CN110016239B - Fluorescent dye containing large conjugated dipyrrole and synthetic method thereof - Google Patents
Fluorescent dye containing large conjugated dipyrrole and synthetic method thereof Download PDFInfo
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- CN110016239B CN110016239B CN201910345087.9A CN201910345087A CN110016239B CN 110016239 B CN110016239 B CN 110016239B CN 201910345087 A CN201910345087 A CN 201910345087A CN 110016239 B CN110016239 B CN 110016239B
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- boron trifluoride
- trimethylindole
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- ULUNQYODBKLBOE-UHFFFAOYSA-N 2-(1h-pyrrol-2-yl)-1h-pyrrole Chemical compound C1=CNC(C=2NC=CC=2)=C1 ULUNQYODBKLBOE-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 238000010189 synthetic method Methods 0.000 title claims description 5
- 239000007850 fluorescent dye Substances 0.000 title description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 150000004032 porphyrins Chemical class 0.000 claims abstract description 13
- FLHJIAFUWHPJRT-UHFFFAOYSA-N 2,3,3-trimethylindole Chemical compound C1=CC=C2C(C)(C)C(C)=NC2=C1 FLHJIAFUWHPJRT-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims abstract description 5
- OVTCUIZCVUGJHS-UHFFFAOYSA-N dipyrrin Chemical compound C=1C=CNC=1C=C1C=CC=N1 OVTCUIZCVUGJHS-UHFFFAOYSA-N 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 32
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 239000000975 dye Substances 0.000 claims description 10
- 238000004440 column chromatography Methods 0.000 claims description 9
- 238000001035 drying Methods 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000009987 spinning Methods 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 238000000799 fluorescence microscopy Methods 0.000 abstract description 4
- 238000001308 synthesis method Methods 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000001228 spectrum Methods 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000002841 Lewis acid Substances 0.000 abstract 1
- 238000006555 catalytic reaction Methods 0.000 abstract 1
- 238000006482 condensation reaction Methods 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- 230000003595 spectral effect Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 4
- 238000002189 fluorescence spectrum Methods 0.000 description 4
- 238000001514 detection method Methods 0.000 description 3
- 238000005286 illumination Methods 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 239000010413 mother solution Substances 0.000 description 2
- 230000000149 penetrating effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 2
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- 241000282414 Homo sapiens Species 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
- 238000010521 absorption reaction Methods 0.000 description 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect 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
- 208000037887 cell injury Diseases 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 230000007547 defect Effects 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
- 238000007865 diluting Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000012632 fluorescent imaging Methods 0.000 description 1
- 150000003278 haem Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000011259 mixed solution 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
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000008832 photodamage Effects 0.000 description 1
- -1 porphyrin compound Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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- 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
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- 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 the technical field of organic chemical industry, and particularly relates to a dipyrromethene dye containing a large conjugated structure, wherein the chemical structural formula is as follows:
the synthesis method is that 2,3, 3-trimethylindole and tetraphenyl N-mixed porphyrin are subjected to condensation reaction under the catalysis of Lewis acid, and a novel dipyrroline (dipyryrin) compound with a large conjugated structure is obtained through a simple synthesis way. The key point is that the structure is simply and efficiently obtained through a one-step method, so that the dipyrrole derivative with excellent spectral performance is obtained, the spectrum of the dipyrrole derivative reaches the range of a near infrared region, and the dipyrrole derivative has important application in the aspect of fluorescence imaging.
Description
Technical Field
The invention relates to the technical field of organic fine chemical engineering, in particular to a dye containing large conjugated dipyrromethene and a synthetic method thereof.
Background
Health is a constant topic pursued by human beings, and with the development of times, how to prevent and treat diseases from the source becomes a subject of increasing attention of people. Fluorescence imaging technology for real-time, in-situ, in vivo biological detection has become the focus of research. The fluorescent dye is the key to the quality of the fluorescence imaging technology, and the performance of the fluorescent dye directly influences the sensitivity and accuracy of detection. The fluorescent dye applied to organisms needs to have the characteristics of low toxicity, high stability, high fluorescence quantum yield, better intracellular dissolving capacity, better cell penetrating capacity and the like, and simultaneously, the fluorescent dye has the advantages of deep penetrating depth of long-wavelength near-infrared light in the organisms, small cell damage and small background fluorescence interference. Because the stability of the organic near-infrared dye in a living body is poor, especially under the illumination and complex conditions in the living body, the organic near-infrared dye is very easy to be degraded by the external illumination and redox substances, and the fluorescence is quenched, the design of the near-infrared fluorescent dye suitable for the fluorescent identification in the living body is always one of the hot points and difficulties in the development of the near-infrared fluorescent imaging technology.
