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Novel symmetric purpurine compound and preparation method and applications thereof

A compound and symmetrical technology, applied in the field of novel symmetrical viologen compounds and their preparation, to achieve the effects of good electron accepting ability, good electron-acquiring performance and easy adjustment

Inactive Publication Date: 2020-02-28
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented novel asymmetric vinifer compound (Vivo) describes various types of chemicals called vibratoene monomers. These chemically active compounds have unique electronic charges attached to them due to certain atoms within it's main chain. They also allow for multiple valences at once when exposed to specific conditions like pH values. By changing these characteristics, they may create useful products including sensors, displays, memory elements, and other applications.

Problems solved by technology

This patented describes different types of chemical substances used for controllably changing physical characteristics such as shape or texture when exposed to certain conditions like heat or pressure. These compounds include organometallics, conductivity polymers, ionochromatic molecules, liquid crystals, metalloids, chloroindoles, carbazones, quinazolinediones, amino acids, peptides, proteins, polysaccharide glycosaminogens, polyphenols, flavonoid agrochemistry agents, dyes, phthalocyanine blue, fluorescein green, rhodamine red, cyanobacteria cell membranes, enzyme catalysts, antimicrobial coatings, electronic displays, batteries, solar cells, gas generators, and other applications where controlled response over time is crucial due to their potential use in various industries including electronics manufacturing processes.

Method used

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  • Novel symmetric purpurine compound and preparation method and applications thereof
  • Novel symmetric purpurine compound and preparation method and applications thereof
  • Novel symmetric purpurine compound and preparation method and applications thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment 1: the preparation of Vio-1-1 and Vio-2-1

[0043]

[0044] (1) Preparation of compound 5: 4,4'-bipyridine (154mg, 1mmol) and 1-chloro-2,4-dinitrobenzene (707mg, 3.5mmol) were refluxed in acetonitrile or ethanol solvent for 24h, cooled Return to room temperature, filter with suction, wash with acetonitrile three times, then wash with ether three times, and dry in vacuum to obtain compound 5. Yield: 74%. 1 H NMR (400MHz,D 2 O) δ(ppm): 9.41(d, J=8Hz, 2H), 9.35(d, J=8Hz, 2H), 8.88(m, 6H), 8.24(d, J=8Hz, 2H). 13 C NMR (100MHz,D 2 O) δ (ppm): 150.7, 148.8, 143.9, 139.9, 134.4, 133.2, 132.6, 123.7, 121.0.

[0045] (2) Preparation of Compound 3: Compound 1, bis(4-tert-butylphenyl)amine (281mg, 1mmol) and sodium hydride (60% in mineral oil) (80mg, 1mmol) in anhydrous DMSO solvent at room temperature Stirred at low temperature for 30min, then added compound 2, p-fluoronitrobenzene (141mg, 1mmol), stirred at 150°C for 18h; cooled to room temperature, poured the...

Embodiment 2

[0053] Embodiment 2: The specific operation steps of the electrochromic and electrochromic light-emitting dual-function devices made of Vio-1-1 or Vio-2-1 are as follows:

[0054] (1) Dissolve Vio-1-1 or Vio-2-1 and polyvinylpyrrolidone (PVP) with a mass ratio of 1:1 in a low-boiling organic solvent, drop-coat it on ITO glass and dry it in a vacuum at 80°C Box drying for 12 hours;

[0055] (2) Dissolve polymethyl methacrylate (PMMA), lithium perchlorate, and propylene carbonate (PC) in a low-boiling point organic solvent, and drop-coat it on the ITO glass with the material coated in (1). The ITO glass is overlapped and dried in a vacuum oven at 80°C for 12 hours to bond the two pieces of ITO glass together.

Embodiment 3

[0056]Embodiment 3: Absorption and emission spectrum test of Vio-1-1 and Vio-2-1

[0057] The spectrum test concentration used in the present invention is 10 μM, and the test solvent is acetonitrile. When measuring the emission spectrum, the excitation wavelength of Vio-1-1 is 405nm, and the excitation wavelength of Vio-2-1 is 350nm.

[0058] Absorption and emission spectra of Vio-1-1 and Vio-2-1 as figure 1 and figure 2 shown. The absorption peak around 300nm is the characteristic absorption peak of viologen. The maximum absorption peak of Vio-1-1 is around 520nm, while the maximum absorption peak of Vio-2-1 is around 480nm; The emission peak is around 425nm and emits green light. This is caused by the difference in the strength of the charge transfer ability in the two molecules.

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Abstract

The invention discloses a novel symmetric purpurine compound, which is composed of an acceptor 4,4'-dipyridine, different donor groups, and different counter anions. The structure of the compound is shown in the description. The invention also discloses a preparation method of the novel symmetric purpurine compound. Different donor groups are introduced into 4,4'-dipyridine, and through ion exchange, purpurine compounds with different counter anions are obtained. The good and reversible redox property of donors and the acceptor unit is utilized, and the charge transfer performances in purpurine molecules are different, so under the action of an external electric field, reversible redox reactions of the purpurine compound happen, during the reaction process, the color and light emitting color change, and the purpurine compound can be made into a bifunctional electrochromic and electrochromic light emitting device with prominent color change.

Description

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Claims

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Application Information

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Owner NANJING UNIV OF POSTS & TELECOMM
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