CN114644562B - Organic small molecule fluorescent compound with red shift fluorescent emission, preparation method and application - Google Patents
Organic small molecule fluorescent compound with red shift fluorescent emission, preparation method and application Download PDFInfo
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- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
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- C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- 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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
Abstract
The invention belongs to the field of fluorescent compound synthesis, and particularly relates to an organic small molecule fluorescent compound with red-shift fluorescent emission, a preparation method and application thereof. The invention is based on the preparation of an organic small molecule fluorescent compound by the click reaction of hydroxyl and alkynyl of an alcohol hydroxyl monomer containing tertiary amine and an activated alkyne monomer without a catalyst. The organic small-molecule fluorescent compound prepared by the invention does not have conventional chromophores such as large pi conjugated groups, only contains non-conventional groups such as tertiary amine, double bonds, vinyl ether and the like, has the characteristics of concentration-enhanced fluorescence, concentration-dependent red shift and excitation wavelength-dependent red shift, and can be used as multicolor fluorescent small-molecule fluorescent dye in the biomedical field. The materials required by the click reaction are all commercial monomers, no catalyst is required to be added, and the method has the advantages of simplicity in operation, environment friendliness, mild conditions, high efficiency, high yield and the like, and is suitable for large-scale production and application.
Description
Technical Field
The invention belongs to the field of fluorescent compound synthesis, and particularly relates to an organic small molecule fluorescent compound with red-shift fluorescent emission, a preparation method and application thereof.
Background
Organic fluorescent compounds are abundant in raw materials and numerous in variety, and have received extensive attention since their discovery in the sixteenth century. Conventional organic fluorescent compounds generally contain a large number of conjugated unsaturated groups or aromatic rings in the molecule. This class of organic fluorescent compounds carrying conventional chromophores has some inherent disadvantages such as complicated preparation process, poor hydrophilicity and toxicity, which seriously hamper their practical application.
In recent years, researchers have discovered a class of non-traditional fluorescent compounds that do not contain conventional chromophores such as large pi conjugated groups. The compound has the advantages of low biotoxicity, high biocompatibility and the like, has great application prospect in the biomedical field and is favored by researchers. However, most of the non-traditional fluorescent materials reported to date have fluorescence emission in the blue region, with very limited reports of green, yellow and red emission. Red-shifted fluorescence, particularly with respect to small molecule fluorescence, is more rarely reported. Therefore, it is very necessary to design and synthesize non-traditional small organic molecule fluorescent compounds with red-shifted fluorescence emission in a new way.
Disclosure of Invention
The invention provides an organic small molecule fluorescent compound with red shift fluorescence emission based on the defects that the types of non-traditional fluorescent small molecules are too few and most of the non-traditional small molecules are in a blue light region, and provides a preparation method of the organic small molecule fluorescent compound. The organic small molecule fluorescent compound provided by the invention can be used as multicolor fluorescent small molecule fluorescent dye in the biomedical field.
The invention provides an organic small molecule fluorescent compound with red shift fluorescence emission, which has the following structural general formula:
wherein R is 1 Methyl, ethyl, alicyclic, or benzene rings; r is R 2 is-H or methyl; r' is methyl, ethyl or isobutyl.
The concentration-induced red shift of the organic small molecule fluorescent compound with red-shifted fluorescence emission of the invention means the combination thereofThe emission wavelength of the material can be changed with the concentration within 420-750nm, and the concentration range is 10 -4 ～1mol/L。
The excitation wavelength of the organic small molecule fluorescent compound with red shift fluorescence emission depends on red shift, and the excitation wavelength range is 380-720 nm.
