CN107056792A - A kind of novel porphyrin class compound and its preparation method and application - Google Patents
A kind of novel porphyrin class compound and its preparation method and application Download PDFInfo
- Publication number
- CN107056792A CN107056792A CN201710273217.3A CN201710273217A CN107056792A CN 107056792 A CN107056792 A CN 107056792A CN 201710273217 A CN201710273217 A CN 201710273217A CN 107056792 A CN107056792 A CN 107056792A
- Authority
- CN
- China
- Prior art keywords
- added
- meso
- tetraphenylporphyrins
- preparation
- triphenylporphyrins
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
Abstract
The invention belongs to the technical field of organic compound synthesis, a kind of novel porphyrin class compound and its preparation method and application is disclosed.Preparation method includes step：Meso tetraphenylporphyrins are synthesized in the environment of propionic acid first with benzaldehyde and pyrroles; then Meso tetraphenylporphyrins are used for raw material; it is mixed solvent from dichloromethane/chloroform system; synthesize 5 (4 chloromethyl phenyls) 10; 15; 20 Triphenylporphyrins; again by 5 (4 chloromethyl phenyls) 10; 15; 20 Triphenylporphyrins and urotropine flow back after being reacted in chloroform solvent in acetic acid, then after column chromatography separating purification, obtain new compound 5 (4 Fonnylphenyl) 10; 15,20 phenyl porphyrins.
Description
Technical field
The invention belongs to the technical field of organic compound synthesis, and in particular to a kind of novel porphyrin class compound and its system
Preparation Method and application.
Background technology
Porphyrin substance contains big ring conjugated structure due to its parent porphines, thus possesses certain armaticity, and spectrum rings
Ying Kuan, stability is good, and the ability with metal complex is strong, is typically rendered as high-melting-point, dark colour crystal.Porphyrin substance
Special construction and property cause it to be widely used.In addition, porphyrin novelty causes its application field rapid growth, in order to meet
It applies rapid growth, thus must synthesize some Novel Porphyrins.The schiff bases porphyrin of currently the majority all passes through
Amino on porphyrin ring forms schiff base compound with carrying out nucleophilic addition containing carbon-based aldehyde, ketone compounds, and new
Not only needed in 5- (4- Fonnylphenyls) -10,15,20- phenyl porphyrins of synthesis containing porphyrin ring but also containing synthesis schiff bases
Aldehyde radical, can add its catalysis with schiff base compound of the porphyrin compound formation containing the big ring of more porphyrins containing amino
Active and each bioactivity, makes its application more extensive.
The content of the invention
In order to overcome the shortcoming and deficiency of prior art, primary and foremost purpose of the invention is to provide a kind of novel porphyrin class
Compound.
Another object of the present invention is to provide a kind of preparation method of above-mentioned porphyrins.The letter of this method technique
It is single, by being relatively easily-synthesized, relatively inexpensive be easy to get) Meso- tetraphenylporphyrins are modified synthesizes inexpensive new list
Replace porphyrin.
It is still another object of the present invention to provide the application of above-mentioned porphyrins.
