CN103666476A - Microwave-assisted synthesis method of macromolecular polydentate ligand CdTe quantum dots - Google Patents

Microwave-assisted synthesis method of macromolecular polydentate ligand CdTe quantum dots Download PDF

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CN103666476A
CN103666476A CN201310550031.XA CN201310550031A CN103666476A CN 103666476 A CN103666476 A CN 103666476A CN 201310550031 A CN201310550031 A CN 201310550031A CN 103666476 A CN103666476 A CN 103666476A
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cadmium
microwave
cdte
solution
cdte quantum
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汪联辉
宇文力辉
薛冰
徐菲
张琦
张磊
翁丽星
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Southeast University
Nanjing University of Posts and Telecommunications
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Nanjing University of Posts and Telecommunications
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Abstract

A microwave-assisted synthesis method of a macromolecular polydentate ligand CdTe quantum dot comprises a method for synthesizing sulfydryl modified polyacrylic acid molecules, taking the macromolecules as ligands, and preparing the CdTe quantum dot in an aqueous phase through microwave-assisted heating. The invention uses cyclodihexylcarbodiimide as a condensing agent to connect mercaptoamine to a polyacrylic acid side chain in N, N' -dimethylformamide. Mixing sulfhydrylated polyacrylic acid and cadmium salt or cadmium oxide in water to obtain a cadmium source solution of the macromolecular polydentate ligand. And injecting a potassium telluride hydride or sodium telluride hydride solution into the cadmium source to obtain a CdTe precursor solution. CdTe quantum dots with various luminous wavelengths are prepared by microwave heating. The CdTe quantum dots prepared by the method have uniform particle size, good dispersibility, high fluorescence quantum yield and good biocompatibility, and can be stably stored for a long time. The method is suitable for labeling and imaging in organisms with high requirements on stability and biocompatibility.

Description

A kind of microwave assisted synthesizing method of macromole polydentate ligand CdTe quantum dot
Technical field
The present invention relates to a kind of microwave assisted synthesizing method of macromole polydentate ligand CdTe quantum dot, belong to nano material and synthesize and bioanalysis detection technique field.
Background technology
The semiconductor material that size is less than its bohr exciton radius presents the photoelectric properties of Size dependence, so be known as quantum dot.With respect to traditional organic fluorescent dye, the plurality of advantages such as II-VI family quantum dot has transmitting half-peak width, and emission wavelength is adjustable, and absorption cross section is large, and absorption region is wide, fast light bleaching.Since the people such as Alivisatos and Nie within 1998, reporting use quantum dot as fluorescent probe for biomarker since (Alivisatos et al. Science, 1998,281,2013-2016; Nie et al. Science, 1998,281,2016-2018), quantum dot is at the application potential widely that demonstrates of the aspects such as molecular biology, immunobiology, clinical medicine.
The method of preparing II-VI family semiconductor-quantum-point comprises organic phase and the large class of water two.People such as Bawendi in 1993, use the method for organic phase high temperature thermolysis that metal complex precursor has been prepared to high-quality II-VI family's semiconductor-quantum-point (J.Am.Chem.Soc., 1993,8706) in thermolysis.The method weak point is: reaction needed high temperature service; protection of inert gas, reagent toxicity is large and price is high, yields poorly; the quantum dot surface obtaining is hydrophobic alkyl chain, especially needs in the application of biological detection in a lot of fields further surface-functionalized.The people such as Weller in 1996 have prepared CdTe quantum dot (Ber.Bunsen-Ges. Phys.Chem., 1996,100 in water, 1772), researchist has been developed ortho-water heat phase method (J. Phys. Chem. B, 2002,106 subsequently, 7177), hydrothermal method (Adv.Mater., 2003,15,1712), microwave assisting method (Chem. Mater. 2007,19,359) the multiple water technology of preparing such as.The method of the synthetic CdTe quantum dot of water utilizes water-soluble thiol molecule as part, can be directly used in the connection of biomolecules, and not need further surface-functionalized.Water is synthetic greatly reduces temperature of reaction with respect to organic phase method, and raw material is also relatively cheap, and environmental pollution reduces, and is conducive to industrialization.Yet in actual use, micromolecular sulfydryl part easily comes off from quantum dot surface, shows as stability not good, is difficult to long storage time or the application in complex biological environment.The macromolecular ligand of Development of Novel, utilizes the synergy enhancing part of a plurality of haptos and the interaction on quantum dot surface can improve stability.
