CN108752354A - A kind of synthesis of porphyrin fluorescence dyestuff and its method - Google Patents
A kind of synthesis of porphyrin fluorescence dyestuff and its method Download PDFInfo
- Publication number
- CN108752354A CN108752354A CN201810594682.1A CN201810594682A CN108752354A CN 108752354 A CN108752354 A CN 108752354A CN 201810594682 A CN201810594682 A CN 201810594682A CN 108752354 A CN108752354 A CN 108752354A
- Authority
- CN
- China
- Prior art keywords
- compound
- nitro
- iii
- porphyrin
- hydrogen
- 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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention belongs to fine field of chemical technology, especially a kind of porphyrin fluorescence dyestuff, the fluorescent dye chemical structural formula is：Wherein, synthetic method is with zinc -5- (4- pyridyl groups) -10,15,20- triaryl porphyrins etc. are initial feed, through N- alkylated reactions, obtained a kind of novel porphyrin fluorescent dye, key point is that the synthetic method yield is high, again because electronic spectrum property is preferable, fluorescence quantum yield is high and biological close friend, be conducive to its application in vivo.
Description
Technical field
The present invention relates to field of chemical technology, the synthesis of especially a kind of porphyrin fluorescence dyestuff and its method.
Background technology
Fluorescent dye shows gratifying application in fields such as biomedical imaging, photochemical therapy and three-dimensional storage data
Foreground.Application especially in terms of fluorescence probe, because its selectivity is good, high sensitivity, testing cost is low, causes vast grind
Study carefully the interest of personnel.As the important component of probe, fluorescent dye plays very important effect.It is glimmering to design synthesizing new
Photoinitiator dye becomes the hot spot of research.
Porphyrin is as a kind of substance being widely present in nature, and because its biology is friendly, photo-thermal chemical stability is good, has
Good spectral response absorbs by force near infrared region, plays an important roll in fluorescent dye.But the fluorescence of porphyrin dye
Quantum yield is low, makes its application by larger limitation.Therefore the porphyrin compound of the design synthesis sub- yield of higher amount has certain
Application value.
Invention content
The main purpose of the present invention is to provide a kind of synthesis of porphyrin fluorescence dyestuff and its methods.
Technical scheme is as follows：
A kind of porphyrin fluorochrome, the dyestuff chemistry structural formula are：
Wherein, substituent R1Including hydrogen, alkyl, aryl, alkoxy, acylamino-, hydroxyl, itrile group, nitro, halogen, ester group
In any one；R2Including any one in ethoxycarbonyl, 4- carbomethoxvphenvls, itrile group, nitro.
The method of the synthesis porphyrin fluorescence dyestuff, the method includes following synthesis paths：
It the described method comprises the following steps：
1) into reaction bulb, addition compound II, III, chloroform are heated to reflux at room temperature, are concentrated to give solid chemical combination
Object；
The compound II is zinc -5- (4- pyridyl groups) -10,15,20- triaryl porphyrins.
2) solid chemical compound in the step 1) is purified to obtain N- alkylates I；
The feeding sequence of the step 1) compound is compound II, compound III and chloroform.
The rate of charge of step 1) the compound II and III are 1：A concentration of 1-100mmol/L of 1-200, compound II.
Step 1) the counterflow condition is to be warming up to 70-90 DEG C, back flow reaction 3-48h, further preferably at 80 DEG C
Back flow reaction is for 24 hours.
Step 2) the way of purification is silica gel, and diatomite chromatography, recrystallization is further purified.
Step 2) the recrystallization purifying solvent is dichloromethane, methanol, n-hexane, pentane.
Complete the synthesis of porphyrin fluorochrome solar cell sensitizer.
The present invention has the beneficial effect that：
1, the porphyrin fluorescence dyestuff biology that the present invention synthesizes is friendly, has water solubility；With good spectral response ability,
There is practical value in application in vivo.
2, a kind of high quantum production rate porphyrin different from classical porphyrins fluorescent dye of present invention synthesis, reachable 15% or more,
A kind of synthetic method that yield is high is provided, there is certain practical value using upper in fluorescence probe.