The purpose of the present invention is achieved through the following technical solutions：
A kind of novel porphyrin class compound, the compound is the phenyl porphyrins of 5- (4- Fonnylphenyls) -10,15,20-, tool
Just like the structure shown in following formula (1)：
The preparation method of above-mentioned novel porphyrin class compound, including following operating procedure：
(1) synthesis of Meso- tetraphenylporphyrins：4.4mL benzaldehydes and 80mL propionic acid, stirring are added in three-neck flask
20min, is then heated to 130 DEG C, and separately the pyrroles that 2mL newly steams is dissolved in 10mL propionic acid, then in dripped in 10min in
After three-neck flask, 1h is heated to reflux, stops heating, when being cooled to room temperature, 10mL methanol stirring is added, lucifuge stands 8h, taken out
Filter obtains the solid of atropurpureus, is washed and is dried in vacuo at filter cake, 60 DEG C with absolute ethyl alcohol, obtains Meso- tetraphenylporphyrins
(TPP)；The mol ratio of the benzaldehyde and pyrroles are 1：4；
(2) synthesis of 5- (4- chloromethyl phenyls) -10,15,20- Triphenylporphyrins：It is separately added into three-neck flask
2.4g paraformaldehydes, 0.3g sodium chloride, 0.29g anhydrous zinc chlorides, then dichloromethanes of the 10mL after drying and distilling is added dropwise thereto
Alkane；Then the system is cooled down and stably to -10 DEG C with ice salt bath, then 4.5mL chlorosulfonic acids is added with 1mL pipettes, stirring is straight
To solid dissolving；The Meso- tetraphenylporphyrins (TPP) that 0.3g has been synthesized are weighed again, are dissolved in the dried chloroforms of 5mL,
In completion of dropping in 5min, then continue to react 15min；Then system is poured into and carrys out terminating reaction in frozen water；Gained is mixed again
Compound is placed in separatory funnel, is extracted with chloroform, and is washed the gas producing formation being collected into neutrality with saturated aqueous common salt, then with nothing
Water Na2SO4Dry crude product；It is finally flushing liquor from methanol, is further purified with column chromatography and obtains 5- (4- chloromethylbenzenes
Base) -10,15,20- Triphenylporphyrins；
(3) preparation of 5- (4- Fonnylphenyls) -10,15,20- phenyl porphyrins：0.6g 5- is added into round-bottomed flask
(4- chloromethyl phenyls) -10,15,20- Triphenylporphyrins, 1.26g urotropine and 35mL chloroforms, is stirred in 45 DEG C
15h is mixed, then solvent is spin-dried for；The acetic acid of 30mL mass concentrations 60% is added immediately, by mixture heating reflux reaction 10h；
Precipitation solid porphyrin is diluted with water after product cooling, is filtered, is washed with water to neutrality, uses anhydrous sodium sulfate drying crude product；Most
It is afterwards 3 from volume ratio:1
Chloroform and petroleum ether be eluant, eluent, use SiO2Column chromatography be further purified obtain 5- (4- Fonnylphenyls)-
10,15,20- phenyl porphyrins.
Above-mentioned novel porphyrin class compound can apply to photoelectric properties and functional material unit block, bionic catalysis and life
In thing antibacterial, with highly important Research Significance, the aldehyde radical in novel porphyrin class compound made from the method can be with one
Level aminated compounds carries out nucleophilic addition formation schiff bases, and schiff base compound has good coordination ability, easily with
Most of metal ion formation metal complex, in terms of catalytic activity, presence of Schiff-base complex can be in Polymer Synthesizing and not right
Claim to be used as catalyst in synthesis.Also due to the conjugated structure of schiff bases, shows certain fluorescence phenomenon, institute in fluorescence spectrum
So that the presence of some compounds can be determined by surveying its fluorescence, for example：Formaldehyde etc..
The present invention has the following advantages and effect relative to prior art：Present invention process is simple, and raw material are easily prepared,
It is few containing accessory substance in synthetic product, and it is high to obtain target product yield.5- (the 4- formoxyl benzene that can be synthesized using the method
Base) -10,15,20- phenyl porphyrins are to produce porphyrin to open up more new approach, and are next step and Meso- tetrakisaminophenyl porphins
Quinoline, which is condensed, to be formed schiff bases and lays the foundation.
Brief description of the drawings
Fig. 1 is that the proton magnetic of 5- (4- Fonnylphenyls) -10,15,20- phenyl porphyrins prepared by embodiment of the present invention is total to
Shake spectrogram.
Fig. 2 is the organic synthesis route map in the present invention.
Embodiment
With reference to embodiment and accompanying drawing, the present invention is described in further detail, but embodiments of the present invention are not limited
In this.
The synthetic route chart that following examples prepare novel porphyrin class compound is as shown in Figure 2.
