LU502960B1 - Mechanochromic and mechanoluminescent photochromic compound, preparation method and application thereof - Google Patents
Mechanochromic and mechanoluminescent photochromic compound, preparation method and application thereof Download PDFInfo
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- LU502960B1 LU502960B1 LU502960A LU502960A LU502960B1 LU 502960 B1 LU502960 B1 LU 502960B1 LU 502960 A LU502960 A LU 502960A LU 502960 A LU502960 A LU 502960A LU 502960 B1 LU502960 B1 LU 502960B1
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- compound
- mechanochromic
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 44
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 239000000243 solution Substances 0.000 claims description 14
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 235000005811 Viola adunca Nutrition 0.000 claims description 6
- 240000009038 Viola odorata Species 0.000 claims description 6
- 235000013487 Viola odorata Nutrition 0.000 claims description 6
- 235000002254 Viola papilionacea Nutrition 0.000 claims description 6
- QNKOCFJZJWOXDE-UHFFFAOYSA-N 2-[4-(trifluoromethyl)phenyl]acetonitrile Chemical class FC(F)(F)C1=CC=C(CC#N)C=C1 QNKOCFJZJWOXDE-UHFFFAOYSA-N 0.000 claims description 5
- JJOPQMAMJLOGFB-UHFFFAOYSA-N 2-hydroxybenzene-1,3-dicarbaldehyde Chemical class OC1=C(C=O)C=CC=C1C=O JJOPQMAMJLOGFB-UHFFFAOYSA-N 0.000 claims description 5
- 239000002244 precipitate Substances 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 230000000638 stimulation Effects 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 239000012670 alkaline solution Substances 0.000 claims description 3
- 239000012298 atmosphere Substances 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000012046 mixed solvent Substances 0.000 claims description 3
- 230000001681 protective effect Effects 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- 239000011540 sensing material Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 23
- ZWKNLRXFUTWSOY-QPJJXVBHSA-N (e)-3-phenylprop-2-enenitrile Chemical compound N#C\C=C\C1=CC=CC=C1 ZWKNLRXFUTWSOY-QPJJXVBHSA-N 0.000 abstract description 6
- 230000008859 change Effects 0.000 abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 5
- 230000002776 aggregation Effects 0.000 abstract description 4
- 238000004220 aggregation Methods 0.000 abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 3
- 125000006575 electron-withdrawing group Chemical group 0.000 abstract description 2
- 239000000843 powder Substances 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 16
- 235000011114 ammonium hydroxide Nutrition 0.000 description 16
- 238000000295 emission spectrum Methods 0.000 description 8
- 238000000862 absorption spectrum Methods 0.000 description 7
- 238000004020 luminiscence type Methods 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 238000010926 purge Methods 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- -1 cyanostyrene compound Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000005166 mechanoluminescence Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/36—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/14—Styryl dyes
- C09B23/148—Stilbene dyes containing the moiety -C6H5-CH=CH-C6H5
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01L—MEASURING FORCE, STRESS, TORQUE, WORK, MECHANICAL POWER, MECHANICAL EFFICIENCY, OR FLUID PRESSURE
- G01L1/00—Measuring force or stress, in general
- G01L1/24—Measuring force or stress, in general by measuring variations of optical properties of material when it is stressed, e.g. by photoelastic stress analysis using infrared, visible light, ultraviolet
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/0009—Materials therefor
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F2202/00—Materials and properties
- G02F2202/14—Materials and properties photochromic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- Optics & Photonics (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Luminescent Compositions (AREA)
Abstract
The invention provides a mechanochromic and mechanoluminescent photochromic compound, a preparation method and application thereof, belonging to the technical field of organic luminescent materials. According to the invention, a molecular structure general formula of a luminescent material is shown, wherein R is H, F, Cl, Br or CH3. According to the mechanoluminescent characteristics of a cyanostyrene material, the introduction of electron-withdrawing groups as well as hydroxyl groups, and the principle of aggregation-induced emission, the invention provides a mechanochromic and mechanoluminescent photochromic material with high contrast change, which is applied in mechanical sensing and acid-base anti-counterfeiting.
Description
MECHANOCHROMIC AND MECHANOLUMINESCENT HU502960
PHOTOCHROMIC COMPOUND, PREPARATION METHOD AND
APPLICATION THEREOF
The invention belongs to the technical field of organic luminescent materials, and in particular relates to a mechanochromic and mechanoluminescent photochromic compound, a preparation method and application thereof.
