CN100558825C - The preparation method of the carbon nanotube of fluorescence ion liquid functionalization - Google Patents
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Abstract
The present invention relates to a kind of preparation method of carbon nanotube of fluorescence ion liquid functionalization of chemical technology field, at first by the synthetic ionic liquid that contains fluorophor of molecular designing, then carbon nanotube is carried out acidifying, salinization processing, by ion exchange reaction fluorescence ion liquid functionalization is arrived carbon nano tube surface, obtain the carbon nanotube of fluorescence ion liquid functionalization.This preparation method is simple, be easy to control, products obtained therefrom excites down at 254nm and sends blue-fluorescence and have higher quantum yield, can be used as the nano-device of specific function, as the nanometer light responsive material, bioprobe, the nano fluorescent transmitter has application widely at electronics and biological field.
Description
Technical field
The present invention relates to the preparation method of a kind of preparation method's of field of nanometer technology, particularly a kind of fluorescence ion liquid functionalization carbon nanotube.
Background technology
Carbon nanotube (Carbon Nanotube, be called for short CNT) be found in recent years a kind of novel carbon structure, it is the seamless hollow carbon pipe that curls and form by the Graphene lamella that carbon atom forms, two ends respectively have the fullerene molecule end-blocking half, are a kind of One-dimensional Quantum materials with height delocalization πDian Zi conjugated system.Carbon nanotube is divided into Single Walled Carbon Nanotube (SWNT) and multi-walled carbon nano-tubes (MWNT).Its preparation method mainly contains catalyse pyrolysis, arc-over, template, chemical Vapor deposition process etc.
Carbon nanotube is since coming out, because its unique electronics and mechanical property and accurate one dimension piped molecular structure become the focus of physics, chemistry, material and even biological study rapidly.Along with carbon nanotube science and the deep of ambit such as biology, electronics intersect, a kind of novel functionalized carbon nano-tube material-fluorescent carbon nanometer tube arises at the historic moment.Fluorescent carbon nanometer tube generally by quantum dot, dye molecule, be with chromophoric polymer and carbon nanotube to be composited.Because it has wide application prospect in fields such as bioprobe, fluorescence nano transmitter, nanometer light active materials.The strategy of preparation fluorescent carbon nanometer tube has two kinds, covalent chemical modification and non-covalent chemical modification at present.
Find through literature search prior art, " interaction between further investigation Single Walled Carbon Nanotube and anthracene and the terphenyl " that Hedderman etc. deliver on " chemical physics magazine B " rolled up 3895 pages in 2006 the 110th, this article proposes to adopt anthracene and terphenyl to increase the solvability of carbon nanotube by non-covalent chemical action, its deficiency is: because fluorescent chromophore directly contacts with carbon nano tube surface, can cause the electronics that is in the excited state chromophoric group mostly to carbon nanotube generation transfer transport, the result will cause serious cancellation.Also find in the retrieval, " energy under the pyrene functionalized Single Walled Carbon Nanotube excited state shifts " that Sun etc. deliver on " photochemistry and photobiology magazine A: chemistry " rolled up 94 pages in 2007 the 185th, this article adopts covalent chemical method modification Single Walled Carbon Nanotube, its deficiency is: the carboxyl functional group on the carbon nanotube need carry out acyl chloride reaction and strengthen its activity, prolonged its reaction time, and condition is relatively more harsh.On the other hand, ionic liquid becomes the focus of recent research owing to characteristics such as having low volatility, high thermostability, high ion-conductivity.Ion liquid structure that more crucial is and character can be by suitably selecting negatively charged ion, and positively charged ion and substituting group thereof and change promptly can design ionic liquid to a certain extent.If the fluorescence ion liquid functionalization that designs is arrived carbon nano tube surface, just can realize fluorescent functional, thereby prepare the carbon nanotube of fluorescence ion liquid functionalization to carbon nanotube.
Summary of the invention
The objective of the invention is at the deficiencies in the prior art, a kind of preparation method of carbon nanotube of fluorescence ion liquid functionalization is provided, make it utilize simple ion exchange method that fluorescence ion liquid functionalization is arrived carbon nano tube surface, obtain the carbon nanotube of fluorescence ion liquid functionalization, target product has higher quantum yield 20%.