Embodiment 1
1st, the synthesis of Meso- tetraphenylporphyrins：
(1) 4.4mL benzaldehyde and 3mL propionic acid are added in three-necked flask, 20min is stirred；
(2) 130 DEG C are then heated to, is dripped in 10min in the pyrroles that the 2mL being dissolved in 10mL propionic acid newly steams,
It is heated to reflux 1h；
(3) stop heating, when being cooled to room temperature, add 10mL methanol stirring, lucifuge stands 8h
(4) suction filtration obtains the solid of atropurpureus, is washed and is dried in vacuo at filter cake, 60 DEG C with absolute ethyl alcohol, obtains product
Meso- tetraphenylporphyrins.
2nd, the synthesis of 5- (4- chloromethyl phenyls) -10,15,20- Triphenylporphyrins：
(1) toward being separately added into 2.4g paraformaldehydes, 0.3g sodium chloride, 0.29g anhydrous zinc chlorides in 100mL three-neck flasks,
10mL dichloromethane after drying and distilling is added dropwise thereto again；
(2) and then with ice salt bath the system is cooled down and stably to -10 DEG C, then 4.5mL chlorine sulphurs are added with 1mL pipettes
Acid, stirring is until solid dissolving；
(3) tetraphenylporphyrin (TPP) that 0.3g has been synthesized is weighed again, is dissolved in the dried chloroforms of 5mL, in 5min
Interior completion of dropping；
(4) then continue to react about 12min, system is then poured into frozen water and carrys out terminating reaction；
(5) gained mixture is extracted as in separatory funnel with chloroform, and with saturated aqueous common salt by the product being collected into
Layer is washed to neutrality, then with anhydrous Na2SO4Dry crude product；
(6) finally select methanol to be flushing liquor, be further purified with column chromatography and obtain 5- (4- chloromethyl phenyls) -10,
15,20- Triphenylporphyrins.
3rd, the preparation of 5- (4- Fonnylphenyls) -10,15,20- phenyl porphyrins
(1) toward the 5- (4- chloromethyl phenyls) -10 of addition 1g in 50mL round-bottomed flask, 15,20- Triphenylporphyrins, 2g
Urotropine, 50mL chloroforms stir 15h in 45 DEG C, then solvent are spin-dried for；
(2) acetic acid of 30mL mass concentrations 50% is added immediately, by mixture heating reflux reaction 10h；
(3) precipitation solid porphyrin is diluted with water after product cooling, filters, be washed with water to neutrality, it is dry with anhydrous sodium sulfate
Dry crude product；
(4) chloroform is finally selected：Petroleum ether=3:1 is eluant, eluent, uses SiO2Column chromatography, which is further purified, obtains product,
Hydrogen nuclear magnetic resonance spectrogram is as shown in Figure 1 to be identified using hydrogen nuclear magnetic resonance to products therefrom：1H NMR(400MHz,CDCl3,
ppm):-2.77(s,2H,NH),7.72–7.77(m,9H,m,p-Ph),8.20–8.65(m,8H,o-Ph),8.88-9.6(s,
8H, b-Ph), 10.41 (s, 1H, CHO) can confirm that products therefrom is 5- (4- Fonnylphenyls) -10,15,20- phenyl porphins
Quinoline, shown in its chemical formula such as formula (1).
Embodiment 2
1st, the synthesis of Meso- tetraphenylporphyrins：
(1) 4.4mL benzaldehyde and 3mL propionic acid are added in three-necked flask, 20min is stirred；
(2) 130 DEG C are then heated to, is dripped in 10min in the pyrroles that the 2mL being dissolved in 10mL propionic acid newly steams,
It is heated to reflux 1h；
(3) stop heating, when being cooled to room temperature, add 10mL methanol stirring, lucifuge stands 8h；
(4) suction filtration obtains the solid of atropurpureus, is washed and is dried in vacuo at filter cake, 60 DEG C with absolute ethyl alcohol, obtains product
Meso- tetraphenylporphyrins.
