention to overcome shortcoming and deficiency present in above-mentioned prior art, it is provided that a kind of Meso-
The preparation method of four (3,4-dihydroxy phenyl) zinc porphyrin.
The purpose of the present invention is achieved through the following technical solutions: a kind of Meso-tetra-(3,4-dihydroxy phenyl) porphin
The preparation method of quinoline zinc, comprises the following steps:
(1) synthesis of Meso-tetra-(3,4-dihydroxy phenyl) porphyrin (OOHPP):
In the three-neck flask equipped with condensing tube, thermometer and constant pressure funnel, add 45mL Nitrobenzol,
Add zeolite, be heated to reflux；Then the 3 of 1.5g are weighed, 4-4-dihydroxy benzaldehyde, it is dissolved in 10mL nitro
Benzene, with the isobutyric mixed solution of 7.5mol, instills in three-neck flask, refluxes at a temperature of 135 DEG C；
After 20min, dropping 1.3mL newly steams pyrroles and the mixed liquor of 25mL Nitrobenzol, and in 30min, dropping is complete；
Reactant liquor quickly by the faint yellow atropurpureus that becomes, back flow reaction 2h, stops heating；Liquid to be mixed is cooled to 80 DEG C
Hereinafter, 8h is stood；Decompression sucking filtration, and with propionic acid wash, obtain dark green solid；It is vacuum dried 1 at 60 DEG C
After h, dissolve with oxolane；It is further purified employing silica gel column chromatography, makees eluant by methanol reagent,
Collect the first kermesinus chromatograph section, concentrate, be evaporated after can obtain sapphirine crystal Meso-tetra-(3,4-dihydroxy phenyl)
Porphyrin；
(2) synthesis of Meso-tetra-(3,4-dihydroxy phenyl) zinc porphyrin (OOHPP-Zn)
Weigh 0.05g Meso-tetra-(3,4-dihydroxy phenyl) porphyrin and 0.40g zinc acetate Zn (OAc)2, it is added to
Equipped with in the condensing tube three-neck flask with thermometer, add 30mL oxolane (THF) stirring and dissolving, and add
Enter 5-10mL methanol hydrotropy, then system is heated with stirring to 75 DEG C, stopped reaction after back flow reaction 2h；
Mixed liquor is poured in beaker, add and the isopyknic distilled water of mixed liquor and 30mL dichloromethane, treat it
After being cooled to room temperature, it is placed in cold preservation 24h in refrigerator；Extract with separatory funnel separatory, after repeatedly washing 3 times
Collected organic layer liquid, removes solvent and obtains thick product, and be vacuum dried；Enter with column chromatography analytic process again
The purification of one step: use CH2Cl2Wet method upper prop, and with CH3OH is leacheate, collects mauve second
Colour band, after evaporation is the most dry, is vacuum dried 24h, obtains product Meso-tetra-(3,4-dihydroxy phenyl) zinc porphyrin.
Silica gel used in silica gel column chromatography described in step (1) is 200-300 mesh.
The present invention has such advantages as relative to prior art and effect:
The invention provides the preparation method of a kind of Meso-tetra-(3,4-dihydroxy phenyl) zinc porphyrin.Described system
Preparation Method is simple, it is thus achieved that the yield of Meso-tetra-(3,4-dihydroxy phenyl) zinc porphyrin high.The present invention's
The synthesis of OOHPP-Zn adds porphyrin and metalloporphyrin class thing qualitative diversity undoubtedly, be also OOHPP with
The complexation of other metals provides certain reference.
Accompanying drawing explanation
Fig. 1 is the synthetic route chart of meso-tetra-(3,4-dihydroxy phenyl) porphyrin of step (1) in embodiment 1；
Fig. 2 is the synthetic route of meso-tetra-(3,4-dihydroxy phenyl) zinc porphyrin of step (2) in embodiment 1
Figure；
Fig. 3 is the uv-visible absorption spectra figure of meso-tetra-(3,4-dihydroxy phenyl) porphyrin in embodiment 1；
Fig. 4 is the uv-visible absorption spectra figure of meso-tetra-(3,4-dihydroxy phenyl) zinc porphyrin in embodiment 1；
Fig. 5 is the infrared spectrogram of meso-tetra-(3,4-dihydroxy phenyl) porphyrin in embodiment 1；
Fig. 6 is the infrared spectrogram of meso-tetra-(3,4-dihydroxy phenyl) zinc porphyrin in embodiment 1；
Fig. 7 is the fluorescence spectrum figure of meso-tetra-(3,4-dihydroxy phenyl) porphyrin in embodiment 1；
Fig. 8 is the fluorescence spectrum figure of meso-tetra-(3,4-dihydroxy phenyl) zinc porphyrin in embodiment 1；
Fig. 9 is the EPR spectrogram of meso-tetra-(3,4-dihydroxy phenyl) porphyrin in embodiment 1；
Figure 10 is the EPR spectrogram of meso-tetra-(3,4-dihydroxy phenyl) zinc porphyrin in embodiment 1.
