CN104531137A - Imidazole fluorescence-emission organic light-emitting material and preparation method thereof - Google Patents
Imidazole fluorescence-emission organic light-emitting material and preparation method thereof Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title abstract description 23
- 239000000463 material Substances 0.000 title abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 36
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000011541 reaction mixture Substances 0.000 claims abstract description 18
- 238000001953 recrystallisation Methods 0.000 claims abstract description 18
- -1 imidazole compound Chemical class 0.000 claims abstract description 17
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000010992 reflux Methods 0.000 claims abstract description 15
- 239000007787 solid Substances 0.000 claims abstract description 13
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical class N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000005695 Ammonium acetate Chemical class 0.000 claims abstract description 12
- 229940043376 ammonium acetate Drugs 0.000 claims abstract description 12
- 235000019257 ammonium acetate Nutrition 0.000 claims abstract description 12
- 238000005406 washing Methods 0.000 claims abstract description 11
- 229960000583 acetic acid Drugs 0.000 claims abstract description 10
- 239000012362 glacial acetic acid Substances 0.000 claims abstract description 9
- 238000010438 heat treatment Methods 0.000 claims abstract description 7
- 150000002460 imidazoles Chemical class 0.000 claims description 41
- 239000011368 organic material Substances 0.000 claims description 41
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 239000000243 solution Substances 0.000 claims description 21
- 239000000047 product Substances 0.000 claims description 19
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 150000003053 piperidines Chemical class 0.000 claims description 15
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 12
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 3
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 2
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 150000003935 benzaldehydes Chemical class 0.000 abstract 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 1
- 239000005457 ice water Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 32
- 238000003756 stirring Methods 0.000 description 21
- 238000001291 vacuum drying Methods 0.000 description 11
- 238000010907 mechanical stirring Methods 0.000 description 10
- 229960004756 ethanol Drugs 0.000 description 9
- 239000012046 mixed solvent Substances 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 7
- 239000005977 Ethylene Substances 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- 239000000975 dye Substances 0.000 description 4
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000007850 fluorescent dye Substances 0.000 description 3
- 239000000990 laser dye Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- QVTPWONEVZJCCS-UHFFFAOYSA-N 2-formylbenzonitrile Chemical compound O=CC1=CC=CC=C1C#N QVTPWONEVZJCCS-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 1
- 0 CCC1=CC*C(C=C[*@@]([C@](C)CC*(CC=C(C)ClC)=C=C)O)C=C1 Chemical compound CCC1=CC*C(C=C[*@@]([C@](C)CC*(CC=C(C)ClC)=C=C)O)C=C1 0.000 description 1
- 235000014493 Crataegus Nutrition 0.000 description 1
- 241001092040 Crataegus Species 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
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- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000000695 excitation spectrum Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 150000004693 imidazolium salts Chemical class 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 1
- 230000005622 photoelectricity Effects 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
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- Plural Heterocyclic Compounds (AREA)
- Luminescent Compositions (AREA)
Abstract
The invention provides an imidazole fluorescence-emission organic light-emitting material and a preparation method and application thereof, and relates to the technical field of organic light-emitting materials. The preparation method of the imidazole fluorescence-emission organic light-emitting material includes the steps that 4-chlorobenzaldehyde and piperidine are dissolved in absolute ethyl alcohol/methyl alcohol to be heated until reflux happens, 2,3-Butanedione is added, reflux is conducted continuously, a reaction mixture is cooled to be at an indoor temperature, solid matter can be precipitated, and after the mixture is subjected to decompress filter and recrystallization, 1,6-2(4-chlorophenyl)-1,5-hexadiene-3,4-butanedione (compound II) can be obtained. The compound II, para-substituted benzaldehyde and ammonium acetate are dissolved into glacial acetic acid, heating and reflux are carried out, the reaction solution is cooled to be at the indoor temperature and then is added into ice water, the pH is adjusted to be neutral, and a head product is precipitated; decompress filter, washing and recrystallization are sequentially conducted. The fluorescence-emission material enriches the variety of the imidazole compound fluorescence-emission organic light-emitting material.
Description
Technical field
The present invention relates to technical field of organic luminescence materials, in particular to a kind of imidazoles fluorescent emission luminous organic material and preparation method thereof.