2nd, the synthesis of 5- (4- chloromethyl phenyls) -10,15,20- Triphenylporphyrins：
(1) toward being separately added into 2.4g paraformaldehydes, 0.3g sodium chloride, 0.29g anhydrous zinc chlorides in 100mL three-neck flasks,
10mL dichloromethane after drying and distilling is added dropwise thereto again；
(2) and then with ice salt bath the system is cooled down and stably to -10 DEG C, then 4.5mL chlorine sulphurs are added with 1mL pipettes
Acid, stirring is until solid dissolving；
(3) tetraphenylporphyrin (TPP) that 0.3g has been synthesized is weighed again, is dissolved in the dried chloroforms of 5mL, in 5min
Interior completion of dropping；
(4) then continue to react about 12min, system is then poured into frozen water and carrys out terminating reaction；
(5) gained mixture is extracted as in separatory funnel with chloroform, and with saturated aqueous common salt by the product being collected into
Layer is washed to neutrality, then with anhydrous Na2SO4Dry crude product；
(6) finally select methanol to be flushing liquor, be further purified with column chromatography and obtain 5- (4- chloromethyl phenyls) -10,
15,20- Triphenylporphyrins.
3rd, the preparation of 5- (4- Fonnylphenyls) -10,15,20- phenyl porphyrins：
(1) toward the 5- (4- chloromethyl phenyls) -10 of addition 0.6g in 50mL round-bottomed flask, 15,20- Triphenylporphyrins,
2g urotropine, 50mL chloroforms stir 15h in 45 DEG C, then solvent are spin-dried for；
(2) acetic acid of 30mL mass concentrations 50% is added immediately, by mixture heating reflux reaction 10h；
(3) precipitation solid porphyrin is diluted with water after product cooling, filters, be washed with water to neutrality, it is dry with anhydrous sodium sulfate
Dry crude product；
(4) chloroform is finally selected：Petroleum ether=3:1 is eluant, eluent, uses SiO2Column chromatography, which is further purified, obtains product,
Hydrogen nuclear magnetic resonance spectrogram is as shown in Figure 1 to be identified using hydrogen nuclear magnetic resonance to products therefrom：1H NMR(400MHz,CDCl3,
ppm):-2.77(s,2H,NH),7.72–7.77(m,
9H,m,p-Ph),8.20–8.65(m,8H,o-Ph),8.88-9.6(s,8H,b-Ph),10.41(s,1H,CHO).
Can confirm that products therefrom is the phenyl porphyrins of 5- (4- Fonnylphenyls) -10,15,20-, shown in its chemical formula such as formula (1).
Embodiment 3
1st, the synthesis of Meso- tetraphenylporphyrins：
(1) 4.4mL benzaldehyde and 3mL propionic acid are added in three-necked flask, 20min is stirred；
(2) 130 DEG C are then heated to, is dripped in 10min in the pyrroles that the 2mL being dissolved in 10mL propionic acid newly steams,
It is heated to reflux 1h；
(3) stop heating, when being cooled to room temperature, add 10mL methanol stirring, lucifuge stands 8h；
(4) suction filtration obtains the solid of atropurpureus, is washed and is dried in vacuo at filter cake, 60 DEG C with absolute ethyl alcohol, obtains product
Meso- tetraphenylporphyrins.
