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Asymmetric squaraine material as well as preparation method and application thereof

A squaraine, asymmetric technology, applied in the field of asymmetric squaraine material and its preparation, can solve the problems that cannot meet the application requirements of blue-green light sensing, and achieve easy control of the reaction process, simple preparation method, strong stability Effect

Active Publication Date: 2018-12-21
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the spectral absorption peaks of the asymmetric squaraine materials disclosed in the prior art are located in the red-orange light absorption region, which cannot meet the application requirements in the fields of blue-green light sensing and multi-channel optical communication. Asymmetric squaraine materials are of great significance for the construction of new high-efficiency squaraine materials and the expansion of their application range

Method used

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  • Asymmetric squaraine material as well as preparation method and application thereof
  • Asymmetric squaraine material as well as preparation method and application thereof
  • Asymmetric squaraine material as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] This embodiment provides the preparation of an asymmetric squaraine material, which has the following structure:

[0040]

[0041] The specific preparation method of the asymmetric squaraine material with the above structure is:

[0042] The first step, the synthesis of intermediates:

[0043] 1. Dissolve 4g of diphenylamine and 3.8g of 3,4-diisopropoxy-3-cyclobutene-1,2,-dione in 160mL of isopropanol, stir and dissolve for 5min, then add 0.8mL of concentrated hydrochloric acid , Refluxed at 90°C for 3h, the solution was bright yellow.

[0044] 2. Filter the reaction solution, remove excess reaction substrate, remove the filtrate by rotary evaporation, and use 200mL of CHCl 3 Dissolved and evaporated to obtain a dried solid.

[0045] 3. Dissolve the above dried solid with 120mL of acetone and 120mL of 6M hydrochloric acid, and reflux at 70°C for 4h, the solution turns dark red.

[0046] 4. Concentrate the reaction solution by rotary evaporation until 50mL, and di...

Embodiment 2

[0060] This embodiment provides an asymmetric squaraine material, which has the following structure:

[0061]

[0062] The specific preparation method of the asymmetric squaraine material with the above structure is:

[0063] The first step, the synthesis of intermediates:

[0064] 1. Dissolve 4g of diphenylamine and 3.8g of 3,4-diisopropoxy-3-cyclobutene-1,2,-dione in 160mL of isopropanol, stir and dissolve for 5min, then add 0.8mL of concentrated hydrochloric acid , Refluxed at 85°C for 3h, the solution was bright yellow.

[0065] 2. Filter the reaction solution, remove excess reaction substrate, remove the filtrate by rotary evaporation, and use 200mL of CHCl 3 Dissolved and evaporated to obtain a dried solid.

[0066] 3. Dissolve the above dried solid with 120mL of acetone and 120mL of 6M hydrochloric acid, and reflux at 70°C for 4h, the solution turns dark red.

[0067] 4. Concentrate the reaction solution by rotary evaporation until 50mL, and dilute with CHCl 3 E...

Embodiment 3

[0075] This embodiment provides an asymmetric squaraine material, which has the following structure:

[0076]

[0077] The specific preparation method of the asymmetric squaraine material with the above structure is:

[0078] The first step, the synthesis of intermediates:

[0079] 1. Dissolve 4g of diphenylamine and 3.8g of 3,4-diisopropoxy-3-cyclobutene-1,2,-dione in 160mL of isopropanol, stir and dissolve for 5min, then add 0.8mL of concentrated hydrochloric acid , Refluxed at 95°C for 3h, the solution was bright yellow.

[0080] 2. Filter the reaction solution, remove excess reaction substrate, remove the filtrate by rotary evaporation, and use 200mL of CHCl 3 Dissolved and evaporated to obtain a dried solid.

[0081] 3. Dissolve the above dried solid with 120mL of acetone and 120mL of 6M hydrochloric acid, and reflux at 65°C for 5h, the solution turns dark red.

[0082] 4. Concentrate the reaction solution by rotary evaporation until 50mL, and dilute with CHCl 3 E...

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Abstract

The invention belongs to the technical field of preparation of squaraine materials and in particular relates to an asymmetric squaraine material as well as a preparation method and application thereof. According to the asymmetric squaraine material, C1 and C2 substituent groups are designed and selected, so that a spectral absorption peak of the material is located in a blue green light absorptionregion and the material is used for preparing an organic green blue light-sensitive device; application requirements in green blue sensing and multi-channel light communication fields; meanwhile, theabsorption half-peak width under an asymmetric squaraine material solution and the absorption half-peak width under a thin film state are less than 110nm and the asymmetric squaraine material has very important application in the aspect of photosensitive diodes. Furthermore, the material provided by the invention has strong stability and can meet various technologies including evaporation, spin-coating, inkjet printing and the like.

Description

technical field [0001] The invention belongs to the technical field of squaraine material preparation, and in particular relates to an asymmetric squaraine material and its preparation method and application. Background technique [0002] Squarine is a class of functional organic dyes, highly delocalized conjugated molecules with cyanine-like structures. Its most notable feature is that it has sharp and strong absorption in the long-wave region, good solubility in low polar solvents and good photothermal stability. Due to its good absorption and emission properties, large molecular rigidity, low excited state recombination energy, and easy structure modification, squaraine has attracted more and more attention, and has been widely studied and applied in organic solar energy in recent years. Batteries, organic photodetectors and photodiodes. [0003] The squaraine compound is formed by condensation of squaraine and electron-rich aromatic ring or heterocycle, which can form ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/335C07D207/36C07D209/14C07D277/28C07D333/20H01L51/46G01N21/31
CPCG01N21/31C07D207/335C07D207/36C07D209/14C07D277/28C07D333/20C07C2601/04H10K85/615H10K85/625H10K85/654H10K85/655H10K85/6572H10K30/00Y02E10/549
Inventor 董桂芳郭航席婵娟
Owner TSINGHUA UNIV
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