The invention also provides a preparation method of the organic small molecule fluorescent compound with red shift fluorescent emission, which comprises the following steps:
the tertiary amine-containing alcohol hydroxyl monomer (the tertiary amine-containing alcohol hydroxyl monomer is tertiary amine-containing primary alcohol or secondary alcohol) and the activated alkyne monomer (C.ident.C-COO-R ', C.ident.C-CO-R') are mixed, and hydroxyl-alkyne click reaction is carried out under stirring conditions. The hydroxyl-alkyne click reaction of the organic small molecule fluorescent compound with red-shift fluorescence emission does not need a catalyst, and is based on the direct simple mixed reaction of an alcohol hydroxyl monomer containing tertiary amine and an activated alkyne monomer.
The temperature and time of the hydroxyl-alkyne click reaction are not particularly limited, the organic small molecular fluorescent compound can be obtained, the temperature can be lower than 25 ℃, the yield of the obtained organic small molecular fluorescent compound after the reaction is finished is generally higher than 90%, the structural regularity is 98% or more of the small molecular compound with E configuration, but in order to obtain higher yield and test convenience, the temperature of the hydroxyl-alkyne click reaction is 25 ℃, and the reaction time is 10min.
Further, the tertiary amine-containing alcoholic hydroxyl monomer is any one of 2-diethylaminoethanol, dimethylethanolamine, 1-piperidineethanol, 1-dimethylamino-2-propanol, 4-methylpiperazine-1-ethanol, 2- (N-ethylanilino) ethanol, N-methyldiethanolamine, and 1, 4-bis (2-hydroxyethyl) piperazine.
Further, the activated alkyne monomer is any one of methyl propiolate, ethyl propiolate and tert-butyl propiolate.
Further, the reaction may proceed spontaneously with or without a solvent.
Compared with the prior art, the invention has the following beneficial effects: the invention provides an organic small molecular fluorescent compound with red-shift fluorescence emission, and provides a preparation method of the organic small molecular fluorescent compound, which is mainly based on the catalytic-free click reaction of hydroxyl and alkynyl to simply prepare the non-traditional organic small molecular fluorescent compound with red-shift fluorescence emission in one step. The organic small-molecule fluorescent compound does not have conventional chromophores such as large pi conjugated groups and the like, only contains non-conventional groups such as tertiary amine, double bonds, vinyl ether and the like, and can be used as multicolor fluorescent small-molecule fluorescent dye in the biomedical field. The raw materials of the organic small molecular fluorescent compound prepared by the method are all commercial monomers, no additional catalyst is required to be added in the reaction, the condition is mild, the reaction system is rapid, and the method is an economic, efficient and environment-friendly method for preparing the organic small molecular fluorescent compound.
Drawings
FIG. 1 is a graph showing the nuclear magnetic resonance spectrum (a) and fluorescence spectra (b and c) at different concentrations and at different excitation wavelengths (d) of the compound obtained in example 1.
FIG. 2 is a graph showing the nuclear magnetic resonance spectrum (a) and fluorescence spectra (b) at different concentrations and (c) at different excitation wavelengths of the compound obtained in example 2.
FIG. 3 is a graph showing the nuclear magnetic resonance spectrum (a) and fluorescence spectra (b) at different concentrations and (c) at different excitation wavelengths of the compound obtained in example 3.
FIG. 4 is a graph showing the nuclear magnetic resonance spectrum (a) and fluorescence spectra (b) at different concentrations and (c) at different excitation wavelengths of the compound obtained in example 4.
FIG. 5 is a graph showing the nuclear magnetic resonance spectrum (a) and fluorescence spectra (b) at different concentrations and (c) at different excitation wavelengths of the compound obtained in example 5.
FIG. 6 is a graph showing the nuclear magnetic resonance spectrum (a) and fluorescence spectra (b) at different concentrations and (c) at different excitation wavelengths of the compound obtained in example 6.
FIG. 7 is a graph showing the nuclear magnetic resonance spectrum (a) and fluorescence spectra (b) at different concentrations and (c) at different excitation wavelengths of the compound obtained in example 7.
