CN109053471A - A kind of synthetic method of [60] fullerene cyclopentene derivatives - Google Patents
A kind of synthetic method of [60] fullerene cyclopentene derivatives Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/08—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
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- C07—ORGANIC CHEMISTRY
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- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
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Abstract
The invention discloses a kind of synthetic methods of [60] fullerene cyclopentene derivatives, belong to the synthesis technical field of fullerene derivate.Synthetic method of the present invention specifically comprises the processes of: under the action of catalyst, using [60] fullerene and 3- methylbutyraldehyd, primary amine as raw material, single step reaction generates [60] fullerene cyclopentene derivatives at a certain temperature.Synthetic method of the present invention has many advantages, such as that raw material are cheap and easily-available, easy to operate, reaction condition is mild and wide application range of substrates.
Description
Technical field
The invention belongs to technical field of organic synthesis, and in particular to a kind of synthesis side of [60] fullerene cyclopentene derivatives
Method.
Background technique
Fullerene has a wide range of applications in fields such as photoelectric material, nano material, supramolecular chemistry and biological medicines, because
The chemical modification of this fullerene has become the important development direction of fullerene research.Fullerene cyclopentene because of its unique structure and
Photoelectric properties also result in the research interest of people.
Yang Haitao in 2013 etc. reports [60] fullerene and Morita-Baylis-Hillman addition product of DMAP catalysis
[3+2] cycloaddition reaction occurs and generates fullerene cyclopentene derivatives (formula 1).
Subsequent Toshiyuki Itoh, which is equal to 2015, carries out the fullerene cyclopentene derivatives of the synthesis such as Yang Haitao
Photoelectric properties research, when R is phenyl, EWG is-CO2When Me, the fullerene cyclopentene for organic photovoltaic battery have with
[C60] the comparable energy conversion efficiency of-PCBM, other fullerene cyclopentene compounds are also all with certain energy conversion effect
Rate.
Chuang etc. reported respectively at 2013 and 2015 yne compounds under the catalysis of alkyl phosphorus compound with
[60] [3+2] cycloaddition reaction generation fullerene cyclopentene derivatives (formula 2 and formula 3) occurs for fullerene.
They have carried out photoelectric properties test to the fullerene cyclopentene derivatives of report in 2015, these fullerene rings penta
The average energy transformation efficiency of ene derivative is 3.79 ± 0.29%, and maximum energy conversion efficiency can achieve 4.1%.
The excellent photoelectric properties of fullerene cyclopentene derivatives imply that it will exist as new a kind of fullerene derivate
Organic photovoltaic material obtains the application of great prospect.
Summary of the invention
The object of the present invention is to provide a kind of raw material is cheap and easily-available, synthesis technology is simple and substrate use scope is wide
[60] synthetic method of fullerene cyclopentene derivatives.
To achieve the goals above, the technical solution used in the present invention are as follows:
A kind of synthetic method of [60] fullerene cyclopentene derivatives is with [60] fullerene and 3- methylbutyraldehyd, primary amine
Raw material, single step reaction generate [60] fullerene cyclopentene derivatives, synthetic reaction equation are as follows:
Wherein, R is one of following group:
The catalyst is Mn (OAc)3·2H2O、Cu(OAc)2·H2O or Cu (OAc)2。
Preferably, the catalyst is Mn (OAc)3·2H2O。
Preferably, the molar ratio of [60] fullerene, 3- methylbutyraldehyd and primary amine is 1:(5~15): (5~15).
Preferably, the molar ratio of [60] fullerene, 3- methylbutyraldehyd and primary amine is 1:10:10.
Preferably, the molar ratio of [60] fullerene and catalyst is 1:(1~3).
Preferably, the molar ratio of [60] fullerene and catalyst is 1:2.
Preferably, the heating temperature of the reaction is 100~130 DEG C.
Preferably, the heating temperature of the reaction is 120 DEG C.
Preferably, the concrete operations of the synthetic reaction are as follows: firstly, [60] fullerene, catalysis are added in round-bottomed flask
Agent, 3- methylbutyraldehyd and primary amine add chlorobenzene and are completely dissolved reactant with Ultrasound Instrument ultrasound, and it is mixed then will to fill reaction
The round-bottomed flask for closing object, which is placed in oil bath, heats reaction, and reaction mixture is first passed through short silicagel column coarse filtration after the reaction was completed, molten
Agent decompression steams, later residue chromatography column chromatography for separation, and using carbon disulfide as eluant, eluent, what is be separated first is not anti-
Then [60] fullerene answered is [60] fullerene cyclopentene derivatives.