Detailed description of the invention
Below in conjunction with embodiment and accompanying drawing, the present invention is described in further detail, but embodiments of the present invention
It is not limited to this.
Embodiment 1
The invention provides the preparation method of a kind of Meso-tetra-(3,4-dihydroxy phenyl) zinc porphyrin, including following
Step:
(1) synthesis (as shown in Figure 1) of Meso-tetra-(3,4-dihydroxy phenyl) porphyrin (OOHPP):
To equipped with in the 250mL three-neck flask of condensing tube, thermometer and constant pressure funnel, add 45mL
Nitrobenzol, adds zeolite, is heated to reflux；Then the 3 of 1.5g are weighed, 4-4-dihydroxy benzaldehyde, it is dissolved in 10
ML Nitrobenzol, with the isobutyric mixed solution of 7.5mol, is slowly dropped in three-neck flask, at 135 DEG C
At a temperature of reflux；After 20min, be slowly added dropwise newly steam pyrroles (1.3mL) and Nitrobenzol (25mL) and mixed liquor,
In 30min, dropping is complete；Reactant liquor quickly by the faint yellow atropurpureus that becomes, back flow reaction 2h, stops heating；
Liquid to be mixed is cooled to less than 80 DEG C, stands 8h；Decompression sucking filtration, and with propionic acid wash, obtain blackish green solid
Body；After 60 DEG C of vacuum drying 1h, dissolve with oxolane.It is further purified and can use silica gel (200-300
Mesh) column chromatography, make eluant by methanol reagent, collect the first kermesinus chromatograph section, concentrate, be evaporated after can obtain
Sapphirine crystal Meso-tetra-(3,4-dihydroxy phenyl) porphyrin (0.13g, yield is 6.5%)；
(2) synthesis (as shown in Figure 2) of Meso-tetra-(3,4-dihydroxy phenyl) zinc porphyrin (OOHPP-Zn):
Weigh 0.05g (0.067mmol) Meso-tetra-(3,4-dihydroxy phenyl) porphyrin and 0.40g (2.18mmol)
Zinc acetate Zn (OAc)2, it is added in the 100mL three-neck flask equipped with condensing tube and thermometer, adds 30mL
Oxolane (THF) stirring and dissolving, and add 5-10mL methanol hydrotropy, then system is heated with stirring to 75 DEG C,
Stopped reaction after back flow reaction 2h；Mixed liquor is poured in 200mL beaker, add 30mL dichloromethane
About isopyknic with mixed liquor distilled water, after it is cooled to room temperature, is placed in cold preservation 24h in refrigerator；
Extract with separatory funnel separatory, collected organic layer liquid after repeatedly washing 3 times, remove solvent and obtain thick product,
And be vacuum dried；Further purified with column chromatography analytic process again: use CH2Cl2Wet method upper prop, and with
CH3OH is leacheate, collects mauve second colour band, after evaporation is the most dry, is vacuum dried 24h, obtains
Pure product zinc-porphyrin, (0.042g, yield is 77.2%).
The sign of embodiment 2 Meso-tetra-(3,4-dihydroxy phenyl) zinc porphyrin
Characterizing method mainly has infrared spectrum, UV-Vis spectra, fluorescence spectrum and electron paramagnetic resonance
Wave spectrum means.When wherein measuring uv-visible absorption spectra, CH selected by solvent2Cl2Or CH3OH, measures model
Enclose for 350-700nm；Infrared spectrum uses Avatar370 type FT-IR infrared spectrometer to detect, and uses bromine
Changing potassium (KBr) tabletting, measurement scope is 4000-400cm-1；Fluorescence spectrum then utilizes Fluorescence-max4
Type fluorescence spectrophotometer detects, and selected solvent has CH2Cl2、CH3OH and DMF, grating spacings is set to 3
nm；Electron paramagnetic resonance spectrum (EPR) is then to be entered porphyrin solid by A200-9.5/12 type electronic paramagnetic resonance spectrometer
Row detects and obtains.
