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A kind of conjugated polyacetylene containing perylene imide and preparation method thereof

A technology of conjugated polyacetylene and peryleneimide, which is applied in the field of preparation of conjugated polyacetylene, can solve the problems of limiting the comprehensive performance of photoelectric devices, poor solution film processing performance, and low utilization rate of sunlight, etc., and achieve excellent spectrum Absorption and energy level regulation performance, good environmental processing performance, and the effect of simple and easy method

Inactive Publication Date: 2017-12-22
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, a variety of n-type materials have obtained acceptable device performance and stability, most of which are based on the copolymerization between donor and acceptor, although a few reports have synthesized pure peryleneimide oligomers, but the reaction type Limited to coupling reactions such as Still and Suzuki, there are only 2-4 perylene imide units in this type of oligomer, and its solution film processing performance is often not as good as that of macromolecular polymer acceptor materials
Only two literatures have reported the preparation of peryleneimide-containing polymers by ring-opening metathesis polymerization (J.Polym.Sci.Part A: Polym.Chem.2012, 50, 1333; Chem.Commun., 2010, 46, 5464-5466), because the main chain of the polymer prepared by ring-opening metathesis polymerization is a non-conjugated structure, which is not conducive to the transmission of electrons; in addition, its ultraviolet-visible absorption range is 250-550nm, and the optical energy band gap ( E. g ) is 2.21eV, and the utilization rate of sunlight is low, which limits the comprehensive performance of optoelectronic devices

Method used

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  • A kind of conjugated polyacetylene containing perylene imide and preparation method thereof
  • A kind of conjugated polyacetylene containing perylene imide and preparation method thereof
  • A kind of conjugated polyacetylene containing perylene imide and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Synthesis of Poly(1), the synthetic route is as follows:

[0064]

[0065] In this example, the reaction tube was always kept under a nitrogen atmosphere, and the solvents used were all dried and purified.

[0066] Add 1,6,7,12-tetrachloro-3,4:9,10-perylenetetracarboxylic dianhydride (2.65g, 5mmol) and 30mL toluene into a 100mL reaction flask, stir well, then add glycine (0.41g , 5.4mmol) and 2-ethylhexylamine (0.69g, 5.4mmol), reflux for 48h. Cool down to room temperature, add 150mL dichloromethane, wash 3 times with water (50mL×3), and wash the organic phase with MgSO 4After drying and removing the solvent, the crude product was separated by column chromatography using dichloromethane / ethyl acetate = 10:1 as the eluent to obtain 1.62 g of dark red solid 1a with a yield of 25%.

[0067] Under a nitrogen atmosphere, add the above product 1a (2.34g, 3.4mmol), 4-hydroxy-1,6-heptadyne (0.83g, 6.8mmol) and 100mL dichloromethane into a 100mL reaction flask, stir to diss...

Embodiment 2

[0070] The polymerization conditions are the same as in Example 1, only the solvent is changed to tetrahydrofuran. 154 mg of black solid poly(1) was obtained with a yield of 96%, and the others were the same as in Example 1.

Embodiment 3

[0072] The synthesis of Po1y(2), the synthetic route is as follows:

[0073]

[0074] Under nitrogen atmosphere, in a 150mL reaction flask, add 1,6,7,12-tetrachloro-3,4:9,10-perylenetetracarboxylic dianhydride (3.01g, 5.6mmol), glycine (3.00g, 40mmol) and 40mL propionic acid, stir until the sample is evenly dispersed, and stop the reaction after 40h of reflux reaction. Cool to room temperature, filter, wash the filter cake with water until the filtrate is neutral, put it in a vacuum drying oven at 80°C and dry to constant weight to obtain 3.20 g of red powder 2a with a yield of 91%. The product is directly put into the next step without further purification dehydration reaction.

[0075] Under a nitrogen atmosphere, in a 100mL reaction flask, add 2a (2.20g, 3.5mmol), 4-hydroxymethyl-1,6-heptadiyne (1.65g, 13.5mmol), 40mLN,N-dimethylformamide and 10 mL of chloroform. Under the condition of ice bath, EDCI.HCl (1.56g, 8.4mmol) and DMAP (0.13g, 1.1mmol) were added, the tempe...

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Abstract

The present invention provides a peryleneimide-containing conjugated polyacetylene, which comprises formula (I) polyacetylene (PA) homopolymer containing peryleneimide (PBI) and formula (II) containing peryleneimide The polyacetylene copolymer acceptor (n‑type) material. The invention also provides its preparation method. The conjugated polyacetylene containing peryleneimide provided by the present invention has excellent photoelectric properties, good thermal stability and environmental stability, and the preparation method is simple and easy, and can be achieved by flexible transformation of substituents on PBI. The energy level matching between materials can realize the regulation of photoelectric performance, which has broad application prospects in the field of photoelectric devices and other fields.

Description

technical field [0001] The invention relates to the preparation technology of conjugated polyacetylene, in particular to the conjugated polyacetylene containing perylene imide and its preparation method by metathesis cyclopolymerization reaction. Background technique [0002] Polyacetylene is the simplest conductive polymer, through Ti(O-Pr) 4 / Et 3 The A1 system is prepared by catalyzing the polymerization of acetylene or the ring-opening metathesis polymerization of cyclooctatetraene. Its poor stability, solubility, and processability in the air bring inconvenience to synthesis and characterization; polyacetylene film has a large third-order polarizability, but it is easy to crystallize, uneven in shape and large in scattering loss, making its optical properties difficult to obtain. Performance is degraded and applications are limited. The introduction of substituent groups on the polyacetylene backbone can effectively improve the solubility, melting and processing prop...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F138/00C08F293/00C08F238/00
Inventor 谢美然宋卫伍建华张莎郭梦方
Owner EAST CHINA NORMAL UNIV
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