Description of the drawings
Fig. 1 is the nucleus magnetic hydrogen spectrum figure of compound I in embodiment 8-10.
Fig. 2 is the nucleus magnetic hydrogen spectrum figure of compound I in embodiment 1-7
Fig. 3 is the steady-state fluorescence spectrum of compound I in embodiment 8-10, R1For hydrogen, R2For ethoxycarbonyl
Fig. 4 is the uv-vis spectra of compound I in embodiment 8-10, R1For hydrogen, R2For ethoxycarbonyl
Fig. 5 is the steady-state fluorescence spectrum of compound I in embodiment 1-7, R1For hydrogen, R2For 4- carbomethoxvphenvls
Fig. 6 is the uv-vis spectra of compound I in embodiment 1-7, R1For hydrogen, R2For 4- carbomethoxvphenvls
Specific implementation mode
It is further illustrated the present invention with reference to embodiment, but the scope of protection of present invention is not limited to implement
The range of example statement.
Embodiment 1
By 1.05g (1.25mmol) compound II (R1Substituent group hydrogen) and 0.21g (1.25mmol) III (R2Substituent group is second
Oxygen formoxyl) it is dissolved in chloroform, for 24 hours, silica gel column chromatography recrystallizes (dichloromethane to heating reflux reaction：N-hexane=1:2)
Purifying, obtains compound I, yield 60%.
Embodiment 2
By 1.05g (1.25mmol) compound II (R1Substituent group hydrogen) and 20.9g (125mmol) III (R2Substituent group is second
Oxygen formoxyl) it is dissolved in chloroform, for 24 hours, silica gel column chromatography recrystallizes (dichloromethane to heating reflux reaction：N-hexane=1:2)
Purifying, obtains compound I, yield 70%.
Embodiment 3
By 1.05g (1.25mmol) compound II (R1Substituent group hydrogen) and 41.8g (250mmol) III (R2Substituent group is second
Oxygen formoxyl) it is dissolved in chloroform, for 24 hours, silica gel column chromatography recrystallizes (dichloromethane to heating reflux reaction：N-hexane=1:2)
Purifying, obtains compound I, yield 85%.
Embodiment 4
By 1.05g (1.25mmol) compound II (R1Substituent group hydrogen) and 10.4g (62.5mmol) III (R2Substituent group is second
Oxygen formoxyl) it is dissolved in chloroform, heating reflux reaction 12h, silica gel column chromatography, recrystallize (dichloromethane：N-hexane=1:2)
Purifying, obtains compound I, yield 80%.
Embodiment 5
By 1.05g (1.25mmol) compound II (R1Substituent group hydrogen) and 10.4g (62.5mmol) III (R2Substituent group is second
Oxygen formoxyl) it is dissolved in chloroform, for 24 hours, silica gel column chromatography recrystallizes (dichloromethane to heating reflux reaction：N-hexane=1:2)
Purifying, obtains compound I, yield 80%.
Embodiment 6
By 1.05g (1.25mmol) compound II (R1Substituent group hydrogen) and 10.4g (62.5mmol) III (R2Substituent group is second
Oxygen formoxyl) it is dissolved in chloroform, heating reflux reaction 48h, silica gel column chromatography, recrystallize (dichloromethane：N-hexane=1:2)
Purifying, obtains compound I, yield 78%.
Embodiment 7
By 1.05g (1.25mmol) compound II (R1Substituent group hydrogen) and 10.4g (62.5mmol) III (R2Substituent group is second
Oxygen formoxyl) it is dissolved in chloroform, heating reflux reaction 48h, silica gel column chromatography, recrystallize (dichloromethane：Methanol=1:2) pure
Change, obtains compound I, yield 85%.
Embodiment 8
By 1.05g (1.25mmol) compound II (R1Substituent group hydrogen) and 14.3g (62.5mmol) III (R2Substituent group is 4-
Carbomethoxvphenvl) it is dissolved in chloroform, heating reflux reaction 48h, silica gel column chromatography, recrystallize (dichloromethane：Methanol=
1:2) it purifies, obtains compound I, yield 82%.