FIG. 8 is a graph showing the nuclear magnetic resonance spectrum (a) and fluorescence spectra (b) at different concentrations and (c) at different excitation wavelengths of the compound obtained in example 8.
FIG. 9 is a photograph of cell images ((a) 0.001mol/L, (b) 0.01mol/L, and (c) 0.05 mol/L) of the compound obtained in example 1 at various concentrations.
Detailed Description
The present invention is not limited to the following embodiments, and those skilled in the art can implement the present invention in various other embodiments according to the present invention, or simply change or modify the design structure and thought of the present invention, which fall within the protection scope of the present invention. It should be noted that, without conflict, the embodiments of the present invention and features of the embodiments may be combined with each other.
The invention is further described in detail below in connection with the examples:
example 1
2-diethylaminoethanol (1.172 g,10 mmol) and methyl propiolate (0.841 g,10 mmol) monomers were mixed and stirred at 25℃for 10min. After the reaction is finished, the mixture is washed and distilled to obtain the micromolecular compound with the yield reaching 98 percent. The nuclear magnetic spectrum is adopted to confirm that 100% of small molecular compounds with E configuration are prepared (figure 1 a). The fluorescence intensity of the compounds obtained by fluorescence spectroscopy increased with increasing concentration (FIG. 1 b), and the maximum excitation wavelengths at different concentrations (0.001, 0.01,0.05,0.1,0.25,1 mol/L) were 370, 480, 520, 560, 600, 650nm, respectively, and the maximum emission wavelengths were 420, 520, 570, 610, 645,750nm (FIG. 1 c), indicating that the non-conventional small organic molecule fluorescent compounds prepared in this way had concentration-enhanced fluorescence and concentration-induced red-shift properties. Meanwhile, the obtained compound also has red shift under different excitation wavelengths (figure 1 d), and the excitation wavelength dependence red shift characteristic is shown. The obtained compound can be imaged in cells, and shows blue (a in figure 9), green (b in figure 9) and red cell imaging (c in figure 9) in cells at different concentrations, and can be used as fluorescent dye in the biomedical field as multicolor fluorescent small molecule dye.
Example 2
2-diethylaminoethanol (1.172 g,10 mmol) was mixed with ethyl propiolate (0.981 g,10 mmol) monomer at 25℃and stirred for 10min. After the reaction is finished, the mixture is washed by water and distilled to obtain the compound with the yield reaching 95 percent. The nuclear magnetic spectrum is adopted to confirm that 100% of small molecular compounds with E configuration are prepared (figure 2 a). The compounds obtained by fluorescence spectroscopy were tested for their maximum excitation wavelengths of 390, 397, 440, 470, 475nm and maximum emission wavelengths of 475, 483, 525, 550, 555nm (FIG. 2 b) at different concentrations (0.05, 0.1,0.25,0.5,1 mol/L), respectively, indicating that the unconventional small organic molecule fluorescent compounds prepared in this way have concentration-induced red-shift properties. Meanwhile, the obtained compound also has red shift under different excitation wavelengths (figure 2 c), and the excitation wavelength dependence red shift characteristic is shown.
Example 3
2-diethylaminoethanol (1.172 g,10 mmol) and t-butyl propiolate (1.262 g,10 mmol) monomers were mixed and stirred at 25℃for 30min. After the reaction is finished, the mixture is washed and distilled to obtain the micromolecular compound with the yield reaching 92 percent. The preparation of a small molecule compound containing 98% E configuration, 2%Z configuration using nuclear magnetic resonance spectroscopy (FIG. 3 a). The maximum excitation wavelengths of the obtained compounds at different concentrations (0.1, 0.25,0.5,1 mol/L) are 403, 415, 418, 426nm respectively, and the maximum emission wavelengths are 482, 494, 498, 501nm respectively (figure 3 b), which shows that the non-traditional small organic molecule fluorescent compounds prepared by the method have concentration-induced red shift characteristics. Meanwhile, the obtained compound also has red shift under different excitation wavelengths (figure 3 c), and the excitation wavelength dependence red shift characteristic is shown.
