CN108794738A - Amphipathic light emitting molecule and preparation method with aggregation-induced emission characteristic - Google Patents
Amphipathic light emitting molecule and preparation method with aggregation-induced emission characteristic Download PDFInfo
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- CN108794738A CN108794738A CN201810706321.1A CN201810706321A CN108794738A CN 108794738 A CN108794738 A CN 108794738A CN 201810706321 A CN201810706321 A CN 201810706321A CN 108794738 A CN108794738 A CN 108794738A
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- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33396—Polymers modified by chemical after-treatment with organic compounds containing nitrogen having oxygen in addition to nitrogen
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterized by the type of post-polymerisation functionalisation
- C08G2650/04—End-capping
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- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/50—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing nitrogen, e.g. polyetheramines or Jeffamines(r)
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Abstract
The present invention discloses a kind of amphipathic light emitting molecule with aggregation-induced emission characteristic, and chemical structural formula is as follows：.Preparation method carries out in accordance with the following steps：Under nitrogen atmosphere, cetylamine is dissolved with solvent, then adds succinic anhydride, for temperature constant magnetic stirring to the reaction was complete, the molar ratio of the cetylamine and succinic anhydride is 1：1~2；After cooling plus water, suction filtration obtain white solid；Obtained white solid is placed in drying box and is dried overnight for 100 DEG C, light yellow solid is obtained；Obtained light yellow solid is mixed with Jeffamine polyetheramines, for magnetic agitation to the reaction was complete, the molar ratio of the Jeffamine polyetheramines and light yellow solid is 1：2-3；Reaction product is placed in drying box and is dried overnight for 100 DEG C, yellow-brown solid, i.e. target product are obtained.
Description
Technical field
The invention belongs to luminous organic material fields, more particularly to one kind having aggregation-induced emission characteristic（AIE）Two
Parent's property light emitting molecule and preparation method.
Background technology
Traditional fluorescent chromophore is mostly to have greatlyThe rigid plane molecule of conjugated system has very high in weak solution
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）.But in practical applications, fluorescent material generally requires that solid or form of film is made, and occurs between fluorescent molecular
Aggregation 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）.
Have however, the AIE systems that disclosure is reported at present focus primarily uponIt is conjugated the organic molecule of group and organic
Polymer（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 bigThere are poorly water-solubles for the molecule of conjugation group, have larger cytotoxicity, easily cause acute inflammation etc.
Defect seriously limits their applications in biomedicine field.On the other hand, at present about amphiphilic AIE molecules
Research and report.In structure, amphipathic light emitting molecule had usually not only contained hydrophobic structure unit but also had contained hydrophilic structural unit.
Therefore, in aqueous solution, amphipathic light emitting molecule can form the nanometer with hydrophobic core and hydrophilic shell structure by self assembly
Micella (J. Phys. Chem. A, 2005,109,10418).In terms of can be applied to chemistry and biology, however existing product
Seldom.
Invention content
The present invention is provided a kind of with aggregation-induced emission to solve the above-mentioned technical problem present in the prior art
The amphipathic light emitting molecule and preparation method of characteristic
Technical solution of the invention is：A kind of amphipathic light emitting molecule with aggregation-induced emission characteristic, feature exist
It is as follows in chemical structural formula：
。
A kind of preparation method of the above-mentioned amphipathic light emitting molecule with aggregation-induced emission characteristic, it is characterised in that successively
It carries out in accordance with the following steps：
A. under nitrogen atmosphere, cetylamine is dissolved with solvent, then adds succinic anhydride, temperature constant magnetic stirring to reaction
Completely, the molar ratio of the cetylamine and succinic anhydride is 1：1~2；
B. after cooling down plus water, suction filtration obtain white solid；
C. obtained white solid is placed in drying box and is dried overnight for 100 DEG C, obtain light yellow solid；
D. obtained light yellow solid is mixed with Jeffamine polyetheramines, magnetic agitation is described to the reaction was complete
The molar ratio of Jeffamine polyetheramines and light yellow solid is 1：2-3；
E. reaction product is placed in drying box and is dried overnight for 100 DEG C, obtain yellow-brown solid, i.e. target product.
