CN109134384A - A kind of preparation method of aggregation-induced emission hydrogen-bonded polymer network - Google Patents
A kind of preparation method of aggregation-induced emission hydrogen-bonded polymer network Download PDFInfo
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- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
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Abstract
A kind of preparation method of aggregation-induced emission hydrogen-bonded polymer network.A kind of tetraphenylethylene bridging urea groups pyrimidinone compound and its synthetic method are related to a kind of organic compound monomer and its synthetic method.The tetraphenylethylene bridging urea groups pyrimidinone compound is the four urea groups pyrimidinone compounds that bridging is aligned based on tetraphenylethylene.Synthetic method: tetraphenylethylene tetra-amino compound is first synthesized, the urea groups pyrimidone precursor compound of activation is then synthesized, is finally synthesizing based on four urea groups pyrimidinone compound of tetraphenylethylene bridging.This method raw material is easy to get, simple process, and application prospect is wide.Meanwhile having many advantages, such as that strong plasticity, easy processing processing, degradable, solid luminescent and mechanical property are good using the fluorescence supermolecule polymer network that the monomer is formed.
Description
Technical field
The invention belongs to the synthesis fields of fluorescence supramolecular polymer material, and in particular to a kind of tetraphenylethylene bridging urea
The synthesis technology of yl pyrimidines ketone (UPy) compound.
Background technique
2001, it was a kind of non-hair that Tang this loyalty academician and its team, which have found the unique effect of aggregation-induced emission (AIE),
If penetrating or emitting, highly luminescent can be become because of aggregation in solution state, (AIQ) is being quenched just with caused by traditional aggregation in this
It is good opposite.Pass through a series of experimental study and theoretical calculation, the limitation campaign (RIM) of intramolecular, the limitation including intramolecular
The main reason for limitation (RIV) of rotation (RIR) and intramolecules vibration has rationally been turned to AIE effect.AIE obeys naturally poly-
Conjunction process, i.e. energy are advantageous, avoid complicated MOLECULE DESIGN and the physical method of formation of the agglomerates is inhibited finally to generate new mould
Formula, new theory, new luminescent material, new research field and new knowledge.It due to its theory significance and has a extensive future, draws
Extensive concern is played.Currently, there is numerous research groups studying.AIE related fields and AIE have become chemistry and material neck
One of the hot research topic in domain.
Tetraphenylethylene is the molecule of most basic aggregation-induced emission, has structure simple, and synthesis is easy, and is easy to chemistry
The advantages that modification and luminosity are good, modification tetraphenylethylene molecule connect urea groups pyrimidone (UPy) unit, form network oversubscription
Sub- polymer.From 1997, E.W.Meijer etc. reported urea groups pyrimidone (UPy) for the first time, made in oversubscription subdomains huge
Contribution.Supermolecule polymer with AIE effect, since there are four interaction of hydrogen bond for urea groups pyrimidone (UPy) molecule, thus
Tridimensional network is further formed by Supramolecular self assembly, there is self-repairability, thorn compared to traditional high molecular polymer
The advantageous properties such as responsiveness are swashed, finally, the physical chemistry that the hydrogen bond supramolecular polymer material with AIE effect will be studied
Matter, and explore its application in photoelectric material.
Summary of the invention
The purpose of the present invention is intended to provide a kind of synthetic method of tetraphenylethylene bridging urea groups pyrimidinone compound.
The compound is four urea groups pyrimidone of tetraphenylethylene ring bridging, is denoted as compound F, chemical structural formula is such as
Under:
The synthetic route of the tetraphenylethylene bridging allophanamide yl pyrimidines ketone compound is as follows:
The synthetic method of the four urea groups pyrimidinone compound of tetraphenylethylene bridging, comprising the following steps:
Step 1: 4 are added in the reactor, 4'- dimethoxy-benzophenone and zinc powder under nitrogen protection, are added super dry
Solvent THF, stirs evenly, and TiCl is added dropwise with constant pressure addition loophole4, continue to stir 20h after being added dropwise, stop reaction and be cooled to
Room temperature.10% sodium carbonate liquor is added and is quenched to no gas releasing, filters to obtain water phase, uses CHCl3Extraction, the anhydrous sulphur of organic phase
Sour magnesium is dry, rotates to obtain white solid.Crude product is chromatographed by column, collects product point, is rotated to get compound A；
Step 2: compound A is added in the reactor, super dry solvent C H is added under nitrogen protection2Cl2, stir evenly, add
Boron tribromide is added in ice salt bath, and dark purple, 15min removes ice salt bath, and 20h is stirred at room temperature, and bath on the rocks is added dropwise methanol and quenches
It goes out, after no white cigarette is released, adds water to and generated without precipitating, collected by suction solid, with water, CH2Cl2Washing, filters to obtain solid, with true
Empty drying box dries to obtain compound B.
