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A kind of porphyrin class supramolecular helical polymer and its synthetic method

A synthesis method and supramolecular technology, which can be used in organic chemistry, photosensitive equipment, etc., can solve the problem of low light capture ability, and achieve the effect of high dye adsorption capacity, wide absorption spectrum, and wide application prospects.

Active Publication Date: 2022-04-19
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to solve the problems in the prior art, the present invention provides a porphyrin-based supramolecular helical polymer and its synthesis method, which solves the problem that porphyrin-based dyes are used in dye-sensitized solar cells in the prior art, but they still exist Problems with low light-harvesting capabilities

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  • A kind of porphyrin class supramolecular helical polymer and its synthetic method
  • A kind of porphyrin class supramolecular helical polymer and its synthetic method
  • A kind of porphyrin class supramolecular helical polymer and its synthetic method

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Experimental program
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Embodiment 1

[0041] 1) Synthesis of Compound 3:

[0042] At room temperature, compound 1 (4.3784g, 20mmol), compound 2 (3.7842g, 20mmol), HOBt (2.9729g, 22mmol), DIPEA (3.48mL, 20mmol) and EDC.HCl (4.2174g, 22mmol) were added to the circle Bottom flask, then add 60ml of dichloromethane, react at 35°C for 6 hours, then extract 3 times with saturated aqueous citric acid solution, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution, and collect organic phase, then dried with anhydrous sodium sulfate, filtered and evaporated, and the residue was purified by 300-400 mesh silica gel column chromatography (petroleum ether / ethyl acetate=1 / 1) to obtain 4.1g of compound 3. The yield was 49.1%. The resulting product is used 1 HNMR (CDCl 3 ,400MHz) for characterization, the following data were obtained: δ H 6.75(s,1H),5.22(s,1H),4.16(q,J=7.0Hz,1H),3.43(t,J=6.6Hz,2H),3.39(m,2H),2.08(q,J =6.5Hz, 2H), 1.45(s, 9H), 1.36(d, J=7.0Hz, 2H).

[0043] 2) Synthesi...

Embodiment 2

[0052] 1) Synthesis of compound 3:

[0053] At room temperature, compound 1 (5.4685g, 25mmol), compound 2 (4.2572g, 22.5mmol), HOBt (4.7566g, 32mmol), DIPEA (5.57mL, 32mmol) and EDC.HCl (6.1344g, 32mmol) were added to In the round-bottomed flask, then add 80ml of dichloromethane, react at 35°C for 7 hours, then extract 3 times with saturated aqueous citric acid solution, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution, and collect The organic phase was then dried with anhydrous sodium sulfate, filtered and then rotary evaporated, and the residue was purified by 300-400 mesh silica gel column chromatography (petroleum ether / ethyl acetate=1 / 1) to obtain 5.9g of compound 3, the yield was 56.3%. The resulting product is compared and characterized by thin-layer chromatography with the above-mentioned Example 1.

[0054] 2) Synthesis of compound 4:

[0055] At room temperature, compound 3 (3g, 9.3mmol) was added to a round-bottomed fl...

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Abstract

The invention discloses a porphyrin-based supramolecular helical polymer and a synthesis method thereof. (1) Acylation reaction of Boc-protected L-type alanine and bromopropanine hydrochloride, and then de-Boc and N-acylation reactions to obtain small molecule aldehydes; (2) through [2+2] Synthetic method, bromination, Heck reaction to obtain hydroxy porphyrins, and then carry out ether-forming reaction and dehydration reaction with the above-mentioned small molecule aldehydes to obtain a porphyrin monomer with cyano branched chain; (3) porphyrin monomer in Ni 2+ Polymerization is carried out under catalysis to obtain the target compound. The present invention designs and synthesizes a porphyrin compound with an isonitrile helical polymer as the skeleton and branched chains with long hydrophobic chains and ester groups. This type of compound can be used as a material in organic photovoltaic materials and organic solar cells. , Catalysis and other fields.

Description

technical field [0001] The invention belongs to the technical field of organic chemical industry, and specifically relates to a porphyrin-based supramolecular helical polymer and a synthesis method thereof. Background technique [0002] The core electronic structure of porphyrin compounds is a sixteen-membered conjugated ring with basic four-fold symmetry, and there are two conjugated structures in a delocalized state of 18π electrons. This unique electronic structure of porphyrin determines the unique spectral absorption bands of porphyrin molecules: Soret absorption band (also known as B band) with strong light absorption and Q absorption band with relatively weak light absorption. At the same time, porphyrin compounds have good photothermal stability, and the four meso-position carbons and eight β-position carbons on the porphyrin ring are also easy to modify. The excellent physical and chemical properties of porphyrin compounds make them widely used in solar cells, cata...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G73/00C07D487/22H01G9/20
CPCC08G73/00C07D487/22H01G9/20
Inventor 张宝冯亚青张宇哲
Owner TIANJIN UNIV
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