Background technology
Luminous organic material is widely used in organic solid laser apparatus, organic photovoltaic battery and organic fluorescence sensor field.Luminous organic material has the features such as fast response time, storage density are high, relative low price, also there is the advantages such as of a great variety, adjustability good, rich color, purity of color are high, molecular designing is relatively flexible simultaneously, become photoelectricity information material of new generation gradually, the development particularly meeting the luminous organic material of various information displaying requirement is particularly rapid.Therefore, designing and developing the luminous organic material with high fluorescence efficiency, Wavelength tunable, is very urgent and necessary for organic optoelectronic industry development and bio-light electronics research and apply, is also simultaneously the work of a challenging and significance.
Glyoxaline compound is the important five member ring heterocyclic compound of a class, is widely used in the aspects such as medicine (antibacterial, anticancer), sterilization, white dyes, laser dyes, fluorescent probe, two-photon absorption, electroluminescent device, photovoltaic cell.In recent years, the synthesis of aryl substituted imidazole compound, photoelectric characteristic and applied research attract attention, and comprise triarylimidazoles compound, single aromatic ethylene base imidazolium compounds, diaryl vinyl imidazolium compounds and three aromatic ethylene base imidazolium compoundss.
In correlation technique, study more compound and be mostly triarylimidazoles fluorescent emission luminous organic material.2012, series two (9-anthryls) and two (2-thienyl) substituted ethylene base imidazoles fluorescent emission luminous organic material have been synthesized in correlative study, the same year, also synthesize two (3,4,5-2,4,5-trimethoxyphenyl) substituted ethylene base imidazoles fluorescent emission luminous organic material, 2013, CN103409134 A reported the two fluorescent emission luminous organic material of a kind of three aromatic ethylene base imidazoles.
But, the above-mentioned imidazoles fluorescent emission luminous organic material kind of lifting is few, cost is higher, still can not meet the application demand in the fields such as medicine, white dyes, laser dyes, fluorescent probe, two-photon absorption, electroluminescent device and photovoltaic cell; Therefore, to develop and to prepare novel imidazoles fluorescent emission luminous organic material very urgent.
In view of this, special proposition the present invention.
Summary of the invention
The first object of the present invention is to provide a kind of novel imidazoles fluorescent emission luminous organic material, this material has enriched the kind of imidazoles fluorescent emissive materials, can meet the application demand in the fields such as medicine, white dyes, laser dyes, fluorescent probe, two-photon absorption, electroluminescent device and photovoltaic cell.The second object of the present invention is the preparation method providing a kind of described imidazoles fluorescent emission luminous organic material, and the method is simple, manipulation is convenient.
In order to realize above-mentioned purpose of the present invention, spy by the following technical solutions:
The invention provides a kind of imidazoles fluorescent emission luminous organic material, its general structure is:
Wherein, R is NO
2, CHO, CN, H, OH, OCH
3, CH
3, N (CH
3)
2in any one.
This imidazoles fluorescent emission luminous organic material provided by the invention, halogen is introduced in aromatic ethylene base, different substituents is introduced in the imidazoles conjugated system formed in the 2-position aryl of imidazoles, and obtain novel imidazoles fluorescent emission luminous organic material; This compound has enriched the kind of glyoxaline compound fluorescent emission luminous organic material, and can make up in luminous organic material field, glyoxaline compound can not meet the defect of application demand.In addition, this compound structure is stablized, and is easy to preserve; It has a closed large π key, the sp of its atom N
2track there is a pair lone-pair electron, belong to non-centrosymmetric structure, the confession of conjugation, electrophilic group, internal energy of molecular generation Charger transfer.Therefore, it is on the basis with aromaticity, both aobvious slightly acidic, weakly alkaline can be shown again, thus there is the characteristic (as having the premium properties such as transmission of ligand complex and electronics, proton) that special chemical reaction occurs, therefore, can be applied to widely in the fields such as chemical sensor, electroluminescent organic material, dye sensitization solar battery.
Optionally, described R is: H, CH
3, N (CH
3)
2in any one.