The present invention is achieved by the following technical solutions, the present invention is at first by the synthetic ionic liquid that contains fluorophor of molecular designing, then carbon nanotube is carried out acidifying, salinization processing, by ion exchange reaction fluorescence ion liquid functionalization is arrived carbon nano tube surface, obtain the carbon nanotube of fluorescence ion liquid functionalization.
The present invention includes following steps:
Step a: N-TMS imidazoles and 9-chloromethyl anthracene are joined in the distilled tetrahydrofuran (THF) with mol ratio 1/2～1/5, stir, product joins washing, separatory in the organic solvent, obtains ionic liquid chlorination 1 after the vacuum-drying, 3-two (9-anthracene methyl) imidazoles ([bamim] Cl).
Step b: 1 weight part exsiccant carbon nanometer tube material and 50～5000 weight part acid with strong oxidizing property are mixed, and ultrasonication, stirring reaction, suction filtration also repeatedly are neutral to solution with the deionized water repetitive scrubbing, obtain the acidifying carbon nanotube after the vacuum-drying;
Step c: the acidifying carbon nanotube of 1 weight part step b gained is joined in the basic solution of 10～1000 weight part 0.1mol/L～1mol/L, ultrasonication, stirring reaction, suction filtration also repeatedly is neutral to solution with the deionized water repetitive scrubbing, obtains the carbon nanotube of salinization after the vacuum-drying;
Steps d: the salt carbon nano tube of step c gained and the ionic liquid of step a gained are joined in the organic solution with weight ratio 1/10～1/100, ultrasonication, stirring reaction, suction filtration is also used the organic solvent repetitive scrubbing, in organic solvent, dialyse, obtain the carbon nanotube of fluorescence ion liquid functionalization after the product vacuum-drying.
Among the above-mentioned steps a, described stirring, its time is 1h～50h, temperature is 20 ℃～100 ℃ during stirring; Described washing, separatory, its operation repeats 5 times.
Among the above-mentioned steps a, described organic solvent is diethyl ether, ether, methyl-sulphoxide, chloroform, tetrahydrofuran (THF), acetone, ethanol, acetonitrile, butanone, pyridine or the mixed solvent that contains these solvents.
Among the above-mentioned steps b, described ultrasonication, stirring reaction are meant: with 0kHz～100kHz ultrasonication 1min～100min, be heated to 20 ℃～200 ℃, stirring reaction 1min～100min.
Among the above-mentioned steps b, described carbon nanotube is the single wall or the multi-walled carbon nano-tubes of catalyse pyrolysis, arc-over, template, the preparation of chemical Vapor deposition process method.
Among the above-mentioned steps b, described acid with strong oxidizing property comprises nitric acid, sulfuric acid, nitric acid and sulfuric acid mixing acid, and is added with potassium permanganate or H
2O
2Hydrochloric acid, nitric acid, sulfuric acid and mixing acid thereof in a kind of.
Among the above-mentioned steps c, described ultrasonication, stirring reaction are meant: step c: with 0kHz～100kHz ultrasonication 1min～100min, be heated to 10 ℃～100 ℃, stirring reaction 20min～200min.
Among the above-mentioned steps c, described alkali comprises a kind of in sodium hydroxide, potassium hydroxide, hydrated barta, cesium hydroxide, calcium hydroxide, aluminium hydroxide, the zinc hydroxide.
Among the above-mentioned steps d, described organic solvent is diethyl ether, ether, methyl-sulphoxide, chloroform, tetrahydrofuran (THF), acetone, ethanol, acetonitrile, butanone, pyridine or the mixed solvent that contains these solvents.
Among the above-mentioned steps d, described ultrasonication, stirring reaction are meant: with 0kHz～100kHz ultrasonication 1min～100min, be heated to 10 ℃～100 ℃, stirring reaction 20min～200min.
Among the above-mentioned steps d, described dialysis, its time is 3 days.
