CN115403747B - Stretchable polymer material based on cyclic UPy quadruple hydrogen bonds and application thereof - Google Patents
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Abstract
The invention discloses a stretchable polymer material based on cyclic UPy quadruple hydrogen bonds and application thereof, which is an A1-D-A2 conjugated polymer prepared by Stille coupling reaction by taking a receptor unit A1, a receptor unit A2 and a donor unit D as raw materials. The invention introduces the annular quadruple hydrogen bond into the conjugated polymer for the first time, and the organic field effect transistor device shows that the polymer semiconductor with the structure has bipolar transmission characteristics under certain conditions, and simultaneously the spectrum absorption covers visible light and extends to the near infrared field; more importantly, compared with a polymer film without a cyclic ureido pyrimidinone (UPy) structure, the film with the structure has fewer microcracks after being stretched to 100%, so that the film is a stretchable conjugated polymer capable of being processed by a solution, and has wide application prospects in the organic electronic fields such as stretchable organic thin film transistors, organic photovoltaics, organic thermoelectric and the like.
Description
Technical Field
The invention belongs to the field of stretchable polymer semiconductor materials, and particularly relates to a stretchable polymer material based on cyclic UPy quadruple hydrogen bonds and application thereof.
Background
As a new generation of semiconductor materials, conjugated polymers have a wide application prospect in the fields of low-cost, large-area, flexible electronic devices such as Organic Field Effect Transistors (OFETs), organic Solar Cells (OSCs), organic Light Emitting Diodes (OLEDs), and the like, and have been receiving a great deal of attention in the past decades. Intrinsically stretchable polymer semiconductors are particularly promising for stretchable electronics due to their low cost, ease of large area printing and high density device fabrication. However, developing an inherently stretchable material that maintains both electrical properties and mechanical stretchability remains a challenge. Therefore, it is of great importance to design a polymer semiconductor material that can still maintain good charge transport properties under mechanical strain.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a stretchable polymer material based on cyclic UPy quadruple hydrogen bonds and application thereof. The invention takes cyclic ureido pyrimidinone (UPy) as a structure to be introduced into the D-A conjugated polymer, the cyclic hydrogen bond structure is composed of a hydrogen bond in the middle part and long alkyl chains on two sides, the stretchability is improved by utilizing the effect of dissipating stress of the hydrogen bond, the effect of protecting the hydrogen bond is achieved by utilizing the cyclic structure on two sides, and when the hydrogen bond effect is opened, the cyclic structure is favorable for promoting the recovery of the hydrogen bond effect, thereby producing the self-repairing effect.
The invention relates to a stretchable polymer based on cyclic UPy quadruple hydrogen bonds, which is an A1-D-A2 conjugated polymer prepared by Stille coupling reaction by taking a receptor unit A1, a receptor unit A2 and a donor unit D as raw materials.
The receptor unit A1 is pyrrolopyrrolidone (DPP), isoindigo (IID) or Benzothiazole (BT).
The receptor unit A2 is a cyclic ureido pyrimidinone (UPy) structure. The number of hydrogen bonds in the middle can be one, two, three or even multiple, preferably four hydrogen bonds. Furthermore, the hydrogen bonds are linked on both sides by a macrocyclic ring consisting of n methylene groups, where n is 19.
The preferred cyclic ureido pyrimidinone (UPy) structure of the invention comprises four hydrogen bonds, has strong intramolecular acting force, and plays a role in dissipating stress with the cyclic structures at two sides in the stretching process. In addition, the ring structures on two sides play a role in protection, and after the hydrogen bonds are opened under the action of external force, the ring structures on two sides can resist partial external force, so that the four-fold hydrogen bond effect is promoted to be recovered, and the self-repairing effect is achieved.
The donor unit D is selenophene bridge, thiophene bridge, bithiophene bridge or thiophene ethylene thiophene bridge.
Further, acceptor unit A1, acceptor unit A2 and donor unit D are each preferably:
r is C 3 -C n H 2n+1 Alkyl chain, where n=10.
