AU2020102310A4 - Ethynylthiophene polymer capable of superassembling with carbon nanotubes (CNTs), and its preparation method - Google Patents
Ethynylthiophene polymer capable of superassembling with carbon nanotubes (CNTs), and its preparation method Download PDFInfo
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- C08K3/041—Carbon nanotubes
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- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y40/00—Manufacture or treatment of nanostructures
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- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
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- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
- C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/54—Inorganic substances
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Abstract
The present invention belongs to the technical field of organic supramolecule
materials, and specifically discloses an ethynylthiophene polymer capable of
forming an ordered supramolecular assembly with carbon nanotubes (CNTs), and
a preparation method thereof. The polymer of the present invention has the main
chain of 2-ethynylthiophene and the side chain of alkoxy including carbon chains
with different lengths. The polymer of the present invention is prepared as follows:
subjecting 3,4-dihydroxythiophene to etherification, and then subjecting the
etherification product to bromination to give 2,5-dibromo-3,4-dialkoxythiophene;
then subjecting the 2,5-dibromo-3,4-dialkoxythiophene and trimethylsilyl
acetylene (TMSA) to reaction to give bis(trimethylsilyl)thiophene; removing
trimethylsilyl (TMS) protecting groups from the bis(trimethylsilyl)thiophene to give
an intermediate of alkynyl-terminated thiophene; and subjecting the intermediate
of alkynyl-terminated thiophene and the 2,5-dibromo-3,4-dialkoxythiophene to
Sonogashira coupling to give an ethynylthiophene polymer. The ethynylthiophene
polymer of the present invention can form a supramolecular assembly system with
CNTs, which involves n-n adsorption of the main chain and entanglement of the
side chain. The composite formed from the supramolecular assembly system
exhibits excellent stability, and has promising application prospects.
1/5
oC4 - I-I -1U nI t1- CDt MOMW( D U
C41-,O 0C4 H9
2a
85 RO 75 TO 65 &O 55 50 45 40 35 30 25 20 15 10J 0.5 0.0
fi(ppm)
FIG. 1
2/5
Wr -wt -t N oowC )M -- wI
C4H-jQ 0C4 H
Br %Br
8.5 8.0 7.5 7.0 65 60 55 Sf0 45 40 3.5 3.0 25 20 15 10 05 f00
fi (ppm)
FIG. 2
3/5
C)o D I r - 1r- -t I 0W t Ut)t OU-t ) U)C
C4H,o OC/I
8 5 OD 7 D 6 D 5 D 45 40D 35 3D) 25 2 D 15 10D 05 0DD
f11(ppm)
FIG. 3
4/5
wr-wC owwwt mC-ow CD CO L
000 ) - -r -r r )V )V WW U) U-h) - Gflm G)
nS 000 ------C D
C4H,O0 OC 4H"A
<s zz
5a
0D 0) 0 0
80 75 70 65 60J 55 50 45 40 35 30 25 2 0 1 5 10 05 00
FIG. 4
5/5
OD CD CD OD CD CO O CO CO O M I- r i -- r-- I-- I-- I-- I-- I-- r--1 uD in -DI DI 0 -D ) m m 03 m m D (n m e oo
. -- - - - - - - - - - . =N (N (N (N (N
C4 gO 0C 4H6 4H9O OC 4Hg
Ga
8.0 75 70 65 60 55 50 45 40 35 30 25 20 15 10 05 0.0
fl (ppm)
FIG. 5
Description
1/5
oC4 - I-I -1U nI t1- CDtD MOMW( U
C41-,O 0C 4 H9
2a
RO 75 TO 65 &O 55 50 45 40 35 30 25 20 15 10J 0.5 0.0 fi(ppm)
FIG. 1
2/5
-t N oowC )M Wr-wt -- wI
C 4H-jQ 0C4 H
Br %Br
8.5 8.0 7.5 7.0 65 60 55 Sf0 45 40 3.5 3.0 25 20 15 10 05 f00 fi (ppm)
FIG. 2
3/5
C)o D I r - 1r- -t I 0W t Ut)t OU-t ) U)C
C4H,o OC/I
OD 7 D 6 D 5 D 45 40D 35 3D) 25 2D 15 10D 05 0DD f11(ppm)
FIG. 3
4/5
wr-wC owwwt mC-ow CD CO L 000 ) - -r -r r )V )V WW U) U-h) - Gflm G) nS 000D ------C
C4H,O0 OC 4H"A
<s zz 5a
0D 0) 0 0
80 75 70 65 60J 55 50 45 40 35 30 25 20 15 10 05 00
FIG. 4
5/5
OD CD CD OD CD CO O CO CO O M I- ri -- r-- I-- I-- I-- I-- I-- r--1 in uD DI 0 -D -DI ) m m 03 m m D (n m e oo . -- - - - - - - - - - .(N=N (N (N (N
C4 gO 0C 4H6 4H9 O OC 4Hg
Ga
8.0 75 70 65 60 55 50 45 40 35 30 25 20 15 10 05 0.0 fl (ppm)
FIG. 5
ETHYNYLTHIOPHENE POLYMER CAPABLE OF SUPERASSEMBLING WITH CARBON NANOTUBES (CNTs), AND ITS PREPARATION METHOD
The present invention belongs to the technical field of organic supramolecule materials, and specifically relates to an ethynylthiophene polymer capable of forming an ordered supramolecular assembly with carbon nanotubes (CNTs), and a preparation method thereof.
