CN101792432A - Pyridine chalcone derivative with aggregation sate fluorescence enhancement and two-photon fluorescence characteristics - Google Patents
Pyridine chalcone derivative with aggregation sate fluorescence enhancement and two-photon fluorescence characteristics Download PDFInfo
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Abstract
The invention relates to a pyridine chalcone derivative which has aggregation sate fluorescence enhancement and two-photon fluorescence characteristics and is connected with different aromatic rings or aromatic heteroatomic rings by using allyl acyl-2-pyridyl as a matrix. The pyridine chalcone derivative has a chemical structural formula as shown below, wherein R1 is selected from one of triphenylamine bases, 4-N-carbazole phenyl and 3-(N-ethyl) carbazyl; R2 is selected from one of triphenylamine groups and 4-bromo-triphenylamine group or 3,8-(N-ethyl) carbazyl; and R3 is selected from the triphenylamine group. The pyridine chalcone derivative has important application values in the fields of organic light-emitting diodes (DLED), two-photon fluorescence microscopy, optical switches, biological fluorescence sensors and the like.
Description
Technical field
The present invention relates to a kind of organism with pyridine chalcone group, be specifically related to a kind of have state of aggregation fluorescence strengthen with the two-photon fluorescence characteristic be different aromatic ring or the fragrant heterocyclic pyridine chalcone derivatives of parent connection with acrylyl-2-pyridyl, have significant application value in fields such as Organic Light Emitting Diode (OLED), two-photon fluorescence micro-imaging, photoswitch and bioluminescence transmitters.
Background technology
A lot of embedded photoluminescent material fluorescent emission intensity height in dilute solution, but very weak or luminous hardly in state of aggregation its luminous intensity when solid-state, this is owing to the cancellation of reunion induced fluorescence.In the two-photon fluorescence of bio-imaging was micro-, it was luminous often to need light emitting molecule to be state of aggregation, and luminescent material is plated to film usually in the making of organic electroluminescence device, and therefore this fluorescent quenching is also inevitable.Therefore, the luminous degree that reduce the state of aggregation fluorescent quenching, improves solid-state material is the difficult problem of field of photovoltaic materials for a long time.
From calendar year 2001, the luminous enhancing of aggregation inducing (Aggregation induced emissionenhancement, AIEE) since this notion proposes, relevant state of aggregation, the solid-state organic materials that presents strong luminosity appear in the newspapers successively, typical material comprises: 1) heterocyclic pentylene (siloles) class of the band aromatic substituent of this loyal study group discovery of Tang, this class material the solution state photoluminescence extremely a little less than, and luminous intensity increases when solid state powder or film; 2) have particular space structure and containing-CN or-CH
3The stilbene compound of group, the state of aggregation of this compounds is luminous relevant with accumulation of H-state of aggregation or J-state of aggregation stacked form; 2003, Wang Xiao plum seminar finds four (N, the N-diethylin) tetraphenyl ethylene molecule solid state fluorescence intensity is compared the enhancing that is the order of magnitude with solution state fluorescence, and reason is that the olefinic double bonds both sides connect four substituting groups, due to sterically hindered the rotating freely of containing two keys of this ortho position group.2008, Wang Xiao plum seminar finds that again the micro-nano solia particle of polyamines-2-replacement-anthracene quasi-molecule has good dispersiveness at aqueous phase, when high density, present the luminous and remarkable red shift of peak position of strong state of aggregation (referring to: application number is 200810021888.1 Chinese invention patent Shen Qing Publication specification sheets).
The enhancing of state of aggregation (solid-state) fluorescence can effectively be lowered energy cancellation effect between compound molecule, be helped to improve the luminous efficiency of device, for new approach has been opened up in the widespread use of luminous organic material in solid state device.But the state of aggregation fluorescence enhanced material category of report is very few at present, has limited its application in photoelectric material and association area thereof.
