CN102874785A - Method for preparing aggregation induced emission (AIE) group functionalized laminar zirconium phosphate material by ion exchange method - Google Patents
Method for preparing aggregation induced emission (AIE) group functionalized laminar zirconium phosphate material by ion exchange method Download PDFInfo
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Abstract
The invention belongs to the technical field of preparation of an inorganic and organic hybrid material with a fluorescence property and particularly relates to an ion exchange method for preparing an aggregation induced emission (AIE) group functionalized laminar zirconium phosphate material. Cation groups containing water-soluble AIE molecules are intercalated into the material by an ion exchange intercalation mode by using zirconium phosphate with a laminar structure as a framework element and organic amine as a pre-swelling agent, so that the inorganic and organic hybrid material with the strong fluorescence can be obtained. The method is suitable for various laminar zirconium phosphate materials which contain the AIE water soluble molecules of the cation groups and have the anion framework structures. The interlamellar spacing and the luminance of the zirconium phosphate can be effectively controlled by changing the varieties and the adding amounts of the AIE molecules or the pre-swelling agents, so that the material can be widely applied to the fields of medicine delivery, bioimaging, explosive detection and the like.
Description
Technical field
The invention belongs to the Inorganic-organic Hybrid Material preparing technical field with photoluminescent property, be specifically related to a kind of employing ion-exchange techniques and prepare the layered zirconium phosphate material of aggregation inducing luminophore (AIE) functionalization, make advantage that the material that obtains not only had an inorganic layer plate structure simultaneously but also have the special photoluminescent property of AIE molecule, thereby represented preferably application prospect in fields such as drug delivery, bio-imaging, explosive detection.
Technical background
Inorganic-organic Hybrid Material has been widely used in the fields such as catalysis, separation, organic and inorganic host-guest chemistry, functional materials as a kind of matrix material of novelty.Wherein the inorganic materials of organic fluorescence molecular modification has represented good character at aspects such as cell imaging, drug delivery, biological detection.But traditional fluorescence molecule such as rhodamine, fluorescein etc. have stronger fluorescence in dilute solution, and phenomenon (the aggregation caused quenching of fluorescent weakening even cancellation occurs at immobilization or when assembling, ACQ), this has limited the further application of this type of functional material to a certain extent.
Calendar year 2001 it is found that the special fluorescence molecule of a class, and it is not luminous when solution state, and when solid-state or state of aggregation, present stronger fluorescence, it is luminous (aggregation induced emission, the AIE) phenomenon of aggregation inducing (Chem.Commun.2001,1740).Wherein, Internal Rotations of Molecules is limited is the major cause that Enhancement of Fluorescence occurs.Since this quasi-molecule is in the news, represented preferably using value in fields such as detection, cell imaging and organic photoelectric diodes.
Zirconium phosphate (ZrP) and derivative thereof are the layered inorganic materials that a class has cation exchange capacity (CEC), have the advantages such as single, synthetic simply, the higher thermostability of composition and chemical stability, are the good matrixes of preparation Pillared Comepound.In previous work, our mode by rear grafting with the AIE molecule immobilized in the mesoporous SBA-15 material (Chem.Commun.2011,47,11077-11079; Chem.Commun.2012,48,7167-7169), make material represent preferably character aspect drug delivery and the explosive detection.At present synthetic about the pillared zirconium phosphate material of AIE molecule also do not have relevant report.
Summary of the invention
The object of the present invention is to provide a kind of synthetic method of simple and fast, namely prepare the layered zirconium phosphate material of AIE radical functino by the method for ion-exchange.It is to have the zirconium phosphate of laminate structure as the skeleton primitive, adopting organic amine is pre-support agent, the cation group that mode by the ion-exchange intercalation will contain water-soluble AIE molecule is inserted in the material, thereby obtains having the Inorganic-organic Hybrid Material than hyperfluorescenceCeng Yongminggaoyingguang.
The method is applicable to all kinds of AIE water soluble molecules of cation group and the layered zirconium phosphate materials with anion frame structure of containing.By changing the AIE molecule or supportting in advance the kind of agent and interlamellar spacing and the luminosities such as fluorescence color and intensity that add-on can be controlled zirconium phosphate effectively, make material in drug delivery, bio-imaging, the fields such as explosive detection have preferably application prospect.