At present, colour-changing materials and luminescent colour-changing materials, which produce photophysical changes under the stimulation of mechanical force, have attracted wide attention because of their potential applications in the fields of sensors, photoelectric devices, multiple anti-counterfeiting, information encryption, light-emitting diodes (LEDs) and so on. In addition, mechanochromism and mechanoluminescence of materials may be realized by adjusting the conjugated structure, electron-withdrawing ability and crystalline state of materials. Up to now, a series of mechanochromic and mechanoluminescent photochromic materials have been reported, such as cyanostyrene, tetrastyrene, polyphenylthio aromatic compounds, spiropyran, etc. Despite the success in the development of mechanochromic and mechanoluminescent photochromic materials, there are still some limitations in the prior art. Firstly, most of them only show a mechanochromic phenomenon or a mechanoluminescent photochromic phenomenon, and can't simultaneously realize mechanochromism and mechanoluminescent photochromism under the stimulation of a mechanical force. Secondly, the contrast of changes before and after mechanical stimulus is low. Therefore, it is still a great challenge to develop a mechanochromic and mechanoluminescent photochromic materials with high contrast, which greatly limits the application of luminescent materials.
In order to overcome the shortcomings of the prior art, the invention aims to 502960 combine mechanical stimulus-responsive compounds with electron-withdrawing functional groups and hydroxyl groups, so as to provide a mechanochromic and mechanoluminescent photochromic compound with high contrast change, a preparation method and application in mechanical stimulus and acid-base anti-counterfeiting materials.
In view of the above objective, the invention adopts a following technical scheme.
A mechanochromic and mechanoluminescent photochromic compound has a following structural formula:
FL” > a # CFs formula I, where R is H, F, Cl, Br or CHs.
The invention also provides a preparation method of the luminescent material, and a synthesis route is shown in the following formula:
R
CHO Fy q en + Q== nd be som HE A HO 1
N Vo È - ECTS or where R is H, F, CI, Br or CHs.
The preparation steps are as follows: adding para-substituted 2-hydroxy isophthalaldehyde and 4-trifluoromethyl phenylacetonitrile into a mixed solvent of ethanol and tetrahydrofuran, stirring, then adding tetrabutylammonium hydroxide (TBAH) and sodium ethoxide (EtONa), carrying out a heating reaction for 4 - 8 hours (h) at 40 - 60 degree Celsius (°C) in protective atmosphere, and stopping the heating reaction; cooling to room temperature, then adding acetic acid to produce precipitate, filtering and recrystallizing to obtain the target compound.
Further, adding para-substituted 2-hydroxy isophthalaldehyde (1 - 2 millimole) 502960 and 4-trifluoromethyl phenylacetonitrile (2 - 4 mmol) into ethanol (10 - 30 milliliter) and tetrahydrofuran (2 - 5 mL), stirring, then adding TBAH (5 - 10 mmol) and EtONa (2 - 4 mmol), carrying out reaction for 4 - 8 h at 40 - 60°C in the protective atmosphere, and stopping the reaction; cooling to room temperature, then adding acetic acid (1 - 3 mL) to produce precipitate, filtering and recrystallizing to obtain the target compound of cyanostyrene.
The mechanochromic and mechanoluminescent photochromic compound is used as solvent, acid-base and mechanical force-responsive sensing material.
According to the invention, the cyanostyrene luminescent material has luminescent characteristics of mechanochromism, mechanoluminescent photochromism, and solvent and acid-base response with high contrast change, that is, cyanostyrene compound shows red fluorescence and bluish-violet appearance in DMF solution, and turns into blue fluorescence and colourless appearance while adding water; solid powder of the cyanostyrene compound shows blue fluorescence and colourless appearance, then changes into red fluorescence and bluish-violet appearance after applying the mechanical force to the solid powder, and turns into red fluorescence and bluish-violet appearance after treating the solid powder with alkaline solution vapor.
According to the above luminescent characteristics, the above luminescent material may be applied to a field of mechanical sensing due to the change of colour and luminescence when the mechanical force is applied.
The luminescent material may also be used for acid-base anti-counterfeiting. The luminescent material shows colourless appearance and blue luminescence when not treated with alkali vapor, but becomes bluish-violet appearance and red luminescence after alkali vapor treatment.
