CN109734736B - Seven-element fluoroboric fluorescent dye and synthetic method thereof - Google Patents
Seven-element fluoroboric fluorescent dye and synthetic method thereof Download PDFInfo
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Abstract
The invention discloses a novel hepta-boron fluoride fluorescent dye containing an electron donor/electron acceptor and a synthesis method thereof, wherein the structure of the compound is as follows:
wherein, the substituent R is electron-donating groups such as alkoxy, amino, hydroxyl and the like, and electron-withdrawing groups such as acyl, aldehyde group, carboxyl, acylamino, sulfonic group, nitrile group, nitro, haloform group, quaternary ammonium group and the like. 2, 3, 3-trimethylindole derivatives and 2-formylpyrrole are taken as raw materials and are subjected to Knoevenagel condensation reaction under the action of an organic catalyst to finally generate the electron-donating/electron-withdrawing heptatomic fluoroboron fluorescent dye. The seven-element boron fluoride fluorescent dye containing the electron donor/electron acceptor has the advantages of simple synthesis method, easily controlled reaction conditions and universal applicability. The material can effectively regulate and control the pi conjugation, the energy band gap and the photoelectric property by selecting a proper fluorophore, an electron donor and an electron acceptor.
Description
Technical Field
The invention discloses a hepta-boron-fluoride fluorescent dye simultaneously containing an electron donor/electron acceptor and a synthesis method thereof, and the dye can be widely applied to the fields of environment, analysis, material science and the like.
Background
Among a wide range of organic pi systems, electron donor/electron acceptor type organic compounds have attracted increasing interest in recent years because they have various excellent photoelectric properties due to a low band gap. Another attractive advantage of these materials is that their pi-conjugation, band gap and photoelectric properties can be effectively manipulated by selecting appropriate fluorophores, electron donors and electron acceptors. The boron fluoride fluorescent dye (BODIPY) has good stability, modifiability, high molar extinction coefficient and good oxidation potential, and optical properties, stability and chemical properties such as absorption wavelength and the like, and physical properties such as solubility and the like of the BODIPY fluorescent dye can be adjusted at the modifiability position by selectively connecting groups with corresponding functions. To date, BODIPY dyes for electron donors and electron acceptors have been developed and used in various fields.
However, the emission center of the common electron donor and electron acceptor BODIPY dyes is six-membered ring, so that the reports of seven-membered ring are few, the full design of molecule and the optimization of reasonable route are lacked, and the problem of single structure exists, so that the preparation of the novel boron fluoride dye with seven-membered ring center from raw materials through a simple synthesis route is a difficult problem to be solved urgently.
The invention designs and synthesizes a series of hepta-boron-fluoride dyes with novel structures and containing electron donors/electron acceptors, optimizes the synthesis method of the compounds, improves the synthesis yield, and reveals the relationship between the molecular structures and the properties by researching the photophysical properties of the compounds.
Disclosure of Invention
The invention mainly aims to provide an electron donor/electron acceptor hepta-boron fluoride fluorescent dye and a synthesis method thereof.
The technical scheme of the invention is as follows:
an electron donor/electron acceptor hepta-boron fluoride fluorescent dye, wherein the chemical structural formula of the compound is as follows:
wherein, the substituent R is an electron-donating group or an electron-withdrawing group, and the electron-donating group comprises any one of alkoxy, amino and hydroxyl; the electron-withdrawing group comprises any one of acyl, aldehyde group, carboxyl, acylamino, sulfonic group, nitrile group, nitro, haloform group and quaternary amine group.
In a further preferred embodiment, the chemical structural formula of the dye is as follows:
A synthetic method for synthesizing said electron donor/electron acceptor heptafluoroboron fluorescent dye, said method comprising the following synthetic route:
the method comprises the following steps:
(1) adding the compound 1, ethanol and the compound 2 into a reaction bottle at room temperature, and heating and refluxing to obtain a solid compound;
(2) purifying the solid compound in the step (1) to obtain a yellow solid compound 3;
(3) respectively adding toluene and triethylamine into the compound 3 in the step (2), slowly dropwise adding a boron trifluoride diethyl etherate complex, heating to 100-130 ℃, stirring and refluxing to obtain a reaction solution;
(4) and (4) respectively washing, extracting, drying and purifying the reaction liquid in the step (3) to obtain a product 3B, namely the electron donor/electron acceptor hepta-boron fluoride fluorescent dye.