Compared with the synthetic method of existing fullerene synthesis cyclopentene derivatives, the invention has the following outstanding advantages:
1,1- amino -3,3- dimethyl-cyclopentene fullerene derivate has been synthesized, this is that cannot synthesize by known method
's；
2, synthesis material 3- methylbutyraldehyd, primary amine and catalyst acetic acid manganese/copper acetate, it is cheap and easily-available；
3, catalyst plays a crucial role in causing the reaction, and the reaction of no catalyst cannot occur；
4, the reaction time is short, it is only necessary to more than ten minutes；
5, easy to operate, wide application range of substrates has excellent functional group compatibility.Amido functional group wherein included
It can further react, provide fullerene derivate more with excellent configuration in organic photovoltaic Material Field for researcher.
Detailed description of the invention
Fig. 1: [60] fullerene cyclopentene derivatives A1H H NMR spectroscopy；
Fig. 2: [60] fullerene cyclopentene derivatives A13C H NMR spectroscopy；
Fig. 3: [60] fullerene cyclopentene derivatives B1H H NMR spectroscopy；
Fig. 4: [60] fullerene cyclopentene derivatives B13C H NMR spectroscopy；
Fig. 5: [60] fullerene cyclopentene derivatives C1H H NMR spectroscopy；
Fig. 6: [60] fullerene cyclopentene derivatives C13C H NMR spectroscopy；
Fig. 7: [60] fullerene cyclopentene derivatives D1H H NMR spectroscopy；
Fig. 8: [60] fullerene cyclopentene derivatives D13C H NMR spectroscopy；
Fig. 9: [60] fullerene cyclopentene derivatives E1H H NMR spectroscopy；
Figure 10: [60] fullerene cyclopentene derivatives E13C H NMR spectroscopy；
Figure 11: [60] fullerene cyclopentene derivatives F1H H NMR spectroscopy；
Figure 12: [60] fullerene cyclopentene derivatives F13C H NMR spectroscopy.
Specific embodiment
Above content of the invention is described in further details by the following examples, but the content invented is not by this reality
Apply the limitation of example.
Embodiment 1
[60] preparation of fullerene cyclopentene derivatives A
Specific preparation step are as follows:
By [60] fullerene (36.0mg, 0.05mmol), Mn (OAc)3·2H2O (26.8mg, 0.10mmol), 3- methyl fourth
Aldehyde (54 μ L, 0.50mmol) and(65 μ L, 0.50mmol) is added in 50mL round-bottomed flask, with ultrasound
Instrument ultrasound makes to be dissolved completely in the chlorobenzene of 10mL, immediately after by mixed liquor be placed in temperature be preset as in 120 DEG C of oil bath plus
Thermal agitation 15 minutes, reaction process was tracked with thin-layer chromatography (TLC) contact plate, until stopping reaction when reaction end.After reaction
Reaction mixture removes insoluble substance by short silicagel column coarse filtration, and solvent depressurizes back-out in Rotary Evaporators, and residue is used
Column chromatography for separation is chromatographed, using carbon disulfide as eluant, eluent, what is be separated first is unreacted [60] fullerene, followed by palm fibre
Color product [60] fullerene cyclopentene derivatives A.The relative productivity of [60] fullerene cyclopentene derivatives A obtained by the present embodiment is
53%.