Step 3: compound B, the potassium carbonate of drying, N- (3- bromopropyl) phenylenediamine and solvent are added in the reactor
DMF is stirred at reflux, and fully reacting is cooled to room temperature, and is diluted with water, and filter cake is washed with water in filtering, and it is complete to solid that chloroform is added
Fully dissolved, dry with anhydrous magnesium sulfate, rotation dry chromatography collects product point, rotates to get compound C；
Step 4: compound C is added in the reaction vessel, catalyst is added and organic solvent, magnetic agitation are heated to reflux
Reaction stops reaction when reacting liquid temperature is down to room temperature, and chloroform dilution and distillation water washing is added, and collects organic phase, anhydrous
Magnesium sulfate dries, filters revolving,
Step 5: the different heptyl iso-cytosine of 6- and N, N'- carbonyl dimidazoles (CDI) are added in the reaction vessel, vacuumize
Inflated with nitrogen afterwards is added haloform reaction, is stirred at room temperature under nitrogen protection, after stopping reaction, successively uses distilled water and saturated common salt
Water washing, anhydrous magnesium sulfate dry, filter to get compound E；
Step 6: compound E is added in the reaction vessel, rear inflated with nitrogen is vacuumized, under nitrogen protection, compound is added
D adds CHCl3Making 0.05~0.08g/mL of total compound quality concentration, magnetic agitation after stopping reaction, removes solvent,
Drying is denoted as compound F to get four urea groups pyrimidinone compound of target product tetraphenylethylene bridging.
In the 4th step, the catalyst is hydrazine hydrate；The additional amount of the catalyst can be by mass percentage reaction
The 5%~6% of system gross mass；The organic solvent is ethyl alcohol；The reaction can react 8~10h at 80~100 DEG C；Institute
It states washing washable 5~7 times；The condition of the drying can dry 2h at 50 DEG C of vacuum.
In the 5th step, the molar ratio of the different pyrimidine of the different heptyl of 6- and N, N'- carbonyl dimidazoles (CDI) can be 1:1.5；
It is described vacuumize rear inflated with nitrogen and can continuously vacuumize rear inflated with nitrogen recycle 3~5 times；The CHCl3To wash 12~15 dryings
Treated CHCl3；The reaction can react 4~6h at room temperature；The washing times are 2~3 times.
In step 6, the molar ratio of the compound D and compound E can be 1:(4.0~4.4)；It is described vacuumize after
Inflated with nitrogen can continuously vacuumize rear inflated with nitrogen and recycle 3~5 times；The CHCl3CHCl after being dried for washing 12~15 times3；
The reaction condition can react at room temperature for 24 hours；The washing times are 1~2 time；The drying temperature is 50 DEG C.
The present invention synthesizes a kind of compound with multiple hydrogen bonding unit, compound bridging four on tetraphenylethylene
A UPy unit to form a highly cross-linked tridimensional network, and then obtains that a plasticity is strong and mechanical property is good
Super molecular compound.
By the above synthesis step, the beneficial effects of the present invention are embodied in:
1, the present invention has synthesized the supermolecule polymer network new material with AIE effect, which has good
Plasticity and bridging property, while also there is aggregation-induced emission characteristic.
2, raw materials used the present invention provides the preparation method of the above-mentioned tetraphenylethylene containing the modification of four urea groups pyrimidones
Cheap and easy to get, simple process, reaction condition is mild, and yield is high.
3, the present invention is the covalent bond using Quadrupolar hydrogen bond as connection site, rather than traditional, has plasticity and easily drop
It the advantages that solution property, has a good application prospect.
Detailed description of the invention
Fig. 1 be compound F in DMSO hydrogen nuclear magnetic resonance (1HNMR) spectrogram, wherein abscissa is chemical shift
(ppm)。
Fig. 2 is the fluorescence radiation image that compound F irradiates in the UV lamp.
Specific embodiment
For a better understanding of the present invention, below by embodiment, the present invention is further illustrated.
Embodiment 1:
Step 1: 4,4'- dimethoxy-benzophenone 5g and zinc powder 6.7g, N are added in the three-necked flask of 250mL2It protects
Under shield, the super dry solvent THF of 100mL is added, stirs evenly, TiCl is added dropwise with constant pressure addition loophole413.7g, after being added dropwise
Continue to stir (20h), stops reaction and be cooled to room temperature.10% sodium carbonate liquor is added and is quenched to no gas releasing, filters to obtain water
Phase uses CHCl3(100mL × 3) extraction, organic phase is dry with anhydrous magnesium sulfate, rotates to obtain white solid.Crude product passes through column layer
It analyses (DCM:PE=1:4 → 1:2) and obtains white solid 2.30g, yield 49.3%.Up to compound A；
Step 2: compound A 0.5g, N are added in 100mL three-necked flask2Protection is lower to be added super dry solvent C H2Cl2
(10mL), stirs evenly, salt bath on the rocks, and Boron tribromide 2.2g is added, dark purple, after 15 minutes, removes ice salt bath, room temperature is stirred
It mixes 20 hours, bath on the rocks, methanol is added dropwise and is quenched, after no white cigarette is released, add water to and generated without precipitating, collected by suction solid uses water
(50mL×2)、CH2Cl2(50mL × 2) washing, filters to obtain solid, dries to obtain violet solid (compound B) with vacuum oven,
Yield 76.1%.