Embodiment 9
By 1.05g (1.25mmol) compound II (R1Substituent group hydrogen) and 28.6g (125mmol) III (R2Substituent group is 4-
Carbomethoxvphenvl) it is dissolved in chloroform, for 24 hours, silica gel column chromatography recrystallizes (dichloromethane to heating reflux reaction：N-hexane
=1:2) it purifies, obtains compound I, yield 80%.
Embodiment 10
By 1.05g (1.25mmol) compound II (R1Substituent group hydrogen) and 28.6g (125mmol) III (R2Substituent group is 4-
Carbomethoxvphenvl) it is dissolved in chloroform, heating reflux reaction 48h, silica gel column chromatography, recrystallize (dichloromethane：Methanol=
1:2) it purifies, obtains compound I, yield 90%.
Embodiment 11
By 1.11g (1.25mmol) compound II (R1Replace ylmethyl) and 20.9g (125mmol) III (R2Substituent group is
Ethoxycarbonyl) it is dissolved in chloroform, for 24 hours, silica gel column chromatography recrystallizes (dichloromethane to heating reflux reaction：N-hexane=1:
2) it purifies, obtains compound I, yield 86%.
Embodiment 12
By 1.18g (1.25mmol) compound II (R1Replace ylmethyl) and 28.6g (125mmol) III (R2Substituent group is
4- carbomethoxvphenvls) it is dissolved in chloroform, for 24 hours, silica gel column chromatography recrystallizes (dichloromethane to heating reflux reaction：Just oneself
Alkane=1:2) it purifies, obtains compound I, yield 83%.
Embodiment 13
By 1.17g (1.25mmol) compound II (R1Replace ylmethoxy) and 20.9g (125mmol) III (R2Substituent group
For ethoxycarbonyl) it is dissolved in chloroform, for 24 hours, silica gel column chromatography recrystallizes (dichloromethane to heating reflux reaction：N-hexane=
1:2) it purifies, obtains compound I, yield 80%.
Embodiment 14
By 1.24g (1.25mmol) compound II (R1Replace ylmethoxy) and 28.6g (125mmol) III (R2Substituent group
For 4- carbomethoxvphenvls) it is dissolved in chloroform, for 24 hours, silica gel column chromatography recrystallizes (dichloromethane to heating reflux reaction：Just
Hexane=1:2) it purifies, obtains compound I, yield 85%.
Embodiment 15
By 1.13g (1.25mmol) compound II (R1Replace ylmethoxy) and 17.5g (125mmol) III (R2Substituent group
Nitro) it is dissolved in chloroform, for 24 hours, silica gel column chromatography recrystallizes (dichloromethane to heating reflux reaction：N-hexane=1:2) pure
Change, obtains compound I, yield 78%.
Embodiment 16
By 1.11g (1.25mmol) compound II (R1Replace ylmethoxy) and 14.9g (125mmol) III (R2Substituent group
Itrile group) it is dissolved in chloroform, for 24 hours, silica gel column chromatography recrystallizes (dichloromethane to heating reflux reaction：N-hexane=1:2) pure
Change, obtains compound I, yield 80%.
The above embodiments are only the preferred technical solution of the present invention, and are not construed as the limitation for the present invention, this Shen
Please in embodiment and embodiment in feature in the absence of conflict, mutually can arbitrarily combine.The protection model of the present invention
Enclose the equivalent replacement side of technical characteristic in the technical solution that should be recorded with claim, including the technical solution of claim record
Case is protection domain.Equivalent replacement i.e. within this range is improved, also within protection scope of the present invention.
Claims (7)
1. a kind of porphyrin fluorescence dyestuff, which is characterized in that the fluorescent dye chemical structural formula is：
Wherein, substituent R1Including hydrogen, alkyl, aryl, alkoxy, acylamino-, hydroxyl, itrile group, nitro, halogen, ester group；R2Packet
Include ethoxycarbonyl, 4- carbomethoxvphenvls, itrile group, nitro.