[60] fullerene cyclopentene derivatives A:1H NMR (500MHz, DMSO-d6/CS2) δ 7.40 (d, J=8.5Hz,
2H), 6.82 (d, J=8.5Hz 2H), 6.50 (s, 1H), 4.85 (s, 2H), 3.76 (s, 3H), 3.01 (m, 1H), 1.40 (d, J
=6.7Hz, 6H)13C NMR (125MHz, DMSO-d6/CS2)(all 2C unless indicated)δ158.12(1C),
149.37,146.72(1C),146.19(1C),145.61,145.06,144.98(4C),144.83(4C),144.79,
144.59,144.36,143.96(4C),143.93,143.44,143.21,142.02,141.62(4C),141.54,
141.32,141.13,141.11,140.96,140.65,139.23,138.41,135.35,134.35,131.09(1C),
129.08(1C),128.99,116.10(1C),113.28,87.50(1C),78.63(1C),54.08(1C),51.94(1C),
26.05(1C),23.70。
Embodiment 2
[60] preparation of fullerene cyclopentene derivatives B
Specific preparation step are as follows:
By [60] fullerene (36.0mg, 0.05mmol), Mn (OAc)3·2H2O (26.8mg, 0.10mmol), 3- methyl fourth
Aldehyde (54 μ L, 0.50mmol) and(51 μ L, 0.50mmol) is added in 50mL round-bottomed flask.With Ultrasound Instrument ultrasound
Make to be dissolved completely in the chlorobenzene of 10mL, mixed liquor is placed in temperature immediately after and is preset as heating stirring in 120 DEG C of oil bath
13 minutes, reaction process was tracked with thin-layer chromatography (TLC) contact plate, until stopping reaction when reaction end.Reaction is mixed after reaction
Object is closed by short silicagel column coarse filtration, removes insoluble substance, solvent depressurizes back-out, residue chromatographic column in Rotary Evaporators
Chromatography, using carbon disulfide as eluant, eluent, what is be separated first is unreacted [60] fullerene, followed by brown product
[60] fullerene cyclopentene derivatives B.The relative productivity of [60] fullerene cyclopentene derivatives B is 45% in the present embodiment.
[60] fullerene cyclopentene derivatives B:1H NMR (500MHz, DMSO-d6/CS2) δ 7.26 (dd, J=5.3,
1.3Hz, 1H), 7.07-7.05 (m, 1H), 6.90 (dd, J=5.0,3.5Hz, 1H), 6.65 (s, 1H), 5.13 (d, J=
0.8Hz, 2H), 3.08-2.98 (m, 1H), 1.44 (d, J=6.7Hz, 6H)13C NMR (125MHz, DMSO-d6/CS2)(all
2C unless indicated)δ149.34,146.77(1C),146.23(1C),145.59,145.10,145.03,
144.99,144.88,144.85(4C),144.64,144.27,144.01(6C),143.47,143.26,142.06,
141.68,141.61,141.59,141.38,141.31,141.17(4C),141.04,140.70,139.26,138.43,
135.36,134.46,131.12(1C),126.02(1C),125.89(1C),125.34(1C),117.35(1C),87.20
(1C),78.66(1C),47.39(1C),26.13(1C),23.72。
Embodiment 3
[60] preparation of fullerene cyclopentene derivatives C
Specific preparation step are as follows:
By [60] fullerene (36.0mg, 0.05mmol), Mn (OAc)3·2H2O (26.8mg, 0.10mmol), 3- methyl fourth
Aldehyde (54 μ L, 0.50mmol) and(63 μ L, 0.50mmol) is added in 50mL round-bottomed flask.It is super with Ultrasound Instrument
Sound makes to be dissolved completely in the chlorobenzene of 10mL, mixed liquor is placed in temperature is immediately after preset as heating in 120 DEG C of oil bath and stir
It mixes 12 minutes, reaction process is tracked with thin-layer chromatography (TLC) contact plate, until stopping reaction when reaction end.It reacts after reaction
Mixture removes insoluble substance by short silicagel column coarse filtration, and solvent depressurizes back-out, residue chromatography in Rotary Evaporators
Column chromatography for separation, using carbon disulfide as eluant, eluent, what is be separated first is unreacted [60] fullerene, followed by brown produces
Object
[60] fullerene cyclopentene derivatives C.The opposite production of [60] fullerene cyclopentene derivatives C prepared by the present embodiment
Rate is 57%.
