CN1687251A - Method for preparing nonlinear optical material of linkage nano carbon tubes of polythiophene methylene - Google Patents
Method for preparing nonlinear optical material of linkage nano carbon tubes of polythiophene methylene Download PDFInfo
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- CN1687251A CN1687251A CN 200510013333 CN200510013333A CN1687251A CN 1687251 A CN1687251 A CN 1687251A CN 200510013333 CN200510013333 CN 200510013333 CN 200510013333 A CN200510013333 A CN 200510013333A CN 1687251 A CN1687251 A CN 1687251A
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- methylene
- octyl group
- amino
- dioxane
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Abstract
The present invention discloses a preparation method of polythiophene methylene bonded carbon nano tube non-linear optical material. Said method includes the following processes: dissolving 3-octyl thiophene and 4-aminobenzaldehyde in dioxane, adding concetnrated sulfuric acid catalyst, under the protection of nitrogen gas synthesizing poly[(3-octyl thiophene)-2,5-di(4-aminobenzane)]; dissolving said compound in dioxane, adding tetrachlorobenzoquinone to obtain poly[(3-octyl thiophene)-2,5-di(4-aminobenzene)], then dissolving said compound in dioxane, and adding multiwall or single-wall carbon nano tube containing acyl chloride group so as to obtain the polythiophene methylene bonded carbon nano tube.
Description
Technical field
The present invention relates to a kind of preparation method of nonlinear optical material of linkage nano carbon tubes of polythiophene methylene, belong to the synthetic technology of organic non linear optical material.
Background technology
The big πDian Zi delocalization structure of carbon nanotube uniqueness causes the interest of people to its nonlinear optical property research.Xie (R.Xie, J.Jiang, Appl.Phys.Lett., 71 (8), 1029-1031,1997), Wan (X.Wan, J.Dong, D.Xing, Phys.Rev.B, 58,6756,1998), Margulis (V.Margulis, T.Sizikova, PhysicaB, 245,173-189,1998) leader's seminar adopts diverse ways that the nonlinear optical property of carbon nanotube has been carried out theoretical modeling respectively, finds that its second order supramolecule polarizability γ can reach 10
-29Esu.Up to the present, people also are in the starting stage to the experimental study of carbon nanotube nonlinear optical property.The leaf pendant string leader's of physics institute of China Chinese Academy of Sciences in 1999 seminar (X.C.Li, J.H.Si, B.H.Chang, G.Xu, Q.G.Yang, P.X.Ye, J.H.Fan, M.X.Wan, Appl.Phys.Lett., 74 (2): 164-166,1999), adopt the method for four-wave mixing, at first measure the third-order nonlinear susceptibility of many walls CNTs, x
(3)=6.460 * 10
-14Esu (30ps, 1024nm).The bright leader's of the Gong Qi of Peking University seminar (S.F.Wang, W.T.Huang, H.Yang, Q.H.Gong, Z.J.Shi, X.H.Zhou, D.Qiang, Z.N.Gu, Chem.Phys.Lett.320,411-414,2000), the third-order nonlinear susceptibility of the colloidal solution of the single wall CNT/DMF of the optical kerr effect commercial measurement gained of employing femtosecond time resolution, x
(3)=4 * 10
-13Esu (120fs, 820nm).
Above-mentioned research is actually to be carried out in the suspension of carbon nanotube, and when concentration was higher, suspension was very unstable, hindered the further research to its performance and application.Therefore people thirst for accessing stable carbon nano-tube solution very much.People find that under study for action carbon nano-tube/polymer composite material shows the good solubility energy in organic solvent, therefore gradually carbon nanotube nonlinear optical property research work emphasis are transferred on the carbon nano-tube/polymer composite material from carbon nano tube suspension.Suat Hong Goh leader's seminar (Zhaoxia Jin, Xuan Sun, Guoqin Xu, Suat Hong Goh, Wei Ji, Chem.Phys.Lett., 318,505-510,2000) matrix material that, has prepared a series of CNT/ polymkeric substance by methods such as physical blending and chemical bondings, as PEG, P2VP, the CNT that P4VP and PVPh coat, and the CNT of PEO bonding (PEO-CNT).Adopt the method for Z-Scan to study its third-order nonlinear optical effect and light limiting effect.Non-linear absorption coefficient β=2.1 * 10 of PEO-CNT wherein
-10MV
-1, nonlinear refractive index n
2=1.2 * 10
-17m
2W
-1The W.J.Blau leader's (S.M.O ' Flaherty of seminar, S.V.Hold, M.E.Brennan, W.J.Blau, Journal of the Optical Society of America B:Optical Physics 20 (1): 49-58,2003), the matrix material (CNT/PmPV) that has prepared PmPV and CNT, adopt the method for Z-Scan to study its third-order nonlinear optical effect and light limiting effect, the imaginary part Im{x of third-order nonlinear susceptibility
(3)1.1 * 10
-10Esu.
