CN104694117A - Ratio-type fluorescent probe based on carbon dot as well as preparation method and application thereof - Google Patents
Ratio-type fluorescent probe based on carbon dot as well as preparation method and application thereof Download PDFInfo
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- CN104694117A CN104694117A CN201310662949.3A CN201310662949A CN104694117A CN 104694117 A CN104694117 A CN 104694117A CN 201310662949 A CN201310662949 A CN 201310662949A CN 104694117 A CN104694117 A CN 104694117A
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- bhhct
- carbon point
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Abstract
The invention discloses a ratio-type fluorescent probe based on a carbon dot and a europium complex, a preparation method of the ratio-type fluorescent probe and an application method of the ratio-type fluorescent probe in a water sample detection technology. A hyperfluorescence rare earth complex and the carbon dot are taken as a double luminous center, a covalent binding manner is adopted for bonding two luminophors together, and ratio-type detection on Cu<2+> ions in a water sample is carried out by virtue of strength ratio of the hyperfluorescence rare earth complex to the carbon dot. The ratio-type fluorescent probe has good selectivity and sensitivity.
Description
Technical field
The present invention relates to nano-luminescent material, specifically a kind of Ratiometric fluorescent probe material based on carbon point and Synthesis and applications thereof.
Background technology
Nano material, as a kind of novel material, causes strong concern and research boom in recent years.And fluorescent nano material due to fluorescence intensity high, the advantages such as good light stability receive much concern especially.In recent years, semiconductor-quantum-point (semiconductorquantum dots) enjoys the concern of investigator due to its distinctive spectral response curve, especially have a good application prospect (document 1:Alivisatos A P Semiconductor clusters in nanocomposite optical device and biology fluorescent mark, nanocrystals, and quantum dots [J] .Science, 1996,271 (5251): 933-937).
Traditional semiconductor-quantum-point, owing to all having certain toxicity containing heavy metal element (such as cadmium) to environment and biologic applications, therefore finds a kind of new nano material thing as an alternative, imperative.Carbon nanomaterial is because its excellent biological safety (hypotoxicity) and biocompatibility are by widely as biomaterial.Take carbon nanotube as carbon material (the Nano graphite crystal of representative, soccerballene etc.) for biological medicine carrying, biosensor (document 2:Guo Y Shi D L, Cho H S, et a1.Invivo imaging and drug storage by quantum-dot-conjugated carbon nanotubes [J] .AdvancedFunctional Materials, 2008,18 (17): 2489-2497).Carbon quantum dot is as the newcomer of the 4th main group carbon family, due to advantages such as its small size, good biocompatibility, low cytotoxicity, light stability and unglazed nictation, there is in biomarker direction good application prospect (document 3:Zhao Q L'Zhang Z L, Huang B H, et a1.Facilepreparation of low cytotoxicity fluorescent carbon nanocrystals by electrooxidation ofgraphite [J] .Chemical Communications, 2008 (41): 5116-51l8).Carbon point, owing to containing a large amount of carboxyls or amino in surface, therefore has passivation modification that is well water-soluble and that be conducive to subsequently, improves its fluorescence property.Since carbon o'clock found from 04 year, its synthetic method has achieved great progress, is mainly used in cell imaging and living imaging, and is still in the junior stage in the application of other field.In recent years, carbon point has the character of upper conversion to have investigator to find, namely at long-wavelength excitation, short wavelength launches.Lower and the life-span shorter development limiting it of the fluorescence quantum yield of carbon point.Recent study finds, carbon point doped with nitrogen has the character of upper conversion, this discovery points out that carbon point can replace rare earth up-conversion fluorescent material in future, further application prospect (the document 4:Wang having opened up carbon point, C., et al., Upconversion fluorescent carbonnanodots enriched with nitrogen for light harvesting.Journal of Materials Chemistry, 2012.22 (31): p.15522).Along with the development of research, the application of carbon point is not only confined to bio-imaging field, expand to LED (document 5:Guo gradually, X., et al., Facile access to versatile fluorescent carbon dots toward light-emittingdiodes.Chem Commun (Camb), 2012.48 (21): p.2692-4), ion probe (document 6:Zhu, A., et al., Carbon-dot-based dual-emission nanohybrid produces a ratiometric fluorescent sensor in vivoimaging of cellular copper ions.Angew Chem Int Ed Engl, p.7185-9) and photochemical catalysis (document 7:Li 2012.51 (29):, H., et al., Water-soluble fluorescent carbon quantum dots and photocatalyst design.AngewChem Int Ed Engl, 2010.49 (26): p.4430-4).