Preparation method provided by the invention is simple, controllability is strong, products obtained therefrom excites down at 254nm and sends blue-fluorescence and have higher quantum yield, the relative quantum productive rate can reach 20%, can be used as the nano-device of specific function, as nanometer light responsive material, bioprobe, the nano fluorescent transmitter can be applied to numerous areas such as electronics and biology.
Description of drawings
Fig. 1: the transmission electron microscope photo of the carbon nanotube of fluorescence ion liquid functionalization;
Fig. 2: fluorescence emission spectrogram: (a) fluorescence ion liquid, (b) carbon nanotube of fluorescence ion liquid functionalization.
Embodiment
Below in conjunction with accompanying drawing embodiments of the invention are elaborated: present embodiment is being to implement under the prerequisite with the technical solution of the present invention, provided detailed embodiment and concrete operating process, but protection scope of the present invention is not limited to following embodiment.
Single Walled Carbon Nanotube with the chemical Vapor deposition process preparation is an initial raw material, acidified, salinization, by ion exchange reaction with chlorination 1,3-two (9-anthracene methyl) imidazoles ([bamim] Cl) functionalization obtains the carbon nanotube of fluorescence ion liquid functionalization to the Single Walled Carbon Nanotube surface.
Step a: in three neck round-bottomed flasks of magnetic agitation rotor are housed, the N-TMS imidazoles of 0.100mol and the 9-chloromethyl anthracene of 0.202mol are joined in the distilled 50mL tetrahydrofuran solvent, take out repeatedly and fill argon gas 3 times, be heated to 60 ℃, stirring reaction 24h, product join washing, separatory in the diethyl ether, repeat 5 times, obtain ionic liquid chlorination 1 after the vacuum-drying, 3-two (9-anthracene methyl) imidazoles ([bamim] Cl);
Step b: in single neck round-bottomed flask of magnetic agitation rotor is housed, add 0.20g carbon nanometer tube material and 150mL nitric acid and sulfuric acid mixed solution, with 40kHz ultrasonication 30min post-heating to 70 ℃, stir reaction 90min down, with ф 0.22 μ m tetrafluoroethylene millipore filtration suction filtration, repeatedly to neutral, obtain acidifying carbon nanotube behind 50 ℃ of vacuum-drying 24h with a large amount of deionized water repetitive scrubbings;
Step c: in single neck round-bottomed flask of magnetic agitation rotor is housed, add the acidifying carbon nanotube of 50mg step b gained and the potassium hydroxide solution of 50g 1mol/L, with 40kHz ultrasonication 30min post-heating to 50 ℃, stir reaction 180min down, with ф 0.22 μ m tetrafluoroethylene millipore filtration suction filtration, repeatedly to neutral, obtain the carbon nanotube of salinization with a large amount of deionized water repetitive scrubbings behind 50 ℃ of vacuum-drying 24h;
Steps d: in single neck round-bottomed flask of magnetic agitation rotor is housed, chlorination 1 with the salt carbon nano tube and the 100mg step a gained of 2mg step c gained, 3-two (9-anthracene methyl) imidazoles ([bamim] Cl) joins in the 50mL ethanolic soln, with 40kHz ultrasonication 30min, be heated to 50 ℃, stirring reaction 180min, suction filtration is also used the ethanol repetitive scrubbing, then in ethanol, dialysed 3 days, obtain the carbon nanotube of fluorescence ion liquid functionalization after the product vacuum-drying.
Fig. 1 has provided the transmission electron microscope photo of fluorescence ion liquid functionalization carbon nanotube, can observe the surface that thickness comparison uniform ion liquid is wrapped in carbon nanotube.Can also estimate the thickness that the Mierocrystalline cellulose coating layer easily and be about 1nm.
From fluorescence emission spectrum data (Fig. 2) as can be seen, the carbon nanotube of fluorescence ion liquid functionalization (b) excites the blue-fluorescence that sends 380～460 wave bands down at 254nm, its spectrum is similar to pure ionic liquid spectrum (a) peak shape, intensity slightly descends, and this is because quenching effect to a certain degree causes.Its fluorescence quantum yield of the carbon nanotube of fluorescence ion liquid functionalization can be up to about 20% as calculated.