[60] fullerene cyclopentene derivatives C:1H NMR (500MHz, DMSO-d6/CS2)δ7.24–7.21(m,4H),
7.15-7.11 (m, 1H), 6.58 (s, 1H), 4.03 (t, J=7.5Hz, 2H), 3.22 (t, J=7.5Hz, 2H), 3.03-2.95
(m, 1H), 1.41 (d, J=7.0Hz, 6H)13C NMR (125MHz, DMSO-d6/CS2)(all 2C unless
indicated)δ149.13,146.64(1C),146.10(1C),145.08,144.93,144.90,144.84,144.71,
144.67,144.65,144.46,144.00,143.81(6C),143.35,143.09,141.94,141.53(4C),
141.43,141.33,141.05,140.96,140.93,140.56,139.11,138.54,138.11(1C),135.19,
134.17,130.71(1C),128.09,127.70,125.61(1C),114.16(1C),87.42(1C),78.43(1C),
48.97(1C),36.32(1C),25.93(1C),23.67。
Embodiment 4
[60] preparation of fullerene cyclopentene derivatives D
Specific preparation step are as follows:
By [60] fullerene (36.0mg, 0.05mmol), Mn (OAc)3·2H2O (26.8mg, 0.10mmol), 3- methyl fourth
Aldehyde (54 μ L, 0.50mmol) and(59 μ L, 0.50mmol) is added in 50mL round-bottomed flask.It is super with Ultrasound Instrument
Sound makes to be dissolved completely in the chlorobenzene of 10mL, mixed liquor is placed in temperature is immediately after preset as heating in 120 DEG C of oil bath and stir
It mixes 18 minutes, reaction process is tracked with thin-layer chromatography (TLC) contact plate, until stopping reaction when reaction end.It reacts after reaction
Mixture removes insoluble substance by short silicagel column coarse filtration, and solvent depressurizes back-out, residue chromatography in Rotary Evaporators
Column chromatography for separation, using carbon disulfide as eluant, eluent, what is be separated first is unreacted [60] fullerene, followed by brown produces
Object [60] fullerene cyclopentene derivatives D.The relative productivity of [60] fullerene cyclopentene derivatives D prepared by the present embodiment is
63%.
[60] fullerene cyclopentene derivatives D:1H NMR (500MHz, DMSO-d6/CS2)δ7.10–7.08(m,1H),
6.88-6.86 (m, 2H), 6.61 (s, 1H), 4.07 (t, J=7.3Hz, 2H), 3.45 (t, J=7.3Hz, 2H), 3.04-2.95
(m, 1H), 1.42 (d, J=6.5Hz, 6H)13C NMR (125MHz, DMSO-d6/CS2)(all 2C unless
indicated)δ149.30,146.82(1C),146.28(1C),145.21,145.11,145.07,145.03,144.89,
144.85,144.81,144.66,144.15,143.99(6C),143.53,143.27,142.11,141.70(4C),
141.61,141.48,141.23,141.14,141.10,140.73,140.33(1C),139.29,138.72,135.44,
134.37,130.81(1C),126.23(1C),124.84(1C),123.39(1C),114.91(1C),87.56(1C),78.59
(1C),49.27(1C),30.45(1C),26.11(1C),23.80。
Embodiment 5
[60] preparation of fullerene cyclopentene derivatives E
Specific preparation step are as follows:
By [60] fullerene (36.0mg, 0.05mmol), Mn (OAc)3·2H2O (26.8mg, 0.10mmol), 3- methyl fourth
Aldehyde (54 μ L, 0.50mmol) and(61.6mg, 0.50mmol) is added in 50mL round-bottomed flask.With super
Sound instrument ultrasound makes to be dissolved completely in the chlorobenzene of 10mL, and mixed liquor is placed in temperature immediately after and is preset as in 120 DEG C of oil bath
Heating stirring 10 minutes, reaction process was tracked with thin-layer chromatography (TLC) contact plate, until stopping reaction when reaction end.Reaction terminates
Reaction mixture removes insoluble substance by short silicagel column coarse filtration afterwards, and solvent depressurizes back-out, residue in Rotary Evaporators
With chromatography column chromatography for separation, using carbon disulfide as eluant, eluent, what is be separated first is unreacted [60] fullerene, followed by
Brown product [60] fullerene cyclopentene derivatives E.[60] fullerene cyclopentene derivatives E's is opposite prepared by the present embodiment
Yield is 90%.