According to the mechanoluminescent characteristics of the cyanostyrene material, introduction of electron-withdrawing groups as well as hydroxyl groups, and the principle of aggregation-induced emission, a mechanochromic and mechanoluminescent photochromic material with high contrast change is provided 502960 and applied in mechanical sensing and acid-base anti-counterfeiting.
According to the invention, the material may change colour from colourless to bluish-violet and luminescence from blue to red under different stimuli.
According to the invention, the luminescent material is simple in synthesis, easily available in raw materials, and thereby diffused and commercialized easily.
FIG. 1 is a nuclear magnetic resonance (NMR) hydrogen spectrum of compound 1 in embodiment 1;
FIG. 2 is an NMR carbon spectrum of compound 1 in embodiment 1;
FIG. 3 is an emission spectrum under different water volume fractions in embodiment 2;
FIG. 4 is an optical photograph of embodiment 2 before and after adding water under ultraviolet light;
FIG. 5 is an absorption spectrum under different water volume fractions in embodiment 3;
FIG. 6 is an optical photograph of embodiment 3 before and after adding water under natural light;
FIG. 7 is an emission spectrum before and after applying mechanical force in embodiment 4:
FIG. 8 is an optical photograph under an ultraviolet lamp before and after applying mechanical force in embodiment 4;
FIG. 9 is an absorption spectrum before and after applying mechanical force in embodiment 5;
FIG. 10 is an optical photograph under natural light before and after applying mechanical force in embodiment 5;
FIG. 11 is an emission spectrum before and after ammonia water vapor treatment in embodiment 6;
FIG. 12 is an absorption spectrum before and after ammonia water vapor 502960 treatment in embodiment 7;
FIG. 13 is an optical photograph under an ultraviolet lamp before and after ammonia water vapor treatment in embodiment 8; 5 FIG. 14 is an optical photograph under natural light before and after ammonia water vapor treatment in embodiment 9.
The invention is further explained by the following embodiments, which are intended only for a better understanding of the invention. Therefore, the following embodiments do not limit the scope of protection of the present invention. As long as improvements are made by adopting the method concept and technical scheme of the invention, or directly applied to other occasions without improvement, they are all within the scope of protection of the present invention.
In the following embodiments, the raw materials and reagents used are commercially available.
Embodiment 1
A mechanochromic and mechanoluminescent photochromic compound has a following structural formula:
FL ON N Ca CF,
The preparation steps of the mechanochromic and mechanoluminescent photochromic compound are as follows:
Adding 2-hydroxy isophthalaldehyde (1 mmol, 0484 gram) and 4-trifluoromethyl phenylacetonitrile (2 mmol, 0.37 g) into ethanol (20 mL) and tetrahydrofuran (4 mL), and at the same time adding TBAH (10 mmol, 0.259 g) and
EtONa (2 mmol, 0.136 g), then carrying out reaction at 50°C in nitrogen atmosphere for 6 h, and stopping the reaction; cooling to room temperature, adding 2 mL acetic 502960 acid to produce precipitate, filtering and recrystallizing the precipitate in ethanol to obtain the target compound of cyanostyrene CNCF;DSB-OH. The hydrogen spectrum and carbon spectrum of the compound CNCF;DSB-OH are shown in FIG. 1 and FIG. 2. 'HNMR (400 MHz, DMSO, 298 K): 5 = 9.33 (s, 1H), 8.08-8.10 (d, 4H), 8.06-8.07 (d, 2H), 7.98-9.00 (d, 4H), 7.52 (s, 2H), 6.68 (t, 1H).>*C NMR (100 MHz, DMSO, 298 K): 5 = 103.75, 116.08, 118.11, 120.03, 125.69, 127.12, 129.05, 131.20, 134.54, 141.76, 149.35, 156.33.
Embodiment 2 (solvent-induced aggregation, luminescence and changing colour)
The DMF solution of the compound CNCF:DSB-OH obtained in embodiment 1 is taken, in which concentration of the compound CNCF;DSB-OH is 10* M. By adding different volumes of deionized water, the water volume fractions (volume ratio of water to DMF solution) are 0, 20 percent (%), 40%, 60%, 80% and 99% respectively, and the concentration of the compound CNCF;DSB-OH is kept at 10° M. 3 mL of each sample is taken in a cuvette, and the emission spectrum with a wavelength ranging from 400 nm to 800 nm is detected by 365 nm of excitation wavelength. The obtained maximum emission wavelength is 675 nm, and at this time, the compound gives off red fluorescence. The emission spectrum is recorded by collecting different volume fractions, and the obtained emission spectrum is shown in
FIG. 3. As can be seen from FIG. 3, the main emission peak of the compound
CNCF:DSB-OH in DMF is at 675 nm. With the addition of water, the emission peak at 675 nm is weakened, and a new emission peak appears at 440 nm. With the increase of the water volume fraction, the emission peak at 440 nm gradually increases. It can be seen from FIG. 4 that the compound CNCF:DSB-OH shows red fluorescence in DMF, and with the water content reaching 99%, the compound shows blue fluorescence.
