CN103373892B - Three-dimensional nanometer graphene based on triptycene and preparation method thereof - Google Patents
Three-dimensional nanometer graphene based on triptycene and preparation method thereof Download PDFInfo
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Abstract
The invention discloses three-dimensional nanometer graphene based on triptycene and a synthetic method thereof. The three-dimensional nanometer graphene based on the triptycene is a novel coronene-modified triptycene derivative. The preparation method comprises the following steps of: firstly carrying out a Sonogashira coupling reaction on triiodo triptycene to obtain a tri-acetenyl triptycene derivative; then carrying out a Diels-Alder reaction on the tri-acetenyl triptycene derivative to obtain a coronene triptycene derivative; finally carrying out an FeCl3 oxidation and cyclization reaction in an organic solvent (dichloromethane) under the conditions of gas protection (Ar) and normal temperature for 15-240 minutes to obtain the three-dimensional nanometer graphene based on the triptycene. The preparation method disclosed by the invention is novel and higher in yield. The prepared three-dimensional nanometer graphene based on the triptycene disclosed by the invention has an outstanding effect on the aspect of cell imaging.
Description
Technical field
The invention belongs to chemical field, relate to three-dimensional manometer Graphene.
Background technology
From nineteen forty-two, the people such as Bartlett (J.Am.Chem.Soc., 1942,64,2649.) first by anthracene, after obtaining a kind of novel cpd-triptycene (triptycene) by the synthesis of polystep reaction low-yield, synthesis and the research of triptycene and derivative thereof just cause the broad interest of people.The unique three-dimensional rigid structure that triptycene and derivative thereof have and distinctive photoelectricity performance, make it be widely used in many fields such as molecule machine, materials chemistry and supramolecular chemistry.
Six benzos cool (Hexa-peri-hexabenzocoronenes) (be called for short HBC) are then that of being formed by 13 phenyl ring has the electron conjugated unit system of super large.Initial by the people such as Clar (Proc.Chem.Soc.1958,150) by after dibenzo-peri-naphthene bromination, by the coupling of self and further Heating Dehydrogenation under heating condition, a kind of yellow solid compound-six benzo of final synthesis is cool.The high-density electron system that this compound has due to itself and strong π-pi-conjugated feature, make it can as an excellent electron acceptor(EA), very advantageous is applied in supramolecular chemistry field, simultaneously also due to its plane, high thermal stability, excellent electron delocalization performance, also has very large potential application in electro-conductive material.
But about using triptycene as skeleton, modify so that six benzos are cool, thus obtain a kind of novel three-dimensional nano-graphite ene derivative based on triptycene and synthetic method also not yet had report.
Summary of the invention
Task of the present invention is to provide a kind of three-dimensional manometer Graphene based on triptycene and preparation method thereof,
Realizing technical scheme of the present invention is: the three-dimensional manometer Graphene based on triptycene provided by the invention, has with structure following formula (I) Suo Shi,
Wherein R=H or t-bu.
The preparation method of the above-described three-dimensional manometer Graphene based on triptycene, comprises the following steps:
Step one: by with compound 2,6, the 14-tri-iodo triptycene shown in following formula IV with join in organic solvent triethylamine, with Pd (PPh with the compound phenylacetylene shown in Formula Il or tert.-butylbenzene acetylene
3)
4/ CuI is catalyzer; under the condition of protection of inert gas; 70-80 DEG C of reaction obtains with the compound three phenylacetylene base triptycene derivative shown in following formula V for 1-36 hour; compound 2; 6,14-tri-iodo triptycene (IV) and compound phenylacetylene or tert.-butylbenzene acetylene, Pd (PPh
3)
4, CuI mol ratio be 1: 3.14: 0.15: 0.25;
Step 2: the compound tetraphenylcyclopentadienone compounds shown in step one gained three phenylacetylene base triptycene derivative and following formula III is added in organic solvent (phenyl ether), under the condition that rare gas element (Ar) is protected, 260 DEG C of reactions obtain with the compound coronene triptycene derivative shown in following formula VI for 0.5-72 hour, and the mol ratio of compound three phenylacetylene base triptycene derivative and compound tetraphenylcyclopentadienone compounds is 1: 3.25;
Step 3: add in organic solvent (methylene dichloride) by step 2 gained coronene triptycene derivative, under the condition of protection of inert gas, adds the FeCl dissolved with Nitromethane 99Min.