Summary of the invention
The object of the invention provides a class and has enhancing of state of aggregation fluorescence and two-photon fluorescence characteristic pyridine chalcone derivative.
For achieving the above object, the concrete technical scheme of the present invention is to be parent with acrylyl-2-pyridyl, connects different aromatic rings or fragrant heterocycle; Contained pyridine ring nitrogen atom, the carbonylic oxygen atom of molecule forms the five-membered ring structure by the hydrogen atom on hydrogen bond and the ortho position carbon-carbon double bond, contained rotating freely of carbon-carbon double bond effectively, obtain state of aggregation fluorescence and strengthen (AIEE) characteristic, the chemical structural formula of described pyridine chalcone derivative is as follows:
Wherein, R
1Be selected from: the triphen amido
4-N-carbazole phenyl
3-(N-ethyl) carbazyl
Or
In a kind of;
Wherein, R
2Be selected from: trianilino group
4-bromo trianilino group
Or 3,8-(N-ethyl) carbazyl
In a kind of; R
3Be selected from trianilino group
Correspondingly, the chemical structural formula of described pyridine chalcone derivative is:
In the technique scheme, described pyridine chalcone derivative is a parent with acrylyl-2-pyridyl, connect different aromatic rings or fragrant heterocycle, precursor skeleton contains carbonyl and pyridyl, in water, has good dispersiveness, and can pass through oxygen, the multiple tooth coordination of nitrogen combines with metal ion is effective, obtains the fluorescent material of different luminous wave bands, has photoluminescent property in solution; Described pyridine chalcone derivative pyridine ring nitrogen atom, carbonylic oxygen atom form intramolecular hydrogen bond by steric effect, effectively check and made rotating freely of carbon-carbon double bond, have state of aggregation fluorescence and strengthen (AIEE) characteristic, state of aggregation and solid-state fluorescence are strengthened significantly with respect to dilute solution, have using value in the organic photoelectrical material field.
Described pyridine chalcone derivative is synthetic: for substituted benzaldehyde and 2-acetopyridine with equimolar amount add in a certain amount of methyl alcohol, stirring at room a few hours under the diluted alkaline catalysis, solution promptly sends bright Huang～ruddiness, water and washed with methanol throw out, draw gorgeous yellow～red precipitate, need not to purify.
Because the technique scheme utilization, the present invention compared with prior art has following advantage:
1. pyridine chalcone derivative of the present invention has state of aggregation fluorescence and strengthens characteristic (seeing Fig. 1～10); With increasing of " pyridine chalcone group " number, its powder glow color under ultra violet lamp is changed by green → Huang → redness, compares with solution state (THF) fluorescence spectrum, and the powder fluorescence intensity increases by 10～100 times of multiples (seeing Figure 14～17);
2. pyridine chalcone derivative of the present invention has strong two-photon fluorescence characteristic (seeing Figure 11～13), in conjunction with its in aqueous phase dispersibility good and aggregation state irradiance characters, have the important application prospect at two-photon fluorescence micro-imaging and bioluminescence sensor field;
3. in the prior art, present most of luminous organic material synthetic routes are grown, complex process, and practicability is difficult; And pyridine chalcone derivative of the present invention, preparation technology is simple, and the productive rate height is easy to purify and industrialization;
4. pyridine chalcone derivative of the present invention, aqueous phase dispersibility and stability are all fine, can combine with metal ion (salt) by the multiple tooth coordination of oxygen, nitrogen in its molecular structure or assemble, obtain the fluorescence strongthener (seeing Fig. 1～10) of different luminous wave bands, can become new and effective " electroluminescent " material.
