CN107857773A - 2-azaaromatic ring substituted quinazolinone borides - Google Patents

2-azaaromatic ring substituted quinazolinone borides Download PDF

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CN107857773A
CN107857773A CN201710088903.3A CN201710088903A CN107857773A CN 107857773 A CN107857773 A CN 107857773A CN 201710088903 A CN201710088903 A CN 201710088903A CN 107857773 A CN107857773 A CN 107857773A
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substituted
quinazolinone
phenyl
boride
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CN107857773B (en
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宋智彬
傅杨
周佳
白雪娇
潘颖
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Jiangxi Normal University
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Abstract

The invention relates to a novel high-efficiency organic fluorescent molecule-2-nitrogen heterocyclic aromatic ring substituted quinazolinone boride, wherein the 2-nitrogen heterocyclic aromatic ring substituted quinazolinone boride can be synthesized by taking 2-nitrogen heterocyclic aromatic ring substituted quinazolinone compounds and boron-containing compounds as raw materials. Because other groups can be introduced into the 2-nitrogen heteroaromatic ring substituted quinazolinone parent body, a novel functional pigment material can be synthesized by reacting with different borides, for example, a conjugated aromatic ring or an aromatic heterocyclic ring is introduced, so that a conjugated system can be enlarged, or electron-donating groups such as triphenylamine, diethylamine and the like are introduced, so that the emission wavelength of the compounds moves towards the long-wave direction, and novel fluorescent molecules with various emission wavelengths are obtained. The fluorescent material prepared by the molecule can be widely applied to the fields of luminescent and display devices, chemical industry, biological medicine, pesticides, military industry, intelligent terminals and the like.

Description

The quinazolinone boride of 2- nitrogen heteroaromatic rings substitution
Technical field
The present invention relates to Functional dye field, and in particular to a kind of new luminescent organic molecule --- 2- nitrogen heteroaromatic rings take The quinazolinone boride in generation.
Background technology
The multiple color and excellent luminescent properties that feature organic pigment molecule can be presented with it, and unique processing Performance, can convenient regulation molecular structure, favored for a long time by researcher, and light emitting diode, solar cell, field effect Answer transistor, multifunctional intellectual display terminal, biomedical imaging, photodynamic therapy, communication and signal transduction, environment inspection The fields such as survey, sensor are widely used, and are one of study hotspots of functional form organic molecule in recent years.
Boron has unique steric configuration and electronic structure, former by introducing boron in functional form organic pigment molecular structure Son, its Photophysics can be effectively adjusted, while boracic organic compound also has special chemical stability.Particularly four The organic B complexs of corrdination type, luminescent properties are superior, because its high molar absorption coefficient, good photostability and chemistry are steady It is qualitative, got in terms of Organic Light Emitting Diode OLED, and metal ion sensing, cell imaging, photodynamic therapy Carry out more applications.But synthesis step is more, purifying is complex, particularly classical BODIPY type boracics complex dye point Son.
By two nitrogen ligands of Quinazolinone-containing construction unit, (or it is corresponding derivative by simple synthesis step by the present invention Thing) it is coordinated with boron, the quinazolinone boride of a kind of new 2- nitrogen heteroaromatic rings substitution is obtained, is a kind of new organic hair Luminescent material.In this way, it can further expand effective conjugated system in quinazolinone molecular structure, realize and improve material Luminous efficiency itself, launch wavelength is adjusted, or even change illumination mode, extend the purpose of luminescent lifetime.Due to the boron after coordination Complex space structure is X-type, can suppress the accumulation between molecule-molecule, and be expected to obtain has preferably under solution and solid-state The luminescent material of luminescent properties.There is potential application value in terms of display device, electronic material, biological medicine.
The content of the invention
It is an object of the invention to provide a kind of new luminescent organic molecule --- the quinazolinone of 2- nitrogen heteroaromatic rings substitution Boride and preparation method thereof.
The quinazolinone boride of a kind of 2- nitrogen heteroaromatic rings substitution, has the general structure such as following formula I or formula II:
Wherein, nitrogen heteroaromatic rings (A rings) can be:Pyrroles, pyridine, quinoline, indoles, thiazole, oxazole, imidazoles, benzothiazole, Benzoxazoles, benzimidazole, pyridazine, pyrazine, pyrimidine, quinoxaline, purine etc..
Functional group X can be halogen atom, alkynyl, phenyl, substituted-phenyl, hydroxyl, alkyl, alkoxy, phenol epoxide, substitution The groups such as phenol epoxide, cyano group, adjacent diphenol epoxide, the adjacent diphenol epoxide of substitution, salicylate, substituted salicylic acid root.
R1~R2 can be alkyl, halogen atom, alkenyl, alkynyl, phenyl, substituted-phenyl, aryl, substituted aryl, hydroxyl, Alkoxy, phenol epoxide, acyl group, aldehyde radical, carboxyl, amide groups, nitro, amino, substituted-amino, heterocyclic radical, substituted heterocyclic radical, cyanogen The groups such as base, sulfonic group, sulfydryl, alkylthio group.