Example 4
1-piperidineethanol (1.292 g,10 mmol) was mixed with methyl propiolate (0.841 g,10 mmol) monomer at 25℃and stirred for 30min. After the reaction is finished, the mixture is washed and distilled to obtain the micromolecular compound with the yield of 90 percent. The nuclear magnetic spectrum is adopted to confirm that 100% of small molecular compounds with E configuration are prepared (figure 4 a). The compounds obtained by fluorescence spectroscopy were found to have maximum excitation wavelengths of 385, 395, 430,435nm, respectively, and maximum emission wavelengths of 456, 469, 499,505nm, respectively, at different concentrations (0.1, 0.25,0.5,1 mol/L), indicating that the non-conventional small organic molecule fluorescent compounds prepared by this method have concentration-induced red-shift characteristics. Meanwhile, the obtained compound also has red shift under different excitation wavelengths (fig. 4 c), and the excitation wavelength dependence red shift characteristic is shown.
Example 5
4-methylpiperazine-1-ethanol (1.442 g,10 mmol) and methyl propiolate (0.841 g,10 mmol) monomers were mixed and stirred at 25℃for 30min. After the reaction is finished, the mixture is washed with water and distilled to obtain the compound with the yield of 90 percent. The nuclear magnetic spectrum is adopted to confirm that 100% of small molecular compounds with E configuration are prepared (figure 5 a). The maximum excitation wavelengths of the obtained compounds at different concentrations (0.1, 0.25,0.5,1 mol/L) are 437,440,475, and 513nm respectively, and the maximum emission wavelengths are 525,540, and 580nm respectively (figure 5 b), which shows that the non-traditional small organic molecule fluorescent compounds prepared by the method have concentration-induced red shift characteristics. Meanwhile, the obtained compound also has red shift under different excitation wavelengths (fig. 5 c), and the excitation wavelength dependence red shift characteristic is shown.
Example 6
1-dimethylamino-2-propanol (1.032 g,10 mmol) was mixed with methyl propiolate (0.841 g,10 mmol) monomer at 25℃for 30min. After the reaction is finished, the mixture is washed with water and distilled to obtain the compound with 92 percent of yield. The nuclear magnetic spectrum is adopted to confirm that 100% of small molecular compounds with E configuration are prepared (figure 6 a). The maximum excitation wavelengths of the obtained compounds at different concentrations (0.05, 0.1,0.25 and 1 mol/L) are respectively 400,404, 421 and 438nm, and the maximum emission wavelengths are respectively 475,475, 485 and 510nm (figure 6 b), which shows that the non-traditional small organic molecule fluorescent compounds prepared by the method have concentration-induced red shift characteristics. Meanwhile, the obtained compound also has red shift under different excitation wavelengths (fig. 6 c), and the excitation wavelength dependence red shift characteristic is shown.
Example 7
N-methyldiethanolamine (0.596 g,5 mmol) and methyl propiolate (0.841 g,10 mmol) monomers were mixed and stirred at 25℃for 30min. After the reaction is finished, the mixture is washed with water and distilled to obtain the compound with 92 percent of yield. The nuclear magnetic spectrum is adopted to confirm that 98% of small molecular compounds with E configuration are prepared (figure 7 a). The maximum excitation wavelengths of the obtained compounds at different concentrations (0.1, 0.25,0.5,1 mol/L) are 384 nm, 402 nm, 404 nm and 453nm, and the maximum emission wavelengths are 454 nm, 460 nm, 462 nm and 518nm (figure 7 b), which shows that the non-traditional small organic molecule fluorescent compounds prepared by the method have concentration-induced red shift characteristics. Meanwhile, the resulting compound also undergoes a red shift at different excitation wavelengths (fig. 7 c), exhibiting excitation wavelength dependent red shift characteristics.