Embodiment 2
Single Walled Carbon Nanotube with the catalytic pyrolysis method preparation is an initial raw material, acidified, salinization, by ion exchange reaction with chlorination 1,3-two (9-anthracene methyl) imidazoles ([bamim] Cl) functionalization obtains the carbon nanotube of fluorescence ion liquid functionalization to the Single Walled Carbon Nanotube surface.
Step a: in three neck round-bottomed flasks of magnetic agitation rotor are housed, the N-TMS imidazoles of 0.200mol and the 9-chloromethyl anthracene of 0.505mol are joined in the distilled 50mL tetrahydrofuran solvent, take out repeatedly and fill argon gas 3 times, be heated to 80 ℃, stirring reaction 12h, product join washing, separatory in the ethanol, repeat 5 times, obtain ionic liquid chlorination 1 after the vacuum-drying, 3-two (9-anthracene methyl) imidazoles ([bamim] Cl);
Step b: in single neck round-bottomed flask of magnetic agitation rotor is housed, add 0.40g carbon nanometer tube material and 200mL nitric acid and sulfuric acid mixed solution, with 40kHz ultrasonication 20min post-heating to 90 ℃, stir reaction 60min down, with ф 0.22 μ m tetrafluoroethylene millipore filtration suction filtration, repeatedly to neutral, obtain acidifying carbon nanotube behind 50 ℃ of vacuum-drying 24h with a large amount of deionized water repetitive scrubbings;
Step c: in single neck round-bottomed flask of magnetic agitation rotor is housed, add the acidifying carbon nanotube of 20mg step b gained and the potassium hydroxide solution of 40g 1mol/L, with 40kHz ultrasonication 20min post-heating to 65 ℃, stir reaction 120min down, with ф 0.22 μ m tetrafluoroethylene millipore filtration suction filtration, repeatedly to neutral, obtain the carbon nanotube of salinization with a large amount of deionized water repetitive scrubbings behind 50 ℃ of vacuum-drying 24h;
Steps d: in single neck round-bottomed flask of magnetic agitation rotor is housed, chlorination 1 with the salt carbon nano tube and the 75mg step a gained of 4mg step c gained, 3-two (9-anthracene methyl) imidazoles ([bamim] Cl) joins in the 50mL acetone soln, with 40kHz ultrasonication 20min, be heated to 65 ℃, stirring reaction 120min, suction filtration is also used the acetone repetitive scrubbing, then in acetone, dialysed 3 days, obtain the carbon nanotube of fluorescence ion liquid functionalization after the product vacuum-drying, measurement result shows that its relative quantum productive rate is 17%.
Embodiment 3
Single Walled Carbon Nanotube with the chemical Vapor deposition process preparation is an initial raw material, acidified, salinization, by ion exchange reaction with chlorination 1,3-two (9-anthracene methyl) imidazoles ([bamim] Cl) functionalization obtains the carbon nanotube of fluorescence ion liquid functionalization to the Single Walled Carbon Nanotube surface.