[60] fullerene cyclopentene derivatives E:1H NMR (800MHz, DMSO-d6/CS2) δ 7.48 (d, J=9.6Hz,
2H), 6.83 (d, J=9.6Hz, 2H), 6.76 (s, 1H), 3.74 (s, 3H), 3.13-3.08 (m, 1H), 1.52 (d, J=
6.5Hz,6H).13C NMR (125MHz, DMSO-d6/CS2)(all 2C unless indicated)δ156.59(1C),
149.07,146.85(1C),146.31(1C),146.22,145.17,145.13,145.11,144.96,144.89,
144.73,144.70,144.66,144.10.144.08,144.05,143.54,143.32,142.10,141.78,141.70,
141.67,141.30(4C),141.26,141.02,140.81,139.34,138.49,136.39(1C),135.30,
134.54,130.69(1C),127.22,119.96(1C),113.94,88.75(1C),78.31(1C),54.35(1C),
26.33(1C),23.89。
Embodiment 6
[60] preparation of fullerene cyclopentene derivatives F
Specific preparation step are as follows:
By [60] fullerene (36.0mg, 0.05mmol), Mn (OAc)3·2H2O (26.8mg, 0.10mmol), 3- methyl fourth
Aldehyde (54 μ L, 0.50mmol) and(56 μ L, 0.50mmol) is added in 50mL round-bottomed flask.With Ultrasound Instrument ultrasound
Make to be dissolved completely in the chlorobenzene of 10mL, mixed liquor is placed in temperature immediately after and is preset as heating stirring in 120 DEG C of oil bath
10 minutes, reaction process was tracked with thin-layer chromatography (TLC) contact plate, until stopping reaction when reaction end.Reaction mixture passes through short
Silicagel column coarse filtration removes insoluble substance, and solvent depressurizes back-out in Rotary Evaporators, and residue, which is used, chromatographs column chromatography for separation,
Using carbon disulfide as eluant, eluent, what is be separated first is unreacted [60] fullerene, followed by brown product [60] fowler
Alkene cyclopentene derivatives F.The relative productivity of [60] fullerene cyclopentene derivatives F is 51% prepared by the present embodiment.
[60] fullerene cyclopentene derivatives F:1H NMR (500MHz, DMSO-d6/CS2)δ7.24–7.15(m,2H),
7.10 (t, J=2.0Hz, 1H), 6.88 (s, 1H), 6.63-6.61 (m, 1H), 3.73 (s, 3H), 3.17-3.09 (m, 1H),
1.53 (d, J=6.5Hz, 6H)13C NMR (125MHz, DMSO-d6/CS2)(all 2C unless indicated)δ
159.46(1C),149.06,146.79(1C),146.23(1C),145.74,145.16,145.08(4C),144.93,
144.83,144.79,144.69,144.62(1C),144.55,144.04(3C),144.01,143.51,143.25,
142.05,141.76,141.64,141.57,141.27(4C),141.19,140.95,140.80,139.34,138.19,
135.43,134.42,129.87(1C),129.22(1C),121.06(1C),117.14(1C),110.95(1C),109.45
(1C),88.07(1C),78.62(1C),54.15(1C),26.29(1C),23.82。
It is obvious to a person skilled in the art that invention is not limited to the details of the above exemplary embodiments, Er Qie
In the case where without departing substantially from spirit or essential attributes of the invention, the present invention can be realized in other specific forms.Therefore, no matter
From the point of view of which point, the present embodiments are to be considered as illustrative and not restrictive, and the scope of the present invention is by appended power
Benefit requires rather than above description limits, it is intended that all by what is fallen within the meaning and scope of the equivalent elements of the claims
Variation is included within the present invention.
In addition, it should be understood that although this specification is described in terms of embodiments, but not each embodiment is only wrapped
Containing an independent technical solution, this description of the specification is merely for the sake of clarity, and those skilled in the art should
It considers the specification as a whole, the technical solutions in the various embodiments may also be suitably combined, forms those skilled in the art
The other embodiments being understood that.
Claims (9)
1. a kind of synthetic method of [60] fullerene cyclopentene derivatives, it is characterised in that: with [60] fullerene and 3- methyl fourth
Aldehyde, primary amine are raw material, and single step reaction generates [60] fullerene cyclopentene derivatives, synthetic reaction equation are as follows:
Wherein, R is one of following group:
The catalyst is Mn (OAc)3·2H2O、Cu(OAc)2·H2O or Cu (OAc)2。
2. synthetic method as described in claim 1, which is characterized in that the catalyst is Mn (OAc)3·2H2O。
3. synthetic method as described in claim 1, which is characterized in that [60] mole of fullerene, 3- methylbutyraldehyd and primary amine
Than for 1:(5~15): (5~15).