The quinazolinone boride of above-mentioned 2- nitrogen heteroaromatic rings substitution can by Quinazolinone-containing construction unit two nitrogen ligands (or Its corresponding derivative) with boron compound be Material synthesis.
The preparation method of the quinazolinone boride of above-mentioned 2- nitrogen heteroaromatic rings substitution:
In the round-bottomed flask of lucifuge, two nitrogen ligands for adding a certain amount of Quinazolinone-containing construction unit (or accordingly spread out Biology), in non-polar solven, back flow reaction some hours, corresponding boride is added according to specific reaction therebetween.Use high pressure Liquid chromatogram (HPLC) and thin-layer chromatography (TLC) track whole course of reaction, judge reaction end.After reaction terminating, reaction solution After the processing such as scrubbed, extraction, obtained extract is concentrated with Rotary Evaporators, removes the mixture obtained after solvent, is utilized Column chromatography chromatogram separates, and obtains target product.
Obtained target product is dissolved in deuterated reagent DMSO-d6 or CDCl3In, it can pass through1H NMR,13C NMR, The methods of HRMS, confirms to product structure.
The fluorescence property measure of the quinazolinone boride of this kind of 2- nitrogen heteroaromatic rings substitution, is mainly included the following steps that:
(1) product is dissolved in acetonitrile solvent, is configured to finite concentration, determine compound most using XRF Big excitation wavelength and maximum emission wavelength, according to maximum excitation wavelength and the maximum emission wavelength numerical measuring product in solution shape Fluorescence quantum yield under state.
(2) solid powder of compound products is directly placed into XRF, determines compound products solid-state like Maximum excitation wavelength and maximum emission wavelength under state, according to maximum excitation wavelength and the maximum emission wavelength numerical measuring product Fluorescence quantum yield under solid states.
The quinazolinone boride of this kind of 2- nitrogen heteroaromatic rings substitution can be used for preparing highly efficient fluorescent material, preparation it is efficient Fluorescent material has the advantages that property is stable, preserve the convenient, visibility of material and brightness is high.
Beneficial effects of the present invention:The quinazolinone boride and other existing boron of the 2- nitrogen heteroaromatic rings substitution of the present invention Compound phase ratio has that fluorescence quantum efficiency is high, all possesses the preferable characteristics of luminescence, synthesis under solution and solid-state two states It is easy, yield is higher, can be the even feather weight large-scale production of gram level the advantages that;Introduced by group, the launch wavelength of compound It can be moved to long wave direction, and then obtain new, the fluorescence molecule with various launch wavelengths, these molecules can be used for preparing Highly efficient fluorescent material;The preparation method of the present invention is simple, raw material is easy to get, yield is higher, and therefore, this new compound can answer For fields such as luminous and display device, chemical industry, biological medicine, agricultural chemicals, military project, intelligent terminals, and it is China in functional material A kind of novel fluorescent material is developed in field.
Brief description of the drawings
Fig. 1 is the quinazolinone boron compound prepared by example 11H NMR spectras.
Fig. 2 is the quinazolinone boron compound prepared by example 113C NMR spectras.
Fig. 3 is the crystal structure figure of the quinazolinone boron compound prepared by example 1.
Fig. 4 is uv absorption spectra of the quinazolinone boron compound in acetonitrile prepared by example 1.
Fig. 5 is fluorescence emission spectrogram of compound of the quinazolinone boron compound in acetonitrile prepared by example 1.
Fig. 6 is fluorescence emission spectrogram of compound of the quinazolinone boron compound under solid states prepared by example 1.
Fig. 7 is luminous photo of the quinazolinone boron compound under solution and solid states prepared by example 1.
Embodiment
With reference to instantiation, the present invention is further elaborated, but patent right is not limited to these embodiments.
Embodiment 1:
In 100mL reactors, 6- bromo- 2- (2- pyridine radicals) -3- hydrogen quinazoline-4-one 3.50g (10mmol) are added, are added It is solvent to enter 50mL toluene, after being uniformly mixed, adds triethylamine 8.5mL (60mmol), is subsequently added into boron trifluoride second Ether compound, backflow is heated to, reacts 24h, reaction material liquid is poured into water by reaction after terminating, and is stood, and layering, uses dichloro Methane extracts, and organic phase uses NaHCO respectively3Several times, organic phase is concentrated with Rotary Evaporators, is removed for the aqueous solution, distillation water washing The mixture obtained after solvent, is separated using column chromatography chromatogram, obtained target product, yield 88%.It is product below Nuclear magnetic resonance, Mass spectrometry experiments data and fluorescence quantum yield:
1H NMR(400MHz,CDCl3) δ=9.14-9.16 (m, 1H), 8.70-8.74 (m, 1H), 8.61-8.63 (m, 1H),8.29-8.30(m,1H),8.20-8.23(m,1H),8.03-8.06(m,1H),7.78-7.80(m,1H)ppm.