3solution, normal-temperature reaction 15-240min obtains the three-dimensional manometer Graphene based on triptycene, compound coronene triptycene derivative (VI) and FeCl
3mol ratio be 1: 64.50.
The reaction times of above-mentioned steps three is 15-240min, and the temperature of reaction of above-mentioned steps three is 25-45 DEG C.
Above-mentioned preparation method's gained based on the three-dimensional manometer Graphene product of triptycene through column chromatography and recrystallization purifying.
Synthetic route of the present invention is as follows:
Three-dimensional manometer Graphene based on triptycene provided by the invention, has strong fluorescence property, in cell imaging, has unusual effect.
Following compound is related in present patent application:
In present patent application, by Compound II per called after phenylacetylene base compounds; By compound III called after tetraphenylcyclopentadienone compounds; By compound IV called after 2,6,14-tri-iodo triptycene; By compound V called after three phenylacetylene base triptycene derivative; By compound VI called after coronene triptycene derivative.
The present invention has following features:
(1) hexaphenyl benzene triptycene derivative under argon shield normal temperature through FeCl
3dehydrocyclization obtains the novel three-dimensional nano-graphite ene derivative based on triptycene, and productive rate is high, can reach 78%-90%, and reaction conditions is simply gentle.
(2) adopt present method to synthesize the compound obtained to be separated with column chromatography, adopt silica gel as stationary phase, eluent can select dichloromethane-petroleum ether, ethyl acetate-light petrol, tetrahydrofuran (THF)-sherwood oil, methylene dichloride-normal hexane, the mixed solvents such as ethyl acetate-hexane.
(3) the novel three-dimensional nano-graphite ene derivative based on triptycene obtained synthesized by, its novel structure, also not yet someone prepares at present.High π cool to the three-dimensional rigid structure of triptycene and six benzos-pi-conjugated system organically combines by the present invention, construct a kind of novel nano Graphene derivative with three-dimensional structure, because it has strong fluorescence property, in cell imaging, there is unusual effect.
Accompanying drawing explanation
Fig. 1 three-dimensional manometer Graphene (R=t-Bu) structural formula;
Fig. 2 three-dimensional manometer Graphene (R=t-Bu) and HepG2 liver cancer cell hatch fluorescence imaging figure altogether.
Embodiment
In order to better understand the present invention, below in conjunction with example the present invention done and describe in detail further, but the scope of protection of present invention being not limited to the scope that example is told about.
Embodiment 12, the synthesis of 6,14-tri-phenylacetylene base triptycene
By 200mg tri-iodo triptycene (0.315mmol), 37mg Pd (PPh
3)
4(0.036mmol) add in 100ml bottle with two necks with 11.6mgCuI (0.061mmol), logical argon gas, add 200ul phenylacetylene (0.99mmol) and 40ml triethylamine, then stirring and refluxing at 70 DEG C, stopped reaction after 48 hours, add methylene chloride dissolving, successively with dilute hydrochloric acid solution, water washing, dichloromethane extraction, anhydrous Na
2sO
4drying, through column chromatography, dichloromethane-petroleum ether (1: 3) selected by eluent, obtains white solid 2,6,14-tri-phenylacetylene base triptycene.
Productive rate: 68.0%. fusing point: 184-185 DEG C
1H NMR(400MHz，CDCl
3)：δ5.45(s，1H)，5.46(s，1H)，7.25(dd，J＝7.6，1.2Hz，3H)，7.33-7.37(m，9H)，7.40(d，J＝7.6Hz，3H)，7.50-7.53(m，6H)，7.60(d，J＝1.2Hz，3H).