Step a: in three neck round-bottomed flasks of magnetic agitation rotor are housed, the N-TMS imidazoles of 0.250mol and the 9-chloromethyl anthracene of 0.606mol are joined in the distilled 50mL tetrahydrofuran solvent, take out repeatedly and fill argon gas 3 times, be heated to 55 ℃, stirring reaction 18h, product join washing, separatory in the acetone, repeat 5 times, obtain ionic liquid chlorination 1 after the vacuum-drying, 3-two (9-anthracene methyl) imidazoles ([bamim] Cl);
Step b: in single neck round-bottomed flask of magnetic agitation rotor is housed, add 0.35g carbon nanometer tube material and 120mL nitric acid and sulfuric acid mixed solution, with 40kHz ultrasonication 45min post-heating to 55 ℃, stir reaction 45min down, with ф 0.22 μ m tetrafluoroethylene millipore filtration suction filtration, repeatedly to neutral, obtain acidifying carbon nanotube behind 50 ℃ of vacuum-drying 24h with a large amount of deionized water repetitive scrubbings;
Step c: in single neck round-bottomed flask of magnetic agitation rotor is housed, add the acidifying carbon nanotube of 35mg step b gained and the potassium hydroxide solution of 70g 1mol/L, with 40kHz ultrasonication 45min post-heating to 55 ℃, stir reaction 120min down, with ф 0.22 μ m tetrafluoroethylene millipore filtration suction filtration, repeatedly to neutral, obtain the carbon nanotube of salinization with a large amount of deionized water repetitive scrubbings behind 50 ℃ of vacuum-drying 24h;
Steps d: in single neck round-bottomed flask of magnetic agitation rotor is housed, chlorination 1 with the salt carbon nano tube and the 80mg step a gained of 6mg step c gained, 3-two (9-anthracene methyl) imidazoles ([bamim] Cl) joins in the 50mL chloroformic solution, with 40kHz ultrasonication 45min, be heated to 55 ℃, stirring reaction 120min, suction filtration is also used the ethanol repetitive scrubbing, then in ethanol, dialysed 3 days, obtain the carbon nanotube of fluorescence ion liquid functionalization after the product vacuum-drying, tem study shows that carbon nano tube surface is coated with one deck ionic liquid equably.
Embodiment 4
Single Walled Carbon Nanotube with the catalytic pyrolysis method preparation is an initial raw material, acidified, salinization, by ion exchange reaction with chlorination 1,3-two (9-anthracene methyl) imidazoles ([bamim] Cl) functionalization obtains the carbon nanotube of fluorescence ion liquid functionalization to the Single Walled Carbon Nanotube surface.
Step a: in three neck round-bottomed flasks of magnetic agitation rotor are housed, the N-TMS imidazoles of 0.350mol and the 9-chloromethyl anthracene of 0.715mol are joined in the distilled 50mL tetrahydrofuran solvent, take out repeatedly and fill argon gas 3 times, be heated to 75 ℃, stirring reaction 10h, product join washing, separatory in the acetonitrile, repeat 5 times, obtain ionic liquid chlorination 1 after the vacuum-drying, 3-two (9-anthracene methyl) imidazoles ([bamim] Cl);
Step b: in single neck round-bottomed flask of magnetic agitation rotor is housed, add 0.30g carbon nanometer tube material and 225mL nitric acid and sulfuric acid mixed solution, with 40kHz ultrasonication 25min post-heating to 80 ℃, stir reaction 55min down, with ф 0.22 μ m tetrafluoroethylene millipore filtration suction filtration, repeatedly to neutral, obtain acidifying carbon nanotube behind 50 ℃ of vacuum-drying 24h with a large amount of deionized water repetitive scrubbings;
Step c: in single neck round-bottomed flask of magnetic agitation rotor is housed, add the acidifying carbon nanotube of 30mg step b gained and the potassium hydroxide solution of 55g 1mol/L, with 40kHz ultrasonication 35min post-heating to 40 ℃, stir reaction 160min down, with ф 0.22 μ m tetrafluoroethylene millipore filtration suction filtration, repeatedly to neutral, obtain the carbon nanotube of salinization with a large amount of deionized water repetitive scrubbings behind 50 ℃ of vacuum-drying 24h;
Steps d: in single neck round-bottomed flask of magnetic agitation rotor is housed, chlorination 1 with the salt carbon nano tube and the 60mg step a gained of 3mg step c gained, 3-two (9-anthracene methyl) imidazoles ([bamim] Cl) joins in the 50mL acetonitrile solution, with 40kHz ultrasonication 25min, be heated to 40 ℃, stirring reaction 100min, suction filtration is also used the acetonitrile repetitive scrubbing, then in acetonitrile, dialysed 3 days, obtain the carbon nanotube of fluorescence ion liquid functionalization after the product vacuum-drying, tem study shows that carbon nano tube surface is coated with one deck ionic liquid equably, and its relative quantum productive rate is 19%.