The inventive method step is as follows:
(1) is dispersed in 10～20mL deionized water 0.4～1.0g ZrP is ultrasonic, then adds 0.07～0.3g organic amine, continue ultrasonic 0.3～1h; (rotating speed is 8000～11000rpm, and the time is repeatedly to wash solid product with deionized water after 15～30min), and then fully drying obtains the presoma of white in centrifugation;
(2) presoma that obtains of weighing 30～60mg step (1) ultrasonicly is distributed in 10～20mL deionized water it fully, obtains the suspension liquid of presoma; The water-soluble AIE molecule of 10～107mg is joined in 30～50mL deionized water, ultrasonic it is dissolved fully, then this solution is joined in the presoma suspension liquid, under 10～50 ℃ of conditions, fully mix 0.5～36h, obtain uniform faint yellow suspension liquid;
(3) centrifugal (rotating speed is 8000～11000rpm with the suspension liquid of step (2), time is 15～30min), and repeatedly wash solid product with deionized water, and do not participate in the AIE molecule of reaction with flush away, obtain the layered zirconium phosphate material of AIE radical functino after the drying.
Zirconium phosphate described in the above-mentioned steps is a kind of among α-ZrP, θ-ZrP, the γ-ZrP; Organic amine is a kind of in methylamine, propylamine, butylamine, Tetramethylammonium hydroxide, tetraethyl ammonium hydroxide, the TBAH.Water miscible AIE molecule is to have a kind of in the quaternary ammonium salt of following general structure, and wherein n is 2～5 integer.
As optimization experiment scope of the present invention, well-mixed mode be ultrasonic, stir, a kind of in the vibration.
The mode of first passage ion-exchange of the present invention prepares the layered zirconium phosphate material of AIE radical functino, and it has following advantage:
1. the ion exchange method of the present invention's proposition prepares the layered zirconium phosphate material of AIE radical functino, need not to use more expensive tensio-active agent to zirconium phosphate material pore-creating, such as cetyl trimethylammonium bromide, P123, F127 etc., and the synthetic method of raw material zirconium phosphate is simple, water dispersible good, Stability Analysis of Structures, the size and the interlamellar spacing that are easy to regulate material.
2. the ion exchange method that proposes of the present invention prepares the layered zirconium phosphate material of AIE radical functino, and the AIE molecule of employing is cheap, be easy to preparation, reduced production cost.
3. the ion exchange method of the present invention's proposition prepares the layered zirconium phosphate material of AIE radical functino, and working method is simple, and generated time is shorter, has reduced the process of removed template method.Be easy to simultaneously regulate amount and the kind of AIE molecule in the interposed layer, thereby change fluorescence intensity and the luminous peak position of matrix material.
Description of drawings:
Fig. 1: be the XRD spectra of the embodiment of the invention 1 raw material α-ZrP;
Fig. 2: be the scanning electron microscope picture of the embodiment of the invention 1 raw material α-ZrP;
Fig. 3: be the XRD spectra of α-ZrP material after the embodiment of the invention 1 butylamine reaming;
Fig. 4: be the scanning electron microscope picture of α-ZrP material after the embodiment of the invention 1 butylamine reaming;
Fig. 5: the XRD spectra of α-ZrP material behind the TPEN intercalation that obtains for the embodiment of the invention 1;
Fig. 6: the scanning electron microscope picture of α-ZrP material behind the TPEN intercalation that obtains for the embodiment of the invention 1;
Fig. 7: the transmission electron microscope picture of α-ZrP material behind the TPEN intercalation that obtains for the embodiment of the invention 1;
Fig. 8: the nitrogen adsorption desorption curve of α-ZrP material behind the TPEN intercalation that obtains for the embodiment of the invention 1;
Fig. 9: the α-fluorogram of ZrP material in the aqueous solution behind the TPEN intercalation that obtains for the embodiment of the invention 1.
Shown in Fig. 1,3,5: first peak position of raw material α-ZrP appears at 2 θ=11.6 °, shows that its interlamellar spacing is
When adopt butylamine pillared as pre-support agent after, first peak position appears at 2 θ=5.9 and ° shows that the interlamellar spacing of pillared rear material is about 1.5nm.After water miscible TPEN molecule inserted in the pillared material, first diffraction peak of finding material continued to move 2 θ=4.3 ° to Small angle, showed that the interlamellar spacing of α-ZrP material is extended to 2.1nm behind the TPEN intercalation.
Shown in Fig. 2,4,6: α-ZrP its pattern before and after intercalation remains unchanged substantially, is the sheet hexagonal structure still, shows that the intercalation process is to the not larger change of basic pattern of material.
As shown in Figure 7: the α of TPEN intercalation-ZrP material has obvious band shape duct, is about 2.1nm by measuring its interlamellar spacing, and the result that this and XRD obtain is basically identical.
As shown in Figure 8: show that by nitrogen adsorption desorption test the BET specific surface area of α-ZrP material is 51.9m behind the TPEN intercalation
2/ g.(deleting former figure nine)
As shown in Figure 9: after the α of TPEN intercalation-the ZrP material evenly spreads to the aqueous solution, under the 360nm ultraviolet excitation, at the 473nm place stronger fluorescence emission peak is arranged, show that the material behind the intercalation is launched blue light.This is because water miscible AIE molecule TPEN and α-ZrP have stronger ionic linkage effect, has suppressed the high speed rotating of TPEN molecule, thereby produces stronger fluorescence.
Embodiment
The present invention will be further described below by embodiment, but embodiments of the present invention are not limited to this, can not be interpreted as limiting the scope of the invention.
With synthetic α-ZrP(New J.Chem.2007,31,39-43) centrifugal, ultra-sonic dispersion repeatedly, fully washing to the pH value of its solution between 5～7, then lyophilize obtains the white solid powder, and is for subsequent use.
Embodiment 1:
With the about 400nm of 0.5g α-ZrP(particle diameter) ultra-sonic dispersion is in the 15mL deionized water, it fully is uniformly dispersed, then the butylamine that adds 0.07g, after continuing ultrasonic 0.5h, centrifugation (10000rpm, 20min), to neutral, obtain solid precursors α-ZrPBA with a large amount of deionized water wash after the lyophilize.
Weighing 50mg α-ZrPBA, ultrasonic evenly spreading in the 17mL aqueous solution; Then 57.6mgTPEN is added in the 33mL deionized water, ultrasonic it is dissolved fully.The aqueous solution of TPEN is added in the suspension liquid of α-ZrP presoma, continue under 40 ℃ of conditions to stir 24h, obtain uniform faint yellow suspension liquid.With supercentrifuge centrifugal (10000rpm, 20min), and repeatedly wash solid with a large amount of deionized waters, do not participate in the TPEN molecule of reaction with flush away, then lyophilize obtains the layered zirconium phosphate material of AIE radical functino, and quality is 55mg.
Embodiment 2:
α-ZrPBA among the weighing 35mg embodiment 1, ultra-sonic dispersion add the TPEN of 10mg in the 30mL deionized water in the 10mL aqueous solution, ultrasonic it are dissolved fully.The aqueous solution of TPEN is added in the suspension liquid of α-ZrPBA, continue under 40 ℃ of conditions to stir 24h, obtain uniform faint yellow suspension liquid.The TPEN molecule of reaction is not participated in centrifugation (10000rpm, 20min), and repeatedly wash solid with a large amount of deionized waters with flush away, then lyophilize obtains the layered zirconium phosphate material of AIE radical functino, and quality is 36mg.
Embodiment 3:
α-ZrPBA among the weighing 50mg embodiment 1, ultra-sonic dispersion add the TPEN of 90mg in the 33mL deionized water in the 17mL aqueous solution, ultrasonic it are dissolved fully.The aqueous solution of TPEN is added in the suspension liquid of α-ZrPBA, continue under 40 ℃ of conditions to stir 24h, obtain uniform faint yellow suspension liquid.The TPEN molecule of reaction is not participated in centrifugation (10000rpm, 20min), and repeatedly wash solid with a large amount of deionized waters with flush away, then lyophilize obtains the layered zirconium phosphate material of AIE radical functino, and quality is 56mg.
Embodiment 4:
α-ZrPBA among the weighing 50mg embodiment 1, ultra-sonic dispersion are in the 17mL aqueous solution, with the TPEO(n=2 of 62.4mg) add in the 33mL deionized water, ultrasonic it is dissolved fully.The aqueous solution of TPEO is added in the suspension liquid of α-ZrPBA, continue under 40 ℃ of conditions to stir 36h, obtain uniform faint yellow suspension liquid.The TPEO molecule of reaction is not participated in centrifugation (8000rpm, 30min), and repeatedly wash solid with a large amount of deionized waters with flush away, then lyophilize obtains the layered zirconium phosphate material of AIE radical functino, and quality is 52mg.
Embodiment 5:
400nm with 1g α-ZrP(particle diameter) ultra-sonic dispersion is in the 20mL deionized water, it is uniformly dispersed, then the butylamine that adds 0.3g, after continuing ultrasonic 0.5h, centrifugation (11000rpm, 15min), to neutral, obtain solid precursors α-ZrP2BA with a large amount of deionized water wash after the lyophilize.
Then weighing 60mg α-ZrP2BA, ultra-sonic dispersion add 107mg TPEN in the 50mL deionized water in the 10mL aqueous solution, ultrasonic it are dissolved fully.The aqueous solution of TPEN is added in the suspension liquid of α-ZrP2BA, continue under 10 ℃ of conditions to stir 24h, obtain uniform faint yellow suspension liquid.The TPEN molecule of reaction is not participated in centrifugation (11000rpm, 15min), and repeatedly wash solid with a large amount of deionized waters with flush away, then lyophilize obtains the layered zirconium phosphate material of AIE radical functino, and quality is 67mg.