2. the method for synthesis porphyrin fluorescence dyestuff described in claim 1, which is characterized in that the method includes following synthesis roads
Diameter：
Wherein, substituent R1Including appointing in hydrogen, alkyl, aryl, alkoxy, acylamino-, hydroxyl, itrile group, nitro, halogen, ester group
Meaning is a kind of；R2Including any one in ethoxycarbonyl, 4- carbomethoxvphenvls, itrile group, nitro；
It the described method comprises the following steps：
1) it is added compound II into reaction bulb at room temperature, III, chloroform, heating reflux reaction 3-48h at 70-90 DEG C,
It is concentrated to give solid chemical compound；
2) solid chemical compound in the step 1) is purified to obtain N- alkylates I.
3. method according to claim 2, it is characterised in that：The compound II is zinc -5- (4- pyridyl groups) -10,15,20-
Triaryl porphyrin, substituent R1Including in hydrogen, alkyl, aryl, alkoxy, acylamino-, hydroxyl, itrile group, nitro, halogen, ester group
Any one.
4. method according to claim 2, it is characterised in that：The feeding sequence of the step 1) compound is compound II, is changed
Object III and chloroform are closed, the wherein rate of charge of compound II and III is 1：1-200, a concentration of 1- of the compound II
100mmol/L。
5. method according to claim 2, it is characterised in that：Step 1) the counterflow condition is to be warming up to 80 DEG C, and reflux 24 is small
When.
6. method according to claim 2, it is characterised in that：Step 2) the way of purification be silica gel, diatomite chromatography,
Recrystallization is further purified.
7. method according to claim 2, it is characterised in that：Step 2) the recrystallization purifying solvent be dichloromethane, methanol,
N-hexane, pentane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810594682.1A CN108752354A (en) | 2018-06-11 | 2018-06-11 | A kind of synthesis of porphyrin fluorescence dyestuff and its method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810594682.1A CN108752354A (en) | 2018-06-11 | 2018-06-11 | A kind of synthesis of porphyrin fluorescence dyestuff and its method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN108752354A true CN108752354A (en) | 2018-11-06 |
Family
ID=64020896
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810594682.1A Pending CN108752354A (en) | 2018-06-11 | 2018-06-11 | A kind of synthesis of porphyrin fluorescence dyestuff and its method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108752354A (en) |
Citations (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02259750A (en) * | 1989-03-31 | 1990-10-22 | Toray Ind Inc | Porphyrin-based recording material |
| US5268371A (en) * | 1990-01-10 | 1993-12-07 | Cis Bio International | Derivatives of porphyrin and metalloporphyrins optionally coupled to a biologically active molecule and pharmaceutical composition containing them |
| US5371122A (en) * | 1992-03-24 | 1994-12-06 | Mitsuboshi Belting Ltd. | Polymer composite, method and polymer composition |
| CN1172485A (en) * | 1994-12-02 | 1998-02-04 | 不列颠哥伦比亚省大学 | Meso-monoiodo-substituted tetramacrocyclic compounds and methods for making and using the same |
| US6107480A (en) * | 1997-07-16 | 2000-08-22 | Dlr, Deutsche Zentrum Fur Luft Und Raumfahrt E.V. | Metallated or unmetallated porphyrin derivatives having amphiphilic properties |
| CN1380292A (en) * | 2001-04-12 | 2002-11-20 | 佳能株式会社 | Porphyrin compound and electronic photographic sensitive unit, photoengraving box and equipment using same |
| CN1450066A (en) * | 2002-04-08 | 2003-10-22 | 巩宪昌 | Porphyrin derivate with macrosubstituent, preparation process thereof and use as small molecule antioxidant |
| CN1879592A (en) * | 2004-12-23 | 2006-12-20 | 莱雅公司 | Use of at least one compound chosen from porphyrin compounds and phthalocyanin compounds for dyeing human keratin materials, compositions comprising them, a dyeing process, and compounds therefor |