Embodiment 3 (solvent-induced aggregation and changing colour)
The DMF solution of the compound CNCF;DSB-OH obtained in embodiment 1 502960 is taken, in which concentration of the compound CNCF;DSB-OH is 10* M. By adding different volumes of deionized water, the water volume fractions (volume ratio of water to DMF solution) are 0, 20%, 40%, 60%, 80% and 99% respectively, and the concentration of the compound CNCF;DSB-OH is kept at 10° M. 3 mL of each sample is taken in a cuvette, the ultraviolet absorption spectrum is collected and recorded by collecting different volume fractions, and the obtained ultraviolet absorption spectrum is shown in FIG. 5. As can be seen from FIG. 5, the main emission peak of the compound CNCF;DSB-OH in DMF is at 595 nm. With the addition of water, the emission peak at 595 nm is weakened, and with the increase of the water volume fraction to 99%, the absorption peak at 595 nm disappears. As can be seen from FIG. 6, the compound CNCF:DSB-OH shows blue-violet appearance in
DMF, and with the water content reaching 99%, the compound CNCF;DSB-OH shows colourless appearance.
Embodiment 4 (Sensing by mechanoluminescent photochromism) 10 milligram (mg) of the solid powder of the compound CNCF;DSB-OH obtained in embodiment 1 is taken, and solid powder emission spectrum with the wavelength range between 400 nm and 800 nm before and after applying the mechanical force is collected by 365 nm of the excitation wavelength. As shown in
FIG. 7, the emission peak is at 445 nm before applying the mechanical force, and the emission peak shifts to 670 nm after applying the mechanical force for grinding for 10 seconds (s). As shown in FIG. 8, the solid powder shows blue fluorescence before applying the mechanical force, and the solid powder shows red fluorescence after applying the mechanical force for grinding for 10 s.
Embodiment 5 (Sensing by mechanochromism) 10 mg of the solid powder of the compound CNCF;DSB-OH obtained in embodiment 1 is taken, and solid powder ultraviolet absorption spectrum with the wavelength range between 300 nm and 700 nm before and after applying the mechanical force is collected. As shown in FIG. 9, there is no absorption peak in 502960 visible light region before applying the mechanical force, and an absorption peak appears at 520 nm after applying the mechanical force for grinding for 10 s. As shown in FIG. 10, the solid powder is colourless before applying the mechanical force, and becomes blue-violet after applying the mechanical force for grinding for 10 s.
Embodiment 6 (Luminescence and changing colour by treating with ammonia water vapor) mg of the solid powder of the compound CNCF;DSB-OH obtained in 10 embodiment 1 is taken, and the solid powder emission spectrum with the wavelength ranging from 400 nm to 800 nm before and after purging with ammonia water vapor is collected by 365 nm of the excitation wavelength, in which the mass fraction of the used ammonia water solution is 28% (the same below). As shown in FIG. 11, the emission peak is at 445 nm before purging the solid powder with ammonia water vapor, and then red-shifts to 670 nm after purging the solid powder for 60 s.
Embodiment 7 (Changing colour by treating with ammonia water vapor) 10 mg of the solid powder of the compound CNCF;DSB-OH obtained in embodiment 1 is taken, and the solid powder ultraviolet absorption spectrum with the wavelength ranging from 300 nm to 700 nm before and after purging with ammonia water vapor is collected, in which the mass fraction of the used ammonia water solution is 28%. As shown in FIG. 12, there is no absorption peak in visible light region before purging the solid powder with ammonia water vapor, and an absorption peak appears at 520 nm after purging the solid powder for 60 s.
Embodiment 8 (Luminescence and changing colour for anti-counterfeiting by treating with ammonia water vapor)
The DMF solution of the compound CNCF:DSB-OH obtained in embodiment 3 is taken, the water volume fraction (volume ratio of water to DMF solution) reaches 99% by adding different volumes of deionized water, and the concentration of the compound CNCF;DSB-OH is kept at 10° M. Letter M and C are written on filter 502960 paper with the solution as anti-counterfeiting ink, where letter F is written by a commercial blue fluorescent tetrastyrene dye which is insensitive to acid and alkali.