The nonlinear optical material that existing organic polymer is carbon nano-tube modified, because the polymkeric substance selected for use is the less conjugated polymers of linear polymer or non-linear optical effect (as PmPV etc.), and do not form the intramolecular charge transmission system, therefore its nonlinear optical response is less, can not satisfy the application requiring of light shutter device.
Summary of the invention
The object of the present invention is to provide a kind of preparation method of nonlinear optical material of linkage nano carbon tubes of polythiophene methylene.With present method synthetic optical material, not only have higher third-order nonlinear optical coefficient, and have good solubility and film-forming properties.
The present invention is realized by following technical proposals, a kind of preparation method of nonlinear optical material of linkage nano carbon tubes of polythiophene methylene, and this method is characterized in that comprising following process:
1. poly-[(3-octyl group thiophene)-2,5-two (4-amino-benzene methane)] (POTAB) synthetic: with 3-octyl group thiophene and 4-aminobenzaldehyde in molar ratio 1: 0.8-1: 1.2 are dissolved in the dioxane, are mixed with the solution that concentration is 60-90mmol/mL.In this solution, drip 1-3mL 96% concentrated sulfuric acid catalyst, under nitrogen protection, in 80-90 ℃ of reaction 25-36h.The product that obtains sedimentation in ammoniacal liquor, more after filtration, dry POTAB.
2. poly-[(3-octyl group thiophene)-2,5-two (4-amino-benzene methylene)] (POTABQ) preparation: the POTAB that step 1 is made is dissolved in the dioxane, be mixed with 0.02-0.05g/mL solution, in this solution, add the 0.20-0.30g tetrachlorobenzoquinone then, at 70-90 ℃ of reaction 10-15h, obtain product and add the methyl alcohol sedimentation, filtration product is at the 60-80 ℃ of dry down POTABQ that gets.
3. the preparation of linkage nano carbon tubes of polythiophene methylene POTABQ-CNT: the POTABQ that step 2 is made is dissolved in dioxane and is mixed with 0.03-0.06g/mL solution, add many walls (n=2-20 layer) or Single Walled Carbon Nanotube (CNT-COCl) 80-120mg that contains acid chloride groups 60-80 ℃ of temperature, under 90-110 ℃ of temperature, react 96-120h.Add sedimentation in the normal hexane, filter,, promptly obtain the carbon nanotube (POTABQ-CNT) of polythiophene methylene bonding with the neutralization of 1mol/mL ammoniacal liquor, washing, drying.
Preparation method's process of the present invention is simple, and obtained POTABQ-CNT has good solubility and film-forming properties, and film forming thickness is about 800nm.(532nm 8ns) records the third-order nonlinear susceptibility x of POTABQ-CNT by the four-wave mixing method
(3)Reach 1.44 * 10
-7Esu.
Embodiment
Embodiment 1:
1. poly-[(3-octyl group thiophene)-2,5-two (4-amino-benzene methane)] (POTAB) synthetic: 3.88g (20mmol) 3-octyl group thiophene and 2.74g (20mmol) 4-aminobenzaldehyde are dissolved in the 50mL dioxane, drip the 2mL96% vitriol oil as catalyzer, at N
2Under the gas shiled condition, be heated to 85 ℃ of reaction 30h.Pour the red-purple reaction solution of gained in 1000mL 1M ammoniacal liquor sedimentation, obtain brown solid precipitation, filter and also use the methanol wash low molecular weight product, then 70 ℃ of vacuum-dryings to constant weight.Promptly obtain the POTAB of eigenstate, productive rate 80%;
2. poly-[(3-octyl group thiophene)-2,5-two (4-amino-benzene methylene)] (POTABQ) synthetic: the POTAB of 1.0g is dissolved in the 30mL dioxane, add tetrachlorobenzoquinone 0.25g then, at 80 ℃ of reaction 12h,, the gained solid product is dissolved with tetrahydrofuran (THF) again the methyl alcohol sedimentation of the brown reaction solution of gained, use the methyl alcohol sedimentation once more, filter the gained solid product and in 70 ℃ of vacuum drying ovens, dry, promptly obtain POTABQ, productive rate 60% to constant weight.