The feeding ratio of the compound 1 to the compound 2 in the step (1) is 1: 1-100. The yield of the compound 3 is greatly improved by changing the charge ratio.
In the step (1), the compound 1 needs to be a protonated salt, otherwise, the reaction does not occur or the yield is low.
The feeding sequence of the step (1) is compound 1, compound 2 and ethanol. If other feeding sequences cause the reaction system to heat up violently, the reaction substrate is not easy to expand.
The reflux condition of the step (1) is that the temperature is raised to 80-90 ℃ and the reflux is carried out for 2-18 hours. When the reflux temperature is reached, the reaction can be smoothly carried out, otherwise, the reaction is insufficient, the yield is low, and the reaction time is long.
The feeding ratio of the compound 3 to the boron trifluoride diethyl etherate in the step (3) is 1: 1-100. The yield of the product can be greatly improved by changing the feed ratio, the range of the feed ratio is large, and the production of fine chemicals is facilitated.
The feeding sequence of the step (3) is compound 3, toluene, triethylamine and boron trifluoride diethyl etherate. The feeding sequence enables the reaction to be carried out smoothly, and boron trifluoride diethyl etherate needs to be added finally.
The heating reaction temperature in the step (3) is 120 ℃, and the reaction time is 0.5-8 h. This reflux temperature enables the reaction to proceed normally. The reaction time is not constant depending on the substrate.
The invention has the following beneficial effects:
(1) the raw material with an electron-donating group or an electron-withdrawing group and formylpyrrole are subjected to Knoevenagel condensation reaction to synthesize an important intermediate 3, and then the important intermediate is subjected to borofluoride to obtain a final product. The dye takes a seven-element fluorine boron complex as a center, and electron-donating or electron-withdrawing groups are introduced into one side of the whole molecule to increase the conjugation of the molecule, thereby being beneficial to charge transmission in the molecule and having good photophysical properties.
(2) The synthesis reaction conditions of the invention are easy to control, the product purification is simpler, and the invention has universal applicability.
(3) The invention has simple synthesis steps and mild reaction conditions.
(4) The compound has high fluorescence quantum yield and large Stokes shift, and can be applied to fluorescence imaging.
Drawings
FIG. 1 is a fluorescence spectrum of the product obtained in example 8.
FIG. 2 is a fluorescence spectrum of the product obtained in example 11.
FIG. 3 is a fluorescence spectrum of the product obtained in example 10.
FIG. 4 is a fluorescence spectrum of the product obtained in example 7.
FIG. 5 is a fluorescence spectrum of the product obtained in example 9.
FIG. 6 is a hydrogen spectrum of the products obtained in examples 1 to 7.
FIG. 7 is a carbon spectrum of the products obtained in examples 1 to 7.
FIG. 8 is a mass spectrum of the products obtained in examples 1 to 7.
Detailed Description
The invention is further illustrated by the following examples, but the scope of the invention as claimed is not limited to the scope of the examples.