Disclosure of Invention
The invention mainly aims to provide a simple synthesis method for obtaining a dipyrrolene fluorescent dye with a large conjugated system and a synthesis method thereof.
The technical scheme of the invention is as follows:
a large conjugated dipyrrole fluorescent dye is disclosed, wherein the chemical structural formula of the dye is as follows:
the synthetic method of the fluorescent dye containing the large conjugated dipyrrole comprises the following synthetic route:
the method comprises the following steps:
1) adding the compound 2,3, 3- trimethylindole 1, 5,10,15, 20-tetraphenyl-N-hybrid porphyrin 2 and toluene into a reaction bottle at room temperature, and stirring for dissolving;
2) heating and refluxing the mixture obtained in the step 1) under the condition of boron trifluoride diethyl etherate catalyst to obtain dark red mixed solution;
3) purifying the solid compound in the step 2) to obtain a deep red solid compound 3;
the synthesis of the large conjugated dipyrrole dye is completed.
The feeding ratio of the compound 1 to the compound 2 in the step 1) is 1.2-5: 1.
The reflux temperature of the reaction solvent toluene in the step 1) is 115-125 ℃, and the reaction time is 0.5-3 hours.
The compound 1 in the step 2) has high reaction activity and reacts under the condition of boron trifluoride diethyl etherate catalyst.
The feeding ratio of boron trifluoride diethyl etherate in the step 2) to the compound 2 is 0.02-0.5: 1.
The separation method in the step 3) is to separate the target product 3 by utilizing a diatomite column chromatography.
The invention has the following beneficial effects:
1. the large conjugated dipyrrolene fluorescent dye is prepared by refluxing 2,3, 3-trimethylindole and 5,10,15, 20-tetraphenyl-N-mixed porphyrin in boron trifluoride ethyl ether and toluene solvent by a one-step method, and the reaction overcomes the defect that a large amount of indole derivatives, various organic acids and bases, reaction solvents and temperature condition screening are required in the preparation process of reaction raw materials. Meanwhile, the obtained product has the characteristic that the ultraviolet spectrum and the fluorescence spectrum reach the near infrared range.
2. The pure dipyrroline compound is generally extremely unstable and is easily oxidized by oxygen in the air, and after N-hybrid porphyrin is selectively introduced under the reflux of boron trifluoride ethyl ether and toluene solvent in the technical scheme of the invention, the conjugated dipyrroline has the characteristics of near-infrared absorption, photo-thermal stability, narrower fluorescence spectrum half-peak width, high molar extinction coefficient, easy modification and the like, and can be applied to near-infrared fluorescent dyes. The method has wide application prospect in the near-infrared fluorescence imaging technology, and has the advantages of deep detection depth and small skin light damage.
Drawings
FIG. 1 Compound of example 1 in CDCl3Nuclear magnetic hydrogen spectrum of (1).
Figure 2 high resolution mass spectrum of the compound of example 1.
FIG. 3 UV-VIS absorption spectrum of the compound of example 1 in DMF.
FIG. 4 fluorescence spectrum of example 1 compound in DMF.
Detailed Description
Example 1
Dissolving 0.15g (0.12mmol) of 2,3, 3-trimethylindole and 0.61g (0.10mmol) of 5,10,15, 20-tetraphenyl-N-hybrid porphyrin in toluene, adding 0.03g (0.02mmol) of boron trifluoride diethyl ether, stirring for 5 minutes, refluxing at 120 ℃ for 0.5 hour, after the reaction is finished, drying, filtering, purifying and performing column chromatography to obtain a purple compound, wherein the yield is 95%, the compound has high stability under illumination, can stably exist for more than 40 days under natural light, is a macrocyclic porphyrin compound similar to a structural matrix of heme iron in blood in vivo, and has extremely low toxicity.
Example 2
0.26g (0.2mmol) of 2,3, 3-trimethylindole and 0.61g (0.10mmol) of 5,10,15, 20-tetraphenyl-N-hybrid porphyrin are dissolved in toluene, 0.03g (0.02mmol) of boron trifluoride diethyl ether is added, the mixture is stirred for 5 minutes and refluxed at 120 ℃ for 0.5 hour, and after the reaction is finished, the purple compound is obtained by filtration and purification column chromatography after spin drying, and the yield is 94%.
Example 3
0.13g (0.1mmol) of 2,3, 3-trimethylindole and 0.61g (0.10mmol) of 5,10,15, 20-tetraphenyl-N-hybrid porphyrin are dissolved in toluene, 0.09g (0.06mmol) of boron trifluoride diethyl ether is added, the mixture is stirred for 5 minutes and refluxed at 120 ℃ for 0.5 hour, and after the reaction is finished, the purple compound is obtained by column chromatography through filtration and purification after the spin-drying, and the yield is 90%.
