Photochromic bi-thiophene six-sugar water-solubility symmetrical octafluorocyclopentene compound and preparation method and application

A thiophene-linked hexavalent sugar, perfluorocyclopentene technology, applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., can solve problems such as application limitations, and achieve the effect of good photochromic performance

Inactive Publication Date: 2013-06-05
JIANGXI SCI & TECH NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, in perfluorocyclopentene diarylethene compounds, the aromatic rings connected to both ends of the ethylene double bond are mainly two five-membered aromatic heterocycles, thiophene and benzothiophene, and there are also a small number of reports using furan, indole , pyrazole and indene as the main structure, but they are fat-soluble diarylethene compounds, which limits the application of such compounds in some fields, such as in biology

Method used

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  • Photochromic bi-thiophene six-sugar water-solubility symmetrical octafluorocyclopentene compound and preparation method and application
  • Photochromic bi-thiophene six-sugar water-solubility symmetrical octafluorocyclopentene compound and preparation method and application
  • Photochromic bi-thiophene six-sugar water-solubility symmetrical octafluorocyclopentene compound and preparation method and application

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Embodiment

[0020] Example: [Compound 1a]:

[0021] In the molecular structural formula, its name is: 1-[2-methyl-5-(β-D-hexaglycosyl)thiophen-3-yl]-2-[2-methyl-5-(β-D- Six-membered glycosyl) thiophen-3-yl] perfluorocyclopentene (a), its synthesis scheme is shown in Scheme 1:

[0022] Scheme 1:

[0023] .

[0024] Its specific synthetic steps are as follows:

[0025] 1. 3-Bromo-2-methyl-5-formylthiophene (2)

[0026] Under ice-bath conditions, 2-methyl-5-formylthiophene (1) (12.6 g, 100 mmol) was dissolved in acetic acid, and acetic acid containing liquid bromine was added dropwise under stirring, and the ice-bath reaction was continued for 8 h , add water solution, the aqueous phase is neutralized with NaOH, and then extracted with ether, the organic phases are combined, and saturated NaOH 2 CO 3 and aqueous solution successively, anhydrous MgSO 4 After drying, filtration, and rotary evaporation to remove the solvent, the residue was separated by silica gel column chromatography...

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Abstract

The invention discloses a photochromic bi-thiophene six-sugar water-solubility symmetrical octafluorocyclopentene compound and a synthetic method and a purpose thereof. A photochromic material can maintain good photochromic performance in solutions or films, the superior performance of a high cyclizing quantum yield, good sensitivity and the like is achieved in a open-loop state (a colorless state) and a closed-loop state (a color generation state), the open-loop state has strong fluorescent light occurs in a 350-550 nm range, luminance of the fluorescent light is reduced along with increasing of ultraviolet light emission time, and the closed-loop state has no fluorescent light, so the compound can be used for fluorescence detection and fluorescence light-operated switches. Compared with symmetrical thiophene or benzo thiophene type octafluorocyclopentene materials, the compound is low in cost of prepared materials and wide in application prospect.

Description

technical field [0001] The invention relates to a photochromic thiophene-linked hexavalent sugar water-soluble symmetrical perfluorocyclopentene compound, a preparation method and an application. Background technique [0002] With the rapid development of information storage technology, higher and higher requirements are put forward for the capacity, data transmission rate and response time of optical information storage materials. Exploring organic photochromic compounds as erasable and rewritable information materials is particularly attractive, because compared with inorganic materials, organic materials have high sensitivity, are easy to form thin films, and can greatly adjust the structure and properties of materials to meet storage requirements. , The price of raw materials is relatively low, but there are also disadvantages such as poor light and heat stability and fatigue resistance. In recent years, photochromic organic compounds with excellent properties have beco...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/26C07H1/00C09K9/02G11B7/26H01L33/50H01L51/54
Inventor 蒲守智童智鹏肖强崔士强刘刚
Owner JIANGXI SCI & TECH NORMAL UNIV
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