Example 1
Taking 2, 3, 3-trimethyl-5-methoxyindole proton salt 1(1.71g, 9.00mmol), weighing 2-formylpyrrole (1.72g, 18.00mmol), weighing 0.15L ethanol solution, mixing, dissolving, heating, stirring, refluxing at 90 ℃ for 4 hours, spinning, filtering and purifying to obtain yellow compound 3, taking compound 3(133.2mg, 0.5mmol), taking 35.00ml toluene solution, 1.00ml triethylamine, slowly dropping boron trifluoride diethyl etherate solution (1.00ml) under electromagnetic stirring, raising the temperature to 120 ℃, refluxing for 30 minutes, detecting by TLC point plate, washing, extracting, drying, spinning, filtering and purifying to obtain the final product, wherein the specific structural formula is as follows:
example 2
Taking 2, 3, 3-trimethyl-5-methoxyindole proton salt 1(3.42g, 18.00mmol), weighing 2-formylpyrrole (1.72g, 18.00mmol), weighing 0.15L ethanol solution, mixing, dissolving, heating, stirring, refluxing at 90 ℃ for 2 hours, spin-drying, filtering and purifying to obtain yellow compound 3, taking compound 3(133.2mg, 0.5mmol), taking 35.00ml toluene solution, 1.00ml triethylamine, slowly dropping boron trifluoride diethyl etherate solution (1.00ml) under electromagnetic stirring, raising the temperature to 120 ℃, refluxing for 30 minutes, detecting by TLC spot plate, washing, extracting, drying, spin-steaming, filtering and purifying to obtain the final product, wherein the specific structural formula is as follows:
example 3
Taking 2, 3, 3-trimethyl-5-methoxyindole proton salt 1(1.71g, 9.00mmol), weighing 2-formylpyrrole (1.72g, 18.00mmol), weighing 0.15L ethanol solution, mixing, dissolving, heating, stirring, refluxing at 90 ℃ for 2 hours, filtering and purifying after spin-drying to obtain yellow compound 3, respectively removing the compound 3(133.2mg, 0.5mmol), taking 35.00ml toluene solution, 1.00ml triethylamine, slowly dropping boron trifluoride diethyl etherate solution (1.00ml) under electromagnetic stirring, raising the temperature to 120 ℃, refluxing for 30 minutes, detecting by TLC spot plate, washing the product with water, extracting, drying, spin-steaming, filtering and purifying to obtain the final product, wherein the specific structural formula is as follows:
example 4
Taking 2, 3, 3-trimethyl-5-methoxyindole proton salt 1(1.71g, 9.00mmol), weighing 2-formylpyrrole (855.9mg, 9.00mmol), weighing 0.15L ethanol solution, mixing, dissolving, heating, stirring, refluxing at 90 ℃ for 2 hours, spinning, filtering and purifying to obtain yellow compound 3, taking compound 3(133.2mg, 0.5mmol), taking 35.00ml toluene solution, 1.00ml triethylamine, slowly dropping boron trifluoride diethyl etherate solution (10.00ml) under electromagnetic stirring, raising the temperature to 120 ℃, refluxing for 30 minutes, detecting by TLC point plate, washing, extracting, drying, spinning, filtering and purifying to obtain the final product, wherein the specific structural formula is as follows:
example 5
Weighing 2-formylpyrrole (855.9mg, 9.00mmol) from 2, 3, 3-trimethyl-5-methoxyindole proton salt 1(1.71g, 9.00mmol), weighing 0.15L ethanol solution, mixing, dissolving, heating, stirring, refluxing at 90 ℃ for 2 hours, spinning, filtering and purifying to obtain yellow compound 3, respectively weighing compound 3(133.2mg, 0.5mmol), weighing 35.00ml toluene solution, 1.00ml triethylamine, slowly dropping boron trifluoride diethyl etherate solution (50.00ml) under electromagnetic stirring, raising the temperature to 120 ℃, refluxing for 30 minutes, detecting by TLC spot plate, washing, extracting, drying, spinning, filtering and purifying to obtain the final product, wherein the specific structural formula is as follows:
example 6
Weighing 2-formylpyrrole (855.9mg, 9.00mmol) from 2, 3, 3-trimethyl-5-methoxyindole proton salt 1(1.71g, 9.00mmol), weighing 0.15L ethanol solution, mixing, dissolving, heating, stirring, refluxing at 90 ℃ for 2 hours, spinning, filtering and purifying to obtain yellow compound 3, removing compound 3(133.2mg, 0.5mmol), respectively, weighing 35.00ml toluene solution, 5.00ml triethylamine, slowly dropping boron trifluoride diethyl etherate solution (100.00m1) under electromagnetic stirring, raising the temperature to 120 ℃, refluxing for 30min, detecting by TLC spot plate, washing, extracting, drying, spinning, filtering and purifying to obtain the final product, wherein the specific structural formula is as follows:
example 7
Taking 2, 3, 3-trimethyl-5-methoxyindole proton salt 1(1.71g, 9.00mmol), weighing 2-formylpyrrole (855.9mg, 9.00mmol), weighing 0.15L ethanol solution, mixing, dissolving, heating, stirring, refluxing at 90 ℃ for 2 hours, spinning, filtering and purifying to obtain yellow compound 3, removing the compound 3(133.2mg, 0.5mmol), respectively, taking 35.00ml toluene solution, 5.00ml triethylamine, slowly dropping boron trifluoride diethyl etherate solution (1.00m1) under electromagnetic stirring, raising the temperature to 120 ℃, refluxing for 30 minutes, detecting by a TLC point plate, washing, extracting, drying, spinning, filtering and purifying to obtain a final product, wherein the specific structural formula is as follows:
example 8
Taking 0.15L of 2, 3, 3-trimethylindole proton salt 1(1.71g, 9.00mmol), 2-formylpyrrole (855.9mg, 9.00mmol) and ethanol solution, mixing, dissolving, heating, stirring, refluxing for 2 hours at 90 ℃, filtering and purifying after spin-drying to obtain yellow compound 3, respectively taking the compound 3(0.5mmol), taking 35.00ml of toluene solution and 5.00ml of triethylamine, slowly dripping boron trifluoride diethyl etherate solution (1.00ml) under electromagnetic stirring, raising the temperature to 120 ℃, refluxing for 30min, detecting by TLC point plates, washing, extracting, drying, spin-steaming, filtering and purifying to obtain the final product, wherein the specific structural formula is as follows:
example 9
Taking 0.15L of 2, 3, 3-trimethyl-5-carbethoxyindole proton salt 1(1.71g, 9.00mmol), 2-formylpyrrole (855.9mg, 9.00mmol) and ethanol solution, mixing, dissolving, heating, stirring, refluxing at 90 ℃ for 2 hours, spinning, filtering and purifying to obtain yellow compound 3, taking the compound 3(0.5mmol), taking 35.00ml of toluene solution and 5.00ml of triethylamine, slowly dripping boron trifluoride diethyl etherate solution (1.00ml) under electromagnetic stirring, raising the temperature to 120 ℃, refluxing for 30min, detecting by TLC (thin layer chromatography) spot plate, washing, extracting, drying, spinning, filtering and purifying to obtain the final product, wherein the specific structural formula is as follows:
example 10
Taking 0.15L of 2, 3, 3-trimethyl-5-bromoindole proton salt 1(1.71g, 9.00mmol), 2-formylpyrrole (855.9mg, 9.00mmol) and ethanol solution, mixing, dissolving, heating, stirring, refluxing at 90 ℃ for 2 hours, drying, filtering and purifying to obtain yellow compound 3, taking the compound 3(0.5mm0L), taking 35.00ml of toluene solution and 5.00ml of triethylamine, slowly dripping boron trifluoride diethyl etherate solution (1.00ml) under electromagnetic stirring, raising the temperature to 120 ℃, refluxing for 30min, detecting by TLC point plates, washing, extracting, drying, rotary steaming, filtering and purifying to obtain the final product, wherein the specific structural formula is as follows:
example 11
Taking 0.15L of 2, 3, 3-trimethyl-5-chloroindole proton salt 1(1.71g, 9.00mmol), 2-formylpyrrole (855.9mg, 9.00mmol) and ethanol solution, mixing, dissolving, heating, stirring, refluxing at 90 ℃ for 2 hours, spinning, filtering and purifying to obtain yellow compound 3, taking above compound 3(133.2mg, 0.5mmol), taking 35.00ml of toluene solution and 5.00ml of triethylamine, slowly dripping boron trifluoride diethyl etherate solution (1.00ml) under electromagnetic stirring, raising the temperature to 120 ℃, refluxing for 30 minutes, detecting by TLC point plate, washing, extracting, drying, spinning, filtering and purifying to obtain the final product, wherein the specific structural formula is as follows:
the above-described embodiments are merely preferred embodiments of the present invention, and should not be construed as limiting the present invention, and features in the embodiments and examples in the present application may be arbitrarily combined with each other without conflict. The protection scope of the present invention is defined by the claims, and includes equivalents of technical features of the claims. I.e., equivalent alterations and modifications within the scope hereof, are also intended to be within the scope of the invention.