The preparation method of described imidazoles fluorescent emission luminous organic material, comprises the following steps:
1), by 4-chlorobenzaldehyde and piperidines be dissolved in dehydrated alcohol/methyl alcohol, after being heated to backflow, add 2,3-dimethyl diketone wherein, and continue backflow, obtain reaction mixture;
2), by described reaction mixture be cooled to room temperature, make it separate out solid matter, and described solid matter is obtained successively after decompress filter and recrystallization 1,6-bis-(4-chloro-phenyl-)-1,5-hexadiene-3,4-dimethyl diketone;
3), by described 1,6-bis-(4-chloro-phenyl-)-1,5-hexadiene-3,4-dimethyl diketone, para-orientation phenyl aldehyde and ammonium acetate are dissolved in glacial acetic acid, heat and join in frozen water after reaction solution being cooled to room temperature after carrying out back flow reaction, and with alkali lye, its pH is adjusted to 6.8-7.2, separate out head product;
Wherein, the structural formula of described para-orientation phenyl aldehyde is:
r is NO
2, CHO, CN, H, OH, OCH
3, N (CH
3)
2in any one;
4), by described head product carry out decompress filter, washing and recrystallization successively, obtain end product.
Optionally, in step 1) in: the mol ratio of described 4-chlorobenzaldehyde, described 2,3-dimethyl diketone and described piperidines is 2:(0.9 ~ 1): (0.01 ~ 0.1);
And/or
In step 3) in: the mol ratio of described 1,6-bis-(4-chloro-phenyl-)-1,5-hexadiene-3,4-dimethyl diketone, described para-orientation phenyl aldehyde and described ammonium acetate is 1:(1 ~ 1.1): (9 ~ 16).
Optionally, in step 1) in;
The temperature of described heating is: 50 ~ 80 DEG C.
Optionally, in step 1) in;
The described time of continuing backflow is: 6-8 hour.
Optionally, in step 1) in;
All reaction solution is stirred in the process that described heating and described continuation reflux.
Optionally, in step 1) in;
Described 2,3-dimethyl diketone adopt the mode dripped to join in the dehydrated alcohol/methyl alcohol being dissolved with described 4-chlorobenzaldehyde and piperidines, and the time dripped is 25 ~ 45 minutes.
Optionally, in step 3) in;
The time of described back flow reaction is 3 ~ 16 hours.
Optionally, in step 3) in;
The temperature of described frozen water is :-5 ~ 5 DEG C;
Described alkali lye comprises: ammoniacal liquor, mass concentration to be 5 ~ 10% aqueous sodium hydroxide solutions or mass concentration be in the potassium hydroxide aqueous solution of 5 ~ 10% any one.
Compared with prior art, beneficial effect of the present invention is:
(1), imidazoles fluorescent emission luminous organic material of the present invention, halogen is introduced in aromatic ethylene base, different substituents is introduced in the imidazoles conjugated system formed in the 2-position aryl of imidazoles, and obtain novel imidazoles fluorescent emission luminous organic material; This compound has enriched the kind of glyoxaline compound fluorescent emission luminous organic material, and can make up in luminous organic material field, glyoxaline compound can not meet the defect of application demand.
(2), imidazoles fluorescent emission luminous organic material of the present invention, this compound structure stablize, be easy to preserve; It has a closed large π key, the SP of its atom N
2track there is a pair lone-pair electron, belong to non-centrosymmetric structure, the confession of conjugation, electrophilic group, internal energy of molecular generation Charger transfer.Therefore, it is on the basis with aromaticity, and both aobvious slightly acidic, can show weakly alkaline again, thus has the characteristic (as having the premium properties such as transmission of ligand complex and electronics, proton) that special chemical reaction occurs.
(3), the preparation method of imidazoles fluorescent emission luminous organic material of the present invention is simple, and reaction conditions is easy to control.
Accompanying drawing explanation
In order to be illustrated more clearly in the embodiment of the present invention or technical scheme of the prior art, be briefly described to the accompanying drawing used required in embodiment or description of the prior art below.
The ultraviolet absorpting spectrum of the imidazoles fluorescent emission luminous organic material that Fig. 1 provides for embodiment of the present invention 1-5;
Fig. 2-6 is respectively the fluorescence emission spectrogram of imidazoles fluorescent emission luminous organic material in DMF that embodiment of the present invention 1-5 provides.
