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Spiropyrane for improving solid photochromic performance by introducing rigid group and synthesis method thereof

A photochromic and synthetic method technology, applied in the direction of color-changing fluorescent materials, chemical instruments and methods, compounds of elements of Group 4/14 of the periodic table, etc., can solve the problem of high commercialization cost and inability to prepare photochromic polymer materials , Organic photochromic materials change color speed and small free volume of molecules, etc., to achieve the effect of improving color changing performance and fatigue resistance.

Active Publication Date: 2020-04-03
ZHEJIANG SCI-TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the photochromic materials that can be commercially applied in the solid state are mainly inorganic materials, and organic photochromic materials can only be used in solvents, which greatly limits the application of organic photochromic materials.
[0003] Current studies have shown that the main factor affecting the discoloration speed of organic photochromic materials is that the free volume of molecules is too small, which leads to the inability of molecules to undergo structural changes smoothly.
Chinese patent CN106046241A discloses the synthesis of a bis-thiopyran photochromic polymer. By introducing double bonds and copolymerizing with acrylate monomers, the bis-pyran photochromic polymer can be obtained, which can effectively increase its photochromic speed , but the use of photochromic materials synthesized by this method is limited, photochromic polymer materials based on different polymers cannot be prepared, and diversified commodities cannot be produced on this basis, and commercialization costs high

Method used

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  • Spiropyrane for improving solid photochromic performance by introducing rigid group and synthesis method thereof
  • Spiropyrane for improving solid photochromic performance by introducing rigid group and synthesis method thereof
  • Spiropyrane for improving solid photochromic performance by introducing rigid group and synthesis method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] In this embodiment, a spiropyran that introduces a rigid group to improve the solid-state photochromic performance, the nitrogen atom of the spiropyran in the indole ring is connected to the ethanol group, and the rigid aromatic ring molecule is introduced into the ethanol group by reacting with the hydroxyl group of the ethanol group. Among spiropyrans; spiropyrans introduced into rigid groups through modification have the following structure:

[0023]

[0024] The synthetic reaction formula is as follows:

[0025]

[0026] A kind of synthetic method that introduces the spiropyran of rigid group of the present embodiment, described method comprises the steps:

[0027] To 10 ml of ultra-dry dichloromethane was added 3,5-bis(benzyloxy)benzoic acid (3.42 mmol, 1.14 g), 1-ethyl-3(3-dimethylpropylamine)carbodiimide (EDCI) (3.42mmol, 0.66g) and 4-dimethylaminopyridine (DMAP) (3.42mmol, 0.42g), stirred under nitrogen until a clear solution. Dissolve 1'-(2-hydroxyethyl...

Embodiment 2

[0031] In this embodiment, a spiropyran that introduces a rigid group to improve the solid-state photochromic performance, the nitrogen atom of the spiropyran in the indole ring is connected to the ethanol group, and the rigid aromatic ring molecule is introduced into the ethanol group by reacting with the hydroxyl group of the ethanol group. Among spiropyrans; spiropyrans introduced into rigid groups through modification have the following structure:

[0032]

[0033] The synthetic reaction formula is as follows:

[0034]

[0035] To 10 ml of ultra-dry dichloromethane was added 3,5-bis(benzyloxy)pentafluorobenzoic acid (0.89 mmol, 0.47 g), 1-ethyl-3(3-dimethylpropylamine)carbodiimide ( EDCI) (2.68mmol, 0.52g) and 4-dimethylaminopyridine (DMAP) (2.68mmol, 0.32g), stirred under nitrogen atmosphere until clear solution. SP (0.89mmol, 0.31g) was dissolved in 10ml of anhydrous dichloromethane, added dropwise to the above clear solution, and reacted at room temperature for 2...

Embodiment 3

[0039] In this embodiment, a spiropyran that introduces a rigid group to improve the solid-state photochromic performance, the nitrogen atom of the spiropyran in the indole ring is connected to the ethanol group, and the rigid aromatic ring molecule is introduced into the ethanol group by reacting with the hydroxyl group of the ethanol group. Among spiropyrans; spiropyrans introduced into rigid groups through modification have the following structure:

[0040]

[0041] The synthetic reaction formula is as follows:

[0042]

[0043] To 10 ml of ultra-dry dichloromethane was added pentafluorobenzoic acid (6.55 mmol, 1.38 g), EDCI (1-ethyl-3(3-dimethylpropylamine) carbodiimide) (9.82 mmol, 1.88 g) and DMAP (4-dimethylaminopyridine) (9.82 mmol, 1.20 g), stirred under nitrogen atmosphere until clear solution. SP (1.31mmol, 0.46g) was dissolved in 10ml of anhydrous dichloromethane, added dropwise to the above clear solution, and reacted at room temperature for 24 hours. Afte...

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Abstract

The invention provides spiropyrane for improving solid photochromic performance by introducing a rigid group. An ethanol group is introduced to a nitrogen atom of an indole ring of spiropyrane, and arigid aromatic ring molecule is introduced into spiropyrane by reacting with a hydroxyl group of the ethanol group. The invention discloses spiropyrane with introduced rigid groups through modification and a synthesis method thereof. According to the spiropyrane molecular modification method used in the invention, a rigid aromatic ring group is introduced to increase the molecular space free volume of spiropyrane, so that spiropyrane has an enough space in a solid state to carry out a ring opening-ring closing reaction, thereby improving the discoloration performance and fatigue resistance.

Description

technical field [0001] The invention relates to the field of organic solid-state photochromic materials, in particular to a spiropyran and a synthesis method for introducing rigid groups to improve solid-state photochromic performance Background technique [0002] Photochromism means that after a compound is stimulated by light of a specific wavelength, the structure of the compound changes, resulting in a change in the absorption wavelength of the compound and the change is reversible. As a new type of smart material, photochromic materials can be applied in the fields of optical information storage, anti-counterfeiting materials, decoration and national defense, so photochromic materials have gradually become a research hotspot. At present, the photochromic materials that can be commercially applied in the solid state are mainly inorganic materials, and organic photochromic materials can only be used in solvents, which greatly limits the application of organic photochromic...

Claims

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Application Information

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IPC IPC(8): C07D491/107C07F7/18C09K9/02
CPCC07D491/107C07F7/1804C07F7/188C09K9/02C09K2211/1007C09K2211/1033Y02P20/55
Inventor 杨玉慧何钧照何哲江国华
Owner ZHEJIANG SCI-TECH UNIV
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