CN110016239A - One kind containing two pyrroles's alkene fluorescent dyes of big conjugation and its synthetic method - Google Patents
One kind containing two pyrroles's alkene fluorescent dyes of big conjugation and its synthetic method Download PDFInfo
- Publication number
- CN110016239A CN110016239A CN201910345087.9A CN201910345087A CN110016239A CN 110016239 A CN110016239 A CN 110016239A CN 201910345087 A CN201910345087 A CN 201910345087A CN 110016239 A CN110016239 A CN 110016239A
- Authority
- CN
- China
- Prior art keywords
- pyrroles
- big
- alkene
- compound
- boron trifluoride
- 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.)
- Granted
Links
- 150000003233 pyrroles Chemical class 0.000 title claims abstract description 18
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 16
- 238000010189 synthetic method Methods 0.000 title abstract description 4
- 239000007850 fluorescent dye Substances 0.000 title description 10
- 230000021615 conjugation Effects 0.000 title description 8
- FLHJIAFUWHPJRT-UHFFFAOYSA-N 2,3,3-trimethylindole Chemical class C1=CC=C2C(C)(C)C(C)=NC2=C1 FLHJIAFUWHPJRT-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000004032 porphyrins Chemical class 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 11
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 5
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 30
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 20
- 229910015900 BF3 Inorganic materials 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 239000000975 dye Substances 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 241000736199 Paeonia Species 0.000 claims description 2
- 235000006484 Paeonia officinalis Nutrition 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 230000000630 rising effect Effects 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- RKCAIXNGYQCCAL-UHFFFAOYSA-N porphin Chemical compound N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 RKCAIXNGYQCCAL-UHFFFAOYSA-N 0.000 claims 1
- 238000005516 engineering process Methods 0.000 abstract description 4
- 238000000799 fluorescence microscopy Methods 0.000 abstract description 3
- 238000001228 spectrum Methods 0.000 abstract description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract 2
- 239000002841 Lewis acid Substances 0.000 abstract 1
- 238000007171 acid catalysis Methods 0.000 abstract 1
- 238000006482 condensation reaction Methods 0.000 abstract 1
- OVTCUIZCVUGJHS-UHFFFAOYSA-N dipyrrin Chemical class C=1C=CNC=1C=C1C=CC=N1 OVTCUIZCVUGJHS-UHFFFAOYSA-N 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- 238000001914 filtration Methods 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 238000002189 fluorescence spectrum Methods 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000004847 absorption spectroscopy Methods 0.000 description 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000005779 cell damage Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N deuterated chloroform Substances [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000001215 fluorescent labelling Methods 0.000 description 1
- 150000003278 haem Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000008832 photodamage Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
-
- 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Abstract
The invention belongs to field of chemical technology, especially a kind of two pyrroles's alkene dyestuffs containing big conjugated structure, the chemical structural formula are as follows:Synthetic method is to mix porphyrin under Lewis acid catalysis with 2,3,3- tri-methyl indoles and tetraphenyl N-, through condensation reaction, novel two pyrroles's alkenes (dipyrrin) compounds with big conjugated structure of one kind obtained by simple route of synthesis.Key point is to be simple and efficient to obtain the structure by one-step method, to obtain the two pyrroles's vinyl derivatives for having spectrum property excellent, spectrum reaches near infrared region range, has important application in terms of fluorescence imaging.
Description
Technical field
The present invention relates to organic fine chemical technology fields, especially a kind of to contain two pyrroles's alkene dyestuffs of big conjugation and its conjunction
At method.
Background technique
Health be the mankind pursue eternal topic, with the development of the times, how from source to disease carry out prevention and
Treatment, becomes the theme of people's growing interest.Carry out real-time, original position, the Imaging-PAM of living body biological detection becomes people
The focus of research.Fluorescent dye is the key that Imaging-PAM quality, and performance directly influences the sensitivity and standard of detection
True property.Low toxicity, high stability, high-fluorescence quantum yield, preferable cell are needed to have applied to the intracorporal fluorescent dye of biology
The features such as interior solvability and cell-penetrating ability, while depth, cellular damage are penetrated in vivo in view of long wavelength's near infrared light
Small, background fluorescence interferes small.Since stability is poor in vivo for organic nir dye, especially in illumination and organism
Interior complex condition is easily degraded by extraneous illumination and redox materials, fluorescence is caused to be quenched, therefore design is suitable for
In organism the near infrared fluorescent dye of fluorescence labelling be always the developing hot and difficult issue of near-infrared fluorescence imaging technology it
One.
Summary of the invention
The main purpose of the present invention is to provide a kind of simple method for synthesizing, the two pyrroles's alkenes for obtaining big conjugated system are glimmering
Photoinitiator dye and its synthetic method.