Embodiment
Below in conjunction with embodiment, embodiment of the present invention are described in detail, but it will be understood to those of skill in the art that the following example only for illustration of the present invention, and should not be considered as limiting the scope of the invention.Unreceipted actual conditions person in embodiment, the condition of conveniently conditioned disjunction manufacturers suggestion is carried out.Agents useful for same or the unreceipted production firm person of instrument, be and can buy by commercially available the conventional products obtained.
The invention provides a kind of imidazoles fluorescent emission luminous organic material, its structural formula is:
Wherein, R is NO
2, CHO, CN, H, OH, OCH
3, CH
3, N (CH
3)
2in any one.Preferably, substituent R used is NO
2, one or more in CHO, CN, OCH3.
The preparation method of the above-mentioned imidazoles fluorescent emission luminous organic material that the present invention also provides, comprises the following steps:
Step 101: 4-chlorobenzaldehyde and piperidines are dissolved in dehydrated alcohol/methyl alcohol, adds 2,3-dimethyl diketone wherein after being heated to backflow, and continues backflow, obtains reaction mixture;
In a step 101, in order to make three kinds of reactants be easy to react, and make sufficient reacting as much as possible, preferably, the mol ratio of described 4-chlorobenzaldehyde, described 2,3-dimethyl diketone and described piperidines is 2:(0.9 ~ 1): (0.01 ~ 0.1); In addition, in order to make 4-chlorobenzaldehyde and piperidines easily molten, preferably, solvent is any one in methyl alcohol or dehydrated alcohol; In order to make speed of response accelerate, and improve the output of reaction mixture, preferably, the temperature of heating controls: between 50 ~ 80 DEG C, and the time of continuing backflow is 6-8 hour; Meanwhile, also all can stir reaction solution in the process of backflow in heating and described continuation, fully react to make reactant.
In addition, the speed that 2,3-dimethyl diketone participates in reaction due to it is comparatively slow, and at high temperature inflammable, therefore, preferably adopt the mode dripped to join in the dehydrated alcohol/methyl alcohol being dissolved with described 4-chlorobenzaldehyde and piperidines, and the time controling dripped is at 25 ~ 45 minutes.
Step 102: described reaction mixture is cooled to room temperature, makes it separate out solid matter, and described solid matter is obtained successively after decompress filter and recrystallization 1,6-bis-(4-chloro-phenyl-)-1,5-hexadiene-3,4-dimethyl diketone;
In above-mentioned steps 101 and 102, the path of 1,6-bis-(4-chloro-phenyl-)-1,5-hexadiene-3,4-dimethyl diketone building-up reactions is:
Step 103: by described 1,6-bis-(4-chloro-phenyl-)-1,5-hexadiene-3,4-dimethyl diketone, para-orientation phenyl aldehyde and ammonium acetate are dissolved in glacial acetic acid, heat and join in frozen water after reaction solution being cooled to room temperature after carrying out back flow reaction, and with alkali lye, its pH is adjusted to 6.8-7.2, separate out head product, obtain crude product.
Preferably, in this step, the mol ratio of described 1,6-bis-(4-chloro-phenyl-)-1,5-hexadiene-3,4-dimethyl diketone, described para-orientation phenyl aldehyde and described ammonium acetate is 1:(1 ~ 1.1): (9 ~ 16); Have the reactant of this mol ratio, it can ensure sufficient reacting, and then improves products collection efficiency.In addition, in order to further realize abundant reaction, preferably, in this step, the time of back flow reaction is 3 ~ 16 hours.
In addition, the temperature of frozen water is :-5 ~ 5 DEG C; And preferred alkali lye is: ammoniacal liquor, mass concentration to be 5 ~ 10% aqueous sodium hydroxide solutions or mass concentration be in the potassium hydroxide aqueous solution of 5 ~ 10% any one; For para-orientation phenyl aldehyde, its structural formula is:
Wherein, R is NO
2, CHO, CN, H, OH, OCH
3, N (CH
3)
2in any one.
Step 104: described head product is carried out decompress filter, washing and recrystallization successively, obtains end product.
In this step, the number of times of washing is preferably 3-5 time, and recrystallization ethanol and DMF mixed solvent carry out, and after vacuum-drying, obtain end product.
