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Alpha-position vinyl bridged BODIPY conjugated polymer and preparation method thereof

A conjugated polymer, ethylene technology, applied in the fields of organic synthesis, dyes and fine chemicals, can solve the problems of limited application, difficult to achieve effective absorption, etc., achieve narrow optical band gap, is conducive to mass production, full application potential effect

Pending Publication Date: 2022-07-08
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the prior art, it is also difficult for BODIPY compounds to achieve effective absorption > 1100nm, which limits their further application

Method used

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  • Alpha-position vinyl bridged BODIPY conjugated polymer and preparation method thereof
  • Alpha-position vinyl bridged BODIPY conjugated polymer and preparation method thereof
  • Alpha-position vinyl bridged BODIPY conjugated polymer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072]

[0073] Under an argon atmosphere, 0.100 mmol of 1a monomer, 0.102 mmol of 1b monomer, 0.003 mmol of tris(dibenzylideneacetone)dipalladium [Pd 2 (dba) 3 ] with 0.012 mmol tris(o-methylphenyl)phosphine [P(o-Tol) 3 ] ligand, take 6 mL of toluene (Toluene) into the bottle, heat up to 120 ° C, stir the reaction under argon protection for 24 hours, then cool to room temperature, pour the reaction solution into methanol, filter the precipitated solid, vacuum dry, The polymer was washed with acetone and n-hexane successively to remove small molecules and catalysts with a Soxhlet extractor, and finally the polymer was extracted with chloroform. Calculated yield: 92%.

[0074] The BODIPY class monomer 1a in Example 1 is detected by hydrogen NMR and carbon NMR, and the results are as follows: Figure 9 and Figure 10 As shown, the ethylene double tin salt monomer 1b in Example 1 was detected by hydrogen nuclear magnetic spectrum, and the results were as follows Figure 1...

Embodiment 2

[0079]

[0080] Under an argon atmosphere, 0.150 mmol of 2a monomer, 0.600 mmol of piperidine and 0.100 mmol of acetic acid were added to a 20 mL pressure bottle, 5 mL of toluene (Toluene) was added to the pressure bottle, and the temperature was raised to 120 ° C. The reaction was stirred for 48 hours, then cooled to room temperature, the reaction solution was poured into methanol, the precipitated solid was filtered, dried in vacuum, the polymer was washed with a Soxhlet extractor with acetone and n-hexane in turn to remove small molecules and catalysts, and finally Chloroform extracted the polymer. Calculated yield: 79%.

[0081] Carry out hydrogen nuclear magnetic spectrum to the BODIPY monomer 2a in embodiment 2, the results are as follows respectively Figure 12 shown.

[0082] Absorption spectrum analysis is carried out to the macromolecule prepared in Example 2, and the test result is as follows Figure 5 shown.

[0083] The prepared polymer was analyzed by gel ...

Embodiment 3

[0087]

[0088] Under an argon atmosphere, 0.100 mmol of 3a monomer, 0.100 mmol of 3b monomer, 0.003 mmol of tris(dibenzylideneacetone)dipalladium [Pd 2 (dba) 3 ] with 0.012 mmol tris(o-methylphenyl)phosphine [P(o-Tol) 3 ] ligand, add 6 mL of toluene (Toluene) into the bottle, heat up to 120°C, stir the reaction under argon for 24 hours, then cool to room temperature, pour the reaction solution into methanol, filter the precipitated solid, and vacuum dry, The polymer was washed with acetone and n-hexane successively to remove small molecules and catalysts with a Soxhlet extractor, and finally the polymer was extracted with chloroform. Calculated yield: 89%.

[0089] The BODIPY class monomer 3a in Example 3 is detected by hydrogen NMR and carbon NMR, and the results are as follows respectively. Figure 13 and Figure 14 shown.

[0090] The absorption spectrum of the polymer prepared in Example 3 is as follows Figure 7 shown.

[0091] The prepared polymer was analyzed b...

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Abstract

The invention relates to an alpha-vinyl bridged BODIPY conjugated polymer and a preparation method thereof, and belongs to the technical fields of organic synthesis, dyes and fine chemical engineering. The BODIPY conjugated polymer has a structural general formula as shown in a formula (I), and in the formula (I), n is an integer of 2-200. The BODIPY type conjugated polymer not only has good photo-thermal stability and chemical stability of BODIPY type materials, but also realizes the characteristics of good planarity and charge delocalization of a conjugated polymer skeleton through ethylene bridging, realizes absorption of a near-infrared long-wave region, and the wavelength distribution of a main absorption peak can be extended from 900nm to 2000nm all the time.

Description

technical field [0001] The invention belongs to the technical fields of organic synthesis, dyes and fine chemicals, in particular to a class of BODIPY-type conjugated polymers with α-position vinyl bridges with near-infrared long-wavelength absorption and a preparation method thereof, in particular to a class of main absorption peaks The invention relates to a BODIPY type conjugated polymer with a wavelength range of 900nm-2000nm and a preparation method thereof. Background technique [0002] Near-infrared (Near Infrared, NIR) absorbing materials, as defined by the American Society for Testing and Materials (ASTM), generally refer to materials that can absorb light with wavelengths ranging from 780 to 2526 nm. The near-infrared region can be divided into two regions: near-infrared short-wave (780-1100nm) and near-infrared long-wave (1100-2526nm). Materials with near-infrared absorption have unique applications in optical fiber communication, energy, medical, national defens...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12
CPCC08G61/122C08G2261/124C08G2261/18C08G2261/1424C08G2261/3247C08G2261/3327C08G2261/414Y02E10/549
Inventor 刘俊邵兴鑫刘孟雨王利祥
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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