Summary of the invention
The object of this invention is to provide and a kind ofly there is highly sensitive and optionally Ratiometric fluorescent probe, for the detection of cupric ion based on stand.
To achieve these goals, technical scheme of the present invention is as follows:
Functional carbon nano fluorescent particulate is two luminescence center with carbon point and rare-earth fluorescent title complex, and carbon point adopts hydrothermal method to be prepared from, and Nano carbon balls surface has the functional group of Chemical bond function, and composite nano materials uses chemical bonding to be prepared from.
Be specially: the fluorescence complex formed with carbon point (CNPs) and rare earth ion europium and beta-diketon class ligand is two luminescence center, and its structure is:
Preparation method is: by 1mgBHHCT and 10mg CNPs, is dissolved in 20mL dehydrated alcohol, and adds 1mL triethylamine wherein, and stirring at normal temperature is synthesized by covalent bonding.
Preparation process (the document 8:Liu of CNPs, Y.L et.al, One-step synthesis of amino-functionalized fluorescentcarbon nanoparticles by hydrothermal carbonization of chitosan.ChemComm.2012, 48, 380-382): chitosan 0.5mg molecular weight being about 25000 joins in the 20mL aqueous solution containing 2% acetic acid, stirring makes chitosan dissolve, transparent solution is poured into containing in teflon-lined reactor, 180 DEG C of reaction 12h in retort furnace, obtain black solid, add about 10mL deionized water, the ultrasonic carbon quantum dot that makes all is dissolved in water, by centrifugal for mixture 14000rpm/min 15 minutes, get supernatant liquor, obtain brown yellow solution.
Tool of the present invention has the following advantages: it is two luminescence center with fluorescent both rare earth compounding and carbon point, is bonded to together, carrys out the Cu in the detection water sample of Ratio-type by the strength ratio of the two in covalently bound mode by two kinds of luminophors
2+ion.The fluorescent probe of this Ratio-type has good selectivity and sensitivity.
Accompanying drawing explanation
Fig. 1 is CNPs, BHHCT and CNPs-BHHCT-Eu
3+conventional fluorescent spectrum and UV spectrum.
Fig. 2 is CNPs, BHHCT and CNPs-BHHCT-Eu
3+infrared spectra.
Fig. 3 is ninhydrin reaction result photo.
Fig. 4 is the CNPs-BHHCT-Eu under different TX-100 content
3+fluorescence spectrum figure and photo.
Fig. 5 is the CNPs-BHHCT-Eu under different ethanol water ratio
3+fluorescence spectrum figure and photo
Fig. 6 is the CNPs-BHHCT-Eu under different PH
3+fluorescence spectrum figure and photo
The fluorescence spectrum of probe and typical curve when Fig. 7 is the cupric ion that there is different concns.
Fig. 8 is Kinetics of Dynamic Quenching curve.
Fig. 9 is Stern-Volmer curve.
Figure 10 is that different ions is to probe response.
Embodiment
Below by embodiment, the invention will be further described.
Embodiment 1
CNPs-BHHCT-Eu
3+preparation
Take 1mgBHHCT and 10mgCNPs, it is fully dissolved in 20mL dehydrated alcohol, and add 1mL triethylamine wherein, stirring at normal temperature 2h, add the EuCl of 0.5mg subsequently
36H
2o, continue to stir 30min, placement is spent the night.Vacuum is revolved and is steamed triethylamine and ethanol, constantly washs solid product with deionized water.