3.POTABQ-CNT preparation: 2gPOTABQ is joined in the 50ml dioxane, is heated to 70 ℃, stir and to make it abundant dissolving.Add the carbon nanotube (CNT-COCl) that 100mg contains acid chloride groups then and be heated to 95 ℃, stir 96h.Pour reaction solution in 500mL normal hexane sedimentation, filter, with the neutralization of 1mol/L ammoniacal liquor, with the normal hexane washing, place 70 ℃ of dry 24h of vacuum drying oven more then, obtain the brown solid powder, be the carbon nanotube (POTABQ-CNT) of POTABQ bonding.
Get aforesaid method synthetic POTABQ-CNT (100mg), be dissolved in the 50ml chloroform, adopt the method (3krpm) of spin-coating to prepare the film that thickness is about 800nm.Adopt the method for four-wave mixing to measure its third-order nonlinear susceptibility x
(3)=1.44 * 10
-7Esu.
Embodiment 2:
1. poly-[(3-octyl group thiophene)-2,5-two (4-amino-benzene methane)] (POTAB) synthetic: 3.88g (20mmol) 3-octyl group thiophene and 2.74g (20mmol) 4-aminobenzaldehyde are dissolved in the 50mL dioxane, drip the 2mL96% vitriol oil as catalyzer, at N
2Under the gas shiled condition, be heated to 85 ℃ of reaction 30h.Pour the red-purple reaction solution of gained in 1000mL1M ammoniacal liquor sedimentation, obtain brown solid precipitation, filter and also use the methanol wash low molecular weight product, then 70 ℃ of vacuum-dryings to constant weight.Promptly obtain the POTAB of eigenstate, productive rate 80%;
2. poly-[(3-octyl group thiophene)-2,5-two (4-amino-benzene methylene)] (POTABQ): the POTAB of 1.0g is dissolved in the 30mL dioxane, add tetrachlorobenzoquinone 0.25g then, at 80 ℃ of reaction 12h,, the gained solid product is dissolved with tetrahydrofuran (THF) again the methyl alcohol sedimentation of the brown reaction solution of gained, use the methyl alcohol sedimentation once more, filter the gained solid product and in 70 ℃ of vacuum drying ovens, dry, promptly obtain POTABQ, productive rate 60% to constant weight.
3.POTABQ-CNT preparation: 2gPOTABQ is joined in the 50ml dioxane, is heated to 70 ℃, stir and to make it abundant dissolving.Add the carbon nanotube (CNT-COCl) that 80mg contains acid chloride groups then and be heated to 95 ℃, stir 96h.Pour reaction solution in 500mL normal hexane sedimentation, filter, with the neutralization of 1mol/L ammoniacal liquor, with the normal hexane washing, place 70 ℃ of dry 24h of vacuum drying oven more then, obtain the brown solid powder, be the carbon nanotube (POTABQ-CNT) of POTABQ bonding.
Get aforesaid method synthetic POTABQ-CNT (100mg), be dissolved in the 50ml chloroform, adopt the method (3krpm) of spin-coating to prepare the film that thickness is about 800nm.Adopt the method for four-wave mixing to measure its third-order nonlinear susceptibility x
(3)=1.22 * 10
-7Esu.
Embodiment 3:
1. poly-[(3-octyl group thiophene)-2,5-two (4-amino-benzene methane)] (POTAB) synthetic: 3.88g (20mmol) 3-octyl group thiophene and 2.74g (20mmol) 4-aminobenzaldehyde are dissolved in the 50mL dioxane, drip the 2mL96% vitriol oil as catalyzer, at N
2Under the gas shiled condition, be heated to 85 ℃ of reaction 30h.Pour the red-purple reaction solution of gained in 1000mL1M ammoniacal liquor sedimentation, obtain brown solid precipitation, filter and also use the methanol wash low molecular weight product, then 70 ℃ of vacuum-dryings to constant weight.Promptly obtain the POTAB of eigenstate, productive rate 80%;
2. poly-[(3-octyl group thiophene)-2,5-two (4-amino-benzene methylene)] (POTABQ): the POTAB of 1.0g is dissolved in the 30mL dioxane, add tetrachlorobenzoquinone 0.25g then, at 80 ℃ of reaction 12h,, the gained solid product is dissolved with tetrahydrofuran (THF) again the methyl alcohol sedimentation of the brown reaction solution of gained, use the methyl alcohol sedimentation once more, filter the gained solid product and in 70 ℃ of vacuum drying ovens, dry, promptly obtain POTABQ, productive rate 60% to constant weight.