Based on the preferred monomers, the structure of the stretchable polymer based on cyclic UPy quadruple hydrogen bonds of the invention is as follows:
wherein R is C 3 -C n H 2n+1 Alkyl chain, n=10.
And x, y and z represent the polymerization degree of different monomers, and the molecular weight ranges from 50000 to 80000.
Further, z/x+y+z=0.1, x/x+y+z=0.4, and y/x+y+z=0.5.
The invention relates to a preparation method of a stretchable polymer material based on cyclic UPy quadruple hydrogen bonds, which comprises the following steps:
pyrrolopyrrolidone (DPP) (80.1 mg,0.07 mmol), selenophene (40.4 mg,0.09 mmol), cyclic ureidopyrimidinone (UPy) (20.3 mg,0.02 mmol), pd 2 (dba) 3 (3.3 mg, 0.04 mmol) and P (o-tolyl) 3 (3.3 mg,0.014 mmol) was dissolved in chlorobenzene (10 ml) and reacted at 130℃for 3 days, and the polymer was purified and collected to give a dark green solid (70.3 mg,75% yield).
The application of the stretchable polymer material based on the cyclic UPy quadruple hydrogen bonds is that the stretchable polymer material is used as a polymer semiconductor material applied to the field of organic electronics and used for preparing materials such as organic thin film transistors, organic photovoltaic cells, organic thermoelectric conversion devices and the like, and the stretchable polymer material has mechanical stretchability and can still keep good charge transmission performance.
The invention relates to a stretchable polymer material based on cyclic UPy quadruple hydrogen bonds, which is a stretchable polymer semiconductor material based on pyrrolopyrrolidone (DPP) and A1-D-A2 type containing cyclic ureido pyrimidinone (UPy) units as acceptor units (A1 and A2) and selenophene as a donor unit (D). The quadruple hydrogen bonds in the UPy structure play a role in dissipating stress in the stretching process, the ring structures on two sides play a role in protecting, and after the hydrogen bonds are opened under the action of external force, the ring structures on two sides can resist part of external force, so that the quadruple hydrogen bonds are restored, and the self-repairing effect is achieved.
The novel stretchable semiconductor material disclosed by the invention utilizes the strong electron deficiency characteristic of thiophene pyrrolopyrrolidone (DPP) and cyclic ureido pyrimidinone (UPy) receptor units and the advantage of containing quadruple hydrogen bonds, and the two receptor units are connected through a selenophene bridge, so that the planar structure of the whole polymer semiconductor material is kept, the intramolecular/intermolecular interaction is strong, the excellent planarity is favorable for orderly accumulation of molecules, and therefore, the excellent photoelectric property is expected to be obtained, and in addition, the cyclic structure formed by the quadruple hydrogen bonds and the alkyl chains at two ends can play a role in dissipating stress in the stretching process. Meanwhile, an alkyl chain is introduced into a pyrrolopyrrole diketone receptor unit so as to ensure excellent solubility of molecules and low-temperature solution processability of a conjugated micromolecular material, and the novel A1-D-A2 type polymer semiconductor material is expected to have application prospects in the organic fields of organic photovoltaics, stretchable organic thin film transistors, organic thermoelectricity and the like.
Drawings
FIG. 1 is a schematic diagram of the synthesis of a novel A1-D-A2 type stretchable polymeric semiconducting material;
FIG. 2 is a schematic diagram of the synthetic route of monomer S1 in example 1;
FIG. 3 is a schematic diagram of the synthetic route of monomer S2 in example 2;
FIG. 4 is a schematic diagram of the synthetic route of monomer S3 in example 3;
FIG. 5 is a schematic diagram of the synthetic route of monomer S4 in example 4;
FIG. 6 is an ultraviolet spectrum of a type A1-D-A2 stretchable polymer semiconductor material P1;
fig. 7 and 8 show the electrical properties of the polymer semiconductor P1 organic field effect transistor device structure at different annealing temperatures.
Fig. 9 is an AFM image of the polymer semiconductor P1 and the control film stretched to 100%.