The present invention provides a kind of with aggregation-induced emission（AIE）The amphipathic light emitting molecule of characteristic, contains only amide groups
Chromophore does not contain traditional conjugated chromophore, water-soluble.When concentration >=critical micelle concentration of aqueous solution, hydrophobic chain
Section is automatically migrated to the inside of micella entrainment of amide groups under multiple hydrogen bonding and strong hydrophobic effect, forms a strong-hydrophobicity
Inner core, hydrophilic segment contacts with water phase, forms the spherical autofluorescence nanometre glue with hydrophobic inner core and hydrophilic outer shell
Beam has very strong blue emission, can be widely applied to every field.Preparation method of the present invention is simple, and purifying is easy.
Description of the drawings
Fig. 1 is the measurement schematic diagram of light emitting molecule critical micelle concentration of the embodiment of the present invention.
Fig. 2 is the micella SEM figures that the amphipathic light emitting molecule of the embodiment of the present invention is self-assembly of in 2 g/L aqueous solutions.
Fig. 3 is the micella that the amphipathic light emitting molecule of the embodiment of the present invention is self-assembly of in 2 g/L aqueous solutions
TEM schemes.
Fig. 4 is the fluorescence emission spectrum of the amphipathic light emitting molecule various concentration aqueous solution of the embodiment of the present invention, and illustration is hair
Photo of the optical molecule solution under ultraviolet light irradiation.
Specific implementation mode
Embodiment 1：
The amphipathic light emitting molecule with aggregation-induced emission characteristic of the present invention, chemical structural formula are as follows：
。
Preparation method carries out in accordance with the following steps successively：
A. under nitrogen atmosphere, DMSO solvents are placed in flask bottle, cetylamine dissolving is added, adds until completely dissolved
Flask is put into temperature constant magnetic stirring heater by succinic anhydride, temperature constant magnetic stirring 4h, that is, ensureing the two, the reaction was complete, and ten
The molar ratio of hexamine and succinic anhydride is 1：1；It is whether complete that amidation process can be detected in reaction process with ehrlich reagent；
B. after cooling down plus water, suction filtration obtain white solid；
C. obtained white solid is placed in drying box and is dried overnight for 100 DEG C, obtain light yellow solid（Intermediate product）；
D. obtained light yellow solid is mixed with Jeffamine polyetheramines and is placed in flask, flask, which is put into constant temperature magnetic force, to be stirred
It mixes in heater, temperature constant magnetic stirring 4h, that is, ensureing the two, the reaction was complete（Amide can be detected in reaction process with ehrlich reagent
Whether complete change reaction）, the molar ratio of the Jeffamine polyetheramines and light yellow solid is 1：2；
Jeffamine polyetheramines have the following structure：
In formula, the integer that X, Z are 3, the integer that Y is 39；
E. reaction product is placed in drying box and is dried overnight for 100 DEG C, obtain yellow-brown solid, i.e. target product.
Reaction process structure change is as follows：
The critical micelle concentration of 1 light emitting molecule of the embodiment of the present invention（CMC）As shown in Figure 1.It will be seen from figure 1 that the present invention is real
The critical micelle concentration for applying example 1 is 0.5g/L.
Experiment：
1. taking the light emitting molecule aqueous solution of a concentration of 2 g/L embodiment of the present invention 1（The concentration of solution is higher than CMC value）, in room temperature
Under, SEM figures are measured respectively, and TEM figures are as a result as shown in Figure 2 and Figure 3 respectively.
It can be seen that from Fig. 2, Fig. 3：The light emitting molecule of the embodiment of the present invention 1 is when concentration of aqueous solution is higher than CMC value, molten
Nanometer spherical micella is formd in liquid, grain size is 40 ~ 60 nm.
2. the fluorescence emission spectrum of 1 amphipathic light emitting molecule various concentration aqueous solution of the embodiment of the present invention as shown in figure 4,
Illustration is photo of the light emitting molecule solution under ultraviolet light irradiation.
From fig. 4, it can be seen that when the concentration of solution is less than critical micelle concentration, it is barely perceivable in fluorescence spectrum
Fluorescence emission peak；But when solution concentration is higher than critical micelle concentration, strong fluorescent emission can be observed at 400 ~ 500 nm
Peak, and fluorescence intensity is dramatically increased with the increase of solution concentration, shows aggregation-induced emission（AIE）Property.Illustration
It is formed by photo it is found that when solution concentration is higher than critical micelle concentration for photo of the light emitting molecule solution under ultraviolet light irradiation
Autofluorescence nano-micelle with blue ray radiation.
