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Fluorine-containing near-infrared absorption conjugated polymer and preparation method thereof

A conjugated polymer, near-infrared technology, applied in the field of functional materials, can solve the problems affecting the singlet oxygen efficiency of photosensitizers, the introduction of perfluorinated segments, etc., and achieve the effect of increasing photodynamic therapy efficiency and high singlet oxygen efficiency.

Active Publication Date: 2022-05-17
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

(HU H, YAN X, WANG H, TANAKAJ, WANG M, YOU W, LI Z. JMater Chem B, 2019, 7(7): 1116-1123.) The above methods are the combination of perfluorocarbon and photosensitive The physical mixing of the photosensitive agent does not directly introduce the perfluorinated segment into the photosensitizer molecule, which will affect the further improvement of the efficiency of the photosensitizer to generate singlet oxygen

Method used

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  • Fluorine-containing near-infrared absorption conjugated polymer and preparation method thereof
  • Fluorine-containing near-infrared absorption conjugated polymer and preparation method thereof
  • Fluorine-containing near-infrared absorption conjugated polymer and preparation method thereof

Examples

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Effect test

Embodiment 1

[0049] (1) Synthesis of 3,6-bis(2-thienyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione

[0050] Add 70mmol potassium tert-butoxide and 40mL tert-amyl alcohol into a 250mL three-necked flask, raise the temperature to 110°C under an argon atmosphere, and stir until the potassium tert-butoxide is completely dissolved. Then, 20 mmol dimethyl succinate was slowly added dropwise, and the reaction was continued for 1 h after the dropwise addition was completed. Then, 50 mmol 2-cyanothiophene was slowly added dropwise, and the reaction was continued for 6 h after the dropwise addition was completed. After the reaction, the reaction solution was poured into a mixed solution of 80 mL of anhydrous methanol, 60 g of ice water and 7 mL of concentrated hydrochloric acid and stirred for 30 min. Filter, wash with water, and dry to obtain a red solid with a yield of 75%.

[0051] (2) Synthesis of 2,5-bis(2-octyldodecyl)-6-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4-dione

[0052] Add 8mmol 3,6-...

Embodiment 2

[0060] (1) Synthesis of 3,6-bis(2-thienyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione

[0061] Add 70mmol potassium tert-butoxide and 40mL tert-amyl alcohol into a 250mL three-necked flask, raise the temperature to 110°C under an argon atmosphere, and stir until the potassium tert-butoxide is completely dissolved. Then, 20 mmol dimethyl succinate was slowly added dropwise, and the reaction was continued for 1 h after the dropwise addition was completed. Then, 50 mmol 2-cyanothiophene was slowly added dropwise, and the reaction was continued for 6 h after the dropwise addition was completed. After the reaction, the reaction solution was poured into a mixed solution of 80 mL of anhydrous methanol, 60 g of ice water and 7 mL of concentrated hydrochloric acid and stirred for 30 min. Filter, wash with water, and dry to obtain a red solid with a yield of 75%.

[0062] (2) Synthesis of 2,5-bis(2-hexyldecyl)-6-(thien-2-yl)pyrrolo[3,4-c]pyrrole-1,4-dione

[0063]Add 8mmol 3,6-di(2-t...

Embodiment 3

[0071] (1) Synthesis of 3,6-bis(2-thienyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione

[0072] Add 70mmol potassium tert-butoxide and 40mL tert-amyl alcohol into a 250mL three-necked flask, raise the temperature to 110°C under an argon atmosphere, and stir until the potassium tert-butoxide is completely dissolved. Then, 20 mmol dimethyl succinate was slowly added dropwise, and the reaction was continued for 1 h after the dropwise addition was completed. Then, 50 mmol 2-cyanothiophene was slowly added dropwise, and the reaction was continued for 6 h after the dropwise addition was completed. After the reaction, the reaction solution was poured into a mixed solution of 80 mL of anhydrous methanol, 60 g of ice water and 7 mL of concentrated hydrochloric acid and stirred for 30 min. Filter, wash with water, and dry to obtain a red solid with a yield of 75%.

[0073] (2) Synthesis of 2,5-di(dodecyl)-6-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4-dione

[0074] Add 8mmol 3,6-di(2-thi...

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Abstract

The invention belongs to the field of functional materials, and particularly relates to a fluorine-containing near-infrared absorption conjugated polymer and a preparation method thereof. The preparation method comprises the following steps: firstly, preparing a 3, 6-bis (5-bromothiophene-2-yl)-2, 5-bis (alkyl) pyrrolo [3, 4-c] pyrrole-1, 4-diketone monomer, then preparing dibromo fluorine-containing fluorene, and finally, reacting the 3, 6-bis (5-bromothiophene-2-yl)-2, 5-bis (alkyl) pyrrolo [3, 4-c] pyrrole-1, 4-diketone monomer with the dibromo fluorine-containing fluorene to prepare the fluorine-containing fluorene dibromo fluorine-containing fluorene. The preparation method comprises the following steps: dissolving a 1, 4-diketone monomer, dibromo fluorine-containing fluorene, a bis (trimethyltin) compound, tris (dibenzylideneacetone) dipalladium and tris (o-tolyl) phosphine in toluene, and reacting at 110 DEG C for 48 hours in an inert gas atmosphere to obtain the fluorine-containing fluorene and diketopyrrolopyrrole copolymer. The fluorine-containing fluorene and diketopyrrolopyrrole copolymer disclosed by the invention has strong absorption in a near-infrared region, and contains a perfluoro side chain, so that the efficiency of generated singlet oxygen is higher, and the photodynamic therapy efficiency can be improved.

Description

technical field [0001] The invention belongs to the field of functional materials, and in particular relates to a fluorine-containing near-infrared absorbing conjugated polymer and a preparation method thereof. Background technique [0002] Photodynamic therapy is a minimally invasive tumor treatment method, which was founded in the early 20th century. Photodynamic therapy is the use of light of a certain intensity and wavelength to irradiate the photosensitizer. The photosensitizer absorbs photon energy and transitions from the ground state to the excited state. The photosensitizer in the excited triplet state transfers energy to the surrounding oxygen to generate highly toxic singlet oxygen. to induce cell death. Compared with traditional tumor treatment methods, photodynamic therapy has the advantages of less trauma, shorter treatment cycle, high selectivity, and less side effects. But for photodynamic therapy, there are still some shortcomings. First of all, tradition...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12
CPCC08G61/126C08G2261/122C08G2261/146C08G2261/3142C08G2261/3223C08G2261/414Y02E10/549
Inventor 李坚张泽栋任强汪称意
Owner CHANGZHOU UNIV
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