2nd, the synthesis of 5- (4- chloromethyl phenyls) -10,15,20- Triphenylporphyrins：
(1) toward being separately added into 2.4g paraformaldehydes, 0.3g sodium chloride, 0.29g anhydrous zinc chlorides in 100mL three-neck flasks,
10mL dichloromethane after drying and distilling is added dropwise thereto again；
(2) and then with ice salt bath the system is cooled down and stably to -10 DEG C, then 4.5mL chlorine sulphurs are added with 1mL pipettes
Acid, stirring is until solid dissolving；
(3) tetraphenylporphyrin (TPP) that 0.3g has been synthesized is weighed again, is dissolved in the dried chloroforms of 5mL, in 5min
Interior completion of dropping；
(4) then continue to react about 12min, system is then poured into frozen water and carrys out terminating reaction；
(5) gained mixture is extracted as in separatory funnel with chloroform, and with saturated aqueous common salt by the product being collected into
Layer is washed to neutrality, then with anhydrous Na2SO4Dry crude product；
(6) finally select methanol to be flushing liquor, be further purified with column chromatography and obtain 5- (4- chloromethyl phenyls) -10,
15,20- Triphenylporphyrins.
3rd, the preparation of 5- (4- Fonnylphenyls) -10,15,20- phenyl porphyrins：
(1) toward the 5- (4- chloromethyl phenyls) -10 of addition 0.6g in 50mL round-bottomed flask, 15,20- Triphenylporphyrins,
1.26g urotropine, 35mL chloroforms stir 15h in 45 DEG C, then solvent are spin-dried for；
(2) acetic acid of 30mL mass concentrations 60% is added immediately, by mixture heating reflux reaction 10h；
(3) precipitation solid porphyrin is diluted with water after product cooling, filters, be washed with water to neutrality, it is dry with anhydrous sodium sulfate
Dry crude product；
(4) chloroform is finally selected：Petroleum ether=3:1 is eluant, eluent, uses SiO2Column chromatography, which is further purified, obtains product,
Hydrogen nuclear magnetic resonance spectrogram is as shown in Figure 1 to be identified using hydrogen nuclear magnetic resonance to products therefrom：1H NMR(400MHz,CDCl3,
ppm):-2.77(s,2H,NH),7.72–7.77(m,9H,m,p-Ph),8.20–8.65(m,8H,o-Ph),8.88-9.6(s,
8H, b-Ph), 10.41 (s, 1H, CHO) can confirm that products therefrom is 5- (4- Fonnylphenyls) -10,15,20- phenyl porphins
Quinoline, shown in its chemical formula such as formula (1).
Above-described embodiment is preferably embodiment, but embodiments of the present invention are not by above-described embodiment of the invention
Limitation, other any Spirit Essences without departing from the present invention and the change made under principle, modification, replacement, combine, simplification,
Equivalent substitute mode is should be, is included within protection scope of the present invention.
Claims (3)
1. a kind of novel porphyrin class compound, it is characterised in that：The compound is 5- (4- Fonnylphenyls) -10,15,20- benzene
Base porphyrin, with the structure as shown in following formula (1)：
2. the preparation method of a kind of novel porphyrin class compound according to claim 1, it is characterised in that including following behaviour
Make step：
(1) synthesis of Meso- tetraphenylporphyrins：4.4mL benzaldehydes and 80mL propionic acid, stirring are added in three-neck flask
20min, is then heated to 130 DEG C, and separately the pyrroles that 2mL newly steams is dissolved in 10mL propionic acid, then in dripped in 10min in
After three-neck flask, 1h is heated to reflux, stops heating, when being cooled to room temperature, 10mL methanol stirring is added, lucifuge stands 8h, taken out
Filter obtains the solid of atropurpureus, is washed and is dried in vacuo at filter cake, 60 DEG C with absolute ethyl alcohol, obtains Meso- tetraphenylporphyrins；It is described
The mol ratio of benzaldehyde and pyrroles are 1：4；
(2) synthesis of 5- (4- chloromethyl phenyls) -10,15,20- Triphenylporphyrins：It is many that 2.4g is separately added into three-neck flask