13CNMR(100MHz，CDCl
3)：δ53.41，53.50，88.77，89.40，120.39，120.42，123.32，123.77，123.80，126.86，128.16，128.31，129.09，131.58，144.47，144.49，144.51，144.57.EI-MS：m/z555(M+).Anal.Calcd for C
44H
26：C，95.28；H，4.72；Found：C，95.01；H，5.08.
Embodiment 22, the synthesis of 6,14-tri-tert phenylacetylene base triptycene
By 200mg tri-iodo triptycene (0.315mmol), 37mg Pd (PPh
3)
4(0.036mmol) add in 100ml bottle with two necks with 11.6mgCuI (0.061mmol), logical argon gas, add 178ul to tert.-butylbenzene acetylene (0.99mmol) and 40ml triethylamine, then stirring and refluxing at 70 DEG C, stopped reaction after 24 hours, add methylene chloride dissolving, successively with dilute hydrochloric acid solution, water washing, dichloromethane extraction, anhydrous Na
2sO
4drying, through column chromatography, dichloromethane-petroleum ether (1:10) selected by eluent, obtains white solid product 2,6,14-tri-tert phenylacetylene base triptycene.
Productive rate: 70.4%. fusing point: 190-193 DEG C
1H NMR(400MHz，CDCl
3)：δ1.310(s，9H)，5.404(s，1H)，5.413(s，1H)，7.210(dd，J＝2.8，2.8Hz，3H)，7.335-7.355(m，9H)，7.421(d，J＝8HZ，6H)，7.556(s，3H).
13C NMR(100MHz，CDCl
3)：δ29.50，29.67，30.31，31，17，34.77，38.97，53.38，53.47，88.77，88.86，120.28，120.58，123.70，125.31，126.81，128.98，131.29，144.35，144.48，151.41.EI-MS：m/z 723(M+).Anal.Calcd for C
56H
50：C，93.03；H，6.97；Found：C，93.38；H，6.61.
Embodiment 32, the synthesis of 6,14-tri-(2,3,4,5,6-pentapheneyl)-phenyl triptycene
By 100mg tri-phenylacetylene base triptycene (0.181mmol), 215mg tetraphenylcyclopentadienone (0.560mmol) and 1.5ml phenyl ether, argon shield, at 260 DEG C, heated and stirred reaction, reacted completely after 48 hours.Through column chromatography, dichloromethane-petroleum ether (1: 3) selected by eluent, obtains yellow solid 2,6,14-tri-(2,3,4,5,6-pentapheneyl)-phenyl triptycene.
Productive rate: 52.0%. fusing point: > 300 DEG C
2,6,14-tri-(2,3,4,5,6-pentapheneyl)-phenyl triptycene
1H NMR(400MHz，CDCl
3)：δ4.05(s，1H)，4.28(s，1H)，6.29-6.36(m，9H)，6.48-6.61(m，9H)，6.72-6.82(m，66H).
13C NMR(100MHz，CDCl
3)：δ52.79，53.00，121.63，125.02，125.10，125.30，125.35，126.10，126.36，126.53，126.67，126.73，127.96，128.10，129.89，129.92，131.15，131.27，131.44，131.58，131.64，131.72，135.84，136.28，139.73，140.04，140.12，140.19，140.23，140.33，140.37，140.40，140.46，140.49，140.68，140.72，140.78，140.82，142.36，143.14，143.66，143.89.MALDI-TOF-MS：m/z 1647(M+Na+)，1663(M+K+).Anal.Calcd for C
128H
86：C，94.66；H，5.34；Found：C，95.02；H，5.50.
Embodiment 42, the synthesis of 6,14-tri-(2,3,4,5,6-five tert-butyl-phenyl)-phenyl triptycene
By the 130mg 4-tertiary butyl-three phenylacetylene base triptycene (0.181mmol); 215mg tetra--4-trimethylphenylmethane base-cyclopentadienone (0.560mmol) and 1.5ml phenyl ether; argon shield, at 260 DEG C, heated and stirred reaction, reacted completely after 48 hours.Dichloromethane-petroleum ether (1: 9) selected by eluent, obtains yellow solid 2,6,14-tri-(2,3,4,5,6-five tert-butyl-phenyl)-phenyl triptycene through column chromatography.