Detailed Description
Examples of the stretchable polymer semiconductor material of the A1-D-A2 type according to the present invention will be described in detail with reference to the accompanying drawings, which show specific structures of the materials, synthetic procedures and related experimental procedures, but the scope of the present invention is not limited to the examples described below.
As shown by P1 in figure 1, the invention uses pyrrolo-pyrrole-dione and UPy as receptor units, selenophene bridge as donor units, the needed polymer is obtained through Stille coupling reaction, and finally, the polymer is subjected to Soxhlet extraction by methanol, acetone, n-hexane and chloroform respectively, so as to obtain the A1-D-A2 type stretchable polymer semiconductor material.
Example 1: synthesis of monomer S1 (as shown in FIG. 2)
Step 1, material S1 is synthesized in reference (Toward a Deformable Two-Dimensional Covalent Organic Network with aNoncovalently Connected Skeleton. Chem. Mater.2020,32,19,8139-8145), monomer 1 and bromoundecene are commercially available and nucleophilic substitution can be used to produce S1. Monomer 1 (8 g,29.5 mmol), K was added separately to a double-necked flask 2 CO 3 (6.1 g,44.3 mmol), solvent DMF (100 mL), nitrogen displacement for 10 min, further bromoundecene (8.3 g,25.4 mmol) was added, the reaction was allowed to proceed for 15 h at 120deg.C, cooled to room temperature, extracted with water and dichloromethane, the organic phase was collected, anhydrous N 2 SO 4 Dried and the final product S1 (6 g) was obtained by column chromatography.
Example 2: synthesis of monomer S2 (as illustrated in FIG. 3)
Step 2, material S2 was obtained by addition reaction in reference (Toward a Deformable Two-Dimensional Covalent Organic Network with aNoncovalently Connected Skeleton. Chem. Mater.2020,32,19,8139-8145), guanidine carbonate was commercially available, monomer S1 (3.3 g,7.8 mmol), guanidine carbonate (1.0 g,10.9 mmol), solvent absolute ethanol (100 ml) were added separately to a double-necked flask, nitrogen was replaced for 10 minutes, reflux reaction was performed at 70℃for three days, cooled to room temperature, ethanol was spin-dried, and directly purified by column chromatography to give monomer S3 (1.6 g).
Example 3: synthesis of monomer S3 (as illustrated in FIG. 4)
Step 3, material S3 is obtained by addition reaction as described in the reference (Toward a Deformable Two-Dimensional Covalent Organic Network with aNoncovalently Connected Skeleton. Chem. Mater.2020,32,19,8139-8145), and undecyl isocyanate is prepared by the Cotose rearrangement (which is susceptible to deterioration and is now available). S2 (1.8 g,4.3 mmol), undecyl isocyanate (1.6 g,8.6 mmol) and triethylamine (2.0 g,19.4 mmol) were added to each flask, dichloromethane (80 ml) was used as a solvent, nitrogen was substituted for 10 minutes, the solvent was dried by spin-drying at room temperature, methanol was added to precipitate a white solid, and the product S3 (2.2 g) was obtained by suction filtration.
Example 4: synthesis of monomer S4 (as illustrated in FIG. 5)
Step 4, material S4 is obtained by olefin metathesis in the reference (Toward a Deformable Two-Dimensional Covalent Organic Network with aNoncovalently Connected Skeleton. Chem. Mater.2020,32,19,8139-8145). S3 (1.0 g,1.7 mmol) and Grubbs generation catalyst (0.06 g,0.08 mmol) are respectively added into a double-mouth bottle, dichloromethane (20 ml) is used as a solvent, nitrogen is used for replacing 10 minutes, the reaction is carried out at room temperature for 2 hours, after the reaction is finished, the mixture is put into a refrigerator for standing for 2 hours, the white solid is obtained through recrystallization, and the product S4 (0.29 g) is obtained through suction filtration.
