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Naphthopyran branched triptycene compound, preparation method and application of naphthopyran branched triptycene compound

A technology of naphthopyran branched triptycene and naphthopyran, applied in chemical instruments and methods, organic chemistry, color-changing fluorescent materials, etc., can solve fast fading speed, low background color, lower device performance, etc. problem, achieve good reversibility, reduce planar stacking, and achieve high quantum efficiency in ring closure

Active Publication Date: 2019-06-14
SHANGHAI GANTIAN OPTICAL MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Naphthopyran compounds have good photoresponsiveness, fast fading speed, good photostability, low background color, excellent photochromic fatigue resistance, easy-to-control discoloration kinetics, open The ring body has the advantages of wide absorption, etc., and has a wide range of applications in many fields such as photochromic mirrors, anti-counterfeiting, decoration, light regulation, optical switches, and photochromic supramolecules. degrade the performance of the device

Method used

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  • Naphthopyran branched triptycene compound, preparation method and application of naphthopyran branched triptycene compound
  • Naphthopyran branched triptycene compound, preparation method and application of naphthopyran branched triptycene compound
  • Naphthopyran branched triptycene compound, preparation method and application of naphthopyran branched triptycene compound

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preparation example Construction

[0047] The preparation method of halogenated naphthopyran compounds 2-7 was synthesized by referring to the literature: Abe, Jiro; Kato, Hirohisa; Shimizu, Takehiro; Nakagawa, Yuki. Decoloration speed adjustment method of naphthopyran compound. Jpn. Kokai Tokkyo Koho (2015), 19pp.CODEN:JKXXAF; JP2015127371.Karine Chamontin,Vladimir Lokshin,Valerie Rossollin,Andre Samat*and Robert Guglielmetti.Synthesis and Reactivity of Formyl-Substituted Photochromic 3,3-Diphenyl-[3H]-naphtho[2,1-b]pyrans .K.Chamontin et al. / Tetrahedron 55(1999)5821-5830.

[0048]7-bromo-2-hydroxynaphthalene, 8-bromo-2-hydroxynaphthalene, 1,1-bis(p-methoxyphenyl)-2-propyl-1-ol, 1-diphenylpropan-2- Alkyn-1-ol and p-toluenesulfonic acid were purchased from Ailean (Shanghai) Chemical Technology Co., Ltd.

[0049] Triptycene, concentrated nitric acid, sodium, glacial acetic acid, Raney nickel, hydrazine hydrate, tetrahydrofuran, ethyl acetate, petroleum ether, dichloromethane, sodium chloride, anhydrous sodium s...

Embodiment 1

[0064] Synthesis of Compound Ia

[0065]

[0066] Add a magneton into a 25mL two-necked flask, under argon protection and under reduced pressure, fully dry the 25mL two-necked flask with an electric oven, and dissolve 2,6-dibromotriptycene (1.0mmol, 410mg) in Into 10mL freshly distilled anhydrous tetrahydrofuran solvent, inject the above solution into the reaction flask with a syringe, stir at -78°C for 5min, then slowly add 2.5M n-BuLi (2.5mmol, 1.0mL) dropwise, and the dropwise addition is completed After continuing to react at -78°C for 1h, inject trimethyl borate (3.0mmol, 0.34mL) at one time, continue to react at -78°C for 1h, and then slowly rise to room temperature for 4h. Without treatment, the obtained three The mixture of trimethyl pterene borate (1) was directly used in the next step of Suzuki coupling reaction.

[0067] Add a magneton into a 50mL two-necked flask, weigh compound 2 (2.0mmol, 0.8g) and dissolve it in 10mL of redistilled tetrahydrofuran and add it...

Embodiment 2

[0071] Synthesis of Compound Ib

[0072]

[0073] Add a magneton into a 25mL two-necked flask, protect it with argon and under reduced pressure, fully dry the 25mL two-necked flask with an electric oven and ventilate it three times, and 2,6-dibromotriptycene (1.0mmol, 410mg) was dissolved in 10mL of freshly distilled anhydrous tetrahydrofuran solvent, and the above solution was injected into the reaction flask with a syringe, and after stirring at -78°C for 5min, 2.5M n-BuLi (2.5mmol, 1.0mL) was slowly added dropwise After the dropwise addition was completed, continue to react at -78°C for 1h, inject trimethyl borate (3.0mmol, 0.34mL) at one time, continue to react at -78°C for 1h, then slowly rise to room temperature for 4h without treatment , the obtained mixture of triptycene borate trimethyl (1) was directly used in the next step of Suzuki coupling reaction.

[0074] Add a magneton into a 50mL two-necked flask, weigh compound 3 (2.0mmol, 0.8g) and dissolve it in 10mL o...

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Abstract

The invention discloses a naphthopyran branched triptycene compound of which the structure is disclosed in the formula I as described in the specification, and the definition of each substituent groupis specifically disclosed in the specification. According to the naphthopyran branched triptycene compound provided by the invention, since the embedding of a triptycene building block of a three-dimensional rigid structure, a target product can be easily subjected to functionalization and device processing. A research indicates that the compound has good reversibility so as to be quickly switched among different ring-opening and ring-closing states under the stimulation of light and heat, in addition, different colors and workability can be displayed, and the naphthopyran branched triptycenecompound can be applied to fields including optical glasses, optical sensors, antifalsification and the like.

Description

technical field [0001] The invention belongs to the technical field of functional materials, and in particular relates to a naphthopyran branched triptycene compound, a preparation method and an application thereof. Background technique [0002] Today's society is an era of big data with massive information. People's demand for information storage and transmission is getting higher and higher. However, the existing hardware conditions make it impossible to put various cutting-edge technologies into application in time. Therefore, high-density, fast-response, and reusable information storage materials have become a research hotspot for the majority of scientific researchers. Photochromic materials have great application potential in information storage and other fields, and have attracted much attention. Among various photochromic materials, naphthopyran compounds are classic photochromic materials and an important class of organic photochromic materials. Can show color cha...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/92C09K9/02
Inventor 甘家安
Owner SHANGHAI GANTIAN OPTICAL MATERIALS
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