4. synthetic method as claimed in claim 3, which is characterized in that [60] mole of fullerene, 3- methylbutyraldehyd and primary amine
Than for 1:10:10.
5. synthetic method as described in claim 1, which is characterized in that [60] molar ratio of fullerene and catalyst is about 1:(1
~3).
6. synthetic method as claimed in claim 5, which is characterized in that [60] molar ratio of fullerene and catalyst is 1:2.
7. synthetic method as described in claim 1, which is characterized in that the heating temperature of the reaction is 100~130 DEG C.
8. synthetic method as claimed in claim 6, which is characterized in that the heating temperature of the reaction is 120 DEG C.
9. such as the described in any item synthetic methods of claim 1-8, which is characterized in that concrete operations are as follows: firstly, in round-bottomed flask
Middle addition [60] fullerene, catalyst, 3- methylbutyraldehyd and primary amine, add chlorobenzene and keep reactant complete with Ultrasound Instrument ultrasound
Then the round-bottomed flask for filling reaction mixture is placed in heat in oil bath and react, after the reaction was completed by reaction mixture by dissolution
Short silicagel column coarse filtration is first passed through, solvent under reduced pressure steams, and residue chromatography column chromatography for separation, is elution with carbon disulfide later
Agent, what is be separated first is unreacted [60] fullerene to get [60] fullerene cyclopentene derivatives.
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| CN110305023A (en) * | 2019-06-25 | 2019-10-08 | 湖北大学 | One kind [60] fullerene cyclopentane derivatives and the preparation method and application thereof |
| CN110444672A (en) * | 2019-07-25 | 2019-11-12 | 武汉理工大学 | A kind of fullerene derivate, preparation method and application |
| CN113004190A (en) * | 2021-03-05 | 2021-06-22 | 湖北大学 | Preparation method of N-phenyl [60] fullerene pyrroline |
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| CN114539151A (en) * | 2022-02-21 | 2022-05-27 | 湖北大学 | Method for preparing [60] fullerene dihydropyridine-3-one derivative by catalyzing p-methoxybenzoic acid and copper acetate and product |
| RU2785692C1 (en) * | 2022-03-11 | 2022-12-12 | Федеральное государственное бюджетное научное учреждение "УФИМСКИЙ ФЕДЕРАЛЬНЫЙ ИССЛЕДОВАТЕЛЬСКИЙ ЦЕНТР РОССИЙСКОЙ АКАДЕМИИ НАУК" | METHOD FOR OBTAINING 1,9-(1',4'-OXATHIANO-4'-OXIDE)-1,9-DIHYDRO-(C60-Ih)[5,6]FULLERENE |
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2018
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| CN110305023A (en) * | 2019-06-25 | 2019-10-08 | 湖北大学 | One kind [60] fullerene cyclopentane derivatives and the preparation method and application thereof |
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| CN110444672A (en) * | 2019-07-25 | 2019-11-12 | 武汉理工大学 | A kind of fullerene derivate, preparation method and application |
| CN110444672B (en) * | 2019-07-25 | 2021-07-02 | 武汉理工大学 | Fullerene derivative, preparation method and application thereof |
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| CN113024464A (en) * | 2021-03-05 | 2021-06-25 | 湖北大学 | Method for preparing [60] fullerene tetrahydroquinoline derivative based on triflic acid/p-toluenesulfonic acid catalysis |
| CN113024464B (en) * | 2021-03-05 | 2022-05-13 | 湖北大学 | Method for preparing [60] fullerene tetrahydroquinoline derivative based on triflic acid/p-toluenesulfonic acid catalysis |
| CN114539151A (en) * | 2022-02-21 | 2022-05-27 | 湖北大学 | Method for preparing [60] fullerene dihydropyridine-3-one derivative by catalyzing p-methoxybenzoic acid and copper acetate and product |
| RU2785692C1 (en) * | 2022-03-11 | 2022-12-12 | Федеральное государственное бюджетное научное учреждение "УФИМСКИЙ ФЕДЕРАЛЬНЫЙ ИССЛЕДОВАТЕЛЬСКИЙ ЦЕНТР РОССИЙСКОЙ АКАДЕМИИ НАУК" | METHOD FOR OBTAINING 1,9-(1',4'-OXATHIANO-4'-OXIDE)-1,9-DIHYDRO-(C60-Ih)[5,6]FULLERENE |
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