Aldehyde-functionalized dithienylethylene conjugated extension versatile molecular skeleton compound and preparation method and application thereof

A dithiophene ethylene, aldehyde functional technology, applied in the direction of inhibiting chemical change compositions, chemical instruments and methods, organic chemistry, etc. Effects of chromogenic properties, good fatigue resistance

Inactive Publication Date: 2019-10-08
LUOYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented technology describes two ways for creation of a new chemical entity called accepterium dibenzocyanine (ADC). These techniques involve adding extra electrons onto certain atoms within one part of the compound's backbone instead of just giving them up with their own atom like this case: they allow for more flexibility when designing photosensitive materials by controllably modifying its spectral characteristics without changing other important physical features such as size or shape. Additionally, these modifications are achieved through redox processes involving different types of radical species formed during decomposition process. Overall, it provides technical benefits over existing chemistry strategies used previously.

Problems solved by technology

The technical problem addressed in this patented text relates to improving the performance of organosilicon compounds that can be activate when exposed to specific wavelengths of electraviolet (UV) rays. This technology could potentially make electronic products more durable against damage caused by UV exposure over longer periods of use compared to existing technologies like phosphors.

Method used

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  • Aldehyde-functionalized dithienylethylene conjugated extension versatile molecular skeleton compound and preparation method and application thereof
  • Aldehyde-functionalized dithienylethylene conjugated extension versatile molecular skeleton compound and preparation method and application thereof
  • Aldehyde-functionalized dithienylethylene conjugated extension versatile molecular skeleton compound and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0034]

[0035] The preparation method of the compound of formula Ⅰ (n=0) is as follows: add (1,3-dioxin-2-ethylmethyl)-triphenylphosphine bromide (1.72 g , 4.0 mmol) and NaOMe (0.74 mL, 5.4 M methanol solution 4.0 mmol), under nitrogen protection, a THF (0.1 M) solution of the compound of formula III (316 mg, 1.0 mmol) was added. The mixture was refluxed for 12 h, cooled to room temperature, extracted with EtOAc (3 x 30 mL). Organic with MgSO 4 Dry, filter and concentrate. The solid was treated with 10% HCl in water (10 mL), stirred at room temperature for 2 hours, and the reaction mixture was neutralized with 2M NaOH. The mixture was extracted with EtOAc (3×30 mL), MgSO 4 Dry on , filter and concentrate under reduced pressure. Column chromatography (silica gel: 200 - 300, PE: EA = 9:1) gave a light yellow solid (Yield: 78%). 1 H NMR (400 MHz, CDCl 3 ) δ 9.57 (d, J = 7.7 Hz,2H), 7.42 (d, J = 15.5 Hz, 2H), 7.02 (s, 2H), 6.35 (dd, J = 15.5, 7.7 Hz,2H), 2.80 (t, ...

Embodiment 2

[0037]The preparation method of the compound of formula Ⅰ (n=1) is as follows: add (1,3-dioxin-2-ethylmethyl)-triphenylphosphine bromide (1.72 g , 4.0 mmol) and NaOMe (0.74 mL, 5.4 M methanol solution, 4.0 mmol), and a THF (0.1 M) solution of the compound of formula I (n=0) (316 mg, 1.0 mmol) was added under nitrogen protection. The mixture was refluxed for 12 h, cooled to room temperature, extracted with EtOAc (3 x 30 mL). Organic with MgSO 4 Dry, filter and concentrate. The solid was treated with 10% HCl in water (10 mL), stirred at room temperature for 2 hours, and the reaction mixture was neutralized with 2M NaOH. The mixture was extracted with EtOAc (3 x 30 mL), MgSO 4 Dry on , filter and concentrate under reduced pressure. Column chromatography (silica gel: 200-300, PE:EA = 9:1) gave a yellow solid (Yield: 61 %). 1 H NMR (400 MHz, CDCl 3 ) δ 9.56 (d, J = 8.0Hz, 2H), 7.15 (dd, J = 15.1, 11.2 Hz, 2H), 6.76 (s, 2H), 6.80- 6.70 (m, 2H),6.55 - 6.45 (m, 2H), 6.16 (dd...

Embodiment 3

[0039] The preparation method of the compound of formula II (n=0) is as follows: add (1,3-dioxin-2-ethylmethyl)-triphenylphosphine bromide (1.72 g , 4.0 mmol) and NaOMe (0.74 mL, 5.4 M methanol solution, 4.0 mmol) solution, under the protection of nitrogen, was added a solution of formula IV compound (644 mg, 2.0 mmol) in THF (0.2M), solution. The resulting mixture was refluxed for 8 h, cooled to room temperature, and extracted with EtOAc (3 x 30 mL). Composite organic layer with MgSO 4 Dry, filter and concentrate. The solid was dissolved in THF (10 mL) and treated with 10% HCl in water (10 mL). After stirring at room temperature for 2 hours, the reaction was neutralized with 2M sodium hydroxide. The mixture was extracted with EtOAc (3 × 30 mL), the organic layer was MgSO 4 Dry, filter and concentrate. Column chromatography (silica gel: 200-300, PE: EA = 9:1) gave a light yellow solid (Yield: 81%). 1 H NMR (400 MHz, CDCl 3 ) δ 9.58 (d, J = 7.7 Hz, 1H), 7.43 (d, J = ...

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Abstract

The invention relates to an aldehyde-functionalized dithienylethylene conjugated extension versatile molecular skeleton compound and a preparation method and application thereof. Electron-withdrawinggroups are introduced into two sides of a dithiophene molecular skeleton to realize construction of a (receptor-dithienylethylene-acceptor)-type photochemical material molecular skeleton, wherein thepresence of the electron-withdrawing groups in a long conjugated system can further reduce an energy difference value between frontier orbitals of a dithienylethylene ring-opening monomer, and the redshift of an absorption wavelength of the molecular occurs. The photochromic material has good photochromic properties, and has good fatigue resistance under ultraviolet or visible light irradiation.

Description

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Claims

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Application Information

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Owner LUOYANG NORMAL UNIV
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