Claims (6)
1. the preparation method of the carbon nanotube of a fluorescence ion liquid functionalization is characterized in that, may further comprise the steps:
Step a: N-TMS imidazoles and 9-chloromethyl anthracene are joined in the distilled tetrahydrofuran (THF) with mol ratio 1/2～1/5, stir, product joins washing, separatory in the organic solvent, obtains ionic liquid chlorination 1 after the vacuum-drying, 3-two (9-anthracene methyl) imidazoles;
Step b: 1 weight part exsiccant carbon nanometer tube material and 10～1000 weight part acid with strong oxidizing property are mixed, and ultrasonication, stirring reaction, suction filtration also repeatedly are neutral to solution with the deionized water repetitive scrubbing, obtain the acidifying carbon nanotube after the vacuum-drying;
Described acid with strong oxidizing property comprises nitric acid, sulfuric acid, nitric acid and sulfuric acid mixing acid, and is added with potassium permanganate or H
2O
2Hydrochloric acid, nitric acid, sulfuric acid and mixing acid thereof in a kind of;
Step c: the acidifying carbon nanotube of 1 weight part step b gained is joined in the basic solution of 10～1000 weight part 0.1mol/L～1mol/L, ultrasonication, stirring reaction, suction filtration also repeatedly is neutral to solution with the deionized water repetitive scrubbing, obtains the carbon nanotube of salinization after the vacuum-drying;
Described alkali comprises a kind of in sodium hydroxide, potassium hydroxide, hydrated barta, cesium hydroxide, calcium hydroxide, aluminium hydroxide, the zinc hydroxide;
Steps d: the salt carbon nano tube of step c gained and the ionic liquid of step a gained are joined in the organic solvent with weight ratio 1/10～1/100, ultrasonication, stirring reaction, suction filtration is also used the organic solvent repetitive scrubbing, in organic solvent, dialyse, obtain the carbon nanotube of fluorescence ion liquid functionalization after the product vacuum-drying;
Described organic solvent is diethyl ether, ether, methyl-sulphoxide, chloroform, tetrahydrofuran (THF), acetone, ethanol, acetonitrile, butanone, pyridine or the mixed solvent that contains these solvents.
2. the preparation method of the carbon nanotube of fluorescence ion liquid functionalization according to claim 1 is characterized in that, among the step a, and described stirring, its time is 1h～50h, temperature is 20 ℃～100 ℃ during stirring; Described washing, separatory, its operation repeats 5 times.
3. the preparation method of the carbon nanotube of fluorescence ion liquid functionalization according to claim 1, it is characterized in that, among the step b, described ultrasonication, stirring reaction, be meant: with 0kHz～100kHz ultrasonication 1min～100min, be heated to 20 ℃～200 ℃, stirring reaction 1min～100min.
4. the preparation method of the carbon nanotube of fluorescence ion liquid functionalization according to claim 1, it is characterized in that, among the step b, described carbon nanotube is the single wall or the multi-walled carbon nano-tubes of catalyse pyrolysis, arc-over, template, the preparation of chemical Vapor deposition process method.
5. the preparation method of the carbon nanotube of fluorescence ion liquid functionalization according to claim 1, it is characterized in that, among the step c, described ultrasonication, stirring reaction, be meant: step c: with 0kHz～100kHz ultrasonication 1min～100min, be heated to 10 ℃～100 ℃, stirring reaction 20min～200min.
6. the preparation method of the carbon nanotube of fluorescence ion liquid functionalization according to claim 1, it is characterized in that, in the steps d, described ultrasonication, stirring reaction, be meant: with 0kHz～100kHz ultrasonication 1min～100min, be heated to 10 ℃～100 ℃, stirring reaction 20min～200min; Described dialysis, its time is 3 days.
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| CN102071019B (en) * | 2010-12-24 | 2014-08-20 | 苏州方昇光电装备技术有限公司 | Preparation method of water-soluble carbon nano particle material with fluorescence property |
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| CN104789215A (en) * | 2014-01-16 | 2015-07-22 | 中国药科大学 | Preparation method of ionic liquid-based fluorescent carbon nanoparticles |
| CN105969333B (en) * | 2016-06-20 | 2018-08-31 | 中国科学院兰州化学物理研究所 | A kind of preparation method of the luminescence generated by light ionic liquid of carbon containing quantum dot |
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