13C NMR (100MHz, DMSO-d6) δ=160.8,150.1,148.0,147.3,145.6,142.6,138.0, 130.6,130.3,129.1,125.0,122.5,121.3ppm.
HRMS m/z[M+H]+calcd:349.9906;found:349.9910.
Fluorescence quantum yield:0.94 (solution), 0.30 (solid-state)
Following table is the associated light performance parameter of the product prepared by embodiment 1:
Embodiment 2:
In 100mL reactors, 2- (2- quinolyls) -3- hydrogen quinazoline-4-one 3.21g (10mmol) are added, are added 50mL toluene is solvent, after being uniformly mixed, adds triethylamine 8.5mL (60mmol), is subsequently added into BFEE Compound, backflow is heated to, reacts 24h, reaction material liquid is poured into water by reaction after terminating, and is stood, and layering, uses dichloromethane Alkane extracts, and organic phase uses NaHCO respectively3Several times, organic phase is concentrated with Rotary Evaporators, is removed molten for the aqueous solution, distillation water washing The mixture obtained after agent, is separated using column chromatography chromatogram, obtained target product, yield 85%.It is the core of product below Magnetic resonance, Mass spectrometry experiments data and fluorescence quantum yield:
1H NMR(400MHz,CDCl3) δ=8.35-8.33 (m, 1H), 8.08-8.06 (m, 1H), 7.88-7.80 (m, 2H),7.60-7.58(m,2H),7.52-7.53(m,1H),7.42-7.45(m,3H)ppm.
13C NMR (100MHz, CDCl3) δ=175.6,163.8,154.3,149.4,147.5,134.9,132.7, 131.6,129.8,129.0,128.0,127.4,126.8,126.3,122.5,121.8,118.6ppm.
HRMS m/z[M+H]+calcd:322.0958;found:322.0963.
Fluorescence quantum yield:0.90 (solution), 0.50 (solid-state)
Embodiment 3:
In 100mL reactors, 6- bromo- 2- (2- pyridine radicals) -3- hydrogen quinazoline-4-one 4.00g (10mmol) are added, are added It is solvent to enter 50mL toluene, after being uniformly mixed, adds triethylamine 8.5mL (60mmol), is subsequently added into boron trifluoride second Ether compound, backflow is heated to, reacts 24h, reaction material liquid is poured into water by reaction after terminating, and is stood, and layering, uses dichloro Methane extracts, and organic phase uses NaHCO respectively3Several times, organic phase is concentrated with Rotary Evaporators, is removed for the aqueous solution, distillation water washing The mixture obtained after solvent, is separated using column chromatography chromatogram, obtained target product, yield 85%.It is product below Nuclear magnetic resonance, Mass spectrometry experiments data and fluorescence quantum yield:
1H NMR(400MHz,CDCl3) δ=8.32-8.34 (m, 1H), 8.05-8.07 (m, 1H), 7.84-7.86 (m, 2H),7.61-7.63(m,2H),7.52-7.53(m,1H),7.42-7.45(m,2H)ppm.
13C NMR (100MHz, CDCl3) δ=175.1,163.0,154.0,149.1,147.5,134.5,132.2, 131.0,129.2,128.6,127.8,127.1,126.3,126.0,122.1,121.5,118.0ppm.
HRMS m/z[M+H]+calcd:400.0063;found:400.0058.
Fluorescence quantum yield:0.82 (solution), 0.56 (solid-state)
Embodiment 4:
In 100mL reactors, 6- dimethylaminos -2- (2- pyridine radicals) -3- hydrogen quinazoline-4-ones 3.64g is added (10mmol), it is solvent to add 50mL toluene, after being uniformly mixed, adds triethylamine 8.5mL (60mmol), is subsequently added into three Boron fluoride ether complex, backflow being heated to, react 24h, reaction material liquid is poured into water by reaction after terminating, and is stood, Layering, is extracted, organic phase uses NaHCO respectively with dichloromethane3The aqueous solution, distill water washing several times, organic phase rotary evaporation Instrument concentrates, and removes the mixture obtained after solvent, is separated using column chromatography chromatogram, obtained target product, yield 85%.With Under be product nuclear magnetic resonance, Mass spectrometry experiments data and fluorescence quantum yield:
1H NMR(400MHz,CDCl3) δ=8.12-8.14 (m, 1H), 8.01-8.03 (m, 1H), 7.74-7.76 (m, 2H),7.51-7.53(m,2H),7.32-7.33(m,1H),7.22-7.25(m,2H),3.35(s,6H)ppm.