Polyformaldehyde, 0.3g sodium chloride, 0.29g anhydrous zinc chlorides, then dichloromethane of the 10mL after drying and distilling is added dropwise thereto；Then
The system is cooled down with ice salt bath and stably to -10 DEG C, then 4.5mL chlorosulfonic acids, stirring are added until solid is molten with 1mL pipettes
Solution；The Meso- tetraphenylporphyrins that 0.3g has been synthesized are weighed again, are dissolved in the dried chloroforms of 5mL, in being dripped in 5min
Finish, then continue to react 15min；Then system is poured into and carrys out terminating reaction in frozen water；Gained mixture is placed in into point liquid again to leak
In bucket, extracted, and washed the gas producing formation being collected into neutrality with chloroform with saturated aqueous common salt, then with anhydrous Na2SO4Dry thick
Product；It is finally flushing liquor from methanol, is further purified with column chromatography and obtains 5- (4- chloromethyl phenyls) -10,15,20-
Triphenylporphyrin；
(3) preparation of 5- (4- Fonnylphenyls) -10,15,20- phenyl porphyrins：0.6g 5- (4- chlorine is added into round-bottomed flask
Aminomethyl phenyl) -10,15,20- Triphenylporphyrins, 1.26g urotropine and 35mL chloroforms are stirred in 45 DEG C
15h, is then spin-dried for solvent；The acetic acid of 30mL mass concentrations 60% is added immediately, by mixture heating reflux reaction 10h；Production
Precipitation solid porphyrin is diluted with water after thing cooling, is filtered, is washed with water to neutrality, uses anhydrous sodium sulfate drying crude product；Finally
It is 3 from volume ratio:1 chloroform and petroleum ether is eluant, eluent, uses SiO2Column chromatography, which is further purified, obtains 5- (4- formoxyls
Phenyl) -10,15,20- phenyl porphyrins.
3. a kind of novel porphyrin class compound according to claim 1 is in photoelectric properties and functional material unit block, imitative
Application in raw catalysis and biological antibiotic.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710273217.3A CN107056792A (en) | 2017-04-24 | 2017-04-24 | A kind of novel porphyrin class compound and its preparation method and application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710273217.3A CN107056792A (en) | 2017-04-24 | 2017-04-24 | A kind of novel porphyrin class compound and its preparation method and application |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN107056792A true CN107056792A (en) | 2017-08-18 |
Family
ID=59603937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710273217.3A Pending CN107056792A (en) | 2017-04-24 | 2017-04-24 | A kind of novel porphyrin class compound and its preparation method and application |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107056792A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111825682A (en) * | 2019-04-17 | 2020-10-27 | 台州学院 | Sulfur-oxygen fluorenyl polyporphyrin and preparation method thereof |
| CN115925746A (en) * | 2022-10-19 | 2023-04-07 | 中山大学 | Porphyrin-based reducible and degradable fluorine-containing surfactant and preparation and application thereof |
| CN116082710A (en) * | 2023-02-09 | 2023-05-09 | 安徽省杰事途新材料有限公司 | Regenerated glass powder composite particles for rubber and preparation method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1903855A (en) * | 2006-08-01 | 2007-01-31 | 浙江大学 | Preparation method of unsym-substituted mcso tetraaryl porphyrin kind compound |
-
2017
- 2017-04-24 CN CN201710273217.3A patent/CN107056792A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1903855A (en) * | 2006-08-01 | 2007-01-31 | 浙江大学 | Preparation method of unsym-substituted mcso tetraaryl porphyrin kind compound |
Non-Patent Citations (4)
| Title |
|---|
| ABDUL R. BHAT等: "Synthesis and Biological Evaluation of Novel 4-Substituted 1-{[4-(10,15,20-Triphenylporphyrin-5-yl)phenyl]methylidene}thiosemicarbazides as New Class of Potential Antiprotozoal Agents", 《CHEMISTRY & BIODIVERSITY》 * |