Description of drawings
Accompanying drawing 1 embodiment 1 reaches and Zn in THF and water
2+, Cu
2+PL spectrogram behind the ion complexation;
Accompanying drawing 2 embodiment 1 PL spectrogram in THF and silver salt solution;
Accompanying drawing 3 embodiment 1 PL spectrogram in THF and silver salt solution in insoluble concentration;
Accompanying drawing 4 embodiment 2 reach and Cu in THF and water
2+, Zn
2+PL spectrogram after the complexing;
The PL spectrogram of accompanying drawing 5 embodiment 2 in the water/acetone mixed solution of different ratios;
Accompanying drawing 6 embodiment 3 reach and Zn in THF and water
2+PL spectrogram after the complexing;
Accompanying drawing 7 embodiment 5 reach and Cu in THF and water
2+PL spectrum after the complexing;
Accompanying drawing 8 embodiment 5 are at THF and water and and Zn
2+PL spectrogram after the complexing;
Accompanying drawing 9 embodiment 6 reach and Cu in THF and water
2+And Zn
2+PL spectrogram after the complexing;
Accompanying drawing 10 embodiment 7 reach and Cu in THF and water
2+PL spectrogram after the complexing;
Accompanying drawing 11 embodiment 1,5 and 7 two-photon fluorescence spectrogram;
The two-photon fluorescence spectrogram of accompanying drawing 12 embodiment 7 under different optical maser wavelengths excite;
Under the accompanying drawing 13800nm laser pumping embodiment 1,5 and 7 respectively with Zn
2+/ short Cu
2+Two-photon fluorescence figure after the complexing;
Accompanying drawing 14 embodiment 3 solution state (THF, 1 * 10
-6Mol/L) and the fluorogram of powder;
Accompanying drawing 15 embodiment 5 solution state (THF, 1 * 10
-6Mol/L) and the fluorogram of powder;
Accompanying drawing 16 embodiment 6 solution state (THF, 1 * 10
-6Mol/L) and the fluorogram of powder;
Accompanying drawing 17 embodiment 7 solution state (THF, 1 * 10
-6Mol/L) and the fluorogram of powder;
Accompanying drawing 18 embodiment 1,2,3,5 and 6 hot weightless pictures (10 ℃ of temperature rise rates/min).
Embodiment
Below in conjunction with drawings and Examples the present invention is further described:
Embodiment 1 (WF1): (E)-N, N-phenylbenzene-4-(2-acrylyl pyridyl) aniline is synthetic.
(1) N, N-diphenyl amino phenyl aldehyde is synthetic: take by weighing the triphenylamine of equimolar amount and DMF in there-necked flask, slowly splash into excessive phosphorus oxychloride under the ice bath again, drip complete temperature rising reflux reaction 1 day, slowly pour in the frozen water after the cooling, with the aqueous sodium hydroxide solution neutralization, leave standstill after the vigorous stirring, get crude product after the filtration.Obtain light yellow crystal by vacuum-sublimation at last, be N, N-diphenyl amino phenyl aldehyde, productive rate 89.5%;
(2) with homemade N, N-diphenyl amino phenyl aldehyde (10.8mmol, 2.95g) join in the alcohol (as methyl alcohol, ethanol etc.) of 20mL, (10.8mmol is 1.31g) with the saturated alkali lye of 8mL (as salt of wormwood, NaOH, the KOH aqueous solution) to add the 2-acetopyridine base more successively; Stirred under the room temperature 24 hours, water/methanol mixed solvent washing number time again after crude product filters, the gorgeous yellow powder of 2.28g, productive rate 56%, purity 98%.
(3) analyze the gained compound: orange-yellow, fusing point: 172 ℃; 180 ℃ of decomposition temperatures.
MS (EI), measured value: 376.2; Calculated value: 376.16.
1H?NMR(CDCl
3，300MHz，Me
4Si)：δ，ppm?9.809(s，1H，o-pyridinyl)；8.168(m，1H，J＝11Hz，m-pyridinyl)；7.904(m，1H，J＝5Hz，p-pyridinyl)；7.580(d，1H，J＝9Hz，m-pyridinyl)；7.678(d，2H。J＝9Hz，-CH＝CH-)；7.334(m，4H，Ph-H)；7.271(d，2H，J＝5Hz，Ph-H)；7.133(m，6H，Ph-H)；7.016(d，2H，J＝9Hz，Ph-H)。
IR (KBr) v:3428cm
-1(wide, in strong, intramolecular hydrogen bond), 1689cm
-1(s, C=O), 1595cm
-1(s, C=C), 824cm
-1(m), 753cm
-1, (m), 690cm
-1(s).