Next, in conjunction with above content, following specific embodiment has been enumerated to preparation method's (product that diverse ways is corresponding different) of imidazoles fluorescent emission luminous organic material of the present invention:
Embodiment 1
The imidazoles fluorescent emission luminous organic material preparation method that the embodiment of the present invention provides comprises:
4-chlorobenzaldehyde (0.3mol) and piperidines (0.015mol) is added in the dry reactor that the low liquid funnel of mechanical stirring, reflux and constant voltage is housed, and dehydrated alcohol 400mL, stir, and be heated to backflow in 50 DEG C, then to this solution, 2 are dripped from constant pressure funnel in 30-40 minute, 3-dimethyl diketone (0.15mol), finishes; Stir lower continuation back flow reaction 6 hours, obtain reaction mixture.Reaction mixture is cooled to room temperature, separate out yellow solid matter, absolute ethanol washing three times are used after decompress filter, with ethanol and N, dinethylformamide mixed solvent recrystallization, under vacuum, drying obtains orange red 1,6-bis-(4-chloro-phenyl-)-1,5-hexadiene-3,4-diketone (compound ii) crystal.Wherein, the productive rate of compound ii is 18.5%, and fusing point is 214-216 DEG C.
1 is added in the dry reactor being provided with mechanical stirring, reflux, 6-bis-(4-chloro-phenyl-)-1,5-hexadiene-3,4-diketone (compound ii, 0.01mol), paranitrobenzaldehyde (0.01mol) and ammonium acetate (0.1mol), and 350mL glacial acetic acid, be heated to backflow under stirring, and react 10 hours, the reaction solution obtained is cooled to room temperature, add under stirring in the frozen water of 5 DEG C, then be adjusted to pH=7 with ammoniacal liquor, separate out head product; After gained head product is carried out decompress filter, wash 5 times with water, ethanol and N is used again after vacuum-drying, dinethylformamide mixed solvent recrystallization, carry out vacuum-drying again, obtain 2-p-nitrophenyl-4,5-bis-[2-(4-chloro-phenyl-) vinyl] imidazoles (chemical compounds I).Wherein, the yield 65% of chemical compounds I, fusing point is 242-245 DEG C.
1H NMR(DMSO-d
6/TMS)，δ：12.084(s，1H)，8.426-8.397(d，J＝8.7Hz，2H)，8.299-8.274(d，J＝8.5Hz，2H)，7.725-7.697(d，J＝8.4Hz，4H)，7.629-7.576(d，J＝15.9Hz，2H)，7.431-7.403(d，J＝8.4，4H)，7.332-7.279(d，J＝15.6Hz，2H)；ESI-MS m/z：462.3。
Make solvent with DMF, being configured to concentration is that 5 × 10-5M mensuration fluorescence property is shown in Fig. 2.
Embodiment 2
The preparation method of the imidazoles fluorescent emission luminous organic material that the embodiment of the present invention provides comprises:
4-chlorobenzaldehyde (2mol) and piperidines (0.05mol) is added in the dry reactor that the low liquid funnel of mechanical stirring, reflux and constant voltage is housed, and dehydrated alcohol 400mL, stir, and be heated to backflow in 55 DEG C, then to this solution, 2 are dripped from constant pressure funnel in 35-40 minute, 3-dimethyl diketone (0.9mol), finishes; Stir lower continuation back flow reaction 6 hours, obtain reaction mixture.Reaction mixture is cooled to room temperature, separate out yellow solid matter, absolute ethanol washing four times are used after decompress filter, with ethanol and N, dinethylformamide mixed solvent recrystallization, under vacuum, drying obtains orange red 1,6-bis-(4-chloro-phenyl-)-1,5-hexadiene-3,4-diketone (compound ii) crystal.Wherein, the productive rate of compound ii is 19.2%, and fusing point is 214-216 DEG C.
1 is added in the dry reactor being provided with mechanical stirring, reflux, 6-bis-(4-chloro-phenyl-)-1,5-hexadiene-3,4-diketone (compound ii, 0.1mol), p-Hydroxybenzaldehyde (0.11mol) and ammonium acetate (1.5mol), and 3500mL glacial acetic acid, be heated to backflow under stirring, and react 10 hours; The reaction solution obtained is cooled to room temperature, adds under stirring in the frozen water of 0 DEG C, then be adjusted to pH=7 with 6.0% aqueous sodium hydroxide solution, separate out head product; After gained head product is carried out decompress filter, wash 4 times with water, ethanol and N is used again after vacuum-drying, dinethylformamide mixed solvent recrystallization, carry out vacuum-drying again, obtain 2-p-hydroxybenzene-4,5-bis-[2-(4-chloro-phenyl-) vinyl] imidazoles (chemical compounds I).Wherein, the yield 72.5% of chemical compounds I, fusing point is 270-271 DEG C.