Self-assembly refers to a technology in which basic structural units (molecules, nanomaterials, micron- or larger-scale substances) spontaneously form an ordered structure. During the process of self-assembly, the basic structural units are spontaneously organized or aggregated into a stable structure with a certain regular geometric appearance under the non-covalent interaction.
Carbon nanotubes (CNTs) are a type of nanomaterials with hexagonal structures as main linking groups, which are rich in n electrons on the surface, and have excellent mechanical, electrical and chemical properties. CNTs are widely used in the preparation of military and civilian composite materials with light weight and high strength. There are single-wall carbon nanotubes (SWCNTs) and multi-wall carbon nanotubes (MWCNTs), which have a relatively-wide size range. Commonly, CNTs have a diameter of 2 nm to 100 nm and a length of 10 pm to 200 pm. Due to the strong van der Waals forces among tube walls, CNTs are often agglomerated, entangled or knotted. Moreover, due to the very stable chemical structure, CNTs, when combined with a composite body, form weak interface binding, which limits the excellent properties of composite materials and also restricts the industrial application of CNTs.
In order to overcome the defects that the existing CNTs are easy to agglomerate and difficult to disperse, the present invention provides a stable ethynylthiophene polymer capable of forming an ordered supramolecular assembly with CNTs, and a preparation method thereof.
The ethynylthiophene polymer capable of forming an ordered supramolecular assembly with CNTs provided in the present invention is a polymer with 2 ethynylthiophene as the main chain and alkoxy as the side chain. The polymer can form a supramolecular assembly system with CNTs of different sizes through n-n adsorption of the main chain and entanglement of the side chain. The ethynylthiophene polymer/CNT composite formed from the supramolecular assembly system exhibits excellent stability, and has promising application prospects in composite materials.
The ethynylthiophene polymer capable of forming an ordered supramolecular assembly with CNTs provided by the present invention has a structure shown in the following general formula:
S n
where, n is a natural number greater than zero, and R is C4H or 6C H1 3
The present invention also provides a method for . preparing the ethynylthiophene polymer capable of forming an ordered supramolecular assembly with CNTs, including the following specific steps:
(1) using 3,4-dihydroxythiophene 1 as a raw material to prepare 3,4 dialkoxythiophene 2a under alkaline conditions, and then subjecting the 3,4 dialkoxythiophene to bromination to give 2,5-dibromo-3,4-dialkoxythiophene 3a;
(2) subjecting the 2,5-dibromo-3,4-dialkoxythiophene 3a and trimethylsilyl acetylene (TMSA) to reaction to give intermediate 4a of bis(trimethylsilyl)thiophene, and then removing trimethylsilyl (TMS) from the intermediate 4a of bis(trimethylsilyl)thiophene to give intermediate 5a of alkynyl terminated thiophene; and
(3) subjecting the intermediate 5a of alkynyl-terminated thiophene and the 2,5-dibromo-3,4-dialkoxythiophene 3a to Sonogashira coupling to give the product of ethynylthiophene polymer 6a.
