CN101798467A - Cholesteryl-contained 2D-pi-A type pyran charge transfer fluorescent dye and synthesizing method thereof - Google Patents
Cholesteryl-contained 2D-pi-A type pyran charge transfer fluorescent dye and synthesizing method thereof Download PDFInfo
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Abstract
The invention relates to a cholesteryl-contained 2D-pi-A type pyran charge transfer fluorescent dye containing a cholesterol group and a synthesizing method thereof. The cholesteryl-based pyran dye has a structure shown as the formula (I). The dye can realize the fluorescent chromogenic wavelengths in different solvents by utilizing the interaction of charge transfer, Van der Waals' force, dipole-dipole, and the like in molecules and can be used for the fields of organic electroluminescence, poisonous and organic compound detection, a molecular sensor, biological probe light, light collection, and the like. In the formula (1), each R and R' can be same, can also be different and are one of hydrogen, C1-C16 alkyl, C1-C16 alkoxyl, C5-C20 cycloalkyl, aromatic ring group or a heterocyclic group, halogen, hydroxyl and a sulfonic acid group; X is S or O; and Y is O, C or NH.
Description
Technical field
The present invention relates to a kind of intramolecular charge and shift fluorescence dye and synthetic method thereof, relate to a kind of cholesteryl 2D-π-A type pyrans class charge transfer fluorescence dye and synthetic method thereof that contain specifically.
Background technology
(D-π-A) compound becomes the focus of research in recent years to have the electron donor(ED)-electron acceptor(EA) of conjugated structure, this compounds of major cause has important use at device for non-linear optical, laser dyes laser apparatus, organic electroluminescent (OLED), toxic organic compound detection, bioprobe, molecular switch and transmitter, dye sensitization solar battery etc. and is worth (Analytical Chemistry, 2006; 78 (11): 3591-600; Angew.Chem.Int.Ed.2007,46,5549-5553; J.AM.CHEM.SOC.2005,127,17799-17802).In this numerous class organic compound, electron donor(ED)-electron acceptor(EA) pyrans class charge transfer functional dye with conjugated structure, because variation and medium pH variation to solvent polarity have high susceptibility, be the fluorescent chromophore (Macromolecules that has potentiality, 2009,42,1733-1738; Dyes and Pigments, 2008,78:25-33).Yet this class dyestuff has big two dimensional structure, forms state of aggregation easily, causes fluorescent quenching.A kind of effective way that overcomes this phenomenon is the gathering behavior that changes molecule by chemically modified, as control molecular configuration, conformation, reduce forming the tendency of ordered aggregation each other and weakening intermolecular ground state and the excited state interaction, thereby eliminate the self-quenching phenomenon effectively.Cholesterol is the important steroidal compounds of a class, can utilize the intermolecular Van der Waals force of cholesterol to realize intermolecular self-assembly, change the parcel and the arrangement of molecule, thereby change molecule photochemistry and optical physics behavior (as: Chem.Eur.J.2007 in solution and solid, 13,8231-8239; Angew.Chem.Int.Ed.2007,46,8005-8009; J.Phys.Chem.B, 2007,111,2000-2007).By appropriate molecular designing, utilize the self-assembly behavior regulation and control pyrans chromophoric luminescent properties of cholesterol group in solvent, the behavior of control molecule self aggregation realizes effective regulation and control of fluorescence.Given this, the technical issues that need to address of the present invention are: design and synthesize a kind of novel cholesteryl 2D-π-A type pyrans class charge transfer fluorescence dye that contains.
Summary of the invention
The objective of the invention is to remedy the deficiency that prior art exists, a kind of cholesteryl 2D-π-A type pyrans class charge transfer fluorescence dye that contains is provided;
Another object of the present invention provides the synthetic method that contains cholesteryl 2D-π-A type pyrans class charge transfer fluorescence dye.
For achieving the above object, the cholesteryl 2D-π-A type pyrans class charge transfer fluorescence dye that contains of the present invention, its general structure is as follows:
In the formula (I), each R and R ' can be identical, also can be different.They are hydrogen, C
1～C
16Alkyl, C
1～C
16Alkoxyl group, C
5～C
20Cycloalkyl, aromatic ring yl or heterocyclic radical, halogen, hydroxyl, sulfonic group; X is S, and O's is a kind of; Y is O, and C's is a kind of.
Each R and R ' can be identical, also can be different, be hydrogen, C
1～C
6Alkyl, C
1～C
6Alkoxyl group, C
5～C
10Cycloalkyl, aromatic ring yl or C
4～C
10Heterocyclic radical; X is S or O; Y is O or C.
Each R is identical with R ', is hydrogen, C
1～C
6Alkyl, C
1～C
6Alkoxyl group, C
5～C
10Cycloalkyl, aromatic ring yl or C
4～C
10Heterocyclic radical; X is S or O; The Y atom is O.
Each R is identical with R ', is hydrogen, C
1～C
6Alkyl, C
1～C
6Alkoxyl group, C
5～C
10Cycloalkyl, aromatic ring yl or C
4～C
10Heterocyclic radical; X is S or O; The Y atom is C.
Each R is identical with R ', is hydrogen, methyl, methoxyl group, cyclohexyl, phenyl or ferrocenyl; X is O; The Y atom is O.
Each R is identical with R ', is hydrogen, methyl, methoxyl group, cyclohexyl, phenyl or ferrocenyl; X is S; The Y atom is O.
This fluorescence dye has different fluorescent emission wavelength in different solvents.
In a preferred design of the present invention, each R is identical with R ', and they are hydrogen, C
1～C
16Alkyl, C
1～C
16Alkoxyl group, C
5～C
20Cycloalkyl, aromatic ring yl or heterocyclic radical, X are S, and O's is a kind of; Y is O, one kind of C.
More preferably: R is identical with R ', and they are C
1～C
6Alkyl, C
1～C
6Alkoxyl group, C
5～C
10Cycloalkyl, aromatic ring yl or heterocyclic radical, X are S, and O's is a kind of; Y is O, one kind of C.
Best R=R ' is ethyl, oxyethyl group, and cyclohexyl, phenyl, X are S; Y is O.
A kind of synthetic method that contains cholesteryl 2D-π-A type pyrans class charge transfer fluorescence dye, with N, N-diethanolaniline, cholesterol acyl chlorides are raw material, through the synthetic key intermediate (II) of over-churning, Vilsmeier-Haack reaction or with aniline and vinylformic acid condensation, then with cholesterol generation esterification, the synthetic key intermediate of Vilsmeier-Haack reaction (II ') further takes place obtain target compound then with after the reaction such as pyrans class chromophoric group (III) condensation condensation.
Specifically comprise the steps:
A) N, N-diethanolaniline, cholesterol acyl chlorides are raw material, under the organic alkali catalyst condition, obtain compound shown in the intermediate 1 in the refluxing toluene reaction, the Vilsmeier-Haack reaction takes place then obtain key intermediate (II)
B) reaction of aniline and vinylformic acid obtains N, and N-two-propionyloxy aniline obtains key intermediate 2 with lentochol reaction then under catalyst action, Vilsmeier-Haack reaction takes place then obtain key intermediate (II ')
C) under pyrone and barbituric acid or the derivative nitrogen protection condition, diacetyl oxide is made solvent refluxing, obtains key intermediate (III)
D) key intermediate (II) or (II ') are placed acetonitrile with intermediate (III), under condition of nitrogen gas, back flow reaction at least 6 hours (obtaining target product).
Synthetic route is as follows:
Synthesizing of cholesteryl 2D-π-A type pyrans class charge transfer fluorescence dye, mainly contain the crucial middle of cholesteryl through prepared in reaction such as esterification, Vilsmeier-Haack, acylations, condensation reaction obtains target product with pyrans class chromophoric group then.
This contains cholesteryl 2D-π-A type pyrans class charge transfer fluorescence dye, utilizes interactions such as intramolecular charge transfer, Van der Waals force, dipole-dipole can be implemented in fluorescence color development wavelength in the different solvents.Such dyestuff can be used as fields such as organic electroluminescent, toxic organics detection, molecule sensor, bioprobe light, light collection.
Embodiment
The present invention is further elaborated below by example, and purpose is better to understand content of the present invention, and therefore, the cited case does not limit protection scope of the present invention:
Embodiment 1
In 100ml single port flask; add N, ' N-two-ethanol based aniline 1.81g, cholesterol acyl chlorides 9.856g, 50ml toluene; the 1ml triethylamine; reflux is 5 hours under the nitrogen protection condition, cooling, rotary evaporation; concentrate and remove toluene; ethanol-chloroform recrystallization obtains the 8.5g white crystalline powder, and productive rate is 81.5%.
1H-NMR (400MHz, CDCl3, ppm): δ 1.01-2.38 (m, 90H), 3.75 (t, 4H ,-CH
2N), 4.4 (t, 4H ,-CH
2O), 6.8 (d, 2H), 7.27 (d, 2H); Ultimate analysis: C, 78.52; H, 10.37; N, 1.28; O, 9.83
In the 250ml there-necked flask, add 5.03g and go up the synthetic intermediate 1 that obtains of step, 60mlN, dinethylformamide, ice-water bath are cooled to 0-10 ℃, drip the 0.756g phosphorus oxychloride then, in 0.5 hour, drip off, remove ice-water bath, stirring at room 1 hour, reflux is 1 hour then, reduce to room temperature, mixture is poured in the frozen water, add salt of wormwood and regulate pH value about 10, separate out precipitation, filter, wash 3 times, oven dry, silica gel column chromatography separates (ethyl acetate: chloroform=1: 5), get white crystalline powder 4.13g.Productive rate 80.5%
1H-NMR (400MHz, CDCl
3, ppm): δ 1.03-2.76 (m, 90H), 3.52 (t, 4H ,-CH
2N), 5.3 (t, 4H ,-CH
2O), 7.0 (d, 2H), 7.2 (d, 2H), 9.8 (1,1H ,-CHO); Ultimate analysis: C, 77.69; H, 9.85; N, 1.20; O, 11.26
In 100ml single port flask, add 2,2 '-dimethyl pyrans ketone 2.48g, barbituric acid 2.6g, 30ml diacetyl oxide; reflux is 5 hours under the nitrogen protection condition, and cooling is filtered; get yellow powder shape solid, ethyl alcohol recrystallization obtains 3.98g yellow crystal sprills.Productive rate is 85%.
1H-NMR (400MHz, d-DMSO, ppm): δ 1.85 (s, 6H), 6.9 (s, 2H), 11.8 (s, 2H), ultimate analysis: 57.0; H, 4.30; N, 10.2,28.5.
In the 100ml there-necked flask; add the pyrone intermediate 0.06g that contains barbituric acid; cholesterol intermediate (II) 0.55g; the 20ml acetonitrile drips several Piperazine anhydrous then, under the nitrogen protection condition; reflux 6 hours; reaction is finished postcooling to room temperature, and filtering-depositing obtains the garnet pressed powder.Ethyl alcohol recrystallization obtains red powder shape solid 0.36g.Productive rate 60.5% ultimate analysis: C, 77.00; H, 9.50; N, 1.50; O, 12.00.
Embodiment 2
In 100ml single port flask, add 2,2 '-dimethyl pyrans ketone 1.24g, N, N-dimethyl barbituric acid 1.56g; the 30ml diacetyl oxide, reflux is 5 hours under the nitrogen protection condition, and cooling is filtered; get yellow powder shape solid, ethyl alcohol recrystallization obtains 2.30g yellow crystal sprills.Productive rate is 88%.
1H?NMR(400MHz，CDCl
3，ppm)d：6.67(s，2H，pyran-H)，3.30(s，6H，NCH
3)，1.56(s，6H，CH3)，EI-MS，m/z?262?Elemental?analysis：C，59.49；H，5.30；N，10.59％.C
13H
14N
2O
4?requires：C，59.54；H，5.38；N，10.68％.
In the 100ml there-necked flask; add and contain N; the pyrone intermediate 0.066g of N-dimethyl barbituric acid, cholesterol intermediate (II) 0.55g, 20ml acetonitrile; drip several Piperazine anhydrous then; under the nitrogen protection condition, reflux 8 hours, reaction is finished postcooling to room temperature; filtering-depositing obtains the garnet pressed powder.Ethyl alcohol recrystallization obtains red powder shape solid 0.36g.Productive rate 60.5% ultimate analysis: C, 76.98; H, 9.40; N, 2.12; O, 11.50.
Embodiment 3
In 100ml single port flask, add 2,2 '-dimethyl pyrans ketone 1.24g, N, N-dicyclohexyl barbituric acid 2.92g; the 50ml diacetyl oxide, reflux is 5 hours under the nitrogen protection condition, and cooling is filtered; get yellow powder shape solid, ethyl alcohol recrystallization obtains 3.38g yellow crystal sprills.Productive rate is 85%.Directly be used in next step.
In the 100ml there-necked flask; add N; the pyrone intermediate 0.11g of N-dicyclohexyl barbituric acid, cholesterol intermediate (II) 0.55g, 20ml acetonitrile; drip several Piperazine anhydrous then; under the nitrogen protection condition, reflux 6 hours, reaction is finished postcooling to room temperature; filtering-depositing obtains silent red solid powder.Ethyl alcohol recrystallization obtains red powder shape solid 0.42g.Productive rate 65.0% ultimate analysis: C, 77.58; H, 9.42; N, 2.00; O, 11.00.
Embodiment 4
In 100ml single port flask, add 2,2 '-dimethyl pyrans ketone 1.24g, N, N-two-phenyl barbituric acid 2.80g; the 30ml diacetyl oxide, reflux is 5 hours under the nitrogen protection condition, and cooling is filtered; get yellow powder shape solid, ethyl alcohol recrystallization obtains 3.28g yellow crystal sprills.Productive rate is 85%.Directly carry out next step.
In the 100ml there-necked flask; add N; the pyrone intermediate 0.10g of N-two-phenyl barbituric acid, cholesterol intermediate (II) 0.55g, 20ml acetonitrile; drip several Piperazine anhydrous then; under the nitrogen protection condition, reflux 6 hours, reaction is finished postcooling to room temperature; filtering-depositing obtains the garnet pressed powder.Ethyl alcohol recrystallization obtains red powder shape solid 0.37g.Productive rate 58.0% ultimate analysis: C, 78.00; H, 9.15; N, 2.19; O, 10.66.
Embodiment 5
In 100ml single port flask, add 2,2 '-dimethyl pyrans ketone 1.24g, N, N-diethyl-thiobarbituricacid 2.0g; the 30ml diacetyl oxide, reflux is 5 hours under the nitrogen protection condition, and cooling is filtered; get yellow powder shape solid, ethyl alcohol recrystallization obtains 2.45g yellow crystal sprills.Productive rate is 80%.Be directly used in next step.
In the 100ml there-necked flask; add the pyrone intermediate 0.08g that contains barbituric acid; cholesterol intermediate (II) 0.55g; the 20ml acetonitrile drips several Piperazine anhydrous then, under the nitrogen protection condition; reflux 6 hours; reaction is finished postcooling to room temperature, and filtering-depositing obtains the garnet pressed powder.Ethanol-benzene mixed solvent recrystallization obtains red powder shape solid 0.33g.Productive rate 53.0% ultimate analysis: C, 76.65; H, 9.60; N, 2.07; O, 10.30; S, 1.38.
Embodiment 6
In 250ml single port flask, add N, ' N-two-propionyloxy aniline 1.0g, cholesterol 3.5g, 60ml tetrahydrofuran (THF), 1.85g dicyclohexyl carbon imide and 0.55g 4-dimethylamine pyridine, room temperature stirring overnight, rotation concentrates, and obtains white solid, adds 100ml methyl alcohol stirring at room, suction filtration obtains the thick product of white solid.Chloroform is done developping agent silica gel group chromatographic separation, obtains pure white powder solid 2.82g, productive rate 68%.
1H-NMR(400MHz，CDCl3，ppm)：δ1.01-2.57(m，90H)，3.68(t，4H)，4.6(t，2H)，5.4(d，2H)，6.72-6.9(d，3H)，7.27(d，2H)。
In the 250ml there-necked flask, add 2.03g and go up the synthetic intermediate that obtains of step, 40mlN, dinethylformamide, ice-water bath are cooled to 0-10 ℃, drip the 0.312g phosphorus oxychloride then, in 0.5 hour, drip off, remove ice-water bath, stirring at room 1 hour, reflux is 1 hour then, reduce to room temperature, mixture is poured in the frozen water, add salt of wormwood and regulate pH value about 10, separate out precipitation, filter, wash 3 times, oven dry, silica gel column chromatography separates (methyl alcohol: chloroform=1: 100), get white crystalline powder 0.82g.Productive rate 40.5%
1H-NMR(400MHz，CDCl
3，ppm)：δ1.03-2.70(m，90H)，3.75(t，4H)，4.6(m，2H)，5.37(d，2H)，6.7(d，2H)7.7(d，2H)，9.8(s，1H)。
In 100ml single port flask, add 2,2 '-dimethyl pyrans ketone 1.24g, N, N-di-t-butyl barbituric acid 2.4g; the 30ml diacetyl oxide, reflux is 5 hours under the nitrogen protection condition, and cooling is filtered; get yellow powder shape solid, ethyl alcohol recrystallization obtains 2.77g yellow crystal sprills.Productive rate is 80%.Be directly used in next step.
In the 100ml there-necked flask; add N; the pyrone intermediate 0.046g of N-di-t-butyl barbituric acid, cholesterol intermediate (II) 0.27g, 10ml acetonitrile; drip several Piperazine anhydrous then; under the nitrogen protection condition, reflux 6 hours, reaction is finished postcooling to room temperature; filtering-depositing obtains the garnet pressed powder.Ethyl alcohol recrystallization obtains red powder shape solid 0.126g.Productive rate 40.0% ultimate analysis: C, 79.68; H, 10.12; N, 2.00; O, 8.20.
Embodiment 7
In 100ml single port flask; add 2; 2 '-dimethyl pyrans ketone 1.24g, N, N-di-t-butyl-thiobarbituricacid 2.56g, 30ml diacetyl oxide; reflux is 5 hours under the nitrogen protection condition; cooling is filtered, and gets yellow powder shape solid; ethyl alcohol recrystallization obtains 2.93g yellow crystal sprills.Productive rate is 81%.Be directly used in next step reaction.
In the 100ml there-necked flask; add the pyrone intermediate 0.047g that contains barbituric acid; cholesterol intermediate (II) 0.27g; the 10ml acetonitrile drips several Piperazine anhydrous then, under the nitrogen protection condition; reflux 6 hours; reaction is finished postcooling to room temperature, and filtering-depositing obtains the garnet pressed powder.Ethanol-benzene mixed solvent recrystallization obtains red powder shape solid 0.14g.Productive rate 45.0% ultimate analysis: C, 78.85; H, 9.92; N, 2.49; O, 7.39; S, 1.35.
Embodiment 8
In 100ml single port flask; add 2,2 '-dimethyl pyrans ketone 1.24g, N; N-two-methyl-thiobarbituricacid 1.72g; the 30ml diacetyl oxide, reflux is 5 hours under the nitrogen protection condition, cooling; filter; get yellow powder shape solid, ethyl alcohol recrystallization obtains 2.22g yellow crystal sprills.Productive rate is 80%.Be directly used in next step reaction.
In the 100ml there-necked flask; add the pyrone intermediate 0.036g that contains barbituric acid; cholesterol intermediate (II) 0.27g; the 20ml acetonitrile drips several Piperazine anhydrous then, under the nitrogen protection condition; reflux 6 hours; reaction is finished postcooling to room temperature, and filtering-depositing obtains the garnet pressed powder.Ethanol-benzene mixed solvent recrystallization obtains red powder shape solid 0.152g.Productive rate 50.5%
Ultimate analysis: C, 78.78; H, 9.82; N, 2.34; O, 7.68; S, 1.38.
Claims (8)
1. one kind contains cholesteryl 2D-π-A type pyrans class charge transfer fluorescence dye, and its structure is shown in (I) formula:
In the formula (I), each R and R ' can be identical, also can be different.They are hydrogen, C
1～C
16Alkyl, C
1～C
16Alkoxyl group, C
5～C
20Cycloalkyl, aromatic ring yl or C
4～C
20A kind of in heterocyclic radical, halogen, hydroxyl, the sulfonic group; X is S, and O's is a kind of; Y is O, one kind of C or NH.
2. according to the described cholesteryl 2D-π-A type pyrans class charge transfer fluorescence dye that contains of claim 1, it is characterized in that: each R and R ' can be identical, also can be different, be hydrogen, C
1～C
6Alkyl, C
1～C
6Alkoxyl group, C
5～C
10Cycloalkyl, aromatic ring yl or C
4～C
10Heterocyclic radical; X is S, and O's is a kind of; Y is O, one kind of C.
3. according to the described cholesteryl 2D-π-A type pyrans class charge transfer fluorescence dye that contains of claim 2, it is characterized in that: each R is identical with R ', is hydrogen, C
1～C
6Alkyl, C
1～C
6Alkoxyl group, C
5～C
10Cycloalkyl, aromatic ring yl or C
4～C
10Heterocyclic radical; X is S, and O's is a kind of; The Y atom is O.
4. according to the described cholesteryl 2D-π-A type pyrans class charge transfer fluorescence dye that contains of claim 2, it is characterized in that: each R is identical with R ', is hydrogen, C
1～C
6Alkyl, C
1～C
6Alkoxyl group, C
5～C
10Cycloalkyl, aromatic ring yl or C
4～C
10Heterocyclic radical; X is S, and O's is a kind of; The Y atom is C.
5. according to the described cholesteryl 2D-π-A type pyrans class charge transfer fluorescence dye that contains of claim 3, it is characterized in that: each R is identical with R ', for hydrogen, methyl, methoxyl group, cyclohexyl, phenyl or ferrocenyl a kind of; X is O; The Y atom is O.
6. according to the described cholesteryl 2D-π-A type pyrans class charge transfer fluorescence dye that contains of claim 3, it is characterized in that: each R is identical with R ', for hydrogen, methyl, methoxyl group, cyclohexyl, phenyl or ferrocenyl a kind of; X is a kind of of S; The Y atom is O.
7. according to any described cholesteryl 2D-π-A type pyrans class charge transfer fluorescence dye that contains in the claim 1～6, it is characterized in that: this fluorescence dye has different fluorescent emission wavelength in different solvents.
8. synthetic method that contains cholesteryl 2D-π-A type pyrans class charge transfer fluorescence dye, it is characterized in that: with N, N-diethanolaniline, cholesterol acyl chlorides are raw material, through the synthetic key intermediate (II) of over-churning, Vilsmeier-Haack reaction or with aniline and vinylformic acid condensation, then with cholesterol generation esterification, the synthetic key intermediate of Vilsmeier-Haack reaction (II ') further takes place obtain target compound then with after the reaction such as pyrans class chromophoric group (III) condensation condensation; Comprise the steps:
A) N, N-diethanolaniline, cholesterol acyl chlorides are raw material, under the organic alkali catalyst condition, obtain compound shown in the intermediate 1 in the refluxing toluene reaction, the Vilsmeier-Haack reaction takes place then obtain key intermediate (II);
B) reaction of aniline and vinylformic acid obtains N, and N-two-propionyloxy aniline obtains key intermediate 2 with lentochol reaction then under catalyst action, Vilsmeier-Haack reaction takes place then obtain key intermediate (II ');
C) under pyrone and barbituric acid or the derivative nitrogen protection condition, diacetyl oxide is made solvent refluxing, obtains key intermediate (III);
D) key intermediate (II) or (II ') are placed acetonitrile with intermediate (III), under condition of nitrogen gas, back flow reaction at least 6 hours obtains target product;
Synthetic route is as follows:
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Application publication date: 20100811 |