Photochromic naphtho-pyrans compounds and synthetic method thereof

A naphthopyran and photochromic technology, applied in chemical instruments and methods, color-changing fluorescent materials, etc., can solve problems such as complex synthesis routes, and achieve the effects of low price, excellent optical density and discoloration effect, and good fading rate.

Inactive Publication Date: 2008-07-09
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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  • Photochromic naphtho-pyrans compounds and synthetic method thereof
  • Photochromic naphtho-pyrans compounds and synthetic method thereof
  • Photochromic naphtho-pyrans compounds and synthetic method thereof

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Embodiment 1

[0032] Add 3.16g (0.012mol) SF1 in a 100ml round bottom flask, then add 50ml of toluene as a solvent, and then add 2.08g (0.01mol) 1,1-diphenyl propargyl alcohol and 0.17g (1mmol) For p-toluenesulfonic acid, stir magnetically, heat to 110°C and monitor the reaction by thin-layer chromatography. After 3 hours, a red reaction mixture is obtained, and the reaction is basically completed. Pour the reaction mixture into 100ml 10% NaOH aqueous solution, separate the organic layer, then wash once with 100ml 10% NaOH aqueous solution, then wash with water, spin dry the solvent on a rotary evaporator to obtain a red solid, and finally use petroleum ether: Ethyl acetate=12:1 eluent was passed through a silica gel column to obtain a light yellow solid pure product. Yield 43.5%.

[0033] MS (m / z): 453.2; IR (KBr, cm -1 ): 3337 (weak, aryl C-H bending out of plane), 3052, 3030 (medium strong, =C-H stretching), 1660 (strong, -C=C- stretching), 1650 (medium strong, stretching vibration),...

Embodiment 2

[0035] In 100ml round bottom flask, add 3.32g (0.012mol) SF2, then add 50ml dichloromethane as solvent, and then add 2.08g (0.01mol) 1,1-diphenyl propargyl alcohol and 0.17g ( 1 mmol) of p-toluenesulfonic acid, stirred by magnetic force, heated to 40° C. and monitored by thin-layer chromatography. After 2 hours, a red reaction liquid substance was obtained, and the reaction was basically completed. Pour the reaction mixture into 100ml 10% NaOH aqueous solution, separate the organic layer, wash once with 100ml 10% NaOH aqueous solution, then wash with water, spin dry the solvent on a rotary evaporator to obtain a light red solid, and finally wash with petroleum ether : Ethyl acetate = 20: 1 eluent passed through a silica gel column to obtain a light yellow solid pure product. Yield 45.2%. MS (m / z): 467.3; IR (KBr, cm -1 ): 3420 (weak, aryl C-H bent out of plane), 2913 (weak, -CH 3 stretching vibration), 1666 (strong, -C=C- stretching), 1650 (medium strong, stretching vibra...

Embodiment 3

[0037] Add 3.56g (0.012mol) SF3 in a 100ml round bottom flask, then add 50ml tetrahydrofuran as a solvent, and then add 2.08g (0.01mol) 1,1-diphenyl propargyl alcohol and 0.17g (1mmol) For p-toluenesulfonic acid, stir magnetically, heat to 66°C and monitor the reaction by thin-layer chromatography. After 4 hours, a gray reaction liquid substance is obtained, and the reaction is basically completed. Pour the reaction mixture into 100ml 10% NaOH aqueous solution, separate the organic layer, then wash once with 100ml 10% NaOH aqueous solution, then wash with water, spin dry the solvent on a rotary evaporator to obtain a gray solid, and finally use sherwood oil: Ethyl acetate=8:1 eluent was passed through a silica gel column to obtain a white solid pure product. Yield 50.6%. MS (m / z): 487.3; IR (KBr, cm -1 ): 3337 (weak, aryl C-H bends out of plane), 1673 (strong, -C=C- stretching), 1655 (moderately strong, stretching vibration), 1220 (medium strength, Ar-O-C-asymmetric stretc...

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Abstract

The invention discloses a photochromic naphthopyrans compound and the synthesis process in the chemical industry technology field. The synthesis process comprises heating up 3 substituted beta naphthol and propargyl alcohol compound under the catalysis condition to reduce into propargyl ether, conducting a Claise rearrangement reaction, finally generating naphthopyrans compound through the cyclization of quinoid compound. The structural general formula is showed as followed, wherein R1 and R2 respectively represent alkyl, nitro, alkoxy and halogen atom. The naphthopyrans compound of the invention is mainly used as photochromic matters of lens such as sunglasses and windscreen of cars and the like.

Description

technical field [0001] The invention relates to a compound in the technical field of chemical industry and a synthesis method thereof, in particular to a photochromic naphthopyran compound and a synthesis method thereof. Background technique [0002] Photochromism is an interdisciplinary and new field formed on the basis of chemistry, physics, materials and optoelectronic technology since the 1990s. Photochromism refers to a reversible chemical change in which a single chemical species is transformed into another chemical species with a significant change in the absorption spectrum due to a change in structure or electronic configuration under the induction of electromagnetic radiation. Photochromism is a reversible switch between colorless and colored substances. One type of application of photochromic substances is based on the different molecular structures, electronic structures and different absorption and emission spectra of species (A), (B), such as anti-counterfeiti...

Claims

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Application Information

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IPC IPC(8): C07D311/92C09K9/02
Inventor 孟庆华符定良张海凤黄德音张万斌
Owner SHANGHAI JIAO TONG UNIV
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