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Photosensitive double helical chiral fluorescent compound based on 5,6-disubstituted phenanthrene and its derivatives and its synthesis method

A technology for fluorescent compounds and derivatives, applied in organic chemistry methods, chemical instruments and methods, organic chemistry, etc., can solve the problem of not exhibiting optical activity and so on

Active Publication Date: 2021-10-19
TIANJIN CHENGJIAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Under ordinary conditions, although the molecule contains an asymmetric center or a helical structure, it will not show optical activity

Method used

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  • Photosensitive double helical chiral fluorescent compound based on 5,6-disubstituted phenanthrene and its derivatives and its synthesis method
  • Photosensitive double helical chiral fluorescent compound based on 5,6-disubstituted phenanthrene and its derivatives and its synthesis method
  • Photosensitive double helical chiral fluorescent compound based on 5,6-disubstituted phenanthrene and its derivatives and its synthesis method

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Experimental program
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Embodiment 1

[0055] 1. Structural characterization and spectral test conditions

[0056] Proton NMR spectrum and C NMR spectrum, using Varian nuclear magnetic resonance (400MHz and 500Mz), deuterated chloroform as a solvent, TMS as an internal standard. Toshiba F-7000 fluorescence spectrophotometer was used for the test of fluorescence spectrum. The ultraviolet absorption spectrum adopts specord 210plus ultraviolet-visible spectrophotometer.

[0057] 2. Synthesis of the target ring compound

[0058] In order to synthesize the target compound with the above structure, the synthetic route adopted is shown below.

[0059]

[0060] Specific steps are as follows:

[0061] 1. Synthesis of intermediate (b)

[0062] Add a small amount of NBS to 500 grams of propionaldehyde diethyl acetal, heat to 50°C, and irradiate with a 200W tungsten lamp until the orange color appears and disappears. Under ice water cooling, add the remaining 672 grams of NBS in batches. After addition, continue to rea...

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Abstract

The invention provides a photosensitive double helical chiral fluorescent compound based on 5,6-disubstituted phenanthrene and its derivatives and a synthesis method thereof, wherein 5,6-disubstituted phenanthrene or 5,6-diaryl heterocycle The ring substitution of 9,10 phenanthroline is the basic structural framework of photoresponsiveness, and a diarylethene-type molecular framework with a double helix structure was synthesized and isolated. The present invention introduces a helical structure with rotation hindrance as a structural unit to increase the specific rotation, and integrates it with a photoresponsive structure, and when the molecule is excited by specific light, energy level transition / or molecular isomerism occurs, resulting in chirality The obvious change of the structure shows the photoresponsiveness of molecular optical activity, which can be applied to the manufacture of special optical films, anti-counterfeiting identification, special optical fiber products and the manufacture of light-emitting film devices.

Description

technical field [0001] The invention relates to the field of chiral optical functional materials, in particular to a photosensitive double helical chiral fluorescent compound and a synthesis method thereof. Background technique [0002] Organic molecules that respond to external energy such as light, electricity, and magnetism are a unique class of organic functional materials, such as molecular switch materials, fluorescent materials, photochromic materials, light-absorbing materials, nonlinear optical materials, etc. In the study of materials, it is found that chirality is also one of the functional elements of materials. [0003] Chirality is a common feature in the universe. The sugar units in sugar, nucleic acid, starch and cellulose that exist in nature are all in D-configuration, and amino acids, the basic materials of biomacromolecules, are in L-configuration. Proteins and DNA have a right-handed helical conformation. In biological systems, there is specific select...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/74C07D495/04C09K11/06
CPCC07B2200/07C07D333/74C07D495/04C09K11/06C09K2211/1092
Inventor 吴边鹏谈廷风李艳霞
Owner TIANJIN CHENGJIAN UNIV