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Application of phenylene bis-vinylidene bis-benzimidazole compound

A technology of phenylenedivinylene and bisbenzimidazole is applied in the field of phenylenedivinylidene bisbenzimidazole compounds, which can solve problems such as large differences, reduce energy difference, and enhance electron cloud delocalization. degree, the effect of increasing the transition moment

Active Publication Date: 2013-05-01
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, no clear structure-activity relationship has been established for up-conversion fluorescence and two-photon absorption materials, and various analysis and speculation based on the structure-activity relationship of known compounds are not necessarily followed. Some results calculated by software theory may be different from actual test results. very big

Method used

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  • Application of phenylene bis-vinylidene bis-benzimidazole compound
  • Application of phenylene bis-vinylidene bis-benzimidazole compound
  • Application of phenylene bis-vinylidene bis-benzimidazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1 Compound (Ⅲ)

[0021] Heat 8.28g (60mmol) of p-xylylene dimethyl ether, 8.10g (270mmol) of paraformaldehyde and 150mL of acetic acid to 60°C, and then add 40mL of 40% mass percent hydrobromic acid solution. React at 60°C for 4 hours, cool, filter the precipitated solid, dissolve it with dichloromethane, wash it with saturated sodium bicarbonate solution several times, and distill off the solvent to obtain 18.75 g of white 1,4-bis(bromomethyl)- 2,5-Dimethoxybenzene. 1 H NMR (500MHz, CDCl 3 ) δ (ppm): 6.89 (s, 2H), 4.55 (s, 4H), 3.89 (s, 6H).

[0022] 12.62g (90mmol) of hexamethylenetetramine and 9.72g (30mmol) of 1,4-bis(bromomethyl)-2,5-dimethoxybenzene were dissolved in 200mL of chloroform, heated to reflux for 4h, and the solvent was evaporated 200mL of 50% acetic acid solution was added to the obtained solid, heated to reflux for 5h, and then a small amount of concentrated hydrochloric acid was added dropwise. After cooling, the mixture was extracted wi...

Embodiment 2

[0023] Example 2 Compound (I)

[0024] Dissolve 7.92 g (0.06 mol) of 2-methylbenzimidazole (Ⅱ) and 10 g of potassium hydroxide in 50 mL of N,N-dimethylformamide, add dropwise 3.88 g (0.02 mol) of compound (Ⅲ) in 30 mL solution in N,N-dimethylformamide. After dropping, heated to reflux for 12 h, cooled to room temperature, a large amount of solid precipitated out, filtered with suction, dried, and separated by silica gel column chromatography to obtain 6.08 g of yellow compound (I). 1 H NMR (500MHz, DMSO-d 6 ) δ (ppm): 13.23(s, 2H), 7.97(d, 2H), 7.57~7.59(m, 4H), 7.44(s, 2H), 7.41(d, 2H), 7.22~7.25(m, 4H ), 3.99(s, 6H). ESI-MS m / z: 423.2 ([M+H] + ). Elem. Anal. Calcd for C 26 h 22 N 4 o 2 : C 73.92, H 5.25, N 13.26; Found: C 74.13, H 5.31, N 13.47.

Embodiment 3

[0025] Example 3 Compound (I)

[0026] Dissolve 6.60 g (0.05 mol) of 2-methylbenzimidazole (Ⅱ) and 8 g of sodium ethoxide in 60 mL of methanol, and add dropwise a solution of 3.88 g (0.02 mol) of compound (Ⅲ) in 60 mL of methanol. After dropping, heated to reflux for 20 h, cooled to room temperature, a large amount of solid precipitated out, filtered with suction, dried, and separated by silica gel column chromatography to obtain 5.32 g of yellow compound (I).

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Abstract

The invention discloses an application of a phenylene bis-vinylidene bis-benzimidazole compound. The chemical name of the phenylene bis-vinylidene bis-benzimidazole compound is (E, E)-2, 2'-[(2, 5-dimethoxy-1, 4-phenylene) bis-2, 1-vinylidene] bis-1H-benzimidazole; and the structure of the compound is shown in the formula (I). The phenylene bis-vinylidene bis-benzimidazole compound is applied as an upconversion fluorescence and two-photon absorption material, and has excellent upconversion fluorescence emitting capacity and two-photon absorption capacity.

Description

(1) Technical field [0001] The present invention relates to a phenylene divinylene bisbenzimidazole compound—(E,E)-2,2'-[(2,5-dimethoxy-1,4-phenylene)bis Application of -2,1-vinylidene]bis-1H-benzimidazole as an upconversion fluorescence and two-photon absorption material. (2) Background technology [0002] The 21st century is a brand-new era of photons. Compared with electrons, photons have excellent characteristics such as large information load, fast response time, strong interconnection ability, strong parallel ability, and high security and confidentiality. Therefore, it is unstoppable to replace electrons with photons to develop photon technology. . At present, photonic technology has become one of the cores of many rapidly developing high-tech in the world. [0003] Nonlinear optical materials are the key materials of photonic technology and the important material basis for realizing optical communication, optical computing, optical information processing, optical s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06G02F1/361C07D235/12
Inventor 蔡志彬李波周茂陈晔
Owner ZHEJIANG UNIV OF TECH
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