1H-NMR(DMSO)-d
6/TMS):δ12.236(s,1H),9.838(s,1H),7.953-7.924(d,J＝8.7Hz,2H),7.736-7.707(d,J＝8.7Hz,4H),7.625-7.572(d,J＝16.8Hz,2H),7.434(s,4H),7.174-7.120(d,J＝16.2Hz,2H),6.906-6.876(d,J＝9Hz,2H)；ESI-MS m/z：432.3。
Make solvent with DMF, being configured to concentration is 5 × 10
-5m measures fluorescence property and sees Fig. 3, in Fig. 3, when 200-300 nanometer, is emmission spectrum in mild curve.
Embodiment 3
The preparation method of the imidazoles fluorescent emission luminous organic material that the embodiment of the present invention provides comprises:
4-chlorobenzaldehyde (0.3mol) and piperidines (0.015mol) is added in the dry reactor that the low liquid funnel of mechanical stirring, reflux and constant voltage is housed, and dehydrated alcohol 400mL, stir, and be heated to backflow in 60 DEG C, then to this solution, 2 are dripped from constant pressure funnel in 35-40 minute, 3-dimethyl diketone (0.15mol), finishes; Stir lower continuation back flow reaction 6 hours, obtain reaction mixture.Reaction mixture is cooled to room temperature, separate out yellow solid matter, absolute ethanol washing four times are used after decompress filter, with ethanol and N, dinethylformamide mixed solvent recrystallization, under vacuum, drying obtains orange red 1,6-bis-(4-chloro-phenyl-)-1,5-hexadiene-3,4-diketone (compound ii) crystal.Wherein, the productive rate of compound ii is 18.5%, and fusing point is 214-216 DEG C.
1 is added in the dry reactor being provided with mechanical stirring, reflux, 6-bis-(4-chloro-phenyl-)-1,5-hexadiene-3,4-diketone (compound ii, 0.01mol), terephthalaldehyde (0.01mol) and ammonium acetate (0.12mol), and 3500mL glacial acetic acid, be heated to backflow under stirring, and react 9 hours; The reaction solution obtained is cooled to room temperature, adds under stirring in the frozen water of 1 DEG C, then be adjusted to pH=7 with 5.0% potassium hydroxide, separate out head product; After gained head product is carried out decompress filter; wash 5 times with water; ethanol and N is used again after vacuum-drying; dinethylformamide mixed solvent recrystallization; carry out vacuum-drying again; obtain 2-to Fonnylphenyl-4,5-bis-[2-(4-chloro-phenyl-) vinyl] imidazoles (chemical compounds I).Wherein, the yield 60.2% of chemical compounds I, fusing point is 242-245 DEG C.
1H-NMR(300 MHz,DMSO)-d
6/TMS):δ10.060(s,1H),8.350-8.377(d,J＝8.1Hz,2H),8.053-8.080(d,J＝8.1Hz,2H),7.720-7.748(d,J＝8.4Hz,4H),7.616-7.670(d,J＝16.2Hz,2H),7.445-7.443(d,J＝8.4Hz,4H),7.333-7.386(d,J＝16.2Hz,2H)；ESI-MS m/z:646.4(M+H)
+。
Make solvent with DMF, being configured to concentration is 5 × 10
-5m measures fluorescence property and sees Fig. 4, in Fig. 4, when 200-400 nanometer, is emmission spectrum in mild curve.
Embodiment 4
The preparation method of the imidazoles fluorescent emission luminous organic material that the embodiment of the present invention provides comprises:
4-chlorobenzaldehyde (0.3mol) and piperidines (0.015mol) is added in the dry reactor that the low liquid funnel of mechanical stirring, reflux and constant voltage is housed, and dehydrated alcohol 400mL, stir, and be heated to backflow in 65 DEG C, then to this solution, 2 are dripped from constant pressure funnel in 30-40 minute, 3-dimethyl diketone (0.15mol), finishes; Stir lower continuation back flow reaction 6 hours, obtain reaction mixture.Reaction mixture is cooled to room temperature, separate out yellow solid matter, absolute ethanol washing three times are used after decompress filter, with ethanol and N, dinethylformamide mixed solvent recrystallization, under vacuum, drying obtains orange red 1,6-bis-(4-chloro-phenyl-)-1,5-hexadiene-3,4-diketone (compound ii) crystal.Wherein, the productive rate of compound ii is 18.5%, and fusing point is 214-216 DEG C.