Productive rate: 43.0%. fusing point: > 300 DEG C
2,6,14-tri-(2,3,4,5,6-five tert-butyl-phenyl)-phenyl triptycene
1H NMR(400MHz，CDCl
3)：δ1.068-1.116(m，135H)，4.239(s，1H)，4.422(s，lH)，6.168(d，J＝7.6HZ，9H)，6.353(d，J＝7.6HZ，6H)，6.542-6.899(m，54H).
13C NMR(100MHz，CDCl
3)：δ52.79，53.04，118.89，120.47，120.78，122.99，123.22，126.37，126.56，128.27，129.74，131.13，131.21，136.63，137.77，138.05，138.18，139.88，140.21，140.35，140.56，142.29，143.04，143.48，143.99，147.24，147.34，147.44，157.25.MALDI-TOF-MS：2466(M+).Anal.Calcd for C
188H
206：C，91.58；H，8.42；Found：C，91.02；H，8.50.
The synthesis of embodiment 5 three-dimensional manometer Graphene (R=H)
By 150mg2,6,14-tri-(2,3,4,5,6-pentapheneyl)-phenyl triptycene (0.082mmol) and 70ml methylene dichloride add in 150ml bottle with two necks, pass into argon gas, then by 882mg FeCl
3(5.292mmol) Nitromethane 99Min. (5ml) solution slowly adds in bottle with two necks, stirs under normal temperature, stopped reaction after reaction 70min, collected by filtration, with methanol wash, obtain brown solid after drying, this product is insoluble to common organic solvents.
Productive rate: 76.0%. fusing point: > 300 DEG C
MALDI-TOF-MS：m/z 1588(M+)，1611(M+Na+).Anal.Calcdfor C128H50：C，96.83；H，3.17；Found：C，97.02；H，2.89.
The synthesis of embodiment 6 three-dimensional manometer Graphene (R=t-bu)
By 205mg 2,6,14-tri-(2,3,4,5,6-five tert-butyl-phenyl)-phenyl triptycene (0.082mmol) and 70ml methylene dichloride add in 150ml bottle with two necks, pass into argon gas, then slowly added in bottle with two necks by Nitromethane 99Min. (5ml) solution of 882mg FeCl3 (5.292mmol), stir under normal temperature, stopped reaction after reaction 125min, removal of solvent under reduced pressure, dissolves with methylene dichloride, washing removing FeCl3, dichloromethane extraction.Through column chromatography, dichloromethane-petroleum ether (1: 9) selected by eluent, obtains yellow three-dimensional manometer Graphene (R=t-Bu) after recrystallization.
Productive rate: 87.0%. fusing point: > 300 DEG C
1H NMR(400MHz，CDCl
3)：δ1.38(s，18H)，1.73(s，9H)，1.75-1.76(d，27H)，1.787-1.797(d，27H)，1.876(s，45H)，1.899(s，45H)，2.307(s，9H)，8.234(s，1H)，8.886(s，1H)，9.179-9.348(m，25H)，9.462(s，3H)，9.517(s，1H)，9.721(s，1H))，9.816(d，J＝10.4HZ，3H).
13C NMR(100MHz，CDCl
3)：δ31.85，31.96，32.00，32.04，32.13，32.31，32.39，32.83，35.40，35.66，35.71，35.75，35.85，35.95，36.36，52.70，53.30，118.93，119.98，120.46，120.56，120.62，120.73，123.86，123.99，125.28，128.87，130.13，130.22，130.46，130.54，140.64，145.94，149.00，149.13，149.31.MALDI-TOF-MS：m/z 2426(M
+).Anal.Calcd for C
128H
86：C，92.95；H，7.05；Found：C，92.62；H，7.28.