Embodiment 2：
Preparation method carries out in accordance with the following steps successively：
A. under nitrogen atmosphere, DMSO solvents are placed in flask bottle, cetylamine dissolving is added, adds until completely dissolved
Flask is put into temperature constant magnetic stirring heater by succinic anhydride, temperature constant magnetic stirring 6h, that is, ensureing the two, the reaction was complete, and ten
The molar ratio of hexamine and succinic anhydride is 1：2；It is whether complete that amidation process can be detected in reaction process with ehrlich reagent；
B. after cooling down plus water, suction filtration obtain white solid；
C. obtained white solid is placed in drying box and is dried overnight for 100 DEG C, obtain light yellow solid（Intermediate product）；
D. obtained light yellow solid is mixed with Jeffamine polyetheramines and is placed in flask, flask, which is put into constant temperature magnetic force, to be stirred
It mixes in heater, temperature constant magnetic stirring 6h, that is, ensureing the two, the reaction was complete（Amide can be detected in reaction process with ehrlich reagent
Whether complete change reaction）, the molar ratio of the Jeffamine polyetheramines and light yellow solid is 1：3；
Jeffamine polyetheramines have the following structure：
In formula, the integer that X, Z are 3, the integer that Y is 39；
E. reaction product is placed in drying box and is dried overnight for 100 DEG C, obtain yellow-brown solid, i.e. target product.
Claims (2)
1. a kind of amphipathic light emitting molecule with aggregation-induced emission characteristic, it is characterised in that chemical structural formula is as follows：
。
2. a kind of preparation method of the amphipathic light emitting molecule with aggregation-induced emission characteristic as described in claim 1, special
Sign is to carry out in accordance with the following steps successively：
A. under nitrogen atmosphere, cetylamine is dissolved with solvent, then adds succinic anhydride, temperature constant magnetic stirring to reaction
Completely, the molar ratio of the cetylamine and succinic anhydride is 1：1~2；
B. after cooling down plus water, suction filtration obtain white solid；
C. obtained white solid is placed in drying box and is dried overnight for 100 DEG C, obtain light yellow solid；
D. obtained light yellow solid is mixed with Jeffamine polyetheramines, magnetic agitation is described to the reaction was complete
The molar ratio of Jeffamine polyetheramines and light yellow solid is 1：2-3；
E. reaction product is placed in drying box and is dried overnight for 100 DEG C, obtain yellow-brown solid, i.e. target product.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110003460A (en) * | 2019-03-26 | 2019-07-12 | 辽宁师范大学 | Amphipathic light emitting molecule and preparation method with aggregation-induced emission characteristic |
| CN115819757A (en) * | 2022-09-27 | 2023-03-21 | 辽宁师范大学 | Atypical luminous compound containing amido and its synthesis method |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105400510A (en) * | 2015-12-15 | 2016-03-16 | 辽宁师范大学 | Self-fluorescent silica microsphere material and preparation method and application thereof |
| CN105440277A (en) * | 2015-11-27 | 2016-03-30 | 辽宁师范大学 | Amphipathic AIE (aggregation-induced emission) molecule, synthetic method thereof, autofluorescence nano-micelle and application |
-
2018
- 2018-07-02 CN CN201810706321.1A patent/CN108794738A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105440277A (en) * | 2015-11-27 | 2016-03-30 | 辽宁师范大学 | Amphipathic AIE (aggregation-induced emission) molecule, synthetic method thereof, autofluorescence nano-micelle and application |
| CN105400510A (en) * | 2015-12-15 | 2016-03-16 | 辽宁师范大学 | Self-fluorescent silica microsphere material and preparation method and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| JUN-ICHI KIKUCHI ET AL.: "Cerasomes: A New Family of Artificial Cell Membranes with Ceramic Surface", 《ADVANCES IN BIOMIMETICS》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110003460A (en) * | 2019-03-26 | 2019-07-12 | 辽宁师范大学 | Amphipathic light emitting molecule and preparation method with aggregation-induced emission characteristic |
| CN115819757A (en) * | 2022-09-27 | 2023-03-21 | 辽宁师范大学 | Atypical luminous compound containing amido and its synthesis method |
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