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A fluorescent anti-counterfeiting material based on mechanical force response
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A technology of mechanical force and fluorescence, applied in the fields of luminescent materials, organic dyes, organic chemistry, etc., can solve problems such as difficulties
Active Publication Date: 2020-04-03
TAIYUAN UNIV OF TECH
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However, it is relatively difficult to obtain the transition of fluorescence from quenching to brightening under the action of mechanical force.
Method used
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Embodiment 1
[0035]
[0036] 2,2'7,7'-tetrabromo-spiro[fluorene-9,9'-xanthene] (1.5g, 2.3mmol), 9,9-dimethylacridine (2.91g, 14.1mmol), Sodium tert-butoxide (1.77g, 18.4mmol) and dry toluene (30mL) were added into a 100mL three-necked flask, and filled with nitrogen to fully exchange the air in the bottle. 10 mg of tris(dibenzylideneacetone) dipalladium and 20 mg of tri-tert-butylphosphine tetrafluoroborate were added, and the reaction solution was heated to 120° C. for 12 h under the protection of nitrogen.
[0037] After the reaction was completed, 50 mL of water was added to the reaction liquid, stirred for 10 min, and filtered. The resulting filter cake was washed twice with 15 mL of methanol. Dry the filter cake, dissolve in dichloromethane and recrystallize to obtain 2,2',7,7'-tetrakis(9,9-dimethylacridine)-spiro[fluorene-9,9'-oxa Anthracene] white powder 1.8g, yield 67%.
[0038] 1 H NMR (600 MHz, C 2 D. 2 Cl 4 , ppm): δ =7.98 (d, J = 7.9 Hz, 2H), 7.47 (dd, J = 11.0, 5....
Embodiment 2
[0045]
[0046] 2,3',6',7-tetrabromo-spiro[fluorene-9,9'-xanthene] (1.5g, 2.3mmol), 9,9-dimethylacridine (2.85g, 13.8mmol) , Sodium tert-butoxide (1.77g, 18.4mmol) and dry toluene (30mL) were added into a 100mL three-necked flask, and filled with nitrogen to fully exchange the air in the bottle. 10 mg of tris(dibenzylideneacetone) dipalladium and 20 mg of tri-tert-butylphosphine tetrafluoroborate were added, and the reaction solution was heated to 120° C. for 12 h under the protection of nitrogen.
[0047] After the reaction was completed, 50 mL of water was added to the reaction liquid, stirred for 10 min, and filtered. The resulting filter cake was washed twice with 15 mL of methanol. Dry the filter cake, dissolve in dichloromethane and recrystallize to obtain 2,3',6',7-tetrakis(9,9-dimethylacridine)-spiro[fluorene-9,9'-oxa Anthracene] white powder 1.75g, yield 65%.
[0048] 1 H NMR (600 MHz, C 2 D. 2 Cl 4 , ppm):δ =8.20 (d, J = 7.9 Hz, 2H), 7.55 –7.45 (m, 8H), 7....
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Abstract
Fluorescent anti-fake materials based on mechanical force responses are disclosed. The materials are microcrystalline-state organic dye shown as a general formula (I), adopting N-substituted 9,9-dimethylacridine as substitutes and adopting spiro[fluorene-9,9'-xanthene] as a core. The materials can be converted from the microcrystalline state into an amorphous state under functions of mechanical force, thus achieving a conversion from fluorescencequenching to fluorescence emitting. In the formula, R is 9,9-dimethylacridine.
Description
technical field [0001] The invention relates to a responsive organic dye. The organic dye of the present invention can be transformed from fluorescencequenching to fluorescence brightening after mechanical grinding. [0002] technical background [0003] Materials that can undergo changes in fluorescence intensity or color when subjected to external stimuli such as light, electricity, and force have good application prospects in the fields of information and anti-counterfeiting technologies. In particular, the obvious change of fluorescence intensity, such as the behavior from quenching to brightening, can provide higher contrast for signal detection, especially in anti-counterfeiting. [0004] Among them, compared with external stimuli such as light and electricity, force stimulation has better implementability in the practical application of anti-counterfeiting. [0005] However, in order to improve the contrast before and after the change of the fluorescent signal of th...
Claims
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