The uv-visible absorption spectra analysis of Meso-tetra-(3,4-dihydroxy phenyl) zinc porphyrin
Both the above compound is dissolved separately in dichloromethane (CH2Cl2), methanol (CH3Or N, N-bis-OH)
A kind of solvent in methylformamide (DMF), is configured with 2 kinds of solution to be measured.Spectral scan scope is set to
350nm-700nm。
Presented 5 absworption peaks from Fig. 3 and Fig. 4, OOHPP in ultraviolet-visible light district, show as one
Soret band the strongest absworption peak (about 421nm at) and Q carry 4 weak absorbing peaks (lay respectively at 517nm,
555nm, 592nm and 651nm).This is the basic feature of porphyrin substance.And when metal center ion
After porphyrin part generation complexation, the Q band peak of the material being newly formed will be reduced to one or two by 4.By
Figure understands, and the number at compound 2 (OOHPP-Zn) Q band peak is reduced to 2 by 4, and this proves that porphyrin is joined
Body has become metalloporphyrin with metal center ion complex.It addition, the peak phase on the Soret band of compound 2
Also there occurs red shift than compound 1, be positioned at 428nm.
The infrared spectrum (IR) of Meso-tetra-(3,4-dihydroxy phenyl) zinc porphyrin is analyzed
As it is shown in figure 5, wherein, 3404.15cm-1It is that on four (3,4-dihydroxy phenyl) porphyrin, the flexible of-OH shakes
Dynamic peak, 2967.04cm-1For the stretching vibration absworption peak of the C-H of-CH2-, 1280.22cm-1For PhC-O's
Stretching vibration peak, 932.62cm-1For the bending vibration peak of the N-H at porphyrin ring center, 1605.51cm-1、
1522.48cm-1And 1421.04cm-1The C=C skeletal vibration of the outer phenyl ring of porphyrin ring is demonstrated at peak, 1344.65
cm-1Etc. peak belong to-CH2C h bond bending vibration peak, 1223.71cm-1It it is the stretching vibration of C-O
Peak, 965.48cm-1For the C-H bending vibration peak of porphyrin ring, 800.69cm-1And 700.06cm-1That locates is strong
Peak is to be caused by the stretching vibration of C-H on phenyl ring and pyrrole ring.
As shown in Figure 6, wherein 3438.50cm-1For-OH the stretching vibration peak of OOHPP, 2962.02cm-1、
2923.67cm-1And 2851.93cm-1For-CH2The asymmetric and symmetrical stretching vibration peak of C-H, 1599.11
cm-1、1541.70cm-1And 1465.47cm-1Peak ownership-the CH at place2C h bond bending vibration peak, 1384.27
cm-1The stronger peak at place is-CH2The bending vibration peak 1261.13cm of upper c h bond-1Flexible for PhC-O shakes
Dynamic peak, 802.19cm-1The extremely strong peak at place is caused by the stretching vibration of C-H on phenyl ring.It additionally can be seen that
OOHPP is at 932.62cm-1The peak at place disappears, and at 1030.68cm-1Place occurs new extremely strong and sharp-pointed
Absworption peak.This is the oxidation-sensitive state of metal ion, it was demonstrated that metallic zinc and porphyrin are coordinated successfully,
OOHPP-Zn successfully synthesizes.
The fluorescence spectrum (FL) of Meso-tetra-(3,4-dihydroxy phenyl) zinc porphyrin is analyzed
From Fig. 7 and Fig. 8, compound 1 (OOHPP) and the fluorescence light of compound 2 (OOHPP-Zn)
Compose near all at 675nm and produce a strong peak, but present position is different.The strong peak of compound 1 is positioned at
At 664nm, and after it is with metallic zinc ion generation complexation, the strong peak of the metalloporphyrin (compound 2) of formation
Position then there occurs blue shift, be moved at 682nm.
Meso-tetra-(3,4-dihydroxy phenyl) zinc porphyrin electron paramagnetic resonance (EPR) analyzes
From Fig. 9 and Figure 10, owing to Porphyrin Molecule exists the situation of zero-field splitting, OOHPP and gold thereof
The epr signal belonging to derivatives of porphyrin does not the most have symmetry.It addition, the EPR spectrogram of compound 1,2 is equal
Occurring spike near 3500G, this is the free radical of pi-conjugated track output of porphyrin and magnetic field occurs mutually
The result of effect.
Additionally, Metalloporphyrins ought to show a big peak near 3000G, this is metal ion
The exclusive characteristic peak in EPR collection of illustrative plates.But the epr signal of OOHPP-Zn with OOHPP compares phase
Seemingly.This is due to central ion Zn2+Do not has into single electronics, it is impossible to measure the feature of metal ion.
Above-described embodiment is the present invention preferably embodiment, but embodiments of the present invention are not by above-mentioned enforcement
The restriction of example, the change made, modifies, replaces under other any spirit without departing from the present invention and principle
In generation, combine, simplify, all should be the substitute mode of equivalence, within being included in protection scope of the present invention.