Example 4
0.13g (0.1mmol) of 2,3, 3-trimethylindole and 0.61g (0.10mmol) of 5,10,15, 20-tetraphenyl-N-hybrid porphyrin are dissolved in toluene, 0.15g (0.10mmol) of boron trifluoride diethyl ether is added, the mixture is stirred for 5 minutes and refluxed at 120 ℃ for 0.5 hour, after the reaction is finished, the purple compound is obtained by column chromatography through filtration and purification after the spin-drying, and the yield is 85%.
Example 5
0.65g (0.5mmol) of 2,3, 3-trimethylindole and 0.61g (0.10mmol) of 5,10,15, 20-tetraphenyl-N-hybrid porphyrin are dissolved in toluene, 0.03g (0.02mmol) of boron trifluoride diethyl ether is added, the mixture is stirred for 5 minutes and refluxed at 120 ℃ for 0.5 hour, and after the reaction is finished, the purple compound is obtained by filtration and purification column chromatography after spin drying, and the yield is 93%.
Example 6
0.15g (0.12mmol) of 2,3, 3-trimethylindole and 0.61g (0.10mmol) of 5,10,15, 20-tetraphenyl-N-hybrid porphyrin are dissolved in toluene, 0.03g (0.02mmol) of boron trifluoride diethyl ether is added, the mixture is stirred for 5 minutes and refluxed at 120 ℃ for 2 hours, and after the reaction is finished, the purple compound is obtained by filtration and purification column chromatography after spin drying, and the yield is 90%.
Example 7
0.15g (0.12mmol) of 2,3, 3-trimethylindole and 0.61g (0.10mmol) of 5,10,15, 20-tetraphenyl-N-hybrid porphyrin are dissolved in toluene, 0.03g (0.02mmol) of boron trifluoride diethyl ether is added, the mixture is stirred for 5 minutes and refluxed at 120 ℃ for 3 hours, and after the reaction is finished, the purple compound is obtained by filtration and purification column chromatography after spin drying, and the yield is 82%.
Example 8
Weighing 0.076g of the compound obtained in example 1, dissolving the compound in 10mLDMF to prepare a 10 mmol/L mother solution, then diluting 10. mu.L of the mother solution into a 10mL dye solution (10. mu. mol/L), and testing the ultraviolet visible spectrum and the fluorescence spectrum by using an ultraviolet visible spectrophotometer and a fluorescence spectrophotometer, wherein the test results are shown in figures 3 and 4, and the results show that the compound has near infrared light absorption and higher fluorescence emission effect, and can be used as a fluorescent dye.
Claims (2)
1. A synthetic method of dipyrrole dye containing large conjugate is characterized in that the chemical structural formula of the dye is as follows:
the method comprises the following steps:
1) adding the compound 2,3, 3-trimethylindole, 5,10,15, 20-tetraphenyl-N-mixed porphyrin and toluene into a reaction bottle at room temperature, and stirring for dissolving;
2) adding boron trifluoride diethyl etherate catalyst into the solution obtained in the step 1), heating and refluxing under the condition of the boron trifluoride diethyl etherate catalyst, after the reaction is finished, drying in a spinning mode, filtering and purifying column chromatography to obtain a purple compound, namely the dipyrroline dye containing a large conjugate;
the mass ratio of the 2,3, 3-trimethylindole to boron trifluoride diethyl etherate to the 5,10,15, 20-tetraphenyl-N-mixed porphyrin is 1.2-5: 0.02-0.5: 1.
2. The method of synthesizing dipyrromethene-containing dyes according to claim 1, wherein: the reflux reaction temperature in the step 2) is 115-125 ℃, and the reaction time is 0.5-3 hours.
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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 |
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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 |
|---|
| An inverted porphyrin with a pendant pyrrole—identification of a tetraphenylsapphyrin isomer in the Rothemund synthesis;Izabela Schmidt et al.;《Tetrahedron Letters》;20011231;第42卷;第1151-1154页 * |
| N-混杂卟啉的合成及其衍生化反应的进展;李筱芳 等;《有机化学》;20111231;第31卷(第2期);第166-175页 * |
| Tautomerism-Induced Cis-Trans Isomerization of Pyridylethenyl N‑Confused Porphyrin;Ryuichi Sakashita et al.;《J. Org. Chem.》;20170726;第82卷;第8686-8696页 * |
| 新型含吲哚基团的光电功能材料;李倩倩 等;《化学进展》;20091231;第21卷(第12期);第2578-2588页 * |
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