As shown in FIG. 13, under the ultraviolet lamp, the letters M, F and C give out blue fluorescence; then, the writing place is purged with ammonia water vapor for 1 s, M and C turn red, and F remains unchanged.
Embodiment 9 (Changing colour for anti-counterfeiting by treating with ammonia water vapor)
The DMF solution of the compound CNCF;DSB-OH obtained in embodiment 3 is taken, the water volume fraction (volume ratio of water to DMF solution) reaches 99% by adding different volumes of deionized water, and the concentration of the compound CNCF;DSB-OH is kept at 10° M. Letter M and C are written on filter paper with the solution as anti-counterfeiting ink, where letter F is written by a commercial blue fluorescent dye which is insensitive to acid and alkali. As shown in
FIG. 14, under natural light, the letters M, F and C is invisible; then, the writing place is purged with ammonia water vapor for 1 s, M and C turn red, and F remains invisible.
Claims (8)
1. A mechanochromic and mechanoluminescent photochromic compound, characterized in that a structural formula is shown as formula I: R Fal ® OH , CF, wherein R is H.
2. A preparation method of the mechanochromic and mechanoluminescent photochromic compound according to claim 1, characterized in that a synthesis route is shown in a following formula: R SHO i en AS en 4 OH + i) ny even - 8 KH, THE ES HO EN N wherein R is H, wherein steps are as follows: adding para-substituted 2-hydroxy isophthalaldehyde and 4-trifluoromethyl phenylacetonitrile into a mixed solvent of ethanol and tetrahydrofuran, stirring, then adding tetrabutylammonium hydroxide (TBAH) and sodium ethoxide (EtONa), carrying out a heating reaction for 4 - 8 hours (h) at 40 - 60 degree Celsius (°C) in protective atmosphere, and stopping the heating reaction; cooling to room temperature, then adding acetic acid to produce precipitate, filtering and recrystallizing to obtain a target compound.
3. The preparation method of the mechanochromic and mechanoluminescent photochromic compound according to claim 1, characterized in that a molar ratio of para-substituted 2-hydroxy isophthalaldehyde, 4-trifluoromethyl phenylacetonitrile, TBAH and EtONa is (1-2):(2-5):(5-10):(2-5).
4. An application of the mechanochromic and mechanoluminescent 7502960 photochromic compound according to claim 1 as solvent, and alkaline and mechanical force-responsive sensing material.
5. The application according to claim 4, characterized in that the solvent is Dimethyl Formamide (DMF) or a mixed solvent of DMF and water.
6. The application according to claim 5, characterized in that the compound shows red fluorescence and blue-violet appearance in the DMF solvent, and turns into blue fluorescence and colourless appearance after adding water.
7. The application according to claim 4, characterized in that the compound changes from blue fluorescence and colourless appearance to red fluorescence and blue-violet appearance under stimulation of alkaline solution, and the compound in DMF solution changes from the red fluorescence and the blue-violet appearance to the blue fluorescence and the colourless appearance under the stimulation of the alkaline solution.
8. The application according to claim 4, characterized in that the compound changes from blue fluorescence and colourless appearance to red fluorescence and blue-violet appearance under action of mechanical force.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202111268538.7A CN113912517B (en) | 2021-10-29 | 2021-10-29 | Mechanochromic and mechanoluminescent photochromic compound and preparation method and application thereof |
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| CN114605317B (en) * | 2022-04-02 | 2023-07-07 | 安徽大学 | Cyanostyrene molecule based on free radical photochromism and application thereof in intelligent glass |
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| JPH03205478A (en) * | 1990-01-05 | 1991-09-06 | Ricoh Co Ltd | Electroluminescent element |
| JPH06123986A (en) * | 1992-10-12 | 1994-05-06 | Ricoh Co Ltd | Single layer type electrophotographic sensitive body |
| JPH06271848A (en) * | 1993-03-24 | 1994-09-27 | Fuji Electric Co Ltd | Organic thin film luminescent element |
| CN1865206A (en) * | 2006-01-20 | 2006-11-22 | 吉林大学 | 2,5-diphenyl-1,4-distyyl benzene derivative and its uses in electroluminescent device |
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| CN113912517B (en) | 2022-08-02 |
| CN113912517A (en) | 2022-01-11 |
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