The embodiment can be obviously applied to fluorescent luminescent materials, the luminous efficiency is high, the fluorescent quantum efficiency is 0.22-0.49 in toluene solution, and the application performance of the fluorescent luminescent materials in biology and luminescent materials is shown.
Claims (10)
1. An electron donor/electron acceptor hepta-boron fluoride fluorescent dye is characterized in that the chemical structural formula of the dye is as follows:
wherein, the substituent R is an electron-donating group or an electron-withdrawing group, and the electron-donating group is any one of alkoxy, amino and hydroxyl; the electron-withdrawing group comprises any one of acyl, aldehyde group, carboxyl, amide group, sulfonic group, nitrile group, nitro group, haloform group and quaternary ammonium group.
2. The electron donor/electron acceptor heptafluoroboron fluorescent dye according to claim 1, wherein the dye has a chemical structural formula of:
3. The method for the synthesis of an electron donor/electron acceptor heptafluoroboron fluorescent dye according to claim 1 or 2, characterized in that it comprises the following synthetic route:
(1) adding the compound 1, ethanol and the compound 2 into a reaction bottle at room temperature, and heating and refluxing to obtain a solid compound;
(2) purifying the solid compound in the step (1) to obtain a yellow solid compound 3;
(3) respectively adding toluene and triethylamine into the compound 3 in the step (2), slowly dropwise adding a boron trifluoride diethyl etherate complex, heating to 100-130 ℃, stirring and refluxing to obtain a reaction solution;
(4) and (4) respectively washing, extracting, drying and purifying the reaction liquid in the step (3) to obtain a product 3B, namely the electron donor/electron acceptor hepta-boron fluoride fluorescent dye.
4. The method for synthesizing an electron donor/electron acceptor heptabasic fluoroboron fluorescent dye according to claim 3, wherein in the step (1), the compound 1 is a proton-activated 2, 3, 3-trimethylindole derivative, and the compound 2 is 2-formylpyrrole; the feeding ratio of the compound 1 to the compound 2 is 1: 1-100.
5. The method for synthesizing an electron donor/electron acceptor heptabasic fluoroboron fluorescent dye according to claim 3, wherein the feeding sequence of the step (1) is compound 1, compound 2 and ethanol.
6. The method for synthesizing an electron donor/electron acceptor heptabasic fluoroboron fluorescent dye according to claim 3, wherein the reflux temperature of the step (1) is 80-90 ℃ and the reflux time is 2-18 hours.
7. The method for synthesizing an electron donor/electron acceptor heptabasic fluoroboron fluorescent dye according to claim 3, wherein the feeding mass ratio of the compound 3 of the step (3) to boron trifluoride ethyl ether complex is 1: 1-100.
8. The method for synthesizing an electron donor/electron acceptor heptabasic fluoroboron fluorescent dye according to claim 3, wherein in the step (3), toluene is used as a solvent, and the feeding molar ratio of triethylamine to boron trifluoride ethyl ether is 1: 1-25.
9. The method for synthesizing an electron donor/electron acceptor heptabasic fluoroboron fluorescent dye according to claim 3, wherein in the step (3), the compound 3, toluene, triethylamine and boron trifluoride diethyl etherate are added in sequence.
10. The method for synthesizing an electron donor/electron acceptor heptabasic fluoroboron fluorescent dye according to claim 3, wherein in the step (3), the heating reaction temperature is 120 ℃, and the reflux reaction time is 0.5-8 h.
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| CN111349109B (en) * | 2020-04-02 | 2022-09-16 | 三峡大学 | Synthetic method of seven-element boron dipyrromethene fluorescent dye |
| CN112442059B (en) * | 2020-12-10 | 2021-09-07 | 青海大学 | Seven-membered ring N, N-chelate boron complex, preparation method thereof, luminescent material and luminescent device |
| CN113105488B (en) * | 2021-03-17 | 2023-10-27 | 三峡大学 | Synthesis method and application of conjugated BOPYAIN fluorescent dye responding to viscosity |
| CN113105487A (en) * | 2021-03-17 | 2021-07-13 | 三峡大学 | Seven-element boron fluoride fluorescent dye and application thereof in fluorescent anti-counterfeiting film |
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