Summary of the invention
The present invention is directed to the deficiencies in the prior art, proposed a kind of method of utilizing macromole polydentate ligand to prepare CdTe quantum dot.
The inventive method, concrete steps are as follows:
A. the preparation of macromole polydentate ligand: polyacrylic acid, mercapto-amine are dissolved in to N, in N '-dimethyl formamide DMF, then drip N, DCC is to N for N'-dicyclohexylcarbodiimide, in N '-dimethyl formamide DMF solution; Polyacrylic acid, mercapto-amine, N, the mol ratio of N'-dicyclohexylcarbodiimide DCC is, hydroxy-acid group: amino: N, N'-dicyclohexylcarbodiimide DCC=25:(1～10): (1～10).At 10～60 ℃, react 1 ~ 12 h.With the mixed solvent sedimentation of chloroform/acetone 1:1～5:1, obtain the sulfhydrylation polyacrylic acid as part.
B. the preparation of cadmium source solution: be dissolved in ultrapure water using sulfhydrylation polyacrylic acid with as cadmium salt, cadmium oxide compound or the cadmium oxyhydroxide in cadmium source, cadmium source, the polyacrylic mol ratio of sulfhydrylation be, Cd 2+: sulfydryl=1:(0.5～5), cadmium concentration is between 0.005 ~ 0.1 mol/L, and the pH value of regulator solution, between 7 ~ 12, is prepared into the cadmium source solution that contains macromole polydentate ligand.
C. the preparation of tellurium source solution: the sodium borohydride that is 1.5:1～5:1 by mol ratio or POTASSIUM BOROHYDRIDE and tellurium powder are placed in ultrapure water is reacted 5～25 hours at 0～30 ℃, obtains NaHTe or the KHTe aqueous solution as tellurium source.
D. CdTe precursor solution preparation: the cadmium source solution of 0.0005～0.1 mol/L that contains macromole polydentate ligand prepared by step b packs in reaction vessel, with high pure nitrogen, drive away the oxygen in solution, the tellurium source solution of preparing in step c is injected, and the mol ratio feeding intake is, Cd 2+: HTe -=1:(0.1 ~ 0.5).
E. the microwave of CdTe quantum dot preparation: the CdTe precursor solution preparing in steps d is injected to microwave reaction pipe, heat in microwave reactor, obtain the CdTe quantum dot solution of different emission wavelengths (visible region); Microwave heating condition: microwave heating power is 10～1000 watts, 1～60 minute heat-up time, 50～160 ℃ of Heating temperatures.
Mercapto-amine of the present invention can be in mercaptoethylamine, sulfydryl propylamine, sulfydryl undecylamine, halfcystine, acthiol-J, ethycysteine, halfcystine isopropyl ester a kind of, or a kind of corresponding hydrochloride wherein, or its mixture.
Cadmium of the present invention source is: Cadmium oxide, cadmium hydroxide, Cadmium chloride fine powder, cadmium bromide, cadmium iodide, Cadmium Sulphate, cadmium nitrate, cadmium carbonate, cadmium acetate, cadmium perchlorate, cadmium chlorate, cadmium bromate, cadmium iodate and their hydrate; Cadmium concentration is 10 -5～10 -1in the concentration range of M.
The present invention uses the inorganicss such as the cadmium salts such as Cadmium chloride fine powder or its oxide compound, oxyhydroxide as raw material, utilizes sulfhydrylation polyacrylic acid as part, has prepared CdTe quantum dot under microwave-assisted.Present method is prepared CdTe quantum dot and in water, is carried out completely, and raw material is easy to get, easy to prepare, and easy handling can be prepared on a large scale.The CdTe quantum point grain diameter homogeneous that adopts present method to prepare, good dispersity, fluorescence quantum yield is high, and good biocompatibility can be preserved long-term and stably.Be applicable to stability and higher organism internal labeling and the imaging of biocompatibility requirement.
Accompanying drawing explanation
Fig. 1 is the uv-visible absorption spectra figure of the CdTe quantum dot prepared of the present invention.
Fig. 2 is the temporal evolution spectrogram of the fluorescence spectrum of the CdTe quantum dot prepared of the present invention.
Fig. 3 is that the TEM figure of PAA-SH as the CdTe quantum dot of polydentate ligand growth usingd in the present invention.
Fig. 4 is that the HRTEM figure of PAA-SH as the CdTe quantum dot of polydentate ligand growth usingd in the present invention.
Fig. 5 is that the powder X-ray RD spectrogram of PAA-SH as the CdTe quantum dot of polydentate ligand growth usingd in the present invention.
Fig. 6 is that the size distribution plot of PAA-SH as the CdTe quantum dot of the different emission wavelengths of polydentate ligand growth usingd in the present invention.
Embodiment
For better understanding content of the present invention, below in conjunction with embodiment and accompanying drawing, further set forth the present invention.The present embodiment be take technology of the present invention as basis enforcement, provided detailed embodiment and operation steps, but protection scope of the present invention is not limited to following embodiment.
The microwave-assisted of the CdTe that macromole polydentate ligand is stable synthesizes and mainly comprises 5 steps: (a) macromole polydentate ligand is synthetic; (b) preparation in cadmium source; (c) preparation in tellurium source; (d) preparation of CdTe precursor; (e) microwave-assisted of CdTe quantum dot growth.
Embodiment 1
(a) preparation of part
In 100 mL flasks, add 10 g polyacrylic acid, 1.87 g mercaptoethylamines, 50 mL DMF, stir 1 hour, and 5.16 g DCC are dissolved in to 15 mL DMF, are slowly added dropwise in flask, and 50 min add.Nitrogen bubble 30 minutes, 50 ℃ of temperature of reaction, after 72 h, most of solvent is removed in decompression, with the sedimentation three times repeatedly of chloroform/acetone=3:1 mixed solvent.Product, with vacuum-drying, is kept in brown bottle and uses nitrogen protection.
(b) preparation in cadmium source
In 1L two neck flasks, add CdCl 2229 mg, ultrapure water 1L, sulfhydrylation polyacrylic acid 1440 mg, add NaOH solution that pH value of solution is adjusted to 8, can obtain the cadmium source of 1.25 mmol/L.
(c) preparation in tellurium source
In thering is the bottle of production well, add 95.7 mg Te powder, 73 mg NaBH 4, 3 mL ultrapure waters, react 12 h at 0 ℃, can obtain the tellurium source of 250 mmol/L.
(d) precursor solution of CdTe
Logical high pure nitrogen 30 min of cadmium source solution at 1.25 mmol/L of 1L, inject tellurium source 1 mL of fresh preparation.
(e) microwave-assisted of CdTe quantum dot preparation
CdTe precursor solution is carried out to microwave heating, and reaction conditions is as follows: heating power 25 W, 100 ℃ of Heating temperatures, 15 minutes heat-up times.
Embodiment 2
(a) preparation of part
In 100 mL flasks, add 10 g polyacrylic acid, 2.25 g mercaptoethylamines, 50 mL DMF, stir 1 hour, and 7.54 g DCC are dissolved in to 15 Ml DMF, are slowly added dropwise in flask, and 30 min add.Nitrogen bubble 30 minutes, 40 ℃ of temperature of reaction, after 72 h, most of solvent is removed in decompression, with the sedimentation three times repeatedly of chloroform/acetone=2:1 mixed solvent.Product, with vacuum-drying, is kept in brown bottle and uses nitrogen protection.
(b) preparation in cadmium source
In 150 mL flasks, add CdCl 245.8 mg, ultrapure water 100 mL, sulfhydrylation polyacrylic acid 432 mg, add NaOH solution that pH value of solution is adjusted to 9, can obtain the cadmium source of 2.5 mmol/L.
(c) preparation in tellurium source
In thering is the bottle of production well, add 95.7 mg Te powder, 73 mg NaBH 4, 3 mL ultrapure waters, react 24 h at 0 ℃, can obtain the tellurium source of 250 mmol/L.
(d) precursor solution of CdTe
Logical high pure nitrogen 30 min of cadmium source solution at 2.5 mmol/L of 100 mL, inject tellurium source 0.5 mL of fresh preparation.
(e) microwave-assisted of CdTe quantum dot preparation
CdTe precursor solution is carried out to microwave heating, and reaction conditions is as follows: heating power 50 W, 110 ℃ of Heating temperatures, 15 minutes heat-up times.
Embodiment 3
(a) preparation of part
In 100 mL flasks, add 10 g polyacrylic acid, 1.4 g mercaptoethylamines, 50 mL DMF, stir 1 hour, and 3.6 g DCC are dissolved in to 15 mL DMF, are slowly added dropwise in flask, and 50 min add.Nitrogen bubble 30 minutes, 40 ℃ of temperature of reaction, after 72 h, most of solvent is removed in decompression, with chloroform/acetone=4:1 mixed solvent sedimentation three times.Product, with vacuum-drying, is kept in brown bottle and uses nitrogen protection.
(b) preparation in cadmium source
In 150 mL flasks, add CdCl 245.8 mg, ultrapure water 100 mL, sulfhydrylation polyacrylic acid 210 mg, add NaOH solution that pH value of solution is adjusted to 10, can obtain the cadmium source of 2.5 mmol/L.
(c) preparation in tellurium source
In thering is the bottle of production well, add 95.7 mg Te powder, 110.5 mg KBH 4, 3 mL ultrapure waters, react 20 h at 0 ℃, can obtain the tellurium source of 250 mmol/L.
(d) precursor solution of CdTe
Logical high pure nitrogen 30 min of cadmium source solution at 2.5 mmol/L of 100 mL, inject tellurium source 0.2 mL of fresh preparation.
(e) microwave-assisted of CdTe quantum dot preparation
CdTe precursor solution is carried out to microwave heating, and reaction conditions is as follows: heating power 70 W, 120 ℃ of Heating temperatures, 5 minutes heat-up times.
Embodiment 4
(a) preparation of part
In 100 mL flasks, add 10 g polyacrylic acid, 0.8 g mercaptoethylamine, 40 mL DMF, stir 1 hour, and 2.06 g DCC are dissolved in to 10 mL DMF, are slowly added dropwise in flask, and 50 min add.Nitrogen bubble 30 minutes, 40 ℃ of temperature of reaction, after 72 h, most of solvent is removed in decompression, with the sedimentation three times repeatedly of chloroform/acetone=3:1 mixed solvent.Product, with vacuum-drying, is kept in brown bottle and uses nitrogen protection.
(b) preparation in cadmium source
In 150 mL flasks, add CdCl 222.9 mg, ultrapure water 100 mL, sulfhydrylation polyacrylic acid 180 mg, add NaOH solution that pH value of solution is adjusted to 11, can obtain the cadmium source of 1.25 mmol/L.
(c) preparation in tellurium source
In thering is the bottle of production well, add 95.7 mg Te powder, 110.5 mg KBH 4, 3 mL ultrapure waters, react 15 h at 5 ℃, can obtain the tellurium source of 250 mmol/L.
(d) precursor solution of CdTe
Logical high pure nitrogen 30 min of cadmium source solution at 1.25 mmol/L of 100 mL, inject tellurium source 0.2 mL of fresh preparation.
(e) microwave-assisted of CdTe quantum dot preparation
CdTe precursor solution is carried out to microwave heating, and reaction conditions is as follows: heating power 100 W, 150 ℃ of Heating temperatures, 5 minutes heat-up times.
According to the method for the invention, the pH value of reacting by change, temperature and time and the microwave power of microwave heating, can obtain having the CdTe quantum dot of different emission.
the description of contents of accompanying drawing 1-6:
Adopt the method for invention, from Fig. 1 and 2, in microwave reaction temperature, it is 130 ℃, under pH=12 condition, uv-visible absorption spectra and the fluorescence spectrum of the CdTe quantum dot of preparing during the time in different heating, along with absorption peak and the emission peak of the visible quantum dot of prolongation in reaction times all has obvious Red Shift Phenomena, the size that shows CdTe quantum dot product increases with the prolongation in reaction times.
Adopting method of the present invention, shown in Fig. 3 and 4, is 130 ℃ in microwave reaction temperature, under pH=12 condition, and the transmission electron microscope of the CdTe quantum dot preparing and high resolving power transmission electron microscope photo.As seen from the figure, the CdTe quantum dot product preparing has good dispersiveness, particle size homogeneous, and lattice fringe is obvious, and the crystal property of quantum dot is good.
Adopting method of the present invention, as shown in Figure 5, is 130 ℃ in microwave reaction temperature, under pH=12 condition, and the X-ray diffraction spectrogram of the CdTe quantum dot product preparing.As seen from the figure, product has characteristic peak at (111), (220) and (311) crystal face, meets the crystalline structure of CdTe, shows that CdTe quantum dot product is cubic structure.
Adopt method of the present invention, as seen from Figure 6, in microwave reaction temperature, it is 130 ℃, under pH=12 condition, the dynamic light scattering of the CdTe quantum dot preparing characterizes, the size of result shows to have different emission wavelengths (ruddiness, orange light, green glow) quantum dot is all at 10 nm left and right, the distribution of sizes homogeneous of quantum dot.

Claims (3)

1.一种大分子多齿配体CdTe量子点的微波辅助合成方法，其特征包括如下步骤： 1. a microwave-assisted synthesis method of macromolecule multidentate ligand CdTe quantum dots, characterized in comprising the steps: 步骤a：大分子多齿配体的制备：将聚丙烯酸、巯基胺溶于N,N’-二甲基甲酰胺（DMF）中，再滴加N,N'-二环己基碳二亚胺（DCC）到N,N’-二甲基甲酰胺（DMF）溶液中；聚丙烯酸、巯基胺、N,N'-二环己基碳二亚胺（DCC）的摩尔比为，羧酸基团：氨基：N,N'-二环己基碳二亚胺（DCC）＝ 25：（1～10）：（1～10）；在10～60℃下反应1~12 h；以氯仿/丙酮1：1～5：1的混合溶剂沉降，得到作为配体的巯基化聚丙烯酸； Step a: Preparation of macromolecular multidentate ligands: dissolve polyacrylic acid and mercaptoamine in N,N'-dimethylformamide (DMF), then add N,N'-dicyclohexylcarbodiimide dropwise (DCC) into N,N'-dimethylformamide (DMF) solution; the molar ratio of polyacrylic acid, mercaptoamine, N,N'-dicyclohexylcarbodiimide (DCC) is, carboxylic acid groups : Amino group: N,N'-dicyclohexylcarbodiimide (DCC) = 25: (1~10): (1~10); react at 10~60°C for 1~12 h; use chloroform/acetone 1 : The mixed solvent of 1～5:1 is settled to obtain the mercaptolated polyacrylic acid as the ligand; 步骤b：镉源溶液的制备：将巯基化聚丙烯酸和作为镉源的镉盐、镉氧化物或者镉氢氧化物溶于超纯水中，镉源、巯基化聚丙烯酸的摩尔比为，Cd2＋：巯基＝1：（0.5～5），镉浓度在0.005~0.1 mol/L之间，调节溶液的pH值在7~12之间，制备成含有大分子多齿配体的镉源溶液； Step b: Preparation of cadmium source solution: dissolve mercaptopolyacrylic acid and cadmium salt, cadmium oxide or cadmium hydroxide as cadmium source in ultrapure water, the molar ratio of cadmium source and mercaptopolyacrylic acid is, Cd 2+ : mercapto group = 1: (0.5~5), the cadmium concentration is between 0.005~0.1 mol/L, the pH value of the solution is adjusted between 7~12, and a cadmium source solution containing a macromolecular multidentate ligand is prepared; 步骤c：碲源溶液的制备：将摩尔比为1.5：1～5：1的硼氢化钠或硼氢化钾和碲粉置于超纯水中，在0～30℃下反应5～25小时，得到作为碲源的NaHTe或者KHTe水溶液； Step c: Preparation of tellurium source solution: put sodium borohydride or potassium borohydride and tellurium powder with a molar ratio of 1.5:1 to 5:1 in ultrapure water, and react at 0 to 30°C for 5 to 25 hours, Obtain NaHTe or KHTe aqueous solution as tellurium source; 步骤d：CdTe前体溶液制备：将步骤b制备的含有大分子多齿配体的0.0005～0.1 mol/L的镉源溶液装入反应容器中，用高纯氮气驱除溶液中的氧气，将步骤c中制备的碲源溶液注入，投料的摩尔比为，Cd2＋：HTe－＝1：（0.1~0.5）； Step d: Preparation of CdTe precursor solution: put the 0.0005-0.1 mol/L cadmium source solution containing the macromolecular multidentate ligand prepared in step b into the reaction vessel, and use high-purity nitrogen to drive off the oxygen in the solution, and the step The tellurium source solution prepared in c is injected, and the molar ratio of feeding is, Cd 2+ : HTe - = 1: (0.1~0.5); 步骤e：CdTe量子点的微波制备：将步骤d中制备好的CdTe前体溶液注入微波反应管中，在微波反应器中加热，得到不同发光波长的CdTe量子点溶液；微波加热条件：微波加热功率为10～1000瓦，加热时间1～60分钟，加热温度50～160℃。 Step e: Microwave preparation of CdTe quantum dots: inject the CdTe precursor solution prepared in step d into a microwave reaction tube and heat in a microwave reactor to obtain CdTe quantum dot solutions with different emission wavelengths; microwave heating conditions: microwave heating The power is 10-1000 watts, the heating time is 1-60 minutes, and the heating temperature is 50-160°C. 2.根据权利要求1所述的一种大分子多齿配体CdTe量子点的微波辅助合成方法，其特征在于： 2. the microwave-assisted synthesis method of a kind of macromolecular multidentate ligand CdTe quantum dot according to claim 1, is characterized in that: 在步骤a中所述的巯基胺可以为巯基乙胺、巯基丙胺、巯基十一胺、半胱氨酸、半胱氨酸甲酯、半胱氨酸乙酯、半胱氨酸异丙酯中的一种，或其中一种的相应的盐酸盐或其混合物。 The mercaptoamine described in step a can be mercaptoethylamine, mercaptopropylamine, mercaptoundecylamine, cysteine, cysteine methyl ester, cysteine ethyl ester, cysteine isopropyl ester One, or one of the corresponding hydrochloride or a mixture thereof. 3.根据权利要求1所述的一种大分子多齿配体CdTe量子点的微波辅助合成方法，其特征在于： 3. the microwave-assisted synthesis method of a kind of macromolecular multidentate ligand CdTe quantum dot according to claim 1, is characterized in that: 在步骤b中所使用的镉盐、镉氧化物或者氢氧化物包括：氧化镉、氢氧化镉、氟化镉、氯化镉、溴化镉、碘化镉、硫酸镉、硝酸镉、碳酸镉、醋酸镉、高氯酸镉、氯酸镉、溴酸镉、碘酸镉以及它们的水合物或混合物；镉浓度在10－5～10－1 M的浓度范围内。 The cadmium salt, cadmium oxide or hydroxide used in step b include: cadmium oxide, cadmium hydroxide, cadmium fluoride, cadmium chloride, cadmium bromide, cadmium iodide, cadmium sulfate, cadmium nitrate, cadmium carbonate , cadmium acetate, cadmium perchlorate, cadmium chlorate, cadmium bromate, cadmium iodate and their hydrates or mixtures; the concentration of cadmium is within the concentration range of 10 -5 ~ 10 -1 M.
CN201310550031.XA 2013-11-08 2013-11-08 Microwave-assisted synthesis method of macromolecular polydentate ligand CdTe quantum dots Pending CN103666476A (en)

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