CN104804739A - Preparation method of POSS (polyhedral oligomeric silsesquioxane) modified up-conversion nanocrystalline - Google Patents
Preparation method of POSS (polyhedral oligomeric silsesquioxane) modified up-conversion nanocrystalline Download PDFInfo
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Abstract
The invention relates to a preparation method of POSS (polyhedral oligomeric silsesquioxane) modified luminescent rare earth up-conversion nanocrystalline. The preparation method comprises steps as follows: firstly, the rare earth up-conversion nanocrystalline doped with different rare earth ions is synthesized in oleic acid and octadecene; secondly, double bonds on the oleic acid on the surface of the nanocrystalline are oxidized by 3-chloroperoxybenzoic acid; finally, POSS is combined with the oleic acid through a ring-opening addition reaction so as to be grafted to the surface of the up-conversion nanocrystalline; the POSS modified up-conversion nanocrystalline with water solubility is obtained through centrifugal washing. The method has the advantages of simple process, convenience in operation and easiness in structure control; the nano fluorescent material has the advantages of uniform size, good monodispersity, good biocompatibility and multi-mode imaging such as fluorescence imaging, magnetic resonance imaging and the like, and can be used in the bio-medical fields such as different modes of imaging and the like.
Description
Technical field
The invention belongs to nano meter biomaterial technical field, be specifically related to the preparation method of the up-conversion luminescence nanometer crystal of a kind of polyhedral oligomeric silsesquioxane (POSS) modification.
Background technology
In the last few years, Medical Imaging Technology as fluorescence imaging, nuclear magnetic resonance, CT imaging etc., clinical medicine detect in obtain great development, this be due to its have highly sensitive, from cell to advantages such as biological tissue's not damaged observations.And the use of contrast medium is absolutely necessary in these image technologies, especially in enhancing scanning.This is because contrast medium can have the effect of enhancing signal to these image technologies, thus cause the density difference of pathological tissues and healthy tissues, allow focus " be completely exposed ".
And in numerous contrast medium, rear-earth-doped up-conversion luminescence nanomaterial causes the extensive concern of people as a kind of potential emerging radiography material, this is because it can not only realize fluorescence imaging, can also by comprehensive to nuclear magnetic resonance, CT imaging etc. in single nano material, thus realize more " material is multiplex ", more accurately can not only locate focus like this, Multifunctional imaging imaging can also be realized.
Although rear-earth-doped up-conversion luminescence nanomaterial has numerous imaging applications, this nano material overwhelming majority obtained under existing synthetic method at present is but oil loving, is unfavorable for the application in organism.So make rear-earth-doped up-conversion luminescence nanomaterial have good wetting ability and Bc by certain modification, to its application organism by significant.Water-soluble modified method at present to such nano material, major part is that polymer modification or mesoporous silicon are coated.Although polymer modification obtains good wetting ability and biocompatibility, nanoparticle is easy to reunite and mr relaxation value is lower.The usual synthesis step of mesoporous silicon method for coating is loaded down with trivial details, and easily introduces the template having certain toxicity, and fluorescence intensity has certain cancellation.Therefore the method for modifying developing new up-conversion luminescence nanometer crystal is extremely important, resulting materials is made to have excellent hydrophilic and biocompatibility, high mr relaxation value, the more important thing is and want synthetic method simply, easily to operate, and nanoparticle can not be caused to reunite and affect luminescent properties.
Summary of the invention
For the deficiency of traditional method of modifying, the object of the present invention is to provide the preparation method with water miscible up-conversion luminescence nanometer crystal of a kind of polyhedral oligomeric silsesquioxane (POSS) modification, obtain the luminescence nanocrystalline of biocompatibility and the application of multi-mode bio-imaging.For achieving the above object, technical scheme provided by the present invention is:
It comprises the following steps:
(1) in oleic acid, octadecylene, on synthesizing rare-earth, conversion nano is brilliant, is then dispersed in hexanaphthene and forms the first dispersion liquid;
(2) joined by the first dispersion liquid 2 ~ 5 mL containing in 5 ~ 10 mg 3-chloroperoxybenzoic acid dichloromethane solutions, above-mentioned mixed solution reacts 3 h at 40 ° of C, is cooled by mixture, obtain the second dispersion liquid after reaction terminates;
(4) in the second dispersion liquid, add 10 ~ 20 mg polyhedral oligomeric silsesquioxane (POSS, C
24h
72n
8o
12si
8), react for some time under room temperature, by centrifugal for gained mixture after reaction terminates, deionized water wash for several times, finally be dispersed in water formation the 3rd dispersion liquid, obtain the up-conversion luminescence nanometer crystal of polyhedral oligomeric silsesquioxane (POSS) modification.
Beneficial effect of the present invention is: the synthetic method of proposition is simple, repeatability is high, and what obtain nanocrystallinely has well water-soluble and biocompatibility.The feature of the inventive method is the up-conversion luminescence nanometer crystal utilizing oligomeric silsesquioxane (POSS) modification, obtain the nano material with multi-modal imaging function, compared to conversion luminescent material traditionally, this nano material has a lot of outstanding advantage: (1) building-up process is simple, repeatability is high; (3) nano material obtained monodispersity, Bc in water is fine; (3) there is the multi-modal imaging such as fluorescence imaging, nuclear magnetic resonance, be expected to be applied to clinical diagnose and targeting diagnosis.
The inventive method specifically a kind of polyhedral oligomeric silsesquioxane (POSS) modification there is the nanocrystalline preparation method of Water-soluble up-conversion luminescence.First, in oleic acid, octadecylene, on synthesizing rare-earth, conversion nano is brilliant; Then at its surperficial continued growth one deck NaGdF
4; Secondly, by 3-chloroperoxybenzoic acid, the double bond on nanocrystal surface oleic acid is oxidized; Finally, polyhedral oligomeric silsesquioxane (POSS) is combined with oleic acid by opening, thus grafting is to the brilliant surface of upper conversion nano; Namely mixture obtains the up-conversion luminescence nanometer crystal of polyhedral oligomeric silsesquioxane (POSS) modification by centrifuge washing.The inventive method has that technique is simple, easy to operate, the advantage of easy control of structure.This nano-luminescent material not only size uniformity, monodispersity is good, Bc is good, and has the advantage such as fluorescence imaging, nuclear magnetic resonance multi-modal imaging, can be used for the biomedical sectors such as the imaging under different mode.
Accompanying drawing explanation
Fig. 1 is that the embodiment of the present invention 1 synthesizes schematic diagram;
Fig. 2 is the TEM photo of the embodiment of the present invention 1 gained sample;
Fig. 3 is the XRD figure of the embodiment of the present invention 1 gained sample; (UCNPs is Upconversion nanoparticles english abbreviation, and the Chinese meaning is upper conversion nano crystalline substance.）
Fig. 4 is the XPS figure of the embodiment of the present invention 1 gained sample;
Fig. 5 is the up-conversion fluorescence spectrogram of the embodiment of the present invention 1 gained sample;
Fig. 6 is the up-conversion fluorescence spectrogram of the embodiment of the present invention 2 gained sample.
Embodiment
Below in conjunction with drawings and Examples, the present invention is described in detail:
embodiment 1:
The present embodiment provides the Er ions of polyhedral oligomeric silsesquioxane (POSS) modification to have the synthesis of the up-conversion luminescence nanometer crystal of nucleocapsid structure, and it comprises the following steps:
(1) preparing 10 ~ 15 mg particle diameters is 30 ~ 35 nm lipophilicity NaYF
4: Yb, ErNaGdF
4be dispersed in hexanaphthene, obtain the first dispersion liquid; Preparation 5 ~ 10 mg 3-chloroperoxybenzoic acids are dispersed in methylene dichloride and form the first mixed solution.
(2) by the first dispersion liquid, the first mixed solution mixed solution, be warming up to 40 ° of C and react 3 h, reaction terminates rear cooling and obtains the second dispersion liquid.
(3) by 10 ~ 20 mg polyhedral oligomeric silsesquioxane (POSS, C
24h
72n
8o
12si
8) join in the second dispersion liquid, react 5 h.Centrifugal for gained mixed solution, washing are finally dispersed in water, obtain the 3rd dispersion liquid, i.e. the Er ions of polyhedral oligomeric silsesquioxane (POSS) modification has the up-conversion luminescence nanometer crystal of nucleocapsid structure.
embodiment 2:
The present embodiment provides the doping of the thulium of polyhedral oligomeric silsesquioxane (POSS) modification to have the synthesis of the up-conversion luminescence nanometer crystal of nucleocapsid structure, and it comprises the following steps:
(1) preparing 10 ~ 15 mg particle diameters is 30 ~ 35 nm lipophilicity NaYF
4: Yb, TmNaGdF
4be dispersed in hexanaphthene, obtain the first dispersion liquid; Preparation 5 ~ 10 mg 3-chloroperoxybenzoic acids are dispersed in methylene dichloride and form the first mixed solution.
(2) the first dispersion liquid, the first mixed solution mixed solution are warming up to 40 ° of C and react 3 h, reaction terminates rear cooling and obtains the 3rd mixed solution.
(3) by 10 ~ 20 mg polyhedral oligomeric silsesquioxane (POSS, C
24h
72n
8o
12si
8) join in the second dispersion liquid, react 5 h.Centrifugal for gained mixed solution, washing are finally dispersed in water, obtain the 3rd dispersion liquid, i.e. the thulium doping of polyhedral oligomeric silsesquioxane (POSS) modification has nucleocapsid structure up-conversion luminescence nanometer crystal.
embodiment 3:
The present embodiment provides the synthesis of the up-conversion luminescence nanometer crystal of the Er ions of polyhedral oligomeric silsesquioxane (POSS) modification, and it comprises the following steps:
(1) preparing 10 ~ 15 mg particle diameters is 30 ~ 35 nm lipophilicity NaYF
4: Yb, Er are dispersed in hexanaphthene, obtain the first dispersion liquid; Preparation 5 ~ 10 mg 3-chloroperoxybenzoic acids are dispersed in methylene dichloride and form the first mixed solution.
(2) the first dispersion liquid, the first mixed solution mixed solution are warming up to 40 ° of C and react 3 h, reaction terminates rear cooling and obtains the 3rd mixed solution.
(3) by 10 ~ 20 mg polyhedral oligomeric silsesquioxane (POSS, C
24h
72n
8o
12si
8) join in the second dispersion liquid, react 5 h.Centrifugal for gained mixed solution, washing are finally dispersed in water, obtain the 3rd dispersion liquid, i.e. the up-conversion luminescence nanometer crystal of the Er ions of polyhedral oligomeric silsesquioxane (POSS) modification.
embodiment 4:
The synthesis of the up-conversion luminescence nanometer crystal that the present embodiment provides the thulium of polyhedral oligomeric silsesquioxane (POSS) modification to adulterate, it comprises the following steps:
(1) preparing 10 ~ 15 mg particle diameters is 30 ~ 35 nm lipophilicity NaYF
4: Yb, Tm are dispersed in hexanaphthene, obtain the first dispersion liquid; Preparation 5 ~ 10 mg 3-chloroperoxybenzoic acids are dispersed in methylene dichloride and form the first mixed solution.
(2) the first dispersion liquid, the first mixed solution mixed solution are warming up to 40 ° of C and react 3 h, reaction terminates rear cooling and obtains the 3rd mixed solution.
(3) by 10 ~ 20 mg polyhedral oligomeric silsesquioxane (POSS, C
24h
72n
8o
12si
8) join in the second dispersion liquid, react 5 h.Centrifugal for gained mixed solution, washing are finally dispersed in water, obtain the 3rd dispersion liquid, be i.e. the up-conversion luminescence nanometer crystal of the thulium doping of polyhedral oligomeric silsesquioxane (POSS) modification.
embodiment 5:
The present embodiment provides the synthesis of the erbium of polyhedral oligomeric silsesquioxane (POSS) modification, the up-conversion luminescence nanometer crystal of thulium codoped, and it comprises the following steps:
(1) preparing 10 ~ 15 mg particle diameters is 30 ~ 35 nm lipophilicity NaYF
4: Yb, Er, Tm are dispersed in hexanaphthene, obtain the first dispersion liquid; Preparation 5 ~ 10 mg 3-chloroperoxybenzoic acids are dispersed in methylene dichloride and form the first mixed solution.
(2) the first dispersion liquid, the first mixed solution mixed solution are warming up to 40 ° of C and react 3 h, reaction terminates rear cooling and obtains the 3rd mixed solution.
(3) by 10 ~ 20 mg polyhedral oligomeric silsesquioxane (POSS, C
24h
72n
8o
12si
8) join in the second dispersion liquid, react 5 h.Centrifugal for gained mixed solution, washing are finally dispersed in water, obtain the 3rd dispersion liquid, i.e. the erbium of polyhedral oligomeric silsesquioxane (POSS) modification, the up-conversion luminescence nanometer crystal of thulium codoped.
Can be found out by Fig. 1 to Fig. 6:
Fig. 1 is that the embodiment of the present invention 1 synthesizes schematic diagram, and the grafting of polyhedral oligomeric silsesquioxane (POSS) covalency is on the brilliant surface of the upper conversion nano of Coated with Oleic Acid as can be seen from Figure.
Fig. 2 is the TEM photo that the Er ions of the embodiment of the present invention 1 gained polyhedral oligomeric silsesquioxane (POSS) modification has the up-conversion luminescence nanometer crystal of nucleocapsid structure, as can be seen from the figure modified nano particle diameter is evenly distributed, and very well dispersed.Illustrate that this method of modifying can obtain the up-conversion nano material that pattern is good, dispersing property is good, and modified nano material median size is about 30-35 nm, because spherical, small size nanoparticle is more easily by cell endocytic, this is used as bioprobe for it and circulates significant in vivo.
Fig. 3 is the XRD figure that the Er ions of the embodiment of the present invention 1 gained polyhedral oligomeric silsesquioxane (POSS) modification has the up-conversion luminescence nanometer crystal of nucleocapsid structure, modified nanoparticle and standard NaYF as seen from the figure
4card is more still six side's phase structures.Having there is the diffraction peak of POSS 20-40 ° of position in what is more important, thus proves that POSS success grafting is on the brilliant surface of upper conversion nano.
The Er ions of Fig. 4 to be the embodiment of the present invention 1 gained sample be polyhedral oligomeric silsesquioxane (POSS) modification has the XPS figure of the up-conversion luminescence nanometer crystal of nucleocapsid structure, from the known resulting materials of figure, there is F, Yb, Er, Y, Gd, Si element, the existence of Si element simultaneously demonstrates POSS success grafting more on the brilliant surface of upper conversion nano.
The Er ions of Fig. 5 to be the embodiment of the present invention 1 gained sample be polyhedral oligomeric silsesquioxane (POSS) modification has the fluorescence spectrum figure of up-conversion luminescence nanometer crystal under 980 nm laser excitations of nucleocapsid structure, be positioned at the emission peak at 550 and 660 nm places as can be observed from Figure, correspond respectively to Er
3+'s
2h
11/2→
4i
15/2,
4s
3/2→
4i
15/2, and
4f
9/2→
4i
15/2the transition of energy level, and still have stronger emissive porwer, shows that the modified up-conversion nano material of polyhedral oligomeric silsesquioxane (POSS) still keeps good up-conversion fluorescence performance, is very suitable for organism fluorescence imaging.
Fig. 6 is that the thulium doping of the embodiment of the present invention 2 polyhedral oligomeric silsesquioxane (POSS) modification has the fluorescence spectrum figure of up-conversion luminescence nanometer crystal under 980 nm laser excitations of nucleocapsid structure, the strong emission peak being positioned at 800 nm can be observed, corresponding to Tm from figure
3+'s
3h
4→
3h
6the transition of energy level, and 800 nm are positioned at " optical window " of biological tissue, show that the up-conversion nano material after POSS functionalization still keeps good fluorescence property, is very suitable for small animal imaging.