CNPs-BHHCT-Eu
3+property representation
(1) CNPs, BHHCT and CNPs-BHHCT-Eu
3+fluorescence Characteristic
Fig. 1 is CNPs and CNPs-BHHCT-Eu
3+fluorescence spectrum and ultra-violet absorption spectrum (1-CNP
sultra-violet absorption spectrum, 2-CNPs-BHHCT-Eu
3+ultra-violet absorption spectrum, the ultra-violet absorption spectrum of 3-BHHCT, the fluorescence spectrum of 4-CNPs, 5-CNPs-BHHCT-Eu
3+fluorescence spectrum).As can be seen from the figure CNPs has absorption at 280nm place, and simultaneously BHHCT has two absorption peaks respectively 260 and 345nm place.And the CNPs-BHHCT-Eu of our synthesis
3+also containing two absorption bands.Fluorescence spectrum points out that 337nm excites lower CNPs-BHHCT-Eu
3+containing two emission peaks, respectively at 410nm and 615nm.
(2) CNPs, BHHCT and CNPs-BHHCT-Eu
3+infrared Characterization
Fig. 2 points out that CNPs is at 3438cm
-1there is the stretching vibration peak of O – H and N – H at place, 1623cm
-1there is the formation vibration peak of N-H at place.And BHHCT is at 1611cm
-1there is the stretching vibration absorption peak of C=O at place, 3052cm
-1place have phenyl ring=C-H stretching vibration peak, 1500cm
-1place has=the formation vibration peak of C-H, and 1241cm
-1and 1181cm
-1place is C-O formation vibration peak.And synthesized CNPs-BHHCT-Eu
3+simultaneously containing O-H and the N-H stretching vibration peak of CNPs, also exist phenyl ring=the stretching vibration absorption peak of C-H stretching vibration peak and C=O and formation vibration peak.
CNPs-BHHCT-Eu
3+fluorescent characteristic
(1) TX-100 of different content is to CNPs-BHHCT-Eu
3+impact
Due to water molecules meeting and BHHCT-Eu
3+in europium ion generation coordination reaction, make its fluorescence generation quencher.TX-100 is a kind of conventional nonionogenic tenside, and water molecules can intercept at CNPs-BHHCT-Eu by it
3+skin, make its cannot with europium generation coordination.Fig. 4 points out, along with the increase of TX-100 content (0.01%, 0.02%, 0.03%, 0.05%), and BHHCT-Eu
3+peak excite the fluorescence intensity at lower 615nm place also to strengthen gradually at 337nm, and can the color of solution have blueness to be transitioned into redness gradually under the irradiation of ultraviolet lamp.
(2) different ethanol water ratios is to CNPs-BHHCT-Eu
3+impact
As can be seen from Figure 5, along with ethanol content (20%, 35%, 40%, 45%, 50%) is increased to 30%, BHHCT-Eu3 from 10%
+peak excite the fluorescence intensity at lower 615nm place significantly to increase at 337nm, and to increases slowly subsequently, reach a ultimate value.I in illustration
615/ I
410must be worth and also show same Changing Pattern and the fluorescence that solution sends under ultraviolet lamp also significantly can be found out from blueness and is transitioned into redness gradually.
(3) PH(5.5,6.0,6.5,7.0,7.5) and to CNPs-BHHCT-Eu
3+impact
Carbon point has good stability to pH, and BHHCT-Eu
3+unstable to pH.Fig. 6 has also reflected this characteristic, along with pH is transitioned into weak base from weak acid, under 337nm excites, and I
615/ I
410the proportional gradually increase of value, and become good linear relationship with corresponding pH value, and the fluorescence that solution sends under the irradiation of ultraviolet lamp is also transitioned into redness from blueness gradually
Cu
2+ion pair CNPs-BHHCT-Eu
3+impact
(1) Cu of different concns
2+ion pair CNPs-BHHCT-Eu
3+impact
Can significantly find out from Fig. 7, along with the Cu added
2+the increase of ionic concn, BHHCT-Eu
3+fluorescence there is quencher gradually, and there is any change in the fluorescence of carbon point hardly.I
615/ I
410ratio within the scope of 0.1-0.5 μM, present good linear relationship, R
2be 0.999, based on the noise ratio of 3 times, calculating Monitoring lower-cut is 20nM.
