CN108046970A - Tritiated Parylene dimer and its application - Google Patents

Tritiated Parylene dimer and its application Download PDF

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CN108046970A
CN108046970A CN201711296035.4A CN201711296035A CN108046970A CN 108046970 A CN108046970 A CN 108046970A CN 201711296035 A CN201711296035 A CN 201711296035A CN 108046970 A CN108046970 A CN 108046970A
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tritiated
parylene
tritium
dimer
parylene dimer
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张子庚
靳文丛
詹芝敏
吕丽娴
张瑜桀
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One Element (guangzhou) Technology Co Ltd
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Abstract

The invention discloses a kind of tritiated Parylene dimer and its application, at least one hydrogen of the substituent group on the phenyl ring or phenyl ring of Parylene dimer of the structural formula as shown in formula I is replaced by tritium：Tritiated Parylene dimer passes through the seamless fine and close application for forming a film, developing photoelectric field that is vapor-deposited by the use of Parylene dimer as the carrier of radioactivity tritium, while using the characteristics of Parylene compact structure is stable, radioresistance is strong, molecular level gaseous state forms a film.

Description

Tritiated Parylene dimer and its application
Technical field：
The present invention relates to tritiated Parylene dimer and its applications.
Background technology：
The entitled Parylene of Parylene (Parylene) Chinese, is a kind of very-high performance polymeric coating material, is army Unique a kind of solids coating in thing standard.
It is as follows that it deposits film forming procedure：
Using vacuum vapor deposition technique, Parylene (Parylene) dimer solid state powder is placed on to the liter of coating equipment In magnificent cavity, first by Parylene (Parylene) dimer solid state powder in 150-170 DEG C of vacuum gasifying under vacuum state, then Chamber is cracked through being cracked into monomer under 650 DEG C of high temperature, then in deposit cavity cohesion synthesising macromolecule copolymer, deposition under normal temperature condition On sample to be protected, protective film is formed.Its deposition growing is a kind of growth course of molecular level, and it is various to be coated to sample The surface of shape, the film thickness of formation uniformly, it is dense non-porous, transparent unstressed, have excellent electrical insulating property and protective, be situated between Electric constant is small, lubricity is good, coefficient of friction is low, insulating properties and anti-corrosive properties are good, capability of resistance to radiation is extremely strong.
The content of the invention：
The object of the present invention is to provide a kind of tritiated Parylene dimer and its applications.
The present invention is achieved by the following technical programs：
A kind of tritiated Parylene dimer, which is characterized in that the phenyl ring of Parylene dimer of the structural formula as shown in formula I or At least one hydrogen of substituent group on phenyl ring is replaced by tritium：
Wherein, A, B, C, D are arbitrary substituent group, and E is selected from hydrogen or halogen.
A, B, C, D are hydrogen or any other conventional substituents, tritium or substituent group containing tritium, and A, B, C, D cannot be tritium simultaneously.
Particularly, when A, B, C, D are selected from hydrogen or ethyl, the synthetic method of tritiated Parylene dimer is including following：
1st, when at least one hydrogen of the phenyl ring of Parylene dimer is replaced by tritium, corresponding halogenated Parylene dimerization is passed through Body tritium halogen under the catalytic conditions such as Pd, Pt, Ni, which exchanges, to be realized：
Wherein X represents halogen, is preferably bromine；
Comprise the following steps, added in round-bottomed flask benzene ring halogenated to the catalyst such as ring benzene alkane, Pd, Pt, Ni, four Then hydrogen THF solvent, liquid nitrogen frozen 5 minutes, fine pumping 5 minutes introduce the tritium gas under 1 atmospheric pressure, remove liquid nitrogen, room When temperature stirring 2 is small, then with liquid nitrogen frozen round-bottomed flask 5 minutes, vacuum transfer absorption method recycles unreacted tritium gas, in flask Residue replys room temperature, is filtered to remove solid matter, and vacuum rotary steam removes solvent, obtains corresponding tritiated Parylene target production Object.
2nd, when at least one hydrogen of the substituent group on the phenyl ring of Parylene dimer is replaced by tritium, by under catalytic condition Side chain unsaturated bond tritium addition passes through halides and tritiated grignard reagent coupling reaction.
Side chain unsaturated bond tritium addition under catalytic condition, a position of double bond can introduce two tritium atoms, three key mapping It puts and fully saturated introduces 4 tritium atoms：
Comprise the following steps：Side chain is added in round-bottomed flask and contains being catalyzed to ring benzene alkane, Pd/C (5%) for unsaturated bond Then agent, tetrahydrofuran solvent, liquid nitrogen frozen 5 minutes, fine pumping 5 minutes introduce the tritium gas under 1 atmospheric pressure, remove liquid Nitrogen, reply room temperature and continue stir about 24 it is small when, then with liquid nitrogen frozen round-bottomed flask 5 minutes, the recycling of vacuum transfer absorption method was not The tritium gas of reaction, the residue in flask reply room temperature, are filtered to remove solid matter, and vacuum rotary steam removes solvent, obtain corresponding Tritiated Parylene target product.
Halides and tritiated grignard reagent coupling reaction：
Comprise the following steps：[double (diphenylphosphine) propane of 1,3-]-nickel chloride of halogenated Parylene dimer and 5%mmol (II)(Ni(dppp)Cl2) be added in round-bottomed flask, adding in anhydrous ether makes its dissolving.Under ice cooling, 4, under stiring The diethyl ether solution of tