CN105440277B - Amphiphilic aggregation-induced emission molecule and its synthetic method and autofluorescence nano-micelle and application - Google Patents
Amphiphilic aggregation-induced emission molecule and its synthetic method and autofluorescence nano-micelle and application Download PDFInfo
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Abstract
The amphiphilic light emitting molecule with aggregation-induced emission characteristic, it is characterised in that:The chemical structural formula of the light emitting molecule is：Or；Wherein X, Z are 0~100 integer, the integer that Y is 5~500, R1And R2Group is any one in alkyl, naphthenic base, Heterocyclylalkyl, alkoxy, alkylamino and the halogenated alkyl of line style or ramiform.Synthetic method is：Under nitrogen atmosphere, by as the polyetheramine of start material and grafting agent heating reflux reaction, brown liquid product is obtained, through organic solvent washing, filtering, dry target product.Light emitting molecule is dissolved in water, forms autofluorescence nano-micelle.The invention also includes the applications of autofluorescence nano-micelle.Solve the problems, such as that the luminescent material in the prior art with aggregation-induced emission characteristic causes because of hydrophobicity and toxicity using limited.
Description
Technical field
The invention belongs to technical field of organic luminescence materials, and in particular to a kind of amphiphilic with aggregation-induced emission
（AIE）The light emitting molecule and its synthetic method and one kind of characteristic are provided by the present invention amphiphilic with aggregation-induced emission
（AIE）The autofluorescence nano-micelle and application that the light emitting molecule of characteristic is self-assembly of.
Background technology
Traditional fluorescent chromophore is mostly the rigid plane molecule with big pi-conjugated system, is had in weak solution very high
Fluorescence quantum yield, but fluorescent weakening does not shine even in the collected state, i.e. and aggregation results in fluorescent quenching
(aggregation caused quenching, ACQ)（Science, 1994, 265, 765; Nature, 1999,
397, 121）.In practical applications, fluorescent material generally requires that solid or form of film is made, and occurs between fluorescent molecular poly-
Collection is inevitable.Tang in 2001 and his co-workers report the aggregation-induced emission of a kind of " unconventional "
（aggregation-induced emission, AIE）Phenomenon：Some organic chromophores do not shine in solution state, but assemble
The fluorescent emission of molecule significantly increases afterwards or in solid-state（Chem. Commun., 2001,1740）.Chemical combination with AIE properties
Object, which fundamentally overcomes aggregation, leads to the problem of fluorescent quenching, causes extensive research interest, has been developed so far from indigo plant
Light covers the AIE systems of entire visible wavelength range to feux rouges, and is widely used in efficient luminescent device, biology
The various fields such as detection and chemical biosensor（Chem. Commun., 2009, 4332； Chem. Soc. Rev.,
2011, 40, 5361； Chem. Commun., 2011, 11273； J. Mater. Chem., 2012, 22, 8622；
Chem. Commun., 2013, 2491； Chem. Soc. Rev., 2014, Doi: 10.1039/c4cs00325j； J.
Am. Chem. Soc. 2013, 135, 4757； Nanoscale 2013, 5, 2065）.
However, the AIE systems being reported at present, organic molecule with pi-conjugated group and organic poly- is focused primarily upon
Close object（J. Mater. Chem. 2010, 20, 1858; Funct. Mater. 2013, 23, 2329; J. Am.
Chem. Soc. 2013, 135, 4757; J. Mater. Chem. 2012, 22, 18505）, for biologic applications
These contain molecules of big pi-conjugated group, and there are poorly water-solubles, have larger cytotoxicity, acute inflammation etc. is easily caused to lack
Fall into, this severely limits they biomedicine field application.Therefore, traditional fluorescent chromophore is not contained, to overcome altogether
The exploitation of the new AIE systems of these disadvantages of compound conjugate, becomes the task of top priority.
On the other hand, few to study and report amphiphilic AIE molecules.In structure, amphipathic molecule had usually both contained
There is hydrophobic structure unit to contain hydrophilic structural unit again.Therefore, in aqueous solution, amphipathic molecule can be formed by self assembly
Nano-micelle (J. Phys. Chem. A, 2005,109,10418) with hydrophobic core and hydrophilic shell structure.It is amphipathic and
The combination of AIE characteristics can generate a series of new fluorescent moleculars for chemistry and biologic applications aspect.
Invention content
The object of the present invention is to provide a kind of amphiphilic with aggregation-induced emission（AIE）The light emitting molecule of characteristic and its
Synthetic method and offer are a kind of provided by the present invention amphiphilic with aggregation-induced emission（AIE）The light emitting molecule of characteristic is certainly
The autofluorescence nano-micelle formed and application are assembled, the luminescent material in the prior art with aggregation-induced emission characteristic is solved
Cause because of hydrophobicity and toxicity using limited problem.
The technical proposal for solving the technical problem of the invention is：It is a kind of amphiphilic special with aggregation-induced emission
The light emitting molecule of property, the chemical structural formula of the light emitting molecule are：
Or；
Wherein X, Z are 0~100 integer, the integer that Y is 5~500, R1And R2Group is the alkane of line style or ramiform
Any one in base, naphthenic base, Heterocyclylalkyl, alkoxy, alkylamino and halogenated alkyl.
A kind of synthetic method of amphiphilic light emitting molecule with aggregation-induced emission characteristic of the present invention, including it is as follows
Step：Under nitrogen atmosphere, by as the polyetheramine of start material and grafting agent heating reflux reaction, the production of brown liquid is obtained
Object, product are dried after being cooled to room temperature through organic solvent washing, filtering, and finally obtained product is brown waxy solid or sugar
Pulpous state.
The synthetic method of a kind of amphiphilic light emitting molecule with aggregation-induced emission characteristic of the present invention, wherein described
The structural formula of start material polyetheramine be：
Or；
The integer that wherein X, Z are 0~100, the integer that Y is 5~500.
The synthetic method of a kind of amphiphilic light emitting molecule with aggregation-induced emission characteristic of the present invention, wherein described
Grafting agent be carboxylic acid, ester and acid anhydrides in any one.
The synthetic method of a kind of amphiphilic light emitting molecule with aggregation-induced emission characteristic of the present invention, wherein described
Organic solvent be ether, tetrahydrofuran and toluene in any one.
Autofluorescence prepared by a kind of light emitting molecule using amphiphilic with aggregation-induced emission characteristic of the present invention is received
Rice glue beam, preparation method are：The amphiphilic light emitting molecule with aggregation-induced emission characteristic is dissolved in water, forms water
The concentration of solution, the aqueous solution is at least up to critical micelle concentration, you can is self-assembly of autofluorescence nano-micelle；Described
The structural formula of the amphiphilic light emitting molecule with aggregation-induced emission characteristic is：
Or。
Autofluorescence prepared by a kind of light emitting molecule using amphiphilic with aggregation-induced emission characteristic of the present invention is received
Rice glue beam, wherein the light emitting molecule, in self assembling process, hydrophobic segment is dredged entrainment of amide groups in multiple hydrogen bonding and by force
It is automatically migrated to the inside of micella under water effect, forms the inner core of a strong-hydrophobicity, hydrophilic segment is contacted with water phase, shape
At autofluorescence nano-micelle.
Autofluorescence prepared by a kind of light emitting molecule using amphiphilic with aggregation-induced emission characteristic of the present invention is received
Rice glue beam contains only unconventional amide groups chromophore, but its wherein the light emitting molecule does not contain traditional conjugated chromophore
Micellar solution but has very strong blue emission, passes through the research to luminescence mechanism, it is proposed that the Internal Rotations of Molecules of hydrogen bond auxiliary
Limited mechanism.
Autofluorescence prepared by a kind of light emitting molecule using amphiphilic with aggregation-induced emission characteristic of the present invention is received
Rice glue beam was detected in the application in terms of biologic pharmacological science or the application in preparing fluorescence chemical sensor or in gene delivery
Application in journey or as pharmaceutical carrier and detect the application in drug release process or the application in cell imaging or
Prepare the application in fluorescence probe.
The amphiphilic light emitting molecule with aggregation-induced emission characteristic of the present invention, solid-state are preparing organic light emission two
Application in pole tube light-emitting layer material.
Implement the present invention amphiphilic aggregation-induced emission molecule and its synthetic method and autofluorescence nano-micelle and its
Using having the advantages that：The present invention's has aggregation-induced emission（AIE）The light emitting molecule of characteristic passes through to commercialization
Polyetheramine carry out graft modification be prepared, preparation method of the invention is simple for process, purifying be easy.The AIE light emitting molecules
Unconventional amide groups chromophore is contained only, this further opens up possible chemical constitution on the basis of original AIE systems
Zhan Liao.The light emitting molecule has amphipathic, and water-soluble, concentration in aqueous solution can be formed when being higher than its critical micelle concentration
Autofluorescence nano-micelle, micellar solution have very strong blue emission.By the research to luminescence mechanism, hydrogen bond auxiliary is proposed
Internal Rotations of Molecules it is limited（Hydrogen bonding aided RIR (restriction of intramolecular
rotations)）Mechanism, to Future Design synthesize this kind of fluorescent material have important directive significance.The luminescent material overcomes
Luminescent material containing traditional fluorescent chromophore has the shortcomings that hydrophobicity and highly toxic, especially suitable for biological medicine neck
The application in domain, can be used as autofluorescence probe for into the cell be imaged, it may also be used for monitoring hydrophobicity gene and drug transport with
Control release.The light emitting molecule has good luminosity in solid-state, can be used for preparing oled device.
Description of the drawings
Fig. 1 be 1-6 of the embodiment of the present invention in AFPEA-18, AFPEA-16, AFPEA-14, AFPEA-12, AFPEA-10,
The synthetic route chart of AFPEA-8 light emitting molecules；
Fig. 2 is light emitting molecule AFPEA-18, AFPEA-16, AFPEA-14, AFPEA- of 1-6 synthesis of the embodiment of the present invention
12, the measurement of AFPEA-10, AFPEA-8 critical micelle concentration；
Fig. 3 is the fluorescence emission spectrum of 2 g/L light emitting molecule AFPEA-16, AFPEA-12, AFPEA-8 aqueous solutions；
Fig. 4 is the TEM figures for the micella that amphipathic AFPEA-16 light emitting molecules are self-assembly of in 2 g/L aqueous solutions, is inserted
Figure is SEM figures；
Fig. 5 is the fluorescence emission spectrum of AFPEA-16 various concentration aqueous solutions, and illustration is light emitting molecule solution in ultraviolet light
Photo under irradiation.
Specific implementation mode
The chemical structural formula of the amphiphilic light emitting molecule with aggregation-induced emission characteristic of the present invention is：
Or；
Wherein X, Z are 0~100 integer, the integer that Y is 5~500, R1And R2Group is the alkane of line style or ramiform
Any one in base, naphthenic base, Heterocyclylalkyl, alkoxy, alkylamino and halogenated alkyl.
A kind of synthetic method of amphiphilic light emitting molecule with aggregation-induced emission characteristic of the present invention, including it is as follows
Step：Under nitrogen atmosphere, by as the polyetheramine of start material and grafting agent heating reflux reaction, the production of brown liquid is obtained
Object, product are dried after being cooled to room temperature through organic solvent washing, filtering, and finally obtained product is brown waxy solid or sugar
Pulpous state.
The synthetic method of a kind of amphiphilic light emitting molecule with aggregation-induced emission characteristic of the present invention, wherein reacting
The structural formula of starting material polyetheramine is：
Or；
The integer that wherein X, Z are 0~100, the integer that Y is 5~500.
The synthetic method of a kind of amphiphilic light emitting molecule with aggregation-induced emission characteristic of the present invention, wherein being grafted
Agent is any one in carboxylic acid, ester and acid anhydrides.
The synthetic method of a kind of amphiphilic light emitting molecule with aggregation-induced emission characteristic of the present invention, wherein organic
Solvent is any one in ether, tetrahydrofuran and toluene.
Autofluorescence prepared by a kind of light emitting molecule using amphiphilic with aggregation-induced emission characteristic of the present invention is received
Rice glue beam, preparation method are：The amphiphilic light emitting molecule with aggregation-induced emission characteristic is dissolved in water, forms aqueous solution,
The concentration of the aqueous solution is at least up to critical micelle concentration, you can is self-assembly of autofluorescence nano-micelle；Amphiphilic tool
There is the structural formula of the light emitting molecule of aggregation-induced emission characteristic to be：
Or。
Autofluorescence prepared by a kind of light emitting molecule using amphiphilic with aggregation-induced emission characteristic of the present invention is received
Rice glue beam, wherein the light emitting molecule, in self assembling process, hydrophobic segment is dredged entrainment of amide groups in multiple hydrogen bonding and by force
It is automatically migrated to the inside of micella under water effect, forms the inner core of a strong-hydrophobicity, hydrophilic segment is contacted with water phase, shape
At autofluorescence nano-micelle.
Autofluorescence prepared by a kind of light emitting molecule using amphiphilic with aggregation-induced emission characteristic of the present invention is received
Rice glue beam contains only unconventional amide groups chromophore, but its wherein the light emitting molecule does not contain traditional conjugated chromophore
Micellar solution but has very strong blue emission, passes through the research to luminescence mechanism, it is proposed that the Internal Rotations of Molecules of hydrogen bond auxiliary
Limited mechanism.
Autofluorescence prepared by a kind of light emitting molecule using amphiphilic with aggregation-induced emission characteristic of the present invention is received
Rice glue beam was detected in the application in terms of biologic pharmacological science or the application in preparing fluorescence chemical sensor or in gene delivery
Application in journey or as pharmaceutical carrier and detect the application in drug release process or the application in cell imaging or
Prepare the application in fluorescence probe.
The amphiphilic light emitting molecule with aggregation-induced emission characteristic of the present invention, solid-state are preparing organic light emission two
Application in pole tube light-emitting layer material.
With reference to the accompanying drawings and examples, to the present invention amphiphilic aggregation-induced emission molecule and its synthetic method and
Autofluorescence nano-micelle and application are further described：
New amphiphilic of the present invention has aggregation-induced emission（AIE）The specific building-up process of the light emitting molecule of characteristic is logical
Following examples are crossed to illustrate.It should be noted that the light emitting molecule synthesized below is only the structural formula protected in claim
Represented light emitting molecule it is several, but the light emitting molecule protected of the present invention is not limited to this.
Wherein embodiment 1-6 building-up processes synthetic route shown in Figure 1.
Embodiment 1：Synthesize AFPEA-18 light emitting molecules
Synthetic method：It weighs a certain amount of Jeffamine ED2003 and stearic acid is put into 50 mL three neck round bottom flask,
Jeffamine ED2003 are 1 with stearic molar ratio:2~1:2.2.Under nitrogen protection, magnetic agitation be heated to 160~
200 °C, react 4~8 h（The reaction time is detected by TLC）, stop heating, obtain brown liquid product.Product is cooled to
It through petroleum ether after room temperature, filters, dry, finally obtained product is brown waxy solid.With1H NMR are to product structure
It is characterized, it was demonstrated that product is compound AFPEA-18.1H NMR (500 MHz, CDCl3) δ 0.83 (t, 6H, J =
5.6 Hz), 1.04~1.12 (m, 21H), 1.20~1.23 (m, 56H), 1.56 (m, 4H), 2.09 (t, 4H,
J = 6.12 Hz), 3.59 (m, 170H)。
Embodiment 2：Synthesize AFPEA-16 light emitting molecules
Synthetic method：Similar to the synthetic method of embodiment 1, except that grafting agent is palmitic acid, product is brown
Waxy solid.With1H NMR characterize product structure, it was demonstrated that product is compound AFPEA-16. 1H NMR (500 MHz,
CDCl3) δ 0.88 (Hz of t, 6H, J=6.75), 1.09~1.18 (m, 21H), 1.25~1.28 (m, 48H),
1.61 (m, 4H), 2.14 (t, 4H, J = 8.45 Hz), 3.60~3.69 (m, 170H)。
Embodiment 3：Synthesize AFPEA-14 light emitting molecules
Synthetic method：Similar to the synthetic method of embodiment 1, except that grafting agent is myristic acid, product is palm fibre
Color waxy solid.With1H NMR characterize product structure, it was demonstrated that product is compound AFPEA-14. 1H NMR (500
MHz, CDCl3) δ 0.87 (t, 6H), 1.1~1.2 (m, 21H), 1.23~1.25 (m, 40H), 1.61 (m,
4H), 2.13 (t, 4H), 3.5~3.8 (m, 170H)。
Embodiment 4：Synthesize AFPEA-12 light emitting molecules
Synthetic method：Similar to the synthetic method of embodiment 1, except that grafting agent is lauric acid, product is brown
Waxy solid.With1H NMR characterize product structure, it was demonstrated that product is compound AFPEA-12. 1H NMR (500 MHz,
CDCl3) δ 0.88 (Hz of t, 6H, J=6.85), 1.11~1.18 (m, 21H), 1.26~1.28 (m, 32H),
1.61 (m, 4H), 2.15 (Hz of t, 4H, J=8.4), 3.60~3.73 (m, 170H).
Embodiment 5：Synthesize AFPEA-10 light emitting molecules
Synthetic method：Similar to the synthetic method of embodiment 1, except that grafting agent is capric acid, product is brown wax
Shape solid.With1H NMR characterize product structure, it was demonstrated that product is compound AFPEA-10. 1H NMR (500 MHz,
CDCl3) δ 0.87 (t, 6H), 1.1~1.2 (m, 21H), 1.20~1.32 (m, 24H), 1.60 (m, 4H),
2.15 (t, 4H), 3.51~3.65 (m, 170H).
Embodiment 6：Synthesize AFPEA-8 light emitting molecules
Synthetic method：Similar to the synthetic method of embodiment 1, except that grafting agent is caprylic acid, product is brown
Syrupy shape.With1H NMR characterize product structure, it was demonstrated that product is compound AFPEA-8. 1H NMR (500 MHz,
CDCl3) δ 0.89 (Hz of t, 6H, J=6.75), 1.11~1.18 (m, 21H), 1.27~1.29 (m, 16H),
1.61 (m, 4H), 2.14 (t, 4H, J = 8.7Hz), 3.64~3.77 (m, 170H)。
Elemental analysis is carried out to the light emitting molecule of embodiment 1-6 synthesis and carries out characterizing further confirmation by infrared spectrum
Its molecular structure, these light emitting molecules are soluble easily in water, highly basic, strong acid, methanol, ethyl alcohol, acetone, dichloromethane, tetrahydrofuran,
DMF and ethyl acetate.
To light emitting molecule AFPEA-18, AFPEA-16, AFPEA-14, AFPEA-12, AFPEA- of embodiment 1-6 synthesis
10, AFPEA-8 carries out amphiphilic Journal of Sex Research.As shown in Fig. 2, utilizing the critical micelle concentration of tensammetric determination light emitting molecule
(CMC)。
Fluorescence property research is carried out to the light emitting molecule that embodiment 2,4,6 synthesizes.The AFPEA- of a concentration of 2 g/L is taken respectively
16, the aqueous solution of AFPEA-12, AFPEA-8 light emitting molecule（The concentration of solution is above their CMC value）, at room temperature, survey
They fixed fluorescence emission spectrum.As shown in figure 3, there are one strong emission peaks at 435 nm for three kinds of light emitting molecules, and with
The increase of grafted chain length, fluorescence intensity increases.
Self assembly research is carried out to the light emitting molecule AFPEA-16 that embodiment 2 synthesizes.When amphiphilic light emitting molecule is in water
When concentration in solution is higher than critical micelle concentration, light emitting molecule can be self-assembly of nanometer spherical micella.As shown in figure 4, being
The aggregated structures of the amphipathic light emitting molecule AFPEA-16 observed by TEM technologies in aqueous solution.Nanosphere size is equal
One, average diameter is about 25 nm, and illustration is schemed for SEM.
Fluorescence property research is carried out to the light emitting molecule AFPEA-16 that embodiment 2 synthesizes.As shown in figure 5, working as the dense of solution
When degree is less than critical micelle concentration, fluorescence emission peak is barely perceivable in fluorescence spectrum, but when solution concentration is higher than critical
Strong fluorescence emission peak can be observed when micellar concentration at 435 nm, and with the increase of solution concentration, fluorescence intensity is notable
Increase, shows aggregation-induced emission（AIE）Property.Illustration is photo of the light emitting molecule solution under ultraviolet light irradiation, by
It is found that when solution concentration is higher than critical micelle concentration, the autofluorescence nano-micelle with blue ray radiation forms photo.
The light emitting molecule of embodiment 1-6 synthesis does not contain traditional conjugated chromophore, all contains only amide in the molecule
Base chromophore, but its micellar solution has very strong blue emission, passes through the research to luminescence mechanism, it is proposed that and hydrogen bond assists
Internal Rotations of Molecules it is limited（Hydrogen bonding aided RIR (restriction of intramolecular
rotations)）Mechanism.In the weak solution less than critical micelle concentration, light emitting molecule is deposited in the form of the single molecular chain stretched
Under the action of exciting energy, C-N singly-bounds are rotated, and lead to the conversion of non-radiative energy, therefore in weak solution not
It shines.When the concentration of solution is higher than critical micelle concentration, amphiphilic light emitting molecule can be by being self-assembly of micellar aggregates
Body.In light emitting molecule self assembling process, the hydrophobic segment at strand both ends entrainment of amide groups in the molecule with it is intermolecular
It is automatically migrated to the inside of micella under multiple hydrogen bonding and strong hydrophobic effect, forms the inner core of a strong-hydrophobicity, it is intermediate
Hydrophilic segment folding take cyclic configuration to be contacted with water phase, form with hydrophobic inner core and this core-shell structure copolymer knot of hydrophilic outer shell
The spherical micelle aggregation of structure.The multiple hydrogen bonding N-H ... O formed between intermolecular amide groups in the molecule is considerably increased
The rigidity of entire aggregate structure, makes the limited swivel of C-N singly-bounds, reduces the nonradiative decay processes of amide groups chromophore,
Improve fluorescence quantum yield.
In biologic pharmacological science application, the autofluorescence nano-micelle of nucleocapsid has preferable dispersibility in water phase,
It is expected to as autofluorescence probe for being imaged into the cell, it may also be used for the transport and control of monitoring hydrophobicity gene and drug are released
It puts.The light emitting molecule also has good luminosity in solid-state, can be used for preparing oled device.
It should be understood that for those of ordinary skills, it can be modified or changed according to the above description,
Within all these improvement or transformation should all belong to the protection domain of appended claims of the present invention.
Claims (3)
1. autofluorescence nano-micelle prepared by a kind of light emitting molecule using amphiphilic with aggregation-induced emission characteristic is in life
Application in terms of object medicine and pharmacology or in the application in preparing fluorescence chemical sensor or the application in gene delivery detection process
Or it as pharmaceutical carrier and is detecting the application in drug release process or the application in cell imaging or is being visited preparing fluorescence
Application in needle；The autofluorescence nanometre glue prepared using the amphiphilic light emitting molecule with aggregation-induced emission characteristic
The preparation method of beam is：The amphiphilic light emitting molecule with aggregation-induced emission characteristic is dissolved in water, is formed water-soluble
The concentration of liquid, the aqueous solution is at least up to critical micelle concentration, you can is self-assembly of autofluorescence nano-micelle；Described two
The structural formula of the light emitting molecule with aggregation-induced emission characteristic of parent's property is：
Or
, wherein X, Z is 0~100 integer, Y be 5~500 it is whole
Number, R1And R2Group is in alkyl, naphthenic base, Heterocyclylalkyl, alkoxy, alkylamino or the halogenated alkyl of line style or ramiform
Any one.
2. light emitting molecule according to claim 1 using amphiphilic with aggregation-induced emission characteristic prepare from glimmering
Light nano-micelle is examined in the application in terms of biologic pharmacological science or the application in preparing fluorescence chemical sensor or in gene delivery
Application during survey as pharmaceutical carrier and is detecting the application in drug release process or the application in cell imaging
Or the application in preparing fluorescence probe, the light emitting molecule is in self assembling process, and hydrophobic segment is entrainment of amide groups more
It is automatically migrated to the inside of micella under deuterium bond and strong hydrophobic effect, forms the inner core of a strong-hydrophobicity, hydrophilic chain
Section is contacted with water phase, forms autofluorescence nano-micelle.
3. light emitting molecule according to claim 1 using amphiphilic with aggregation-induced emission characteristic prepare from glimmering
Light nano-micelle is examined in the application in terms of biologic pharmacological science or the application in preparing fluorescence chemical sensor or in gene delivery
Application during survey as pharmaceutical carrier and is detecting the application in drug release process or the application in cell imaging
Or the application in preparing fluorescence probe, the light emitting molecule do not contain traditional conjugated chromophore, contain only unconventional acyl
Amido chromophore, but its micellar solution has very strong blue emission, passes through the research to luminescence mechanism, it is proposed that hydrogen bond is auxiliary
The mechanism that the Internal Rotations of Molecules helped is limited.
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