Triphyene derivative and application thereof

A derivative, triptycene technology, applied in the field of triptycene derivatives, to achieve the effects of fast light response time, good thermal stability and high quantum efficiency

Inactive Publication Date: 2015-04-22
EAST CHINA UNIV OF SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few reports on the construction of star-shaped functional materials u...

Method used

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  • Triphyene derivative and application thereof
  • Triphyene derivative and application thereof
  • Triphyene derivative and application thereof

Examples

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preparation example Construction

[0024] The method for the compound shown in the preparation formula I provided by the present invention specifically comprises the following steps:

[0025] (1) In the presence (protection) of an inert gas (a gas that does not participate in the reaction, such as argon, etc.) and under light-shielding conditions, the compound shown in Formula IV and the solvent are placed in a dry round-bottomed flask, at (-15 ° C) ~-10°C), add n-BuLi cyclohexane solution to the round bottom flask, after the addition is complete, stir at room temperature for at least 45 minutes, then add trimethyl borate, and continue stirring for at least 4 hours to obtain the formula III Compound shown (no need for separation and purification, can be directly used in the next step);

[0026] (2) In the presence (protection) of an inert gas (a gas that does not participate in the reaction, such as argon, etc.), add an aqueous solution of potassium carbonate to the tetrahydrofuran (THF) solution of the corresp...

Embodiment 1

[0033] Synthesis of compounds shown in formula Ia

[0034]

[0035] Under reduced pressure, the compound shown in formula IIa (1.0mmol, 328mg) and 10mL of freshly distilled anhydrous tetrahydrofuran were placed in a dry reaction flask, and placed in an ice-salt bath Under the condition of stirring, 2Mn-BuLi (1.2mmol, 0.6mL) was added dropwise, after the addition was completed, the ice-salt bath was removed, and after stirring at room temperature for 45 minutes, trimethyl borate (1.2mmol, 0.134mL) was added, and After that, the stirring reaction was continued for 4 hours to obtain the compound represented by formula IIIa, which was directly used in the next coupling reaction without isolation.

[0036] In a two-necked flask, add 0.21 g of triiodotriptycene (0.33 mmol) shown in formula A and freshly distilled anhydrous tetrahydrofuran, then add tetrakis triphenylphosphine palladium (35 mg, 0.03 mmol), 2 mL of potassium carbonate aqueous solution (2M), vacuum, argon protecti...

Embodiment 2

[0039] Synthesis of compound shown in formula Ib

[0040]

[0041] Except that the compound shown in Formula IIa in Example 1 was replaced by the compound shown in Formula IIb, the other steps were the same as in Example 1 to obtain 123 mg of the compound shown in Formula Ib as a solid with a yield of 25.5%.

[0042] 1 H NMR (400MHz, CDCl 3 ,ppm):δ=7.54(t,J=7.0Hz,3H),7.36-7.32(m,3H),7.18-7.10(m,3H),7.04(s,3H),6.88(s,3H), 5.42(d,J=6.9Hz,2H),2.40(s,9H),2.09(s,9H),1.95(s,9H).HRMS[C 71 h 71 f 18 S 6 ]:calcd for[M+H] + :1458.3671, found 1458.3682.

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Abstract

The invention relates to a triphyene derivative containing diarylethene and an application thereof. The triphyene derivative is obtained by the way that triphyene derivative halogeneated triphyene and bisthienylethenes containing trimethyl borate are in coupled reaction. The designed and compounded triphyene derivative has the characteristics of being good in heat stability, high in quantum efficiency, short in light response time and the like. In addition, a unique solvation color development phenomenon is shown in triphyene derivative alkane chloride. Consequently, the triphyene derivative containing the diarylethene not only can be used for full color display and information storage but also can be used for trace detection of the alkane chloride.

Description

technical field [0001] The invention relates to a triptycene derivative and its application, in particular to a triptycene derivative containing diarylene and its application. Background technique [0002] In today's society, science and technology continue to develop rapidly. The application of various advanced information technologies has been closely related to people's work, study and life. We are in an era of information explosion. However, the existing hardware conditions make it impossible for various cutting-edge technologies to be put into application in time, and it is increasingly unable to meet people's growing demand for information storage and transmission. Therefore, information storage materials with high density, fast response, and reusability have become the research focus of many scientific researchers. Photochromic materials have great application potential in information storage and other fields, and have attracted much attention. Among various photoc...

Claims

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Application Information

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IPC IPC(8): C07D333/28C07D333/12C07D333/08C09K9/02G01N21/33
CPCC07D333/08C07D333/12C07D333/28C09K9/02C09K2211/1092G01N21/33
Inventor 罗千福刘新超蔡训志刘茂启鲍书敏
Owner EAST CHINA UNIV OF SCI & TECH
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