Technical scheme is as follows:
A kind of two pyrroles's alkene fluorescent dyes of big conjugation, the dyestuff chemistry structural formula are as follows:
The above-mentioned method containing two pyrroles's alkene fluorescent dyes of big conjugation is synthesized, synthesis path is as follows:
Specific method the following steps are included:
1) 2,3,3- tri-methyl indole of compound, 1,5,10,15,20- tetraphenyl-N- is added into reaction flask at room temperature
Mix porphyrin 2 and toluene, stirring and dissolving；
2) by the step 1) under conditions of boron trifluoride ether catalyst, temperature rising reflux obtains peony mixed liquor；
3) solid chemical compound in Xiang Suoshu step 2) purifies to obtain dark red solid compound 3；
Complete the synthesis of two pyrroles's alkene dyestuffs of big conjugation.
The feed ratio of the step 1) compound 1 and compound 2 is 1.2-5:1.
Step 1) the reaction dissolvent refluxing toluene temperature is 115-125 DEG C DEG C, and the reaction time is 0.5-3 hours.
The reactivity of the step 2) compound 1 is higher, is reacted under boron trifluoride ether catalysts conditions.
The feed ratio of the step 2) boron trifluoride ether and compound 2 is 0.02-0.5:1.
Step 3) the separation method is to obtain purpose product 3 using siliceous earth column chromatography.
The present invention has the beneficial effect that:
1, the present invention is to mix porphyrin in boron trifluoride with 2,3,3- tri-methyl indole and 5,10,15,20- tetraphenyl-N-
Two pyrroles's alkene fluorescent dyes of big conjugation have been prepared in the reflux next step method of ether and toluene solvant, which overcomes reaction
Raw material needs the sieve by a large amount of indole derivatives, various organic acids and bases and reaction dissolvent and its temperature condition during the preparation process
Choosing.The product obtained simultaneously has both the characteristics of ultraviolet and fluorescence spectrum reaches near infrared range.
2, two simple pyrroles's vinyl compounds are generally extremely unstable, easily by the dioxygen oxidation in air, skill of the invention
Art scheme is selectively introducing after N- mixes porphyrin under the reflux of boron trifluoride ether and toluene solvant, two pyrroles's alkene of the conjugation
Class has the characteristics that near infrared absorption, and photo and thermal stability, relatively narrow fluorescence spectrum half-peak breadth, height rub extinction coefficient, easily modification etc.
Characteristic can be applied near infrared fluorescent dye.It can be with a wide range of applications in near-infrared fluorescence imaging technology, have and visit
Depth measurement degree is deep, the advantage small to dermal photodamage.
Detailed description of the invention
1 compound of Fig. 1 embodiment is in CDCl3In nucleus magnetic hydrogen spectrum.
The high resolution mass spectrum of 1 compound of Fig. 2 embodiment.
Ultraviolet-visible absorption spectroscopy of 1 compound of Fig. 3 embodiment in DMF.
Fluorescence spectrum of 1 compound of Fig. 4 embodiment in DMF.
Specific embodiment
Embodiment 1
2,3,3- tri-methyl indole 0.15g (0.12mmol) and 5,10,15,20- tetraphenyl-N- is taken to mix porphyrin 0.61g
(0.10mmol) is dissolved in toluene, and boron trifluoride ether 0.03g (0.02mmol) then is added, and is stirred 5 minutes, is returned in 120 DEG C
Stream 0.5 hour, after reaction, is spin-dried for rear Purification by filtration column and chromatographs to obtain violet compound, yield 95%, the compound is in light
The stability with higher according under can be stabilized 40 days or more under natural light, and for big ring porphyrin-like compound and in vivo
The structural matrix of heme iron is close in blood, and toxicity is minimum.
Embodiment 2
2,3,3- tri-methyl indole 0.26g (0.2mmol) and 5,10,15,20- tetraphenyl-N- is taken to mix porphyrin 0.61g
(0.10mmol) is dissolved in toluene, and boron trifluoride ether 0.03g (0.02mmol) then is added, and is stirred 5 minutes, is returned in 120 DEG C
Stream 0.5 hour, after reaction, is spin-dried for rear Purification by filtration column and chromatographs to obtain violet compound, yield 94%.
Embodiment 3
2,3,3- tri-methyl indole 0.13g (0.1mmol) and 5,10,15,20- tetraphenyl-N- is taken to mix porphyrin 0.61g
(0.10mmol) is dissolved in toluene, and boron trifluoride ether 0.09g (0.06mmol) then is added, and is stirred 5 minutes, is returned in 120 DEG C
Stream 0.5 hour, after reaction, is spin-dried for rear Purification by filtration column and chromatographs to obtain violet compound, yield 90%.