The compound molecule formula that present embodiment obtains is:
Fig. 2 shows that embodiment 1 (1 * 10
-6M) be dispersed in and contain silver salt (1 * 10
-6M) aqueous phase, the former fluorescence intensity have increased 1 times (embodiment under the same concentrations 1 fluorescence in THF on year-on-year basis), luminous peak position blue shift 30nm, the halfwidth degree has shunk 30nm; If add electronegative nanometer metallic silver salt particle again, then fluorescence intensity strengthens～5 times.As shown in Figure 3, the embodiment 1 of different solubility is dispersed in different concns (from 10
-5M to 10
-9M) in the silver salt solution, fluorescence strengthens up to 6～10 times.
Embodiment 2 (WW1): (E)-N-[4-(2-acrylyl pyridyl)] phenyl carbazole is synthetic.
(1) N-carbazyl phenyl aldehyde is synthetic: take by weighing the carbazole of equimolar amount and p-Fluorobenzaldehyde in there-necked flask, the hexadecyl trimethyl ammonium bromide that adds excessive salt of wormwood and catalyst levels again, 136 ℃ of reactions of heating are 3 days in the DMF solvent, slowly pour in the frozen water after the cooling, stir afterwards with DCM extraction three times, get crude product after concentrating, obtain yellow crystals by vacuum-sublimation at last, be N-carbazyl phenyl aldehyde, productive rate 85.2%;
(2) adopt with embodiment 1 in similar method, only need according to the compound that obtains the N in the step 2, N-diphenyl amino phenyl aldehyde makes N-carbazyl phenyl aldehyde, productive rate 56.3% into;
(3) analyze the gained compound: yellow, fusing point: 200 ℃, 210 ℃ of decomposition temperatures.
MS (EI), measured value: 374.1; Calculated value: 374.14.
1H?NMR(CDCl
3，300MHz，Me
4Si)：δ，ppm?8.788(d，4H，J＝5Hz，pyridinyl-H)；8.292(t，4H，J＝9Hz，carbazyl-H)；7.993(d，4H，J＝10Hz，Ph-H)；7.720(d，4H，J＝8Hz，carbazyl-H)；7.190，7.163(d，2H，J＝8Hz，-CH＝CH-).
IR (KBr) v:3407cm
-1(wide, s, intramolecular hydrogen bond), 1663cm
-1(m, C=O); 1593cm
-1(s, C=C); 990cm
-1(m, E-CH=CH) 724cm
-1(s), 749cm
-1(s).
The compound molecule formula that obtains is:
Embodiment 3 (WW2): (E)-N-ethyl-[3-(2-acrylyl pyridyl)] carbazole is synthetic.
(1) N-ethyl-3-carbazole formaldehyde: the DMF of 3ml joined fill in 3.5g (18mmol) the N-ethyl carbazole flask ice bath and N
2Under the atmosphere, dropwise add the POCl of 0.09mol
3Dropwise, be warming up to 90 ℃ of reactions 24 hours, be chilled to room temperature, slowly to going in the frozen water, the diluted acid neutralization is used dichloromethane extraction, anhydrous MgSO with reaction solution
4After the drying, silica gel dress post purify 2.4g N-ethyl-3-carbazole formaldehyde, productive rate is 63%.
(2) synthetic method is similar to Example 1, only need be according to the compound that obtains with the N in the step (2), and N-diphenyl amino phenyl aldehyde makes N-ethyl-3-carbazole formaldehyde, productive rate 64.3% into.