| WO2011099602A1 (en) * | 2010-02-12 | 2011-08-18 | 学校法人日本大学 | Porphyrin derivative and use thereof in radiation induced photodynamic therapy |
| BRPI1000790A2 (en) * | 2010-03-31 | 2011-11-22 | Univ Minas Gerais | use of substituted porphyrins as fluorescent indicator of nanoparticles and nanomaterials |
| CN103874490A (en) * | 2011-08-15 | 2014-06-18 | 工业研究与发展基金会有限公司 | Combinations of corroles and statins |
| BRPI1001299A2 (en) * | 2010-04-16 | 2015-03-03 | Fundacao De Ampara A Pesquisa Do Estado De Sao Paulo Fapesp | Polymeric Formulations for the Treatment of Skin Tumors by Photodynamic Therapy |
| CN106939004A (en) * | 2017-01-23 | 2017-07-11 | 河南师范大学 | The method of mixed solvent system synthesizing cationic type water-soluble porphyrin and metal porphyrinses |
| CN108047234A (en) * | 2017-12-28 | 2018-05-18 | 湖南科技大学 | A kind of amino and hydroxyl substitution porphyrin fluorescence parent and preparation method |
-
2018
- 2018-06-11 CN CN201810594682.1A patent/CN108752354A/en active Pending
Patent Citations (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02259750A (en) * | 1989-03-31 | 1990-10-22 | Toray Ind Inc | Porphyrin-based recording material |
| US5268371A (en) * | 1990-01-10 | 1993-12-07 | Cis Bio International | Derivatives of porphyrin and metalloporphyrins optionally coupled to a biologically active molecule and pharmaceutical composition containing them |
| US5371122A (en) * | 1992-03-24 | 1994-12-06 | Mitsuboshi Belting Ltd. | Polymer composite, method and polymer composition |
| CN1172485A (en) * | 1994-12-02 | 1998-02-04 | 不列颠哥伦比亚省大学 | Meso-monoiodo-substituted tetramacrocyclic compounds and methods for making and using the same |
| US6107480A (en) * | 1997-07-16 | 2000-08-22 | Dlr, Deutsche Zentrum Fur Luft Und Raumfahrt E.V. | Metallated or unmetallated porphyrin derivatives having amphiphilic properties |
| CN1380292A (en) * | 2001-04-12 | 2002-11-20 | 佳能株式会社 | Porphyrin compound and electronic photographic sensitive unit, photoengraving box and equipment using same |
| CN1450066A (en) * | 2002-04-08 | 2003-10-22 | 巩宪昌 | Porphyrin derivate with macrosubstituent, preparation process thereof and use as small molecule antioxidant |
| CN1879592A (en) * | 2004-12-23 | 2006-12-20 | 莱雅公司 | Use of at least one compound chosen from porphyrin compounds and phthalocyanin compounds for dyeing human keratin materials, compositions comprising them, a dyeing process, and compounds therefor |
| WO2011099602A1 (en) * | 2010-02-12 | 2011-08-18 | 学校法人日本大学 | Porphyrin derivative and use thereof in radiation induced photodynamic therapy |
| BRPI1000790A2 (en) * | 2010-03-31 | 2011-11-22 | Univ Minas Gerais | use of substituted porphyrins as fluorescent indicator of nanoparticles and nanomaterials |
| BRPI1001299A2 (en) * | 2010-04-16 | 2015-03-03 | Fundacao De Ampara A Pesquisa Do Estado De Sao Paulo Fapesp | Polymeric Formulations for the Treatment of Skin Tumors by Photodynamic Therapy |
| CN103874490A (en) * | 2011-08-15 | 2014-06-18 | 工业研究与发展基金会有限公司 | Combinations of corroles and statins |
| CN106939004A (en) * | 2017-01-23 | 2017-07-11 | 河南师范大学 | The method of mixed solvent system synthesizing cationic type water-soluble porphyrin and metal porphyrinses |
| CN108047234A (en) * | 2017-12-28 | 2018-05-18 | 湖南科技大学 | A kind of amino and hydroxyl substitution porphyrin fluorescence parent and preparation method |
Non-Patent Citations (4)
| Title |
|---|
| DAIANA K. DEDA,ET AL.: "Correlation of photodynamic activity and singlet oxygen quantum yields in two series of hydrophobic monocationic porphyrins", 《JOURNAL OF PORPHYRINS AND PHTHALOCYANINES》 * |
| ICHIRO OKURA, ET AL.: "Photoinduced Hydrogen Evolution with Viologen-Linked Zinc Porphyrins", 《BULL. CHEM. SOC. JPN.》 * |