Step 3: potassium carbonate 2.09g, N- (3- bromine third of compound B 0.75g, drying are added in 50mL three-necked flask
Base) phenylenediamine 2.23g and 20mL DMF, be stirred at reflux, fully reacting is cooled to room temperature, add water 50mL dilute, filtering, use water
Filter cake is washed, yellow solid is obtained, chloroform to solid is added and is completely dissolved, it is dry with anhydrous magnesium sulfate, revolve dry chromatography: DCM:
MeOH=400:1 → 200:1 obtains yellow powder (compound C) yield 57.9%.
Step 4: compound A 0.40g is added in 50mL three-necked flask, vacuumized by continuous 3~5 times, inflated with nitrogen
Circulation, oxygen and moisture in discharge system.Under nitrogen protection, compound B 0.98g is added, adds washing 15 times and does
Dry treated CHCl35mL is stirred at room temperature reaction 4h, stops reaction.Separation obtains organic phase, dries to get target product,
Product is faint yellow solid (compound D), yield 65.83%.
Step 5: the different pyrimidine 0.75g and N of the different heptyl of 6-, N'- carbonyl dimidazoles (CDI) are added in 50mL three-necked flask
1.08g is vacuumized, the circulation of inflated with nitrogen by continuous 3~5 times, the oxygen and moisture in discharge system.Under nitrogen protection,
The CHCl after being dried is added washing 15 times320mL is stirred at room temperature reaction 6h, stops reaction.(30mL × 2) successively are washed,
Saturated common salt water washing (30mL × 2) collects organic phase, and anhydrous magnesium sulfate dries, filters, and product is yellow solution
(compound E), yield 90%.
Step 6: compound D is added in the reaction vessel, rear inflated with nitrogen is vacuumized, under nitrogen protection, compound is added
E adds CHCl3Making 0.05~0.08g/mL of total compound quality concentration, magnetic agitation after stopping reaction, removes solvent,
Drying is denoted as compound F to get four urea groups pyrimidinone compound of target product tetraphenylethylene bridging.
Claims (4)
1. a kind of tetraphenylethylene bridging urea groups pyrimidinone compound, it is characterised in that be four urea groups pyrimidine of tetraphenylethylene bridging
Ketone is denoted as compound F, and chemical structural formula is as follows:
The tetraphenylethylene bridging urea groups pyrimidinone compound is synthesized by following methods:
1): it is added 4,4'- dimethoxy-benzophenone and zinc powder in the reactor, under nitrogen protection, super dry solvent THF is added,
It stirs evenly, TiCl is added dropwise with constant pressure addition loophole4, continue to stir 20h after being added dropwise, stop reaction and be cooled to room temperature.Add
Enter 10% sodium carbonate liquor and be quenched to no gas releasing, filters to obtain water phase, use CHCl3Extraction, organic phase are dry with anhydrous magnesium sulfate
It is dry, rotate to obtain white solid.Crude product is chromatographed by column, collects product point, is rotated to get compound A；
2): compound A being added in the reactor, super dry solvent C H is added under nitrogen protection2Cl2, stir evenly, salt bath on the rocks adds
Enter Boron tribromide, dark purple, 15min removes ice salt bath, and 20h is stirred at room temperature, and bath on the rocks is added dropwise methanol and is quenched, and no white cigarette is put
After out, adds water to and generated without precipitating, collected by suction solid, with water, CH2Cl2Washing, filters to obtain solid, is dried with vacuum oven
Obtain compound B.
3): compound B, the potassium carbonate of drying, N- (3- bromopropyl) phenylenediamine and solvent DMF being added in the reactor, stirs back
Fully reacting is flowed, is cooled to room temperature, is diluted with water, is filtered, filter cake is washed with water, chloroform to solid is added and is completely dissolved, with nothing
Water magnesium sulfate is dry, and rotation dry chromatography collects product point, rotates to get compound C；
4): addition compound C in the reaction vessel, addition catalyst and organic solvent, magnetic agitation, heating reflux reaction, when
Reacting liquid temperature stops reaction when being down to room temperature, and chloroform dilution and distillation water washing is added, and collects organic phase, and anhydrous magnesium sulfate is dry
Dry, filtering revolving obtains D.