1 is added in the dry reactor being provided with mechanical stirring, reflux, 6-bis-(4-chloro-phenyl-)-1,5-hexadiene-3,4-diketone (compound ii, 0.01mol), to cyanobenzaldehyde (0.01mol) and ammonium acetate (0.1mol), and 100mL glacial acetic acid, backflow is heated under stirring, and react 7 hours, the reaction solution obtained is cooled to room temperature, add under stirring in the frozen water of 2 DEG C, then be adjusted to pH=7 with 5.0% potassium hydroxide aqueous solution, separate out head product; After gained head product is carried out decompress filter, wash 5 times with water, after vacuum-drying, use sherwood oil again, ethyl acetate washing for several times, carry out vacuum-drying again, obtain brown color 2-to cyano-phenyl-4,5-bis-[2-(4-chloro-phenyl-) vinyl] imidazoles (chemical compounds I); The yield 60.2% of chemical compounds I; Fusing point is 282-283 DEG C.
1H-NMR(300 MHz,DMSO-d
6/TMS):δ12.770(s,1H),8.295-8.266(d,J＝8.7Hz,2H),8.012-7.984(d,J＝8.4Hz,2H),7.762-7.733(d,J＝8.7Hz,4H),7.673-7.620(d,J＝15.9Hz,2H),7.488-7.460(d,J＝8.4Hz,4H),7.356-7.304(d,J＝15.6Hz,2H)；ESI-MS m/z:441.3(M+H)
+。
Make solvent with DMF, being configured to concentration is 5 × 10
-5m measures fluorescence property and sees Fig. 5, in Fig. 5, when 200-400 nanometer, is emmission spectrum in mild curve.
Embodiment 5
The preparation method of the imidazoles fluorescent emission luminous organic material that the embodiment of the present invention provides comprises:
4-chlorobenzaldehyde (0.3mol) and piperidines (0.015mol) is added in the dry reactor that the low liquid funnel of mechanical stirring, reflux and constant voltage is housed, and dehydrated alcohol 400mL, stir, and be heated to backflow in 65 DEG C, then to this solution, 2 are dripped from constant pressure funnel in 35-40 minute, 3-dimethyl diketone (0.15mol), finishes; Stir lower continuation back flow reaction 8 hours, obtain reaction mixture.Reaction mixture is cooled to room temperature, separate out yellow solid matter, absolute ethanol washing three times are used after decompress filter, with ethanol and N, dinethylformamide mixed solvent recrystallization, under vacuum, drying obtains orange red 1,6-bis-(4-chloro-phenyl-)-1,5-hexadiene-3,4-diketone (compound ii) crystal.Wherein, the productive rate of compound ii is 18.5%, and fusing point is 214-216 DEG C.
1 is added in the dry reactor being provided with mechanical stirring, reflux, 6-bis-(4-chloro-phenyl-)-1,5-hexadiene-3,4-diketone (compound ii, 0.005mol), aubepine (0.005mol) and ammonium acetate (0.05mol), and 50mL glacial acetic acid, backflow is heated under stirring, and react 8 hours, vacuum rotary steam part acetic acid, is cooled to room temperature by the reaction solution obtained, and adds in the frozen water of 1 DEG C under stirring, be adjusted to pH=7 with 5.0% potassium hydroxide aqueous solution again, separate out head product; After gained head product is carried out decompress filter, wash 5 times with water, use methylene dichloride recrystallization again after vacuum-drying again, then carry out vacuum-drying, obtain yellow 2-p-methoxyphenyl-4,5-bis-[2-(4-chloro-phenyl-) vinyl] imidazoles (chemical compounds I).Wherein, the yield of chemical compounds I is 74.2%; Fusing point is 128-130 DEG C.