Embodiment 4
2,3,3- tri-methyl indole 0.13g (0.1mmol) and 5,10,15,20- tetraphenyl-N- is taken to mix porphyrin 0.61g
(0.10mmol) is dissolved in toluene, and boron trifluoride ether 0.15g (0.10mmol) then is added, and is stirred 5 minutes, is returned in 120 DEG C
Stream 0.5 hour, after reaction, is spin-dried for rear Purification by filtration column and chromatographs to obtain violet compound, yield 85%.
Embodiment 5
2,3,3- tri-methyl indole 0.65g (0.5mmol) and 5,10,15,20- tetraphenyl-N- is taken to mix porphyrin 0.61g
(0.10mmol) is dissolved in toluene, and boron trifluoride ether 0.03g (0.02mmol) then is added, and is stirred 5 minutes, is returned in 120 DEG C
Stream 0.5 hour, after reaction, is spin-dried for rear Purification by filtration column and chromatographs to obtain violet compound, yield 93%.
Embodiment 6
2,3,3- tri-methyl indole 0.15g (0.12mmol) and 5,10,15,20- tetraphenyl-N- is taken to mix porphyrin 0.61g
(0.10mmol) is dissolved in toluene, and boron trifluoride ether 0.03g (0.02mmol) then is added, and is stirred 5 minutes, is returned in 120 DEG C
Stream 2 hours, after reaction, is spin-dried for rear Purification by filtration column and chromatographs to obtain violet compound, yield 90%.
Embodiment 7
2,3,3- tri-methyl indole 0.15g (0.12mmol) and 5,10,15,20- tetraphenyl-N- is taken to mix porphyrin 0.61g
(0.10mmol) is dissolved in toluene, and boron trifluoride ether 0.03g (0.02mmol) then is added, and is stirred 5 minutes, is returned in 120 DEG C
Stream 3 hours, after reaction, is spin-dried for rear Purification by filtration column and chromatographs to obtain violet compound, yield 82%.
Embodiment 8
The compound 0.076g that embodiment 1 obtains is weighed, is dissolved in 10mLDMF, is configured to the mother of 10 mmol/L
Then liquid takes 10 μ L mother liquors to be diluted to the dye solution (10 μm of ol/L) of 10mL, utilize ultraviolet-uisible spectrophotometer and glimmering
Light spectrophotometer carries out testing its ultraviolet-visible spectrum and fluorescence spectrum, testing result are as shown in Figure 3,4, the results showed that,
Compound has near-infrared absorption, and has higher fluorescent emission effect, can be used as fluorescent dye use.
Claims (4)
1. one kind contains big two pyrroles's alkene dyestuff of conjugated body, which is characterized in that the dyestuff chemistry structural formula are as follows:
2. synthesizing the method described in claim 1 containing big two pyrroles's alkene dyestuff of conjugated body, which is characterized in that the method packet
Include following steps:
1) 2,3,3- tri-methyl indole of compound is added into reaction flask at room temperature, 5,10,15,20- tetraphenyl-N- mix porphin
Quinoline and toluene, stirring and dissolving；
2) boron trifluoride ether catalyst will be added in the solution of the step 1), in the condition of boron trifluoride ether catalyst
Under, temperature rising reflux obtains peony mixed liquor；
3) solid chemical compound in the step 2) purifies to obtain dark red solid compound, as contains big two pyrroles of conjugated body
Alkene dyestuff.
3. synthesis according to claim 2 contains the method for big two pyrroles's alkene dyestuff of conjugated body, which is characterized in that the step
It is rapid 1) in 2,3,3- tri-methyl indole, boron trifluoride ether and 5,10,15,20- tetraphenyl-N- mix the mass ratio that feeds intake of porphyrin
For 1.2-5:0.02-0.5:1.