5): the different pyrimidine of the different heptyl of 6- and N, N'- carbonyl dimidazoles (CDI) are added in the reaction vessel, vacuumize rear inflated with nitrogen,
Under nitrogen protection, haloform reaction is added, is stirred at room temperature, after stopping reaction, successively uses distilled water and saturated common salt water washing, it is anhydrous
Magnesium sulfate dries, filters to get compound E；
6): compound D being added in the reaction vessel, vacuumizes rear inflated with nitrogen, under nitrogen protection, compound E is added, adds
CHCl3 makes 0.05~0.08g/mL of total compound quality concentration, and magnetic agitation after stopping reaction, removes solvent, dry, i.e.,
Four urea groups pyrimidinone compound of target product tetraphenylethylene bridging is obtained, compound F is denoted as.
2. tetraphenylethylene bridging urea groups pyrimidinone compound according to claim 1, it is characterised in that in step 5),
The molar ratio of the different pyrimidine of the different heptyl of 6- and N, N'- carbonyl dimidazoles (CDI) can be 1:1.5；It is described to vacuumize rear inflated with nitrogen
Rear inflated with nitrogen can be continuously vacuumized to recycle 3~5 times；The CHCl3CHCl after being dried for washing 12~15 times3；It is described anti-
It can should react at room temperature 4~6h；The washing times are 2~3 times.
3. tetraphenylethylene bridging urea groups pyrimidinone compound according to claim 1, it is characterised in that in step 4),
The catalyst is hydrazine hydrate；The additional amount of the catalyst by mass percentage can for reaction system gross mass 5%~
6%；The organic solvent is ethyl alcohol；The reaction can react 8~10h at 80~100 DEG C；The washing washable 5~7
It is secondary；The condition of the drying can dry 2h at 50 DEG C of vacuum.
4. tetraphenylethylene bridging urea groups pyrimidinone compound according to claim 1, it is characterised in that in step 6),
The molar ratio of the compound D and compound E can be 1:(4.0~4.4)；It is described to vacuumize after rear inflated with nitrogen vacuumize continuously
Inflated with nitrogen recycles 3~5 times；The CHCl3CHCl after being dried for washing 12~15 times3；The reaction condition can be in room temperature
Lower reaction is for 24 hours；The washing times are 1~2 time；The drying temperature is 50 DEG C.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109879858A (en) * | 2019-04-12 | 2019-06-14 | 常州大学 | A kind of preparation method of the supermolecule polymer network based on tetraphenylethylene |
| CN111205472A (en) * | 2020-02-16 | 2020-05-29 | 常州大学 | Preparation method of solid fluorescent dye based on multiple hydrogen bonds |
| CN111269173A (en) * | 2020-02-16 | 2020-06-12 | 常州大学 | Preparation and application of solid fluorescent test paper material |
| CN111303049A (en) * | 2020-02-16 | 2020-06-19 | 常州大学 | Preparation method of water-dispersible fluorescent supramolecular polymer nanospheres |
| CN111826153A (en) * | 2020-06-08 | 2020-10-27 | 上海大学 | Temperature-sensitive amphiphilic dendritic macromolecule based on tetraphenylethylene and preparation method thereof |
| CN111965147A (en) * | 2019-05-20 | 2020-11-20 | 中国科学院理化技术研究所 | Ratio type nanosphere sensor based on pure organic room temperature phosphorescence and preparation method and application thereof |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109879858A (en) * | 2019-04-12 | 2019-06-14 | 常州大学 | A kind of preparation method of the supermolecule polymer network based on tetraphenylethylene |
| CN111965147A (en) * | 2019-05-20 | 2020-11-20 | 中国科学院理化技术研究所 | Ratio type nanosphere sensor based on pure organic room temperature phosphorescence and preparation method and application thereof |
| CN111205472A (en) * | 2020-02-16 | 2020-05-29 | 常州大学 | Preparation method of solid fluorescent dye based on multiple hydrogen bonds |
| CN111269173A (en) * | 2020-02-16 | 2020-06-12 | 常州大学 | Preparation and application of solid fluorescent test paper material |
| CN111303049A (en) * | 2020-02-16 | 2020-06-19 | 常州大学 | Preparation method of water-dispersible fluorescent supramolecular polymer nanospheres |
| CN111826153A (en) * | 2020-06-08 | 2020-10-27 | 上海大学 | Temperature-sensitive amphiphilic dendritic macromolecule based on tetraphenylethylene and preparation method thereof |
| CN111826153B (en) * | 2020-06-08 | 2022-11-22 | 上海大学 | Temperature-sensitive amphiphilic dendritic macromolecule based on tetraphenylethylene and preparation method thereof |
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Application publication date: 20190104 |