Example 5: synthesis of A1-D-A2-type Polymer semiconductor Material P1 (shown in FIG. 1)
Step 5, the A1-D-A2 type polymer semiconductor material P1 is prepared by Stille coupling reaction: pyrrolopyrrolidone (DPP) (80.1 mg,0.07 mmol), selenophene (40.4 mg,0.09 mmol), cyclic ureidopyrimidinone (UPy) (20.3 mg,0.02 mmol), pd 2 (dba) 3 (3.3 mg, 0.04 mmol) and P (o-tolyl) 3 (3.3 mg,0.014 mmol) was dissolved in chlorobenzene (10 ml), reacted at 130℃for 3 days, and the polymer was subjected to Soxhlet extraction with methanol, acetone, n-hexane, chloroform solvents, respectively (methanol extraction temperature: room temperature, acetone, n-hexane, chloroform)The extraction temperature was 100℃) and the dark green solid (70.3 mg,75% yield) was collected.
Fig. 6 shows the ultraviolet absorption spectrum in the state of a solution of the polymer semiconductor material P1 (z/x+y+z=0.1, x/x+y+z=0.4, y/x+y+z=0.5), with a maximum absorption peak of 832nm.
Fig. 7 shows a bottom gate top contact field effect transistor device structure prepared by using P1 as a semiconductor layer.
FIG. 8 shows the transfer curves of a polymer semiconductor material P1 (z/x+y+z=0.1, x/x+y+z=0.4, y/x+y+z=0.5) at different annealing temperatures, with increasing temperature, mobility showing a trend of increasing followed by decreasing, reaching a maximum mobility of 0.16cm at 150 ℃ 2 V -1 s -1 And there is a tendency for bipolar transmission at lower temperatures.
Figure 9 shows AFM images of polymer films (control) and P1 films that did not incorporate cyclic quadruple hydrogen bonding structures, with better stretchability P1 exhibiting fewer cracks, both unstretched and stretched to 100%.
The novel A1-D-A2 type stretchable polymer semiconductor material designed by the invention is a semiconductor material which can be processed by solution and has better stretching performance, and can be applied to the organic electronics fields such as stretchable organic thin film transistors, organic photovoltaic devices, organic thermoelectricity and the like.
Claims (5)
1. A stretchable polymeric material based on cyclic UPy quadruple hydrogen bonds, characterized in that:
the stretchable polymer based on the cyclic UPy quadruple hydrogen bonds is an A1-D-A2 conjugated polymer prepared by Stille coupling reaction by taking a receptor unit A1, a receptor unit A2 and a donor unit D as raw materials;
the receptor unit A1 is pyrrolopyrrolidone, isoindigo or benzothiazole;
the receptor unit A2 is of a cyclic ureido pyrimidinone structure, and the structure is shown as follows:
the donor unit D is selenophene bridge, thiophene bridge, bithiophene bridge or thiophene ethylene thiophene bridge.
2. The stretchable polymeric material based on cyclic UPy quadruple hydrogen bonding according to claim 1, characterized in that:
the acceptor unit A1 and the donor unit D are respectively:
r is C 3 -C n H 2n+1 Alkyl chain, wherein n=10;
3. the stretchable polymeric material based on cyclic UPy quadruple hydrogen bonding according to claim 2, characterized in that:
the structure of the stretchable polymer based on the cyclic UPy quadruple hydrogen bonds is as follows:
wherein R is C 3 -C n H 2n+1 Alkyl chain, n=10;
and x, y and z represent the polymerization degree of different monomers, and the molecular weight ranges from 50000 to 80000.
4. Use of a stretchable polymeric material based on cyclic UPy quadruple hydrogen bonds according to claim 1, 2 or 3, characterized in that:
the stretchable polymer material based on the cyclic UPy quadruple hydrogen bonds is applied to the field of electronics as a polymer semiconductor material.
5. The use according to claim 4, characterized in that:
the stretchable polymer material based on the cyclic UPy quadruple hydrogen bonds is used for preparing organic thin film transistor, organic photovoltaic cell or organic thermoelectric conversion device materials.
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