Embodiment 6:
Then α-ZrP2BA among the weighing 50mg embodiment 5, ultra-sonic dispersion add 57.6mg TPEN in the 33mL deionized water in the 17mL aqueous solution, ultrasonic it are dissolved fully.The aqueous solution of TPEN is added in the suspension liquid of α-ZrP2BA, and room temperature continues ultrasonic 0.5h, obtains uniform faint yellow suspension liquid.The TPEN molecule of reaction is not participated in centrifugation (11000rpm, 15min), and repeatedly wash solid with a large amount of deionized waters with flush away, then lyophilize obtains the layered zirconium phosphate material of AIE radical functino, and quality is 52mg.
Embodiment 7:
150nm with 0.5g α-ZrP(particle diameter) ultra-sonic dispersion is in the 10mL deionized water, it fully is uniformly dispersed, then the butylamine that adds 0.14g, after continuing ultrasonic 0.3h, centrifugation (11000rpm, 20min), to neutral, obtain solid precursors nano-α-ZrPBA with a large amount of deionized water wash after the lyophilize.
Then weighing 50mg nano-α-ZrPBA, ultra-sonic dispersion add 14.4mgTPEN in the 30mL deionized water in the 20mL aqueous solution, ultrasonic it are dissolved fully.The aqueous solution of TPEN is added in the suspension liquid of nano-α-ZrPBA, continue under 50 ℃ of conditions to stir 24h, obtain uniform faint yellow suspension liquid.The TPEN molecule of reaction is not participated in centrifugation (11000rpm, 20min), and repeatedly wash solid with a large amount of deionized waters with flush away, then lyophilize obtains the layered zirconium phosphate material of AIE radical functino, and quality is 51mg.
Embodiment 8:
400nm with 0.4g α-ZrP(particle diameter) ultra-sonic dispersion is in the 10mL deionized water, it fully is uniformly dispersed, then the TBAH that adds 0.08g, after continuing ultrasonic 1h, centrifugation (8000rpm, 30min), to neutral, obtain solid precursors α-ZrPTBA with a large amount of deionized water wash after the lyophilize.
Weighing 30mg α-ZrPTBA, ultra-sonic dispersion is in the 10mL aqueous solution; Then 34.6mg TPEN is added in the 30mL deionized water, ultrasonic it is dissolved fully.The aqueous solution of TPEN is added in the suspension liquid of α-ZrPTBA, continue under 40 ℃ of conditions to stir 36h, obtain uniform faint yellow suspension liquid.With supercentrifuge centrifugal (8000rpm, 30min), and repeatedly wash solid with a large amount of deionized waters, do not participate in the TPEN molecule of reaction with flush away, then lyophilize obtains the layered zirconium phosphate material of AIE radical functino, and quality is 33mg.
Claims (5)
1. ion exchange method prepares the layered zirconium phosphate material of aggregation inducing luminous (AIE) radical functino, and its step is as follows:
(1) is dispersed in 10～20mL deionized water 0.4～1.0g ZrP is ultrasonic, then adds 0.07～0.3g organic amine, continue ultrasonic 0.3～1h; Repeatedly wash solid product with deionized water after the centrifugation, then fully drying obtains white presoma;
(2) presoma that obtains of weighing 30～60mg step (1) ultrasonicly is distributed in 10～20mL deionized water it fully, obtains the suspension liquid of presoma; The water-soluble AIE molecule of 10～107mg is joined in 30～50mL deionized water, ultrasonic it is dissolved fully, then this solution is joined in the presoma suspension liquid, under 10～50oC condition, fully mix 0.5～36h, obtain uniform faint yellow suspension liquid;
(3) suspension liquid of step (2) is centrifugal, and repeatedly wash solid product with deionized water, do not participate in the AIE molecule of reaction with flush away, obtain the layered zirconium phosphate material of AIE radical functino after the drying.
2. ion exchange method as claimed in claim 1 prepares the layered zirconium phosphate material of aggregation inducing luminophore functionalization, it is characterized in that: zirconium phosphate is a kind of among α-ZrP, θ-ZrP, the γ-ZrP.
3. ion exchange method as claimed in claim 1 prepares the layered zirconium phosphate material of aggregation inducing luminophore functionalization, it is characterized in that: organic amine is a kind of in methylamine, propylamine, butylamine, Tetramethylammonium hydroxide, tetraethyl ammonium hydroxide, the TBAH.
4. ion exchange method as claimed in claim 1 prepares the layered zirconium phosphate material of aggregation inducing luminophore functionalization, it is characterized in that: water miscible AIE molecule is to have a kind of in the quaternary ammonium salt of following general structure, and wherein n is 2～5 integer,
5. ion exchange method as claimed in claim 1 prepares the layered zirconium phosphate material of aggregation inducing luminophore functionalization, it is characterized in that: in the step (2) fully hybrid mode be ultrasonic, stir, a kind of in the vibration.
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