4. synthesis according to claim 2 contains the method for big two pyrroles's alkene dyestuff of conjugated body, it is characterised in that: the step
It is rapid 2) in back flow reaction temperature be 115-125 DEG C, the reaction time be 0.5-3 hours.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910345087.9A CN110016239B (en) | 2019-04-26 | 2019-04-26 | Fluorescent dye containing large conjugated dipyrrole and synthetic method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910345087.9A CN110016239B (en) | 2019-04-26 | 2019-04-26 | Fluorescent dye containing large conjugated dipyrrole and synthetic method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN110016239A true CN110016239A (en) | 2019-07-16 |
| CN110016239B CN110016239B (en) | 2021-02-02 |
Family
ID=67192525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910345087.9A Active CN110016239B (en) | 2019-04-26 | 2019-04-26 | Fluorescent dye containing large conjugated dipyrrole and synthetic method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110016239B (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108558893A (en) * | 2018-06-11 | 2018-09-21 | 三峡大学 | A kind of synthesis of porphyrin sensitizer and its method |
-
2019
- 2019-04-26 CN CN201910345087.9A patent/CN110016239B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108558893A (en) * | 2018-06-11 | 2018-09-21 | 三峡大学 | A kind of synthesis of porphyrin sensitizer and its method |
Non-Patent Citations (4)
| Title |
|---|
| IZABELA SCHMIDT ET AL.: "An inverted porphyrin with a pendant pyrrole—identification of a tetraphenylsapphyrin isomer in the Rothemund synthesis", 《TETRAHEDRON LETTERS》 * |
| RYUICHI SAKASHITA ET AL.: "Tautomerism-Induced Cis-Trans Isomerization of Pyridylethenyl N‑Confused Porphyrin", 《J. ORG. CHEM.》 * |
| 李倩倩 等: "新型含吲哚基团的光电功能材料", 《化学进展》 * |
| 李筱芳 等: "N-混杂卟啉的合成及其衍生化反应的进展", 《有机化学》 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN110016239B (en) | 2021-02-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109294569A (en) | A kind of preparation method of the adjustable carbon dots of fluorescence color | |
| CN111995580B (en) | Fluorescent dye with tetraphenyl ethylene imidazole ring structure and application thereof | |
| CN110128430B (en) | 8-hydroxyquinolyl corrole gallium complex pH fluorescent probe and preparation method thereof | |
| CN106084873B (en) | A kind of efficiently near-infrared fluorescent material and its biologic applications | |
| CN108102408B (en) | A kind of preparation and application of the nir dye based on azepine fluorine borine | |
| CN110229120B (en) | Long-wavelength fluorescent dye molecule and preparation method thereof | |
| CN111995579B (en) | Preparation method and application of tetraphenylethylene derivative containing imidazole ring structure | |
| CN113861156B (en) | Near-infrared aggregation-induced emission organic fluorescent dye and preparation method and application thereof | |
| Sun et al. | A novel colorimetric and fluorometric probe for the detection of CN− with high selectivity in aqueous media | |
| CN110272734A (en) | A kind of high quantum production rate carbon quantum dot preparation method and applications for NO detection | |
| CN104861039B (en) | A kind of phthalocyanine compound, preparation method and the application as single, double photon fluorescence probe in cancer targeting and mitochondrial markers | |
| CN110256218A (en) | A kind of aggregation-induced emission dye molecule and its synthetic method | |
| CN110305026B (en) | Solid fluorescent dye and preparation method thereof | |
| CN109796483A (en) | A kind of water-soluble cationic photosensitizer and its preparation and application | |
| CN106831719B (en) | A kind of more pyridine naphthalimide fluorescence dendrimers and its preparation method and application | |
| Han et al. | A diphenylacrylonitrile conjugated porphyrin with near-infrared emission by AIE–FRET | |
| CN111548363B (en) | Intelligent photosensitizer and preparation method and application thereof | |
| CN111793371B (en) | 3, 5-asymmetrically modified BODIPY near-infrared fluorescent dye and preparation method thereof | |
| CN111849196B (en) | Near-infrared two-region dye and synthetic method thereof | |
| CN110256339B (en) | Organic fluorescent dye molecule and preparation method thereof | |
| CN105199422B (en) | Sulfhydryl group-containing bithiophene benzoindoles dye as well as preparation method and application thereof | |
| CN117165284A (en) | Ratio fluorescent probe and test strip for detecting tetracycline as well as preparation methods and applications thereof | |
| CN110016239A (en) | One kind containing two pyrroles's alkene fluorescent dyes of big conjugation and its synthetic method | |
| CN106892870A (en) | Lysosome targeted two-photon viscosity fluorescent probe and preparation method and application thereof | |
| CN114106027B (en) | Fluoroboron fluorescent dye-tetrazine fluorescent probe and preparation method and application 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 | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20240605 Address after: 443200 Qixingtai Shipbuilding Industrial Park, Zhijiang City, Yichang City, Hubei Province Patentee after: Yichang Xinhui Shipbuilding Co.,Ltd. Country or region after: China Address before: 443002 No. 8, University Road, Xiling District, Yichang, Hubei Patentee before: CHINA THREE GORGES University Country or region before: China |
|
| TR01 | Transfer of patent right | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A fluorescent dye containing a large conjugated dipyrrole and its synthesis method Granted publication date: 20210202 Pledgee: China Postal Savings Bank Co.,Ltd. Zhijiang Branch Pledgor: Yichang Xinhui Shipbuilding Co.,Ltd. Registration number: Y2024980038030 |
|
| PE01 | Entry into force of the registration of the contract for pledge of patent right |