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Selenium/tellurium-containing heterocyclic polymer as well as preparation method and conversion method thereof

A polymer and heterocyclic technology, applied in the fields of polymer chemistry and materials science, can solve the problems of hindering the development and application of polyselenophene materials, harsh reaction conditions, and many reaction steps, and achieves high atom utilization and polymerization efficiency. The effect of high and high thermal stability

Inactive Publication Date: 2021-09-24
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the synthesis of this kind of very valuable polyselenophene organic semiconductor materials is relatively difficult. Asit Patra et al. published a paper on the synthesis method of polyselenophene in Polym.Chem. (2020, 11, 7275-7292) in 2020. In summary, these methods mainly involve problems such as selenophene monomers, metal catalysts, toxic reagents, harsh reaction conditions, and many reaction steps, which hinder the development and application of polyselenophene materials to a certain extent.
The synthesis of polytellophene is rarely reported

Method used

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  • Selenium/tellurium-containing heterocyclic polymer as well as preparation method and conversion method thereof
  • Selenium/tellurium-containing heterocyclic polymer as well as preparation method and conversion method thereof
  • Selenium/tellurium-containing heterocyclic polymer as well as preparation method and conversion method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] A poly-1,4-diselenene polymer, the structural formula of which is shown in P1:

[0069]

[0070] The poly-1,4-diselenene polymer is prepared by direct reaction of acetylenone and elemental selenium, and the reaction equation is as formula (1):

[0071]

[0072] M1 is elemental selenium, which can be purchased from the market. In this example, it was purchased from Merrill Chemical Reagents. M2 is acetylene, and its synthesis method is as described in the literature (Macromolecules 2015,48,1941-1951);

[0073] The synthesis steps of the poly-1,4-diselenene polymer are as follows:

[0074] Add 47.4mg (0.6mmol) monomer M1 and 90.1mg (0.2mmol) monomer M2 successively in the polymerization tube of 10 milliliters, add 16.8mg (0.3mmol) potassium hydroxide again, then vacuumize and change nitrogen 3 times, use Inject 1.0ml of N,N-dimethylformamide into the syringe, react at 60°C, and stir at a rate of 300rpm for 1.5h; after the reaction is completed, dissolve the reacti...

Embodiment 2

[0077] A poly-1,4-diselenene polymer, the structural formula of which is shown in P1:

[0078]

[0079] The poly-1,4-diselenene polymer is prepared by direct reaction of acetylenone and elemental selenium, and the reaction equation is as formula (1):

[0080]

[0081] M1 is elemental selenium, which can be purchased from the market. In this example, it was purchased from Merrill Chemical Reagents. M2 is acetylene, and its synthesis method is as described in the literature (Macromolecules 2015,48,1941-1951);

[0082] The synthesis steps of the poly-1,4-diselenene polymer are as follows:

[0083] Add 47.4mg (0.6mmol) of monomer M1 and 90.1mg (0.2mmol) of monomer M2 in sequence in a 10ml polymerization tube, then add 97.6mg (0.3mmol) of cesium carbonate, then vacuum and change nitrogen for 3 times, use a syringe Inject 1.0mL of N,N-dimethylformamide, react at 60°C, and stir at a rate of 300rpm for 1.5h; after the reaction, dissolve the reaction mother liquor in 4mL of tet...

Embodiment 3

[0086] A poly-1,4-diselenene polymer whose structural formula is as shown in P2:

[0087]

[0088] The poly-1,4-diselenene is prepared by direct reaction of cyclooctadiyne and elemental selenium, and the reaction equation is as formula (2):

[0089]

[0090] M1 is elemental selenium, which can be purchased from the market. In this example, it was purchased from Merrill Chemical Reagents. M3 is cyclooctadiyne, and its synthesis method is as described in the literature (ACS Macro Lett., 2019, 8, 948-954);

[0091] The synthesis steps of the poly-1,4-diselenene polymer are as follows:

[0092] Add 47.4mg (0.6mmol) of monomer M1 and 20.8mg (0.2mmol) of monomer M3 in sequence to a 10ml polymerization tube, then add 97.6mg (0.3mmol) of cesium carbonate, then vacuumize and change nitrogen for 3 times, use a syringe Inject 1.0mL of N,N-dimethylformamide, react at 60°C, and stir at a rate of 300rpm for 1.5h; after the reaction, dissolve the reaction mother liquor in 4mL of tetr...

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Abstract

The invention discloses a selenium / tellurium-containing heterocyclic polymer as well as a preparation method and a conversion method thereof. The selenium / tellurium-containing heterocyclic polymer comprises a poly (1, 4-diselenide / tellurene) polymer and a poly (selenium / tellurophene) polymer; according to the method, the elemental selenium / tellurium can be activated under the condition of alkali induction, and then the elemental selenium / tellurium is polymerized with activated internal alkyne under the regulation and control of temperature to selectively obtain poly (1, 4-diselenide / tellurene) and poly (selenium / tellurophene). Meanwhile, poly (1, 4-diselenide / tellurene) is converted into poly (selenium / tellurophene) under the condition of high temperature or oxidation. The method is mild in reaction condition, simple to operate, green, economical, energy-saving and environment-friendly, and has the characteristics of high reaction efficiency, high atom economy and high regioselectivity. The synthesized poly (1, 4-diselenide / tellurene) can be converted into poly (selenium / tellurophene). And the synthesized poly (1, 4-diselenide / tellurene) and poly (selenium / tellurophene) have relatively high thermal stability.

Description

technical field [0001] The invention belongs to the field of polymer chemistry and material science, and specifically relates to a selenium / tellurium-containing heterocyclic polymer and a preparation method and a conversion method thereof. Background technique [0002] Conjugated chalcogen-containing heterocyclic polymers, such as polythiophene, polyselenophene, and polytellophene, as a special class of chalcogen-containing polymers, have strong thermal stability, strong electron transport ability and easy processing And other advantages, and widely used in organic light-emitting diodes, solar cells, thermoelectric materials, fluorescent sensing, magnetic nanomaterials, memory materials, etc. Compared with polythiophene, polyselenophene has lower aromaticity, higher stability after oxidation, lower band gap, lower redox potential, better electrochromic performance, stronger quinoid characteristics, and is not easy to Twisted, tends to be more planar, and stronger Se-Se inte...

Claims

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Application Information

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IPC IPC(8): C08G79/00
CPCC08G79/00
Inventor 唐本忠胡蓉蓉彭建文秦安军赵祖金
Owner SOUTH CHINA UNIV OF TECH
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