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Chiral binaphthopyran photochromic compound as well as preparation method and application thereof

A photochromic and compound technology, applied in chemical instruments and methods, color-changing fluorescent materials, organic chemistry, etc., can solve the problems of slow fading rate, lack of optical activity, slow fading, etc., and achieve rapid discoloration and fading speed, Wide application prospects and excellent fatigue resistance

Active Publication Date: 2021-10-15
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the above methods have solved the problem of slow fading rate to a certain extent, the synthesis is complicated and costly, which reduces the practical value
At present, the shortcomings of naphthopyran-based photochromic materials such as slow fading and lack of optical activity have not been resolved.

Method used

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  • Chiral binaphthopyran photochromic compound as well as preparation method and application thereof
  • Chiral binaphthopyran photochromic compound as well as preparation method and application thereof
  • Chiral binaphthopyran photochromic compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: the preparation of photochromic compound (R)-Ia

[0032] Step 1: the preparation of compound (R)-2, the reaction formula is as follows:

[0033]

[0034] N 2 Under protection, chiral 9-bromo-dinaphtho[2,1-d:1',2'-f][1,3]dioxepin(R)-1 (1.90g , 5.09mmol) and tetrahydrofuran (15mL). The reaction system was cooled to -78°C and n-butyllithium (1.6M, 4.85ml, 7.76mmol) was added slowly. Slowly warm up to 0°C and stir for 1.5h. Cool to -78°C and add trimethyl borate (1.20 mL, 10.8 mmol). Stir at room temperature for 18h, add hydrogen peroxide (30%, 1.6ml), heat to 50°C and stir for 6h. Cool to room temperature, add saturated Na to the reaction solution 2 SO 3 solution (20 mL), and extracted with ethyl acetate (50 mL×2). Combine the organic phases and wash with anhydrous Na 2 SO 4 dry. The solvent was removed by concentration, and the residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate=50:1) to obtain a reddish-brow...

Embodiment 2

[0042] The preparation of embodiment 2 photochromic compound (R)-Ib, reaction formula is as follows:

[0043]

[0044] Into a 100 mL round bottom flask was added (R)-2 (0.24 g, 0.77 mmol), toluene (20 mL), 1-(4-biphenyl)-1-phenylprop-2-yn-1-ol ( 0.28g, 1.00mmol) and 2 drops of dodecylbenzenesulfonic acid. Heated to 40°C for 3h. After the reaction was completed, the reaction solution was concentrated under reduced pressure to remove the solvent. The residue was separated by silica gel column chromatography (petroleum ether / ethyl acetate=80:1) to obtain a yellow solid product (R)-Ib with a yield of 86%.

[0045] The proton nuclear magnetic resonance spectrum characterization data of (R)-Ib is: 1 H NMR (400MHz, CDCl 3 )δ(ppm)8.02(d,J=8.0Hz,1H),7.90–7.77(m,2H),7.57–7.37(m,10H),7.37–7.26(m,7H),7.25–7.00(m, 4H), 6.95(d, J=8.0Hz, 1H), 6.25(d, J=10Hz, 1H), 5.54(s, 2H).

[0046] The carbon nuclear magnetic resonance spectrum characterization data of (R)-Ib is: 13 C NMR (100MH...

Embodiment 3

[0047] The preparation of embodiment 3 photochromic compound (R)-Ic, reaction formula is as follows:

[0048]

[0049] Into a 100 mL round bottom flask was added (R)-2 (0.24 g, 0.77 mmol), toluene (20 mL), 1,1-bis(4-methoxyphenyl)prop-2-yn-1-ol ( 0.27g, 1.00mmol) and 2 drops of dodecylbenzenesulfonic acid. Heated to 40°C for 3h. After the reaction was completed, the reaction solution was concentrated under reduced pressure to remove the solvent. The residue was separated by silica gel column chromatography (petroleum ether / ethyl acetate=50:1) to obtain the pink product (R)-Ic with a yield of 79%.

[0050] The characterization data of (R)-Ic proton nuclear magnetic resonance spectrum is: 1 H NMR (400MHz, CDCl 3 )δ(ppm)8.10(d,J=8.0Hz,1H),7.95–7.89(m,2H),7.52–7.39(m,6H),7.38–7.28(m,5H),7.01–6.95(m, 1H),6.92–6.87(m,2H),6.82–6.77(m,2H),6.25(d,J=10.0Hz,1H),5.64(s,2H),3.81(s,3H),3.75(s ,3H).

[0051] The carbon NMR spectrum characterization data of (R)-Ic is: 13 C NMR (100...

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Abstract

The invention relates to a chiral binaphthopyran photochromic compound as well as a preparation method and application thereof. The compound has a structure shown as a formula (R)-I, (S)-I, (R)-II or (S)-II defined in the description, wherein R1 and R2 are the same or different, and each independently represents hydrogen, a straight chain or branched chain alkyl group containing 1-6 carbon atoms, a straight chain or branched chain alkoxy group containing 1-6 carbon atoms, phenyl or substituted phenyl or halogen. The invention also provides a preparation method of the compound. The compound prepared by the invention has the characteristics of high fading rate, good fatigue resistance, optical activity and the like.

Description

technical field [0001] The invention relates to the field of organic optical functional materials, in particular to a chiral binaphthopyran photochromic compound and a preparation method and application thereof. Background technique [0002] Organic photochromic compounds mainly include spirooxazines, fulgid anhydrides, diarylethenes, azobenzenes, and naphthopyrans. Among them, naphthopyran-based photochromic compounds have the characteristics of easy synthesis, high chromaticity, and fast photoresponse. They have application value in the fields of color-changing glasses, smart windows, color-changing clothing, and anti-counterfeiting materials, and continue to attract extensive research interest. In practical applications, naphthopyran-based photochromic materials still have some limitations, such as slow fading rate, which limits the practical application range of this type of materials. Furthermore, optically active naphthopyran photochromic compounds are rarely reported...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04C09K9/02
CPCC07D493/04C09K9/02C09K2211/1088
Inventor 韩杰杨俊生杜思毅
Owner NANKAI UNIV
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