3.POTABQ-CNT preparation: 2gPOTABQ is joined in the 50ml dioxane, is heated to 70 ℃, stir and to make it abundant dissolving.Add the carbon nanotube (CNT-COCl) that 60mg contains acid chloride groups then and be heated to 95 ℃, stir 96h.Pour reaction solution in 500mL normal hexane sedimentation, filter, with the neutralization of 1mol/L ammoniacal liquor, with the normal hexane washing, place 70 ℃ of dry 24h of vacuum drying oven more then, obtain the brown solid powder, be the carbon nanotube (POTABQ-CNT) of POTABQ bonding.
Get aforesaid method synthetic POTABQ-CNT (100mg), be dissolved in the 50ml chloroform, adopt the method (3krpm) of spin-coating to prepare the film that thickness is about 800nm.Adopt the method for four-wave mixing to measure its third-order nonlinear susceptibility x
(3)=9.76 * 10
-8Esu.
Embodiment 4:
1. poly-[(3-octyl group thiophene)-2,5-two (4-amino-benzene methane)] (POTAB) synthetic: 3.88g (20mmol) 3-octyl group thiophene and 2.74g (20mmol) 4-aminobenzaldehyde are dissolved in the 50mL dioxane, drip the 2mL96% vitriol oil as catalyzer, at N
2Under the gas shiled condition, be heated to 85 ℃ of reaction 30h.Pour the red-purple reaction solution of gained in 1000mL1M ammoniacal liquor sedimentation, obtain brown solid precipitation, filter and also use the methanol wash low molecular weight product, then 70 ℃ of vacuum-dryings to constant weight.Promptly obtain the POTAB of eigenstate, productive rate 80%;
2. poly-[(3-octyl group thiophene)-2,5-two (4-amino-benzene methylene)] (POTABQ): the POTAB of 1.0g is dissolved in the 30mL dioxane, add tetrachlorobenzoquinone 0.25g then, at 80 ℃ of reaction 12h,, the gained solid product is dissolved with tetrahydrofuran (THF) again the methyl alcohol sedimentation of the brown reaction solution of gained, use the methyl alcohol sedimentation once more, filter the gained solid product and in 70 ℃ of vacuum drying ovens, dry, promptly obtain POTABQ, productive rate 60% to constant weight.
3.POTABQ-CNT preparation: 2gPOTABQ is joined in the 50ml dioxane, is heated to 70 ℃, stir and to make it abundant dissolving.Add the carbon nanotube (CNT-COCl) that 40mg contains acid chloride groups then and be heated to 95 ℃, stir 96h.Pour reaction solution in 500mL normal hexane sedimentation, filter, with the neutralization of 1mol/L ammoniacal liquor, with the normal hexane washing, place 70 ℃ of dry 24h of vacuum drying oven more then, obtain the brown solid powder, be the carbon nanotube (POTABQ-CNT) of POTABQ bonding.
Get aforesaid method synthetic POTABQ-CNT (100mg), be dissolved in the 50ml chloroform, adopt the method (3krpm) of spin-coating to prepare the film that thickness is about 800nm.Adopt the method for four-wave mixing to measure its third-order nonlinear susceptibility x
(3)=5.41 * 10
-8Esu.
Embodiment 5:
1. poly-[(3-octyl group thiophene)-2,5-two (4-amino-benzene methane)] (POTAB) synthetic: 3.88g (20mmol) 3-octyl group thiophene and 2.74g (20mmol) 4-aminobenzaldehyde are dissolved in the 50mL dioxane, drip the 2mL96% vitriol oil as catalyzer, at N
2Under the gas shiled condition, be heated to 85 ℃ of reaction 30h.Pour the red-purple reaction solution of gained in 1000mL1M ammoniacal liquor sedimentation, obtain brown solid precipitation, filter and also use the methanol wash low molecular weight product, then 70 ℃ of vacuum-dryings to constant weight.Promptly obtain the POTAB of eigenstate, productive rate 80%;
2. poly-[(3-octyl group thiophene)-2,5-two (4-amino-benzene methylene)] (POTABQ): the POTAB of 1.0g is dissolved in the 30mL dioxane, add tetrachlorobenzoquinone 0.25g then, at 80 ℃ of reaction 12h,, the gained solid product is dissolved with tetrahydrofuran (THF) again the methyl alcohol sedimentation of the brown reaction solution of gained, use the methyl alcohol sedimentation once more, filter the gained solid product and in 70 ℃ of vacuum drying ovens, dry, promptly obtain POTABQ, productive rate 60% to constant weight.