Claims (2)
1. the preparation method of Meso-tetra-(3, a 4-dihydroxy phenyl) zinc porphyrin, it is characterised in that: include
Following steps:
(1) synthesis of Meso-tetra-(3,4-dihydroxy phenyl) porphyrin:
In the three-neck flask equipped with condensing tube, thermometer and constant pressure funnel, add 45mL Nitrobenzol,
Add zeolite, be heated to reflux；Then the 3 of 1.5g are weighed, 4-4-dihydroxy benzaldehyde, it is dissolved in 10mL nitro
Benzene, with the isobutyric mixed solution of 7.5mol, instills in three-neck flask, refluxes at a temperature of 135 DEG C；
After 20min, dropping 1.3mL newly steams pyrroles and the mixed liquor of 25mL Nitrobenzol, and in 30min, dropping is complete；
Reactant liquor quickly by the faint yellow atropurpureus that becomes, back flow reaction 2h, stops heating；Liquid to be mixed is cooled to 80 DEG C
Hereinafter, 8h is stood；Decompression sucking filtration, and with propionic acid wash, obtain dark green solid；It is vacuum dried 1 at 60 DEG C
After h, dissolve with oxolane；It is further purified employing silica gel column chromatography, makees eluant by methanol reagent,
Collect the first kermesinus chromatograph section, concentrate, be evaporated after can obtain sapphirine crystal Meso-tetra-(3,4-dihydroxy phenyl)
Porphyrin；
(2) synthesis of Meso-tetra-(3,4-dihydroxy phenyl) zinc porphyrin
Weigh 0.05g Meso-tetra-(3,4-dihydroxy phenyl) porphyrin and 0.40g zinc acetate, be added to equipped with condensing tube
With the three-neck flask of thermometer, add 30mL oxolane stirring and dissolving, and add 5-10mL methanol
Hydrotropy, then system is heated with stirring to 75 DEG C, stopped reaction after back flow reaction 2h；Pour mixed liquor into burning
In Bei, add and the isopyknic distilled water of mixed liquor and 30mL dichloromethane, after it is cooled to room temperature,
It is placed in cold preservation 24h in refrigerator；Extract with separatory funnel separatory, collected organic layer liquid after repeatedly washing 3 times,
Remove solvent and obtain thick product, and be vacuum dried；Further purified with column chromatography analytic process again: use
CH2Cl2Wet method upper prop, and with CH3OH is leacheate, collects mauve second colour band, and evaporation is near dry
After, it is vacuum dried 24h, obtains product Meso-tetra-(3,4-dihydroxy phenyl) zinc porphyrin.
The preparation method of Meso-tetra-(3,4-dihydroxy phenyl) zinc porphyrin the most according to claim 1,
It is characterized in that: silica gel used in the silica gel column chromatography described in step (1) is 200-300 mesh.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109282836A (en) * | 2018-08-23 | 2019-01-29 | 浙江理工大学 | A kind of preparation method of tetrasulfonic acid phenyl manganoporphyrin nanotube-cadmium sulfide nano piece complex light sensitive sensing material |
| CN110627799A (en) * | 2019-09-25 | 2019-12-31 | 浙江理工大学 | Preparation method of tetra (hydroxyphenyl) zinc porphyrin-AIE fluorescent molecule composite photosensitive sensing material |
| CN113956284A (en) * | 2021-11-18 | 2022-01-21 | 任元林 | Porphyrin structure derivative, preparation method thereof and dyeing-flame-retardant-anti-dripping integrated polyester |
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| CN1944447A (en) * | 2006-10-27 | 2007-04-11 | 北京工业大学 | Synthetic method for metal porphyrin |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109282836A (en) * | 2018-08-23 | 2019-01-29 | 浙江理工大学 | A kind of preparation method of tetrasulfonic acid phenyl manganoporphyrin nanotube-cadmium sulfide nano piece complex light sensitive sensing material |
| CN109282836B (en) * | 2018-08-23 | 2020-08-11 | 浙江理工大学 | Preparation method of phenylsulfate manganoporphyrin nanotube-cadmium sulfide nanosheet composite photosensitive sensing material |
| CN110627799A (en) * | 2019-09-25 | 2019-12-31 | 浙江理工大学 | Preparation method of tetra (hydroxyphenyl) zinc porphyrin-AIE fluorescent molecule composite photosensitive sensing material |
| CN113956284A (en) * | 2021-11-18 | 2022-01-21 | 任元林 | Porphyrin structure derivative, preparation method thereof and dyeing-flame-retardant-anti-dripping integrated polyester |
| CN113956284B (en) * | 2021-11-18 | 2023-10-03 | 任元林 | Porphyrin structure derivative and preparation method thereof, and dyeing-flame-retardant-anti-dripping integrated polyester |
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Application publication date: 20160921 |