(2) Fluorescence quenching effect
I can be found out in Fig. 9
0/ I and [Cu
2+] in nonlinear relationship, in other words, after adding cupric ion, quenching of fluorescence exists static quenching and dynamic quenching two kinds of forms simultaneously.And the quenching of fluorescence curve of Fig. 8 is pointed out, after adding cupric ion, the fluorescence wink speed quencher at 615nm place.
(3) ion selectivity test
As can be seen from Figure 10, only have cupric ion to cause the obvious quencher of probe, other metal ions almost do not affect, and illustrate that the Ratio-type probe synthesized by us has good selectivity to cupric ion.
(4) rate of recovery rate of recovery table of cupric ion (in tap water and the deionized water)
Table 1
The rate of recovery in tap water
Table 2
The rate of recovery in deionized water
Have selected tap water and deionized water as water sample, test the tolerance range that probe detects cupric ion.Cu
2+the ultimate density of ion is 0.25 and 0.3 μM.By fluorescence spectrum record carbon point and BHHCT-Eu
3+intensity rate, then according to the concentration that typical curve equation is calculated finally.As can be seen from the table, the probe synthesized by us may be used for the Cu well detected in actual water sample
2+ion.
Claims (5)
1., based on a Ratiometric fluorescent probe for carbon point, it is characterized in that:
By 10mg containing amino carbon point and 1mg beta-diketon complex compound, in 20mL alcohol solvent, the effect of 1mL triethylamine basic catalyst issues biochemical reaction, makes containing BHHCT on amino carbon point surface bond, add 0.5mg europium chloride again, stir half hour more than; After completion of the reaction, revolve and steam removing ethanol and triethylamine, remove unreacted carbon point with deionized water wash.
2. a preparation method for Ratiometric fluorescent probe described in claim 1, is characterized in that:
By 10mg containing amino carbon point and 1mg BHHCT, in 20mL alcohol solvent, under the effect of 1mL triethylamine basic catalyst there is chemical reaction with amino in chlorosulfonyl group, makes BHHCT on carbon point surface bond, add 0.5mg europium chloride again, more than stirring half hour make itself and BHHCT complexing; After completion of the reaction, revolve and steam removing ethanol and triethylamine, remove unreacted carbon point with deionized water wash.
3., according to the preparation method of Ratiometric fluorescent probe described in claim 2, it is characterized in that:
By 10mg containing amino carbon point and 1mg BHHCT, in 20mL alcohol solvent, under the effect of 1mL triethylamine basic catalyst there is chemical reaction with amino in chlorosulfonyl group, makes BHHCT on carbon point surface bond, add 0.5mg europium chloride again, more than stirring half hour make itself and BHHCT complexing; After completion of the reaction, revolve and steam removing ethanol and triethylamine, remove unreacted carbon point with deionized water wash.
4. an application for the Ratiometric fluorescent probe described in right 1, it is for the detection of copper ion concentration in water.
5., according to the application of Ratiometric fluorescent probe described in claim 4, it is characterized in that:
By BHHCT-Eu
3+pass through together with chemical bonding with carbon point, and BHHCT-Eu
3+can directly as detection moiety, there is not any change in carbon point, by the ratio of the two fluorescence intensity under 337nm excites for determining copper ion concentration in water, BHHCT-Eu
3+be inversely proportional to the concentration of cupric ion in the fluorescence intensity ratio of carbon point and water.
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| CN105154069A (en) * | 2015-09-21 | 2015-12-16 | 山东农业大学 | Multi-colored adjustable light-emitting material of nitrogen-doped carbon dot coordination rare earth and preparation method thereof |
| CN105223174A (en) * | 2015-09-23 | 2016-01-06 | 山东大学 | A kind of detection method based on fluorescent quenching copper ion |
| CN105255487A (en) * | 2015-10-19 | 2016-01-20 | 南京医科大学 | Amino alcohol functional CDs (carbon dots), preparation method and application of amino alcohol functional CDs in copper ion measurement |
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