1H-NMR(300 MHz,DMSO-d
6/TMS):δ：12.330(s，1H)，8.070-8.040(d，J＝9.0Hz，2H)，7.751-7.569(m，6H)，7.469-7.440(d，J＝8.7Hz，4H)，7.435-7.407(d，J＝8.7Hz，2H)，3.840(s，3H)。
Make solvent with DMF, being configured to concentration is 5 × 10
-5m measures fluorescence property and sees Fig. 6.
Table 1 R is respectively H, CH
3with N (CH
3)
2the ultraviolet of compound, excitation and emission spectra data
Can be found out by table 1 and Fig. 1-6, this imidazoles fluorescent emission luminous organic material provided by the invention, its fluorescing frequencies coverage is comparatively wide, has potential using value.
Although illustrate and describe the present invention with specific embodiment, however it will be appreciated that can to make when not deviating from the spirit and scope of the present invention many other change and amendment.Therefore, this means to comprise all such changes and modifications belonged in the scope of the invention in the following claims.
Claims (10)
1. an imidazoles fluorescent emission luminous organic material, is characterized in that, its general structure is:
Wherein, R is NO
2, CHO, CN, H, OH, OCH
3, CH
3, N (CH
3)
2in any one.
2. imidazoles fluorescent emission luminous organic material according to claim 1, is characterized in that,
Described R is: H, N (CH
3)
2, CH
3in any one.
3. a preparation method for imidazoles fluorescent emission luminous organic material according to claim 1, is characterized in that, comprise the following steps:
1), by 4-chlorobenzaldehyde and piperidines be dissolved in dehydrated alcohol/methyl alcohol, after being heated to backflow, add 2,3-dimethyl diketone wherein, and continue backflow, obtain reaction mixture;
2), by described reaction mixture be cooled to room temperature, make it separate out solid matter, and described solid matter is obtained successively after decompress filter and recrystallization 1,6-bis-(4-chloro-phenyl-)-1,5-hexadiene-3,4-dimethyl diketone;
3), by described 1,6-bis-(4-chloro-phenyl-)-1,5-hexadiene-3,4-dimethyl diketone, para-orientation phenyl aldehyde and ammonium acetate are dissolved in glacial acetic acid, heat and join in frozen water after reaction solution being cooled to room temperature after carrying out back flow reaction, and with alkali lye, its pH is adjusted to 6.8-7.2, separate out head product;
Wherein, the structural formula of described para-orientation phenyl aldehyde is:
R is NO
2, CHO, CN, H, OH, OCH
3, N (CH
3)
2 in any one;
4), by described head product carry out decompress filter, washing and recrystallization successively, obtain end product.
4. preparation method according to claim 3, is characterized in that, in step 1) in: the mol ratio of described 4-chlorobenzaldehyde, described 2,3-dimethyl diketone and described piperidines is 2:(0.9 ~ 1): (0.01 ~ 0.1);
And/or
In step 3) in: the mol ratio of described 1,6-bis-(4-chloro-phenyl-)-1,5-hexadiene-3,4-dimethyl diketone, described para-orientation phenyl aldehyde and described ammonium acetate is 1:(1 ~ 1.1): (9 ~ 16).
5. the preparation method according to claim 3 or 4, is characterized in that, in step 1) in;
The temperature of described heating is: 50 ~ 80 DEG C.
6. preparation method according to claim 5, is characterized in that, in step 1) in;
The described time of continuing backflow is: 6 ~ 8 hours.
7. preparation method according to claim 5, is characterized in that, in step 1) in;
All reaction solution is stirred in the process that described heating and described continuation reflux.
8. preparation method according to claim 5, is characterized in that, in step 1) in;
Described 2,3-dimethyl diketone adopt the mode dripped to join in the dehydrated alcohol/methyl alcohol being dissolved with described 4-chlorobenzaldehyde and piperidines, and the time dripped is 25 ~ 45 minutes.
9. preparation method according to claim 5, is characterized in that, in step 3) in;
The time of described back flow reaction is 3 ~ 16 hours.
10. preparation method according to claim 5, is characterized in that, in step 3) in;
The temperature of described frozen water is :-5 ~ 5 DEG C;
Described alkali lye comprises: ammoniacal liquor, mass concentration to be 5 ~ 10% aqueous sodium hydroxide solutions or mass concentration be in the potassium hydroxide aqueous solution of 5 ~ 10% any one.
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