The cell imaging experiment of embodiment 7 three-dimensional manometer Graphene (R=t-bu):
The three-dimensional manometer Graphene (R=t-Bu) that we select embodiment 6 to prepare, its structural formula is shown in Fig. 1, first by this Graphene compound dissolution in tetrahydrofuran (THF), be mixed with the tetrahydrofuran solution that concentration is 0.2mg/ml, by pluronic F68, (poly (ethylene glycol)-block-poly (propylyene glycol)-block-poly (ethylene glycol) is dissolved in water, is mixed with the aqueous solution that concentration is 1mg/ml simultaneously.The tetrahydrofuran solution getting 0.5ml Graphene compound drops in the aqueous solution of 5ml pluronic F68, then revolves after steaming removing THF, is finally settled to 10ml with water, obtains nanoparticle.Cell imaging research is carried out with this sample, concrete operations are: after HepG2 liver cancer cell creep plate 24h, (F68 concentration is 500ug/ml to the substratum adding containing sample, Graphene compound concentration is 10ug/ml), 37 DEG C of degree hatch 0.5h, after 1.5,3h, cold pbs washes 3 times, and 4% paraformaldehyde fixes 20min.Again with 50% glycerine pbs mounting, laser confocal microscope film making (488nm laser excitation, 525nm launches spectral filter, exposure 2s).Result shows (see Fig. 2), and along with the growth of time, the Fluorescence Increasing of cell, illustrates that the content that nanoparticle enters cell increases gradually, have time effect.This three-dimensional manometer Graphene based on triptycene of this result display has strong fluorescence property, in cell imaging, have unusual effect.
Claims (7)
1., based on a three-dimensional manometer Graphene for triptycene, there is structure shown in formula I,
2. according to claim 1 have with the preparation method of the three-dimensional manometer Graphene based on triptycene of structure shown in following formula I,
Comprise the following steps:
Step one: by with compound 2,6, the 14-tri-iodo triptycene shown in following formula IV with join in organic solvent triethylamine, with Pd (PPh with the compound phenylacetylene shown in Formula Il or tert.-butylbenzene acetylene
3)
4/ CuI is catalyzer, and under the condition of protection of inert gas, 70-80 DEG C of reaction obtains with the compound three phenylacetylene base triptycene derivative shown in following formula V for 1-36 hour;
Step 2: the compound tetraphenylcyclopentadienone compounds shown in step one gained three phenylacetylene base triptycene derivative and following formula III is added in organic solvent phenyl ether; under the condition of protection of inert gas; 260 DEG C of reactions obtain with the compound coronene triptycene derivative shown in following formula VI for 0.5-72 hour
Step 3: add in organic solvent dichloromethane by step 2 gained coronene triptycene derivative, under the condition of protection of inert gas, adds the FeCl dissolved with Nitromethane 99Min.
3solution, normal-temperature reaction 15-240min obtains the three-dimensional manometer Graphene based on triptycene.
3. the preparation method of the three-dimensional manometer Graphene based on triptycene according to claim 2, is characterized in that, in step one, and compound 2,6,14-tri-iodo triptycene and compound phenylacetylene or tert.-butylbenzene acetylene, Pd (PPh
3)
4, CuI mol ratio be 1: 3.14: 0.15: 0.25.
4. the preparation method of the three-dimensional manometer Graphene based on triptycene according to claim 2, is characterized in that, in step 2, the mol ratio of compound three phenylacetylene base triptycene derivative and compound tetraphenylcyclopentadienone compounds is 1: 3.25.
5. the preparation method of the three-dimensional manometer Graphene based on triptycene according to claim 2, is characterized in that, in step 3, and compound coronene triptycene derivative and FeCl
3mol ratio be 1: 64.50.
6. the preparation method of the three-dimensional manometer Graphene based on triptycene according to claim 2, is characterized in that, the rare gas element described in step one to three is Ar or nitrogen.
7. the preparation method of the three-dimensional manometer Graphene based on triptycene according to claim 2, is characterized in that the three-dimensional manometer Graphene of gained based on triptycene is through column chromatography and recrystallization purifying.
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