(3) analyze the gained compound: yellow, 169 ℃ of decomposition temperatures;
Mass spectrum (EI), measured value: 326.23, calculated value: 326.14;
1H?NMR(CDCl
3，300MHz，Me
4Si)：δppm?8.792(t，1H，J＝2Hz，o-pyridinyl)；8.620(m，1H，m-pyridinyl)；8.469(t，1H，J＝8Hz，p-pyridinyl)；8.370(d，1H，J＝5Hz，m-pyridinyl)；8.236(d，1H，J＝6Hz，carbazyl-H)；8.165(d，1H，J＝7Hz，-CH＝CH-)；8.084(d，1H，J＝11Hz，carbazyl-H)；7.448(m，2H，carbazyl-H)；7.291(s，1H，carbazyl-H)；7.136(m，2H，carbazyl-H)；5.646(d，1H，J＝11Hz，-CH＝CH-)；4.258(t，2H，-CH
2)；1.464(t，3H，J＝7Hz，-CH
3)。
IR (KBr) v:3427cm-1 (wide, s, intramolecular hydrogen bond), and 1652cm-1 (w, C=O), 1603cm
-1(s, C=C), 776cm
-1(s), 752cm
-1(s).
The compound molecule formula that obtains is:
Recording embodiment 3 gained (E)-N-ethyl-[3-(2-acrylyl pyridyl)] carbazole reaches and Zn in THF and water
2+(concentration of embodiment 3 gained (E)-N-ethyl-[3-(2-acrylyl pyridyl)] carbazole and metal ion is 1 * 10 to PL spectrogram after the complexing
-3M, embodiment 3 consumption 2mL), luminous very weak in the THF dilute solution as shown in Figure 6, state of aggregation (in the water) fluorescence intensity strengthens 20 times and Zn
2+The fluorescence intensity maximum can strengthen about 30 times after the complexing.The peak position red shift more than the 40nm, the intramolecularly group freely rotates and is obstructed during state of aggregation, fine structure appears in spectrum.
Embodiment 4 (WW3): (E)-the N-ethyl-[3,8-two (acrylyl-2-pyridyl)] carbazole is synthetic.
(1) N-ethyl-3,8-azepine fluorenes dialdehyde: the DMF of 5ml joined fill in 3.5g (18mmol) the N-ethyl azepine fluorenes flask ice bath and N
2Under the atmosphere, dropwise add the POCl of 0.18mol
3Dropwise, be warming up to 90 ℃ of reactions 24 hours, be chilled to room temperature, slowly to going in the frozen water, the diluted acid neutralization is used dichloromethane extraction, anhydrous MgSO with reaction solution
4After the drying, silica gel dress post purify 2.4g N-ethyl 2.8-azepine fluorenes dialdehyde, productive rate is 53%.
m/z(EI)251；
1H?NMR(CDCl
3，ppm)：δ1.463-1.500(t，3H，J＝7.4Hz，CH
3)，4.402-4.455(q，2H，J＝7.1Hz，CH
2)，7.487-7.508(d，4H，J＝8.4Hz，Ar-H)，8.630(s，2H，Ar-H)，10.112(s，2H)。
(2) synthetic method is similar to Example 1, only need be according to the compound that obtains with the N in the step (2), and N-diphenyl amino phenyl aldehyde makes N-ethyl-3 into, and 8-azepine fluorenes dialdehyde gets gorgeous orange powder, productive rate 50.2%;
(3) analyze the gained compound:
Fusing point: 153-155 ℃;
Mass spectrum (EI), measured value: 457.1; Calculated value: 457.18.
1H?NMR(CDCl
3，300MHz，Me
4Si)：δ，ppm?9.672(s，2H，o-pyridinyl)；7.681(d，8H，J＝9Hz，pyridinyl-H；-CH＝CH-)；6.548(d，8H，J＝9Hz，carbazyl-H，-CH＝CH-)；4.070(d，2H，J＝7Hz，-CH
2)；1.208(t，3H，-CH
3).