13C NMR (100MHz, CDCl3) δ=170.1,160.0,151.0,145.1,142.5,130.5,130.2, 129.8,128.2,127.5,126.4,125.1,124.3,123.0,122.1,121.5,118.0,45.2ppm.
HRMS m/z[M+H]+calcd:365.1380;found:365.1386.
Fluorescence quantum yield:0.89 (solution), 0.41 (solid-state)
Embodiment 5:
In 100mL reactors, 6- phenylacetylene bases -2- (2- pyridine radicals) -3- hydrogen quinazoline-4-ones 4.21g is added (10mmol), it is solvent to add 50mL toluene, after being uniformly mixed, adds triethylamine 8.5mL (60mmol), is subsequently added into three Boron fluoride ether complex, backflow being heated to, react 24h, reaction material liquid is poured into water by reaction after terminating, and is stood, Layering, is extracted, organic phase uses NaHCO respectively with dichloromethane3The aqueous solution, distill water washing several times, organic phase rotary evaporation Instrument concentrates, and removes the mixture obtained after solvent, is separated using column chromatography chromatogram, obtained target product, yield 85%.With Under be product nuclear magnetic resonance, Mass spectrometry experiments data and fluorescence quantum yield:
1H NMR(400MHz,CDCl3) δ=8.22-8.24 (m, 1H), 8.05-8.07 (m, 1H), 7.78-7.80 (m, 2H),7.59-7.60(m,2H),7.49-7.51(m,2H),7.41-7.43(m,2H),7.35-7.37(m,2H),7.22-7.25 (m,2H),3.35(s,6H)ppm.
13C NMR (100MHz, CDCl3) δ=171.1,161.0,150.0,144.1,141.5,132.8,130.6, 129.2,128.8,127.9,127.2,126.5,125.9,125.4,124.8,124.0,123.5 122.8,121.7, 120.5,116.2,100.1,96.2ppm
HRMS m/z[M+H]+calcd:422.1271;found:422.1265.
Fluorescence quantum yield:0.70 (solution), 0.65 (solid-state)
Embodiment 6:
In 100mL reactors, 6- phenylacetylene bases -2- (2- pyridine radicals) -3- hydrogen quinazoline-4-ones 4.21g is added (10mmol), it is solvent to add 50mL tetrahydrofurans, after being uniformly mixed, adds triethylamine 8.5mL (60mmol), then adds Entering the tetrahydrofuran solution of triphenyl borine, be heated to backflow, react 24h, reaction material liquid is poured into water by reaction after terminating, Stand, layering, extracted with dichloromethane, organic phase uses NaHCO respectively3Several times, organic phase rotates for the aqueous solution, distillation water washing Evaporimeter concentrates, and removes the mixture obtained after solvent, is separated using column chromatography chromatogram, obtained target product, yield is 85%.It is nuclear magnetic resonance, Mass spectrometry experiments data and the fluorescence quantum yield of product below:
1H NMR(400MHz,CDCl3) δ=8.12-8.14 (m, 1H), 8.01-8.03 (m, 1H), 7.75-7.80 (m, 6H),7.56-7.57(m,2H),7.49-7.51(m,2H),7.41-7.47(m,6H),7.32-7.36(m,4H),7.21-7.23 (m,2H)ppm.
13C NMR (100MHz, CDCl3) δ=171.1,161.0,150.0,144.1,141.5,132.8,130.6, 129.2,128.8,128.5,128.2,128.0,127.8,127.4,126.8,126.0,125.5 124.8,123.7, 122.5,119.2ppm
HRMS m/z[M+H]+calcd:438.1772;found:438.1763.
Fluorescence quantum yield:0.56 (solution), 0.42 (solid-state)
Embodiment 7:
In 100mL reactors, 2- (2- pyridine radicals) -3- hydrogen quinazoline-4-one 2.23g (10mmol) are added, are added 50mL toluene is solvent, after being uniformly mixed, adds catechol 1.1g (10mmol), triethylamine 8.5mL (60mmol), connects Addition BFEE compound, is heated to backflow, reacts 24h, reacts and reaction material liquid is poured into water after terminating In, stand, layering, extracted with dichloromethane, organic phase uses NaHCO respectively3Several times, organic phase is used for the aqueous solution, distillation water washing Rotary Evaporators concentrate, and remove the mixture obtained after solvent, are separated using column chromatography chromatogram, obtained target product, yield For 89%.It is nuclear magnetic resonance, Mass spectrometry experiments data and the fluorescence quantum yield of product below:
1H NMR (400MHz, DMSO-d6) δ=8.32-8.33 (m, 1H), 8.09-8.10 (m, 1H), 7.77-7.78 (m, 1H),7.62-7.63(m,1H),7.41-7.21(m,1H),7.35-7.31(m,1H),7.06-7.02(m,1H),6.65(d,J =8Hz, 2H), 6.56 (d, J=8Hz, 2H) ppm.
