Photochromic compound and preparation method and application thereof
What is Al technical title?
Al technical title is built by PatSnap Al team. It summarizes the technical point description of the patent document.
A photochromic and compound technology, applied in chemical instruments and methods, color-changing fluorescent materials, luminescent materials, etc., can solve the problems of reducing the effect of photochromic fluorescent switches, achieve high yield, simple preparation method, and easy industrialization Effect
Active Publication Date: 2017-08-22
EAST CHINA UNIV OF SCI & TECH +1
View PDF2 Cites 12 Cited by
Summary
Abstract
Description
Claims
Application Information
AI Technical Summary
This helps you quickly interpret patents by identifying the three key elements:
Problems solved by technology
Method used
Benefits of technology
Problems solved by technology
[0006] However, most photochromic groups, such as spiropyran, dithiopheneethylene, stilbene, and azobenzene, basically have maximum absorption wavelengths in the ultraviolet region, while the maximum absorption wavelengths of
Method used
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more
Image
Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
Click on the blue label to locate the original text in one second.
Reading with bidirectional positioning of images and text.
Smart Image
Examples
Experimental program
Comparison scheme
Effect test
Example Embodiment
[0058] Example 1 Synthesis of Compound A1
[0059] synthetic route
[0060]
[0061] (a): Synthesis of compound 2 (9-anthracene borate pinacol ester)
[0062] Take 9-bromoanthracene (1.7g, 6.6mmol), pinacol diborate (2g, 7.9mmol) and dissolve in 1,4-dioxane (20mL), add anhydrous potassium acetate (1.9g, 19.8 mmol) and [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (0.6g, 0.7mmol), added to the above system, heated to reflux at 100°C for 2h, TLC (thin layer chromatography ) Follow up and monitor the reaction to completion. Suction filtration, rotary evaporation to remove 1,4-dioxane, wash with saturated brine, extract three times with dichloromethane, combine the organic phases, dry with anhydrous sodium sulfate, spin dry, and separate by column chromatography (eluent is petroleum Ether: ethyl acetate = 100:1) to obtain a light yellow powder, namely compound 2 (1.8 g, yield 90%).
[0063] (b): Synthesis of compound 3 (5-(9-anthryl)indoline)
[0080] Take 4-bromo-N-ethyl-1,8-naphthimide (2.2g, 6.6mmol), pinacol diborate (2g, 7.9mmol) and dissolve in 1,4-dioxane (20mL ), add anhydrous potassium acetate (1.9g, 19.8mmol) and [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (0.6g, 0.7mmol) to the above system After heating at 100°C under reflux for 2h, TLC (Thin Layer Chromatography) tracked and monitored the reaction to completion. Suction filtration, rotary evaporation to remove 1,4-dioxane, wash with saturated brine, extract three times with dichloromethane, combine the organic phases, dry with anhydrous sodium sulfate, spin dry, and separate by column chromatography (eluent is petroleum Ether: ethyl acetate = 100:1) to obtain a light yellow powder, namely compound 7 (2.1 g, yield 85%).
[0081] (b): Synthesis of compound 8 (5-(N-n-butyl-1,8-na...
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more
PUM
Login to view more
Abstract
The invention discloses a photochromic compound. The structure of the photochromic compound is represented by a formula A (shown in the description), wherein R represents a fluorescence group and represents substituted or unsubstituted naphthalene, anthracene, xanthenes, pyrene 1,8-naphthalimide, coumarin or pyran nitrile, and a substituent group on R is C1-C4 alkyl, halogen, hydroxide radical, C1-C4 alkoxy or C1-C4 alkyl amino; X represents oxygen, and Y represents C(CH3)2; or X represents N(CH3), and Y represents C(O). The invention further discloses an isomer of the photochromic compound, a mixture of the photochromic compound and the isomer and a preparation method and an application of the photochromic compound. The maximum absorption wavelength of a color-changing group of the photochromic compound is in a visible light region, but the maximum absorption wavelength of the fluorescence group is in an ultraviolet region and a near visible light region, so that the overlapping of the maximum absorption wavelengths of the two groups is effectively avoided. The photochromic compound has remarkable and special absorption and emitting properties in the ultraviolet region and the visible light region and can be used for producing photochromic fluorescence switches and molecular logic gates.
Description
technical field [0001] The invention belongs to the technical field of photochromic materials, in particular to a photochromic compound and its preparation method and application. Background technique [0002] The discoloration of photochromic compounds is basically caused by photoisomerization, bond breaking, or redox and dimerization of the compound. Among them, the triene compounds represented by Donor-Acceptor Stenhouse Adducts (DASA) are a class of excellent photochromic compounds, especially in the range of 450-750nm, 4∏ electrocyclization can occur, making it from colored to It becomes colorless, and can be changed from colorless to colored by heating or avoiding light in a variety of organic solvents (Hemmer J R, Poelma S O, Treat N, et al. Tunable Visible and Near Infrared Photoswitches. J. Am. Chem. Soc ., 2016, 138:13960-13966.). DASA-like photochromic materials have the advantages of being sensitive to visible light, high sensitivity, fast reaction speed, and f...
Claims
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more
Application Information
Patent Timeline
Application Date:The date an application was filed.
Publication Date:The date a patent or application was officially published.
First Publication Date:The earliest publication date of a patent with the same application number.
Issue Date:Publication date of the patent grant document.
PCT Entry Date:The Entry date of PCT National Phase.
Estimated Expiry Date:The statutory expiry date of a patent right according to the Patent Law, and it is the longest term of protection that the patent right can achieve without the termination of the patent right due to other reasons(Term extension factor has been taken into account ).
Invalid Date:Actual expiry date is based on effective date or publication date of legal transaction data of invalid patent.
Login to view more 
Login to view more