According to preparation method provided by the present invention, not only size is little for the product obtained, Stability Analysis of Structures, and has the advantages such as multi-modal imaging simultaneously, and particularly gained nano material can be applicable to cell imaging, nuclear magnetic resonance and animalcule in-vivo imaging.And this its surface can functionalization further, can be applicable to the transport of targeting diagnosis and targeted drug.
The inventive method has simple, the easy to operate advantage of technique, the preparation method with water miscible up-conversion luminescence nanometer crystal of specifically a kind of polyhedral oligomeric silsesquioxane (POSS) modification.First, the rare earth NaYF of synthesizing blender different rare earth ions in oleic acid, octadecylene
4in matrix, conversion nano is brilliant; Secondly, by 3-chloroperoxybenzoic acid, the double bond on nanocrystal surface oleic acid is oxidized; Finally, polyhedral oligomeric silsesquioxane (POSS) to be combined with oleic acid by opening thus grafting to the brilliant surface of upper conversion nano; By centrifuge washing, namely obtain the up-conversion luminescence nanometer crystal of polyhedral oligomeric silsesquioxane (POSS) modification.The inventive method has that technique is simple, easy to operate, the advantage of easy control of structure.This nano-luminescent material not only size uniformity, monodispersity is good, Bc is good, and has the advantage of the multi-modal imaging such as fluorescence imaging, nuclear magnetic resonance, can be used for the biomedical sectors such as the imaging under different mode.
As described in the above embodiment the present invention, adopt from its same or similar method obtain the modified different up-conversion luminescence nanometer crystals of polyhedral oligomeric silsesquioxane (POSS) all in scope.
Claims (2)
1. the preparation method of the upper conversion nano crystalline substance of polyhedral oligomeric silsesquioxane modification, is characterized in that the method comprises following technological process:
The brilliant NaYF of conversion nano in synthesis in high boiling solvent oleic acid, octadecylene
4: Yb, ErNaGdF
4, or NaYF
4: Yb, TmNaGdF
4or NaYF
4: Yb, Er, TmNaGdF
4, be dispersed in hexanaphthene, form the first dispersion liquid; Secondly, by 3-chloroperoxybenzoic acid by the double bond oxidation on nanocrystal surface oleic acid, the second dispersion liquid is obtained; Finally, polyhedral oligomeric silsesquioxane is combined with oleic acid by opening, thus grafting is to the brilliant surface of upper conversion nano, what namely obtain polyhedral oligomeric silsesquioxane modification by centrifugal, washing has water miscible up-conversion luminescence nanometer crystal, products therefrom is dispersed in water, obtains the 3rd dispersion liquid.
2. the preparation method of the upper conversion nano crystalline substance of polyhedral oligomeric silsesquioxane modification according to claim 1, is characterized in that the preparation of the 3rd dispersion liquid specifically comprises the following steps:
(1) preparing 10 ~ 15 mg particle diameters is the brilliant NaYF of conversion nano in 30 ~ 35 nm lipophilicities
4be dispersed in hexanaphthene, obtain the first dispersion liquid;
(2) prepare the 3-chloroperoxybenzoic acid of 5 ~ 10 mg, be dispersed in methylene dichloride and form the first mixed solution;
(3) by the first dispersion liquid and the mixing of the first mixed solution, be warming up to 40 ° of C, react 3 h, reaction terminates rear cooling, obtains the second dispersion liquid;
(4) 10 ~ 20 mg polyhedral oligomeric silsesquioxanes are joined in the second dispersion liquid, react 5 h, by centrifugal for gained mixed solution, wash and be dispersed in water, obtain the 3rd dispersion liquid, namely polyhedral oligomeric silsesquioxane modification to have water miscible upper conversion nano brilliant.
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2015
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Application publication date: 20150729 |