| STEFAN AIGNER等: "On synthesis and properties of hypericin-porphyrin hybrids", 《MONATSH CHEM》 * |
| XUEJUN ZHANG: "Meso-Schiff-base substituted porphyrin dimer dyes for dye-sensitized solar cells: synthesis, electrochemical,and photovoltaic properties", 《RES CHEM INTERMED》 * |
| 夏梅君等: "取代四苯基卟啉的紫外、荧光光谱及电化学性质", 《郑州大学学报(理学版)》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111825682A (en) * | 2019-04-17 | 2020-10-27 | 台州学院 | Sulfur-oxygen fluorenyl polyporphyrin and preparation method thereof |
| CN115925746A (en) * | 2022-10-19 | 2023-04-07 | 中山大学 | Porphyrin-based reducible and degradable fluorine-containing surfactant and preparation and application thereof |
| CN115925746B (en) * | 2022-10-19 | 2024-04-12 | 中山大学 | Porphyrin-based reducible and degradable fluorine-containing surfactant and preparation and application thereof |
| CN116082710A (en) * | 2023-02-09 | 2023-05-09 | 安徽省杰事途新材料有限公司 | Regenerated glass powder composite particles for rubber and preparation method thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105859622B (en) | The method of palladium chtalyst asymmetric hydrogenation synthesis of chiral fluoro pyrazolone derivatives | |
| CN107056792A (en) | A kind of novel porphyrin class compound and its preparation method and application | |
| CN109651202A (en) | Utilize the method for dimethyl sulfoxide ylide, amine and carbon dioxide synthesis of carbamates | |
| CN101462935A (en) | Process for synthesizing alpha-bromoacetophenone compound | |
| CN106831691B (en) | A kind of catalysis oxidation synthetic method of heterochromatic full -4- ketone compounds | |
| CN104592313B (en) | Difunctional hydrogen bond organic catalyst based on ferrocene and its preparation method and application | |
| CN106986886B (en) | A kind of preparation method of the fluoro- 3- Trifluoromethoxyphen-l pinacol borate of 4- | |
| CN110449183A (en) | Ionic iron (III) complex is preparing the application in allylic amines compound | |
| CN115806504B (en) | Asymmetric chiral ligand and preparation method thereof, prepared catalyst, synthesis method and application | |
| CN110078622A (en) | A kind of synthetic method of 4- ethyoxyl -1,1,2,4,5,6- hexahydro cyclobutane and naphthalene -2- benzoic ether | |
| CN106866480B (en) | Polycyclic virtue selenide analog derivative and preparation method thereof | |
| CN105348044B (en) | A kind of synthetic method of hemlock extract (S)-Virol A | |
| CN109651385A (en) | A kind of preparation method of pyrans [3,2-a] carbazole compound | |
| CN101967075A (en) | Method for synthesizing terminal alkyne compound by using 3-aryl-2,3-dibromopropionic acid | |
| CN106365962B (en) | The synthetic method of 1,3- dihydroxy -3,7- dimethyl -6- octene-2-ketone | |
| CN111533707B (en) | Preparation method of polysubstituted oxazole-2 (3H) -ketone compound | |
| CN101092377A (en) | Method for preparing 4 -methoxy - benzonitrile through 'one pot metho | |
| CN108727323B (en) | Method for catalytically synthesizing trifluoromethyl substituted homoisoflavone compound by using N-heterocyclic carbene | |
| CN101580446B (en) | Method for preparing aryl methylene double (3-hydroxide radical-5, 5-dimethyl-2-cyclohexene-1-ketone) terpenoids | |
| CN107954966B (en) | Preparation method for synthesizing 2, 3-disubstituted-4H-benzopyran by Sc (III) catalysis | |
| CN106905205B (en) | One step of one kind constructing Bifunctionalized product of C-O and C-S keys and preparation method thereof | |
| CN105294416B (en) | A kind of 1,5 Dicarbonyl derivatives and preparation method thereof | |
| CN106279114B (en) | A kind of synthetic method of Taladegib | |
| CN109251227A (en) | Chipal compounds of the one kind comprising ferrocene frame having ferrocene frame and rigid spirane structure and synthesis and application | |
| CN110172015A (en) | α-quaternary carbon trifluoromethyl ketone compound and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20170818 |