Example 8
1, 4-bis (2-hydroxyethyl) piperazine (0.871 g,5 mmol) and methyl propiolate (0.841 g,10 mmol) monomers were dissolved in dichloromethane (0.5 mL) and mixed and stirred at 25℃for 30min. After the reaction is finished, the mixture is washed with water and distilled to obtain the compound with the yield of 90 percent. The nuclear magnetic spectrum is adopted to confirm that 100% of small molecular compounds with E configuration are prepared (figure 8 a). The maximum excitation wavelength of the compound C-8 obtained by the fluorescence spectrum test under different concentrations (0.05, 0.1,0.25 and 0.5 mol/L) is 374, 375,399 and 458nm respectively, and the maximum emission wavelength is 455,457,475 and 540nm respectively (figure 8C), and the non-traditional small organic molecule fluorescent compound prepared by the method has concentration-induced red shift property. Meanwhile, the obtained compound also has red shift under different excitation wavelengths (fig. 8 c), and the excitation wavelength dependence red shift characteristic is shown.
The foregoing is only a preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art, who is within the scope of the present invention, should make equivalent substitutions or modifications according to the technical scheme and the concept of the present invention, and should be covered by the scope of the present invention.
Claims (6)
1. An organic small molecule fluorescent compound having red-shifted fluorescent emission, characterized by: the structural general formula is shown in formula 1, formula 2 or formula 3:
wherein R is 1 Methyl or ethyl; r is R 2 is-H or methyl; r' is methyl, ethyl or isobutyl;
alternatively, the organic small molecule fluorescent compound having red-shifted fluorescence emission is one of the following compounds:
2. the method for preparing the organic small molecule fluorescent compound with red-shifted fluorescence emission according to claim 1, wherein: the method comprises the following steps: mixing an alcohol hydroxyl monomer containing tertiary amine with an activated alkyne monomer, and carrying out hydroxyl-alkyne click reaction under the stirring condition; the alcohol hydroxyl monomer containing tertiary amine is primary alcohol or secondary alcohol containing tertiary amine, and the structural formula of the activated alkyne monomer is C.ident.C-COO-R'.
3. The method for preparing the organic small molecule fluorescent compound with red-shifted fluorescence emission according to claim 2, wherein the method comprises the following steps: the temperature of the hydroxyl-alkyne clicking reaction is less than or equal to 25 ℃ and the time is 1-30 min.
4. The method for preparing the organic small molecule fluorescent compound with red-shifted fluorescence emission according to claim 2, wherein the method comprises the following steps: the temperature of the hydroxyl-alkyne click reaction is 25 ℃ and the reaction time is 10min.
5. The method for preparing the organic small molecule fluorescent compound with red-shifted fluorescence emission according to claim 2, wherein the method comprises the following steps: the alcohol hydroxyl monomer containing tertiary amine is any one of 2-diethylaminoethanol, dimethylethanolamine, 1-piperidineethanol, 1-dimethylamino-2-propanol, 4-methylpiperazine-1-ethanol, N-methyldiethanolamine and 1, 4-bis (2-hydroxyethyl) piperazine.
6. Use of the organic small molecule fluorescent compound with red-shifted fluorescence emission of claim 1 in the preparation of a multicolor fluorescent small molecule fluorescent dye.
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| CN105980367A (en) * | 2014-01-24 | 2016-09-28 | 阿斯利康(瑞典)有限公司 | (2S)-N-[(1S)-1-cyano-2-phenylethyl]-1,4-oxazepane-2-carboxamides as dipeptidyl peptidase 1 inhibitors |
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| "Synthesis of Benzo[1,4]heterocycles using Palladium Catalyzed Heck Reaction to Vinylogous Carbonates/Carbamates: Unexpected Formation of Indoles via Carbopalladation Intercepted by Nucleopalladation";Santosh J. Gharpure，et.;《Org. Lett.》;第19卷;第6136−6139页 * |
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