| NUONUO ZHANG，ET AL.: "Synthesis and photoelectric property of N-confused porphyrins bearing an ethynylbenzoic and benzoic acid moiety", 《RES CHEM INTERMED》 * |
| 赵文伯 等: "meso-苯基-4-吡啶基取代卟啉混合物的正相高效液相色谱定量分析方法的建立", 《化学试剂》 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105669529B (en) | A kind of fulleropyrrolidine derivative and preparation method thereof | |
| Bonacorso et al. | Synthesis, 11B-and 19F NMR spectroscopy, and optical and electrochemical properties of novel 9-aryl-3-(aryl/heteroaryl)-1, 1-difluoro-7-(trifluoromethyl)-1H-[1, 3, 5, 2] oxadiazaborinino [3, 4-a][1, 8] naphthyridin-11-ium-1-uide complexes | |
| CN104710816A (en) | Large Stokes shift and near infrared fluorescence emitting new rhodamine fluorescent dye and synthetic method thereof | |
| CN110372735B (en) | Aza-BODIPY derivative with photothermal effect and synthesis and application thereof | |
| Stephenson et al. | Significantly enhanced DNA thermal stability resulting from porphyrin H-aggregate formation in the minor groove of the duplex | |
| CN103709202B (en) | Ruthenium (II) complex and preparation method thereof and its it is used as the application of cell fluorescence dyestuff | |
| CN102040617B (en) | Organic boron difluoride complex and preparation method thereof | |
| Eçik et al. | Novel Bodipy-triazine conjugates: Synthesis and the generation of singlet oxygen | |
| Long et al. | Boosting the turn-on fluorescent signaling ability of thiazole orange dyes: the effectiveness of structural modification site and its unusual interaction behavior with nucleic acids | |
| WO2013131235A1 (en) | Two-photon fluorescent probe using naphthalene as matrix and preparation method and use thereof | |
| CN113462187A (en) | Heptamethine indocyanine dye and preparation method and application thereof | |
| CN106867271A (en) | The naphthalimide fluorescent dyestuff and its synthetic method and application of a kind of big Stokes shift and launch wavelength long | |
| CN106632063A (en) | Compound I and compound II based on phenanthroimidazole, and preparation method and applications thereof | |
| Ievlev et al. | Synthesis and Luminescence Spectral Properties of New Cyano-Substituted 2, 2′-Bipyridine Derivatives | |
| CN112358493B (en) | Micromolecular photothermal reagent based on boron-fluorine complex and preparation method and application thereof | |
| CN107043372B (en) | A kind of flavones fluorescence probe of targetted mitochondria and the preparation method and application thereof | |
| CN106748879A (en) | P-nitrobenzaldehyde Schiff base derivative and preparation method and application thereof | |
| US6541628B1 (en) | Process for the preparation of corroles and several such new compounds, including chiral derivatives, and the use thereof | |
| CN105693590B (en) | A kind of photothermal reagent and its preparation method and application of pH control tumor cell | |
| CN106188149B (en) | A kind of near-infrared metal iridium complex and its preparation method and application | |
| CN108752354A (en) | A kind of synthesis of porphyrin fluorescence dyestuff and its method | |
| Murugesan et al. | One-pot synthesis of Claisen–Schmidt reaction through (E)-chalcone derivatives: Spectral studies in human serum albumin protein binding and molecular docking investigation | |
| Ghasemi et al. | Synthesis of highly fluorescent (E)-Stilbene derivatives containing polysubstituted imidazole scaffold | |
| CN105037359B (en) | A kind of have the half flower compound of cyanines-naphthalimide structure, its preparation method and application | |
| CN111548373A (en) | Iridium complex azapyrrolidone photo-diagnosis and treatment reagent 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 | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20181106 |
|
| RJ01 | Rejection of invention patent application after publication |