13C NMR (100MHz, DMSO-d6) δ=171.9,162.41,154.6,149.7,145.6,140.9,137.8, 133.4,128.6,125.7,122.5 120.9,119.69,116.92,112.9,110.21ppm.
HRMS m/z[M+H]+calcd:342.1044;found:342.1052.
Fluorescence quantum yield:0.64 (solution), 0.10 (solid-state)
Embodiment 8:
In 100mL reactors, 2- (2- pyridine radicals) -3- hydrogen quinazoline-4-one 2.23g (10mmol) are added, are added 50mL toluene is solvent, after being uniformly mixed, adds salicylic acid 1.40g (10mmol), triethylamine 8.5mL (60mmol), connects Addition BFEE compound, is heated to backflow, reacts 24h, reacts and reaction material liquid is poured into water after terminating In, stand, layering, extracted with dichloromethane, organic phase uses NaHCO respectively3Several times, organic phase is used for the aqueous solution, distillation water washing Rotary Evaporators concentrate, and remove the mixture obtained after solvent, are separated using column chromatography chromatogram, obtained target product, yield For 90%.It is nuclear magnetic resonance, Mass spectrometry experiments data and the fluorescence quantum yield of product below:
1H NMR (400MHz, DMSO-d6) δ=8.22-8.25 (m, 1H), 8.15-8.18 (m, 1H), 7.96-7.97 (m, 1H),7.85-7.89(m,1H),7.76-7.78(m,1H),7.54-7.58(m,1H),7.44-7.48(m,2H),7.05-7.07 (m,1H),6.95-7.03(m,3H)ppm.
13C NMR (100MHz, DMSO-d6) δ=174.1,170.2,164.2,147.8,145.6,135.5,133.5, 131.5,129.6,127.8,126.8,125.3,122.6,121.3,120.5,117.4,115.7,115.3,108.9, 102.6ppm.
HRMS[M+H]+calcd:370.0994;found:370.0102.
Fluorescence quantum yield:0.54 (solution), 0.12 (solid-state)
Embodiment 9:
In 100mL reactors, 2- (2- pyrrole radicals) -3- hydrogen quinazoline-4-one 2.11g (10mmol) are added, are added 50mL toluene is solvent, after being uniformly mixed, adds triethylamine 8.5mL (60mmol), is subsequently added into BFEE Compound, backflow is heated to, reacts 24h, reaction material liquid is poured into water by reaction after terminating, and is stood, and layering, uses dichloromethane Alkane extracts, and organic phase uses NaHCO respectively3Several times, organic phase is concentrated with Rotary Evaporators, is removed molten for the aqueous solution, distillation water washing The mixture obtained after agent, is separated using column chromatography chromatogram, obtained target product, yield 75%.It is the core of product below Magnetic resonance, Mass spectrometry experiments data and fluorescence quantum yield:
1H NMR (400MHz, DMSO-d6) δ=8.12 (d, J=8Hz, 1H), 7.87-7.89 (m, 1H), 7.72 (d, J= 8Hz,1H),7.49-7.53(m,1H),7.45-7.41(m,1H),7.12-7.16(m,1H),6.32-6.30(m,1H)ppm.
13C NMR (100MHz, DMSO-d6) δ=172.3,156.9,144.9,136.9,136.4,135.7,134.7, 134.3,130.9,123.0,120.2,110.0ppm.
HRMS:m/z[M+H]+calcd:260.0801;found:260.0805.
Fluorescence quantum yield:0.74 (solution), 0.25 (solid-state)
Embodiment 10:
In 100mL reactors, 2- (6- propyl group -2- quinolyls) -3- hydrogen quinazoline-4-one 3.59g (10mmol) are added, It is solvent to add 50mL toluene, after being uniformly mixed, adds catechol 1.1g (10mmol), triethylamine 8.5mL (60mmol), BFEE compound is subsequently added into, is heated to backflow, react 24h, reaction will reaction after terminating Feed liquid is poured into water, and is stood, and layering, is extracted with dichloromethane, organic phase uses NaHCO respectively3The aqueous solution, distillation water washing number Time, organic phase is concentrated with Rotary Evaporators, is removed the mixture obtained after solvent, is separated using column chromatography chromatogram, obtained mesh Mark product, yield 89%.It is nuclear magnetic resonance, Mass spectrometry experiments data and the fluorescence quantum yield of product below:
1H NMR (400MHz, DMSO-d6) δ=10.5 (br s, 2H), 8.42-8.43 (m, 1H), 8.05-8.06 (m, 1H),7.72-7.74(m,1H),7.65-7.66(m,1H),7.41-7.42(m,2H),7.30-7.31(m,2H),7.06-7.08 (m,1H),2.62-2.64(m,2H),1.65-1.67(m,2H),0.92-0.94(m,3H)ppm.