The compound molecule formula that obtains is:
Embodiment 5 (WF2): (E)-N, N-two [4-(acrylyl-2-pyridyl) phenyl] aniline synthetic.
(1) N, N-two (4-phenyl aldehyde) aniline is synthetic: synthetic method is similar to Example 1, only needs to make the mole proportioning of triphenylamine in the step (1) and DMF into productive rate 50.2% 1: 2.5 according to the compound that obtains;
(2) (E)-N, N-two [4-(acrylyl-2-pyridyl) phenyl] aniline: similar method among employing and the embodiment 1, only need the N in the step (2) according to the compound that obtains, N-diphenyl amino phenyl aldehyde makes N into, N-two (4-phenyl aldehyde) aniline, the glassy yellow precipitation, recrystallization gets product productive rate 76.5%, purity 98% twice;
(3) analyze the gained compound: fusing point: 220 ℃; 250 ℃ of decomposition temperatures decompose 10% in the time of 300 ℃;
Mass spectrum (MALDI-TOF-TOF) measured value: 507.19; Calculated value: 507.19.
1H?NMR(CDCl
3，300MHz，Me
4Si)：δ，ppm?8.744(t，2H，o-pyridinyl)；8.205(m，4H，pyridinyl)；7.891(m，2H，m-pyridinyl)；7.640(d，4H，J＝9Hz，-CH＝CH-)；7.484(m，2H，Ph-H)；7.356(t，3H，J＝8Hz，Ph-H)；7.184(m，4H，Ph-H)；7.121(d，4H，J＝9Hz，Ph-H).
The compound molecule formula that obtains is:
Embodiment 6 (WF3): (E)-N, N-two [4,4 '-(acrylyl-2-pyridyl) phenyl]-4 ' bromaniline synthetic.
(1) (E)-N, N-two [4-(acrylyl-2-pyridyl) phenyl] aniline: similar method among employing and the embodiment 5, only need the N in the step (2) according to the compound that obtains, N-two (4-phenyl aldehyde) aniline makes N into, N-two (4,4 '-phenyl aldehyde) 4 ' bromaniline, the glassy yellow precipitation, recrystallization gets product productive rate 70.5%, purity 98% twice.
(2) analyze the gained compound: fusing point: 197 ℃.
Mass spectrum (MALDI-TOF-TOF) measured value: 585.456, calculated value (585.11);
The compound molecule formula that obtains is:
Embodiment 7 (WF4): (E)-4,4 ', 4 "-three (acrylyl-2-pyridyl) triphenylamine synthetic.
(1) 4,4 ', 4 "-three (formyl radical) triphenylamine is synthetic: synthetic method is similar to Example 1, only needs to make the mole proportioning of triphenylamine in the step (1) and DMF into productive rate 20.2% 1: 10 according to the compound that obtains;
(2) with embodiment 1 in similar method, only need according to the compound that obtains the N in the step (2), N-two (4-phenyl aldehyde) aniline makes 4 into, 4 ', 4 "-three (formyl radical) triphenylamine, the deep red pressed powder, productive rate 56.5%, purity 98%.
(3) analyze the gained compound: fusing point: 153-155 ℃;
Mass spectrum (MALDI-TOF-TOF) measured value: 638.408; Calculated value: 638.23.
1H?NMR(CDCl
3，300MHz，Me
4Si)：δ，ppm?10.011(m，3H，o-pyridinyl)；8.737(t，3H，J＝5Hz，p-pyridinyl)；8.592(s，3H，p-pyridinyl)；8.474(d，3H，J＝3Hz，m-pyridinyl)；8.328(d，3H，J＝16，-CH＝CH-)；8.159(m，6H，J＝8Hz，Ph-H)；7.443(t，3H，J＝7Hz，-CH＝CH-，Ph-H)；7.370(t，6H，J＝6Hz，Ph-H)。
IR (KBr) v:3407cm
-1(wide, s, intramolecular hydrogen bond), 1689cm
-1(s, C=O), 1584cm
-1, (s, C=C), 825cm
-1(w), 790cm
-1, (m), 742cm
-1(s).