3.POTABQ-CNT preparation: 2g POTABQ is joined in the 50ml dioxane, is heated to 70 ℃, stir and to make it abundant dissolving.Add the carbon nanotube (CNT-COCl) that 20mg contains acid chloride groups then and be heated to 95 ℃, stir 96h.Pour reaction solution in 500mL normal hexane sedimentation, filter, with the neutralization of 1mol/L ammoniacal liquor, with the normal hexane washing, place 70 ℃ of dry 24h of vacuum drying oven more then, obtain the brown solid powder, be the carbon nanotube (POTABQ-CNT) of POTABQ bonding.
Get aforesaid method synthetic POTABQ-CNT (100mg), be dissolved in the 50ml chloroform, adopt the method (3krpm) of spin-coating to prepare the film that thickness is about 800nm.Adopt the method for four-wave mixing to measure its third-order nonlinear susceptibility x
(3)=1.82 * 10
-8Esu.
Claims (1)
1. the preparation method of a nonlinear optical material of linkage nano carbon tubes of polythiophene methylene, this method is characterized in that comprising following process:
1) poly-[(3-octyl group thiophene)-2,5-two (4-amino-benzene methane)] synthetic: with 3-octyl group thiophene and 4-aminobenzaldehyde example 1: 0.8-1 in molar ratio: 1.2 are dissolved in the dioxane, be mixed with the solution that concentration is 60-90mmol/mL, in this solution, drip 1-3mL 96% concentrated sulfuric acid catalyst, under nitrogen protection, in 80-90 ℃ of reaction 25-36h, the product that obtains sedimentation in ammoniacal liquor, dry must gathering [(3-octyl group thiophene)-2,5-two (4-amino-benzene methane)] more after filtration;
2) poly-[(3-octyl group thiophene)-2,5-two (4-amino-benzene methylene)] synthetic: poly-[(the 3-octyl group thiophene)-2 that step 1) is made, 5-two (4-amino-benzene methane)] be dissolved in the dioxane, be mixed with 0.02-0.05g/mL solution, in this solution, add the 0.20-0.30g tetrachlorobenzoquinone then,, obtain product and add the methyl alcohol sedimentation at 70-90 ℃ of reaction 10-15h, filtration product is at 60-80 ℃ of following dry must gathering [(3-octyl group thiophene)-2,5-two (4-amino-benzene methylene)];
3) poly-[(the 3-octyl group thiophene)-2 that the preparation of linkage nano carbon tubes of polythiophene methylene: with step 2) makes, 5-two (4-amino-benzene methylene)] be dissolved in dioxane and be mixed with 0.03-0.06g/mL solution, add many walls or the Single Walled Carbon Nanotube 80-120mg that contains acid chloride groups 60-80 ℃ of temperature, under 90-110 ℃ of temperature, react 96-120h, add sedimentation in the normal hexane, filter, neutralize with 1mol/mL ammoniacal liquor, washing, drying promptly obtains the carbon nanotube of polythiophene methylene bonding.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101298510B (en) * | 2008-06-19 | 2010-06-02 | 同济大学 | Polythiofuran-carbon nanotube composite photosensitive film material and preparation thereof |
| WO2010062717A1 (en) * | 2008-11-03 | 2010-06-03 | University Of Houston | Composites comprising biologically-synthesized nanomaterials |
| CN108047407A (en) * | 2017-12-15 | 2018-05-18 | 福州大学 | A kind of preparation method of carbon nano-tube/poly pyrroles methylene third-order nonlinear optical composite material |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20020025101A (en) * | 2002-01-10 | 2002-04-03 | (주) 나노텍 | mass production of carbon nanotubes by pyrolysis |
| CN1283723C (en) * | 2004-07-13 | 2006-11-08 | 南京大学 | Poly-3,4-ethylenedioxy thiophene/multi-wall carbon nanotube compositions and their preparation process and use |
-
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101298510B (en) * | 2008-06-19 | 2010-06-02 | 同济大学 | Polythiofuran-carbon nanotube composite photosensitive film material and preparation thereof |
| WO2010062717A1 (en) * | 2008-11-03 | 2010-06-03 | University Of Houston | Composites comprising biologically-synthesized nanomaterials |
| AU2009320026B2 (en) * | 2008-11-03 | 2015-08-20 | University Of Houston | Composites comprising biologically-synthesized nanomaterials |
| CN108047407A (en) * | 2017-12-15 | 2018-05-18 | 福州大学 | A kind of preparation method of carbon nano-tube/poly pyrroles methylene third-order nonlinear optical composite material |
| CN108047407B (en) * | 2017-12-15 | 2019-04-02 | 福州大学 | A kind of preparation method of carbon nano-tube/poly pyrroles methylene third-order nonlinear optical composite material |
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