13C NMR (100MHz, DMSO-d6) δ=170.5,160.2,151.4,145.6,142.7,130.8,130.1, 129.5,128.6,127.1,126.5,125.3,124.7,123.3,122.5,121.1,118.4,28.3,19.6, 12.5ppm.
HRMS m/z[M+H]+calcd:360.1514;found:360.1519.
Fluorescence quantum yield:0.24 (solution), 0.20 (solid-state)
Embodiment 11:
In 100mL reactors, 2- (2- indyls) -3- hydrogen quinazoline-4-one 2.61g (10mmol) are added, are added 50mL toluene is solvent, after being uniformly mixed, adds triethylamine 8.5mL (60mmol), is subsequently added into BFEE Compound, backflow is heated to, reacts 24h, reaction material liquid is poured into water by reaction after terminating, and is stood, and layering, uses dichloromethane Alkane extracts, and organic phase uses NaHCO respectively3Several times, organic phase is concentrated with Rotary Evaporators, is removed molten for the aqueous solution, distillation water washing The mixture obtained after agent, is separated using column chromatography chromatogram, obtained target product, yield 70%.It is the core of product below Magnetic resonance, Mass spectrometry experiments data and fluorescence quantum yield:
1H NMR(400MHz,CDCl3) δ=8.5 (br s, 1H), 7.91-7.92 (m, 1H), 7.70-7.71 (m, 1H), 7.45-7.48(m,1H),7.33-7.35(m,2H),7.26-7.28(m,3H),7.11-7.13(m,1H)ppm.
13C NMR (100MHz, DMSO-d6) δ=175.2,163.98,147.68,146.9,136.2,133.85, 128.6,127.78,126.93,122.4,121.8,120.6,117.98,115.58,115.17,102.6ppm.
HRMS:[M+H]+calcd:310.0958;found:310.0967.
Fluorescence quantum yield:0.84 (solution), 0.35 (solid-state)
Embodiment 12:
In 100mL reactors, 2- (2-[4-morpholinodithio base) -3- hydrogen quinazoline-4-one 2.79g (10mmol) are added, are added It is solvent to enter 50mL toluene, after being uniformly mixed, adds triethylamine 8.5mL (60mmol), is subsequently added into boron trifluoride second Ether compound, backflow is heated to, reacts 24h, reaction material liquid is poured into water by reaction after terminating, and is stood, and layering, uses dichloro Methane extracts, and organic phase uses NaHCO respectively3Several times, organic phase is concentrated with Rotary Evaporators, is removed for the aqueous solution, distillation water washing The mixture obtained after solvent, is separated using column chromatography chromatogram, obtained target product, yield 95%.It is product below Nuclear magnetic resonance, Mass spectrometry experiments data and fluorescence quantum yield:
1H NMR(400MHz,CDCl3) δ=8.23-8.25 (m, 1H), 7.95-7.96 (m, 1H), 7.63-7.59 (m, 2H),7.48-7.45(m,3H),7.34-7.35(m,1H)ppm.
13C NMR (100MHz, DMSO-d6) δ=176.1,163.98,156.3,152.9,147.68,146.92, 133.8,130.5 127.7,126.9,122.6,122.1 117.9,115.5,115.1ppm.
HRMS(ESI):m/z[M+H]+calcd:328.0522;found:328.0525.
Fluorescence quantum yield:0.90 (solution), 0.60 (solid-state)
Embodiment 13:
In 100mL reactors, 2- (2- quinazolyls) -3- hydrogen quinazoline-4-one 2.79g (10mmol) are added, are added 50mL toluene is solvent, after being uniformly mixed, adds triethylamine 8.5mL (60mmol), is subsequently added into BFEE Compound, backflow is heated to, reacts 24h, reaction material liquid is poured into water by reaction after terminating, and is stood, and layering, uses dichloromethane Alkane extracts, and organic phase uses NaHCO respectively3Several times, organic phase is concentrated with Rotary Evaporators, is removed molten for the aqueous solution, distillation water washing The mixture obtained after agent, is separated using column chromatography chromatogram, obtained target product, yield 86%.It is the core of product below Magnetic resonance, Mass spectrometry experiments data and fluorescence quantum yield:
1H NMR (400MHz, DMSO-d6) δ=9.50 (s, 1H), 8.42-8.43 (m, 1H), 7.85-7.86 (m, 2H), 7.66-7.68(m,2H),7.62-7.58(m 1H),7.26-7.23(m,1H),6.76(m,1H)ppm.
13C NMR (100MHz, DMSO-d6) δ=178.1,165.5,163.7,156.2,150.0,147.7,133.9, 132.8,128.2,127.8,122.1,119.0,117.0,115.7,114.9,111.9ppm.
HRMS(ESI):m/z[M+H]+calcd:323.0910;found:323.0915.