The compound molecule formula that obtains is:
Record embodiment 7 gained (E)-4,4 ', 4 "-three (acrylyl-2-pyridyl) triphenylamine in THF and water and and Cu
2+PL spectrogram after the complexing (embodiment 7 gained (E)-4,4 ', 4 " concentration of-three (acrylyl-2-pyridyl) triphenylamines and metal ion is 1 * 10
-3M, embodiment 7 consumption 2mL), with respect to the luminous intensity of solution state, the intensity of state of aggregation slightly increases as shown in Figure 10, slightly descends with luminous intensity behind the Cu ion complexation, more than the peak position blue shift 40nm.
Record embodiment 7 gained (E)-4,4 ', 4 "-three (acrylyl-2-pyridyl) triphenylamine solution state (THF, 1 * 10
-6Mol/L) and the fluorescence spectrum figure of powder, as shown in Figure 17, to compare with the fluorescence intensity of solution state (THF), the fluorescence intensity of pressed powder strengthened～and 80 times, luminous peak position red shift～25nm.
Record embodiment 7 gained (E)-4,4 ', 4 " the two-photon fluorescence spectrogram (test condition: femtosecond ti sapphire laser, 300mW, repetition rate 140Hz, sample concentration 1 * 10 of-three (acrylyl-2-pyridyl) triphenylamine under different optical maser wavelengths excite
-4M, THF), referring to Figure 12.
Record the two-photon fluorescence spectrogram of embodiment 1 (WF1), 5 (WF2) and 7 (WF4), as shown in Figure 11, along with " pyridine chalcone " unitary number increases to 3 to 2 by 1, two-photon fluorescence intensity strengthens in 1: 4: 9 ratio, the also obvious red shift (test condition: femtosecond ti sapphire laser, 300mW, repetition rate 140Hz of peak position, 740nm excites, sample concentration 1 * 10
-4M, THF).
According to ordinary method, record the hot weightless picture (temperature rise rate 100C/min is under the nitrogen atmosphere) of embodiment 1,2,3,5 and 6, referring to Figure 18.
Claims (1)
1. one kind has state of aggregation fluorescence and strengthens pyridine chalcone derivative with the two-photon fluorescence characteristic, it is characterized in that the chemical structural formula of described pyridine chalcone derivative is as follows:
Wherein, R
1Be selected from: the triphen amido
4-N-carbazole phenyl
3-(N-ethyl) carbazyl
In a kind of;
Wherein, R
2Be selected from: trianilino group
4-bromo trianilino group
Or 3,8-(N-ethyl) carbazyl
In a kind of; R
3Be selected from trianilino group
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| CN101037410A (en) * | 2007-04-11 | 2007-09-19 | 安徽大学 | Triphenylamine derivative double-photon optical storage material and preparation method thereof |
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| CN104447504A (en) * | 2014-11-03 | 2015-03-25 | 北京工业大学 | Carbazole group-containing m-phthalic acid fluorescence chemosensor and preparation and application thereof |
| CN104447504B (en) * | 2014-11-03 | 2016-10-26 | 北京工业大学 | A kind of carbazolyl-containing group M-phthalic acid fluorescence chemical sensor, prepare and apply |
| CN105085375A (en) * | 2015-08-28 | 2015-11-25 | 陕西科技大学 | Preparing method of 4-carbazole-9-group-benzaldehyde |
| CN105131220A (en) * | 2015-09-30 | 2015-12-09 | 华南理工大学 | Sulfonated arylphenol-acetone-formaldehyde fluorescent polymer with aggregation-induced emission reinforcing effect and preparing method thereof |
| CN105753871A (en) * | 2016-04-19 | 2016-07-13 | 安徽大学 | Indole [3,2-b ] carbazole derivative containing cyano stilbene structural unit and preparation method thereof |
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