In some embodiments, the Sonogashira coupling is conducted by the following specific steps: under a nitrogen atmosphere, adding the 2,5-dibromo-3,4 dialkoxythiophene 3a, the intermediate 5a of alkynyl-terminated thiophene, CuI, tetrakis(triphenylphosphine)palladium() and triphenylphosphine to a reaction flask, and then adding toluene and triethylamine (TEA); after nitrogen replacement is conducted, subjecting the mixture to reaction at a high temperature (65 0C to 750 C (preferably 70 0 C)); then subjecting the reaction solution to extraction, drying and concentration to give a yellow viscous liquid; and then subjecting the yellow viscous liquid to methanol/tetrahydrofuran (THF) precipitation to give a yellow solid powder.
In some embodiments, the 3,4-dialkoxythiophene 2a is 3,4 dibutoxythiopheneor3,4-dihexoxythiophene.
In some embodiments, the 3,4-dialkoxythiophene 2a and bromine water have a molar ratio of 1:(2.1-2.5).
The present invention also provides an ethynylthiophene polymer synthesized by the above method.
The present invention also provides a supramolecular self-assembly system of CNTs, and the functional substance in the self-assembly system is any one of the ethynylthiophene polymers described above.
The present invention also provides the use of any one of the ethynylthiophene polymers described above in the preparation of CNT composite materials.
Beneficial effects of the present invention:
(1) The ethynylthiophene polymer provided in the present invention adsorbs CNTs by the main chain and entangles CNTs by side chains, which achieves the supramolecular self-assembly of CNTs through the n-n interaction without damaging CNTs, thereby realizing the dispersion of CNTs.
(2) In order to ensure the intrinsic characteristics of CNTs and improve the dispersion of CNTs without destroying the surface structure of CNTs, the present invention provides a polymer based on ethynylthiophene, which can effectively disperse CNTs under the action of a conventional organic solvent, thereby promoting the application of CNTs in composite materials. The present invention has great application potential in the fields of instruments and medical devices.
(3) The synthesis method of the present invention has advantages, such as simple operations, controllable process parameters, and low cost in raw materials and equipment.
FIG. 1 shows the nuclear magnetic resonance (NMR) spectrum for 3,4 dialkoxythiophene 2a.
FIG. 2 shows the NMR spectrum for 2,5-dibromo-3,4-dialkoxythiophene 3a.
FIG. 3 shows the NMR spectrum for the intermediate 4a of bis(trimethylsilyl)thiophene.
FIG. 4 shows the NMR spectrum for the intermediate 5a of alkynyl-terminated thiophene.
FIG. 5 shows the NMR spectrum for the ethynylthiophene polymer 6a.
It should be noted that the following detailed description is exemplary and aims to further describe the present invention. The accompany drawings of the specification are provided for further explanation of the present application. The schematic examples of the present application and description thereof are provided to illustrate the present application and do not constitute an undue limitation to the present application.
Unless otherwise specified, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the technical field to which the present application belongs.
Example 1
HO OH C4 H 9O OC 4 H9 C4 H9 O OC 4 H 9 CHBrDCM r500 Br Br Pd(O)/Cu/PPh3 S Acetone tolune/TEA=9/1 1 2a 3a
C 4 H 9O OC 4 H9 C 4 H 9O OC 4 H9 C4 90 OC 4 H1 4 H 9O OC4 H 9 I / KF/K 200 3 ~Pd(O)/Cul/PPh3 I\__ \__ Si S TKFF/tOH tolune/TEA=9/1 / 4a 5a 6a
Preparation process of the ethynylthiophene polymer 6a
Intermediates 2a to 5a were synthesized according to the steps reported in Chem. Eur. J. 2011, 17, 1473-1484.
The intermediate 2a was a colorless liquid. 1H NMR (500 MHz, Chloroform d) 5 6.34 (s, 2H), 4.02 (t, J = 6.1 Hz, 4H), 1.81 - 1.69 (m, 4H), 1.58 - 1.46 (m, 4H), 0.96 (t, J = 7.6 Hz, 6H).
The intermediate 3a was a white solid. 1H NMR (500 MHz, Chloroform-d) 5 4.08 (t, J = 6.1 Hz, 4H), 1.79 - 1.69 (m, 4H), 1.58 - 1.49 (m, 4H), 0.97 (t, J= 7.6 Hz, 6H).
The intermediate 4a was a white solid. 1H NMR (500 MHz, Chloroform-d) 5 4.09 (t, J = 6.1 Hz, 4H), 1.77 - 1.67 (m, 4H), 1.49 - 1.39 (m, 4H), 0.95 (t, J= 7.6 Hz, 6H), 0.25 (s, 18H).
The intermediate 5a was a white solid. 1H NMR (500 MHz, Chloroform-d) 5 4.07 (t, J = 6.1 Hz, 4H), 3.32 (s, 2H), 1.79 - 1.72 (m, 4H), 1.57 - 1.47 (m, 4H), 0.96 (t, J = 7.6 Hz, 6H).
Polymer 6a: Under a nitrogen atmosphere, the intermediate 3a (3.84 g, 10 mmol), the intermediate 5a (2.76 g, 10 mmol), CuI (0.19 g, 1 mmol), tetrakis(triphenylphosphine)palladium(0) (0.24 g, 0.2 mmol) and triphenylphosphine (0.13 g, 0.5 mmol) were added to a dry 250 mL three-necked flask, and then 100 mL of dried toluene and 20 mL of TEA were added; after the nitrogen replacement was conducted three times, and the mixture reacted at 700 C for 24 h; the reaction system was cooled to room temperature, then subjected to extraction, dried, and concentrated by rotary evaporation to give a yellow viscous liquid; and the yellow viscous liquid was subjected to methanol/THF recrystallization to give 4.4 g of yellow-green solid powder. H NMR (500 MHz, Chloroform-d) 5 4.03 (ddt, J = 9.1, 6.3, 3.4 Hz, 20H), 2.20 (s, 2H), 1.99 (s, 2H), 1.79-1.73 (m, 20H), 1.55-1.49 (m, 20H), 0.99-0.94 (m, 30H).
Claims (5)
1. An ethynylthiophene polymer capable of forming an ordered supramolecular assembly with carbon nanotubes (CNTs), having a general structure shown in the following formula:
RO OR RO OR
S S n
wherein, n is a natural number greater than zero, and R is 4CH or C 6 H1 3
.
2. A method for preparing the ethynylthiophene polymer according to claim 1, comprising the following specific steps:
(1) using 3,4-dihydroxythiophene 1 as a raw material to prepare 3,4 dialkoxythiophene 2a under alkaline conditions, and then subjecting the 3,4 dialkoxythiophene to bromination to give 2,5-dibromo-3,4-dialkoxythiophene 3a;
(2) subjecting the 2,5-dibromo-3,4-dialkoxythiophene 3a and trimethylsilyl acetylene (TMSA) to reaction to give intermediate 4a of bis(trimethylsilyl)thiophene, and then removing trimethylsilyl (TMS) from the intermediate 4a of bis(trimethylsilyl)thiophene to give intermediate 5a of alkynyl terminated thiophene; and
(3) subjecting the intermediate 5a of alkynyl-terminated thiophene and the 2,5-dibromo-3,4-dialkoxythiophene 3a to Sonogashira coupling to give the product of ethynylthiophene polymer 6a.
3. The preparation method according to claim 2, wherein, the Sonogashira coupling is conducted by the following specific steps: under a nitrogen atmosphere, adding the intermediate 5a of alkynyl-terminated thiophene, the 2,5-dibromo 3,4-dialkoxythiophene 3a, CuI, tetrakis(triphenylphosphine)palladium(O) and triphenylphosphine to a reaction flask, and then adding toluene and triethylamine (TEA); after nitrogen replacement is conducted, subjecting the mixture to reaction at a high temperature; then subjecting the reaction solution to cooling, extraction, drying and concentration to give a yellow viscous liquid; and then subjecting the yellow viscous liquid to methanol/tetrahydrofuran (THF) precipitation to give a yellow solid powder.
4. The preparation method according to claim 3, wherein, the 3,4 dialkoxythiophene 2a is 3,4-dibutoxythiophene or 3,4-dihexoxythiophene; wherein, the 3,4-dialkoxythiophene 2a and bromine water have a molar ratio of 1:(2.0-2.5).
5. A supramolecular self-assembly system of CNTs, with the ethynylthiophene polymer according to claim 1 as a functional substance.
FIG. 1 1/5
FIG. 2 2/5
FIG. 3 3/5
FIG. 4 4/5
FIG. 5 5/5
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