Fluorescence quantum yield:0.84 (solution), 0.43 (solid-state)
Embodiment 14:
In 100mL reactors, 2- (6- nitro -2- quinazolyls) -3- hydrogen quinazoline-4-ones 3.67g is added (10mmol), it is solvent to add 50mL toluene, after being uniformly mixed, adds triethylamine 8.5mL (60mmol), is subsequently added into three Boron fluoride ether complex, backflow being heated to, react 24h, reaction material liquid is poured into water by reaction after terminating, and is stood, Layering, is extracted, organic phase uses NaHCO respectively with dichloromethane3The aqueous solution, distill water washing several times, organic phase rotary evaporation Instrument concentrates, and removes the mixture obtained after solvent, is separated using column chromatography chromatogram, obtained target product, yield 86%.With Under be product nuclear magnetic resonance, Mass spectrometry experiments data and fluorescence quantum yield:
1H NMR (400MHz, DMSO-d6) δ=9.50 (s, 1H), 8.72-8.73 (m, 2H), 8.21-8.23 (m, 1H), 7.76-7.78(m,2H),7.65-7.67(m 1H),7.36-7.35(m,1H),7.21-7.23(m,1H)ppm.
13C NMR (100MHz, DMSO-d6) δ=178.1,170.5,167.7,159.8,155.0,149.7,142.9, 138.8, 135.2,133.8,129.5,128.1,126.0,125.3,124.4,120.8.ppm.
HRMS(ESI):m/z[M+H]+calcd:368.0761;found:368.0753.
Fluorescence quantum yield:0.34 (solution), 0.12 (solid-state)
Embodiment 15:
In 100mL reactors, 6- methoxyl groups -2- (6- cyano group -2- quinazolyls) -3- hydrogen quinazoline-4-ones are added 3.72g (10mmol), it is solvent to add 50mL toluene, after being uniformly mixed, adds triethylamine 8.5mL (60mmol), then Boric acid is added, is heated to backflow, reacts 24h, reaction material liquid is poured into water by reaction after terminating, and is stood, and layering, uses dichloro Methane extracts, and organic phase uses NaHCO respectively3Several times, organic phase is concentrated with Rotary Evaporators, is removed for the aqueous solution, distillation water washing The mixture obtained after solvent, is separated using column chromatography chromatogram, obtained target product, yield 86%.It is product below Nuclear magnetic resonance, Mass spectrometry experiments data and fluorescence quantum yield:
1H NMR (400MHz, DMSO-d6) δ=10.5 (br s, 2H), 8.36-8.38 (m, 1H), 8.10-8.11 (m, 1H),7.80-7.81(m,1H),7.62-7.63(m,1H),7.39-7.40(m,1H),7.30-7.31(m,2H),7.01-7.02 (m,1H),3.85(s,3H)ppm.
13C NMR (100MHz, DMSO-d6) δ=171.5,161.2,152.4,146.6,143.7,131.8,131.1, 129.8,128.6,128.1,127.5,126.3,125.7,124.3,123.5,122.1,119.4,118.5,56.2ppm
HRMS(ESI):m/z[M+H]+calcd:373.1103;found:373.1109.
Fluorescence quantum yield:0.36 (solution), 0.30 (solid-state).

Claims (5)

  1. The quinazolinone boride of 1.2- nitrogen heteroaromatic rings substitution, has such as following formula I or the general structure of formula II:
    Wherein, nitrogen heteroaromatic rings (A rings) are selected from:Pyrroles, pyridine, quinoline, indoles, thiazole, oxazole, imidazoles, benzothiazole, benzo are disliked Azoles, benzimidazole, pyridazine, pyrazine, pyrimidine, quinoxaline, purine etc.;
    Functional group X is selected from:Halogen atom, alkynyl, phenyl, substituted-phenyl, hydroxyl, alkyl, alkoxy, phenol epoxide, substituted phenol oxygen The groups such as base, cyano group, adjacent diphenol epoxide, the adjacent diphenol epoxide of substitution, salicylate, substituted salicylic acid root;
    R1It is selected from:Alkyl, halogen atom, alkenyl, alkynyl, phenyl, substituted-phenyl, aryl, substituted aryl, hydroxyl, alkoxy, phenol Epoxide, acyl group, aldehyde radical, carboxyl, amide groups, nitro, amino, substituted-amino, heterocyclic radical, substituted heterocyclic radical, cyano group, sulfonic group, The groups such as sulfydryl, alkylthio group;
    R2It is selected from:Alkyl (including cycloalkyl), alkyl heterocycle, halogen atom, alkenyl, alkynyl, phenyl, substituted-phenyl, aryl, take For aryl, hydroxyl, alkoxy, phenol epoxide, acyl group, aldehyde radical, carboxyl, amide groups, nitro, amino, substituted-amino, heterocyclic radical, take For groups such as heterocyclic radical, cyano group, sulfonic group, sulfydryl, alkylthio groups.
  2. 2. the preparation method of the quinazolinone boride of 2- nitrogen heteroaromatic rings substitution according to claim 1, including following step Suddenly:
    (1) two nitrogen ligands (or corresponding derivative) of a certain amount of Quinazolinone-containing construction unit are added, in non-polar solven, The raw materials such as corresponding boride and catechol, salicylic acid are added according to specific reaction therebetween, with triethylamine adjust reaction solution to Alkalescence, back flow reaction 24 hours;
    (2) reaction material liquid is poured into water, stood, layering, extracted with dichloromethane, organic phase uses NaHCO respectively3The aqueous solution, steaming Distilled water is washed several times, and organic phase is concentrated with Rotary Evaporators, removes the mixture obtained after solvent, utilizes column chromatography chromatogram point From obtained sterling.
  3. 3. preparation method according to claim 2, it is characterised in that:The phenodiazine of described Quinazolinone-containing construction unit is matched somebody with somebody Body (or corresponding derivative), there is the structure such as following formula III or formula IV:
    Wherein, nitrogen heteroaromatic rings (A rings) are selected from:Pyrroles, pyridine, quinoline, indoles, thiazole, oxazole, imidazoles, benzothiazole, benzo are disliked Azoles, benzimidazole, pyridazine, pyrazine, pyrimidine, quinoxaline, purine etc.;
    R1And R2It is selected from:Alkyl (including cycloalkyl), alkyl heterocycle, halogen atom, alkenyl, alkynyl, phenyl, substituted-phenyl, virtue Base, substituted aryl, hydroxyl, alkoxy, phenol epoxide, acyl group, aldehyde radical, carboxyl, amide groups, nitro, amino, substituted-amino, heterocycle The groups such as base, substituted heterocyclic radical, cyano group, sulfonic group, sulfydryl, alkylthio group.
  4. 4. preparation method according to claim 2, it is characterised in that:Described boride is that BFEE is compound Thing, boric acid, triphenyl borine or tri-substituted phenyl boron.
  5. 5. application of the quinazolinone boride of 2- nitrogen heteroaromatic rings substitution according to claim 1 in fluorescent material.
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CN109694372A (en) * 2018-12-11 2019-04-30 湖南大学 A kind of two-photon fluorescence probe and the preparation method and application thereof
CN113461914A (en) * 2021-06-21 2021-10-01 上饶师范学院 D-pi-A type polymer fluorescent material containing 2, 6-diphenyl-4-aryl pyridine structure and synthetic method thereof
CN113583031A (en) * 2021-07-06 2021-11-02 江西师范大学 Endoplasmic reticulum positioning imaging/photoinduced iron death dual-function probe
CN113980039A (en) * 2021-11-19 2022-01-28 杭州师范大学 Photothermal agent and preparation method and application thereof
CN115850308A (en) * 2022-11-07 2023-03-28 淮阴工学院 BODIPY near-infrared fluorescent probe containing electron donor and acceptor group recognition Abeta fibers and preparation method thereof
CN116003448A (en) * 2022-11-07 2023-04-25 淮阴工学院 BODIPY near infrared fluorescent probe containing indoline polyethylenically recognized Abeta fiber and preparation method thereof

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CN109503550A (en) * 2018-11-20 2019-03-22 江西师范大学 2- azepine aryl-6-substituted-amino quinazolinones and its preparation method and application
CN109503550B (en) * 2018-11-20 2022-11-29 江西师范大学 2-azaaryl-6-substituted amino quinazolinone compound and preparation method and application thereof
CN109694372A (en) * 2018-12-11 2019-04-30 湖南大学 A kind of two-photon fluorescence probe and the preparation method and application thereof
CN109694372B (en) * 2018-12-11 2021-08-24 湖南大学 Two-photon fluorescent probe and preparation method and application thereof
CN113461914A (en) * 2021-06-21 2021-10-01 上饶师范学院 D-pi-A type polymer fluorescent material containing 2, 6-diphenyl-4-aryl pyridine structure and synthetic method thereof
CN113583031B (en) * 2021-07-06 2022-07-26 江西师范大学 Endoplasmic reticulum positioning imaging/photoinduced iron death dual-function probe
CN113583031A (en) * 2021-07-06 2021-11-02 江西师范大学 Endoplasmic reticulum positioning imaging/photoinduced iron death dual-function probe
CN113980039A (en) * 2021-11-19 2022-01-28 杭州师范大学 Photothermal agent and preparation method and application thereof
CN113980039B (en) * 2021-11-19 2023-08-18 杭州师范大学 Photothermal agent and preparation method and application thereof
CN115850308A (en) * 2022-11-07 2023-03-28 淮阴工学院 BODIPY near-infrared fluorescent probe containing electron donor and acceptor group recognition Abeta fibers and preparation method thereof
CN116003448A (en) * 2022-11-07 2023-04-25 淮阴工学院 BODIPY near infrared fluorescent probe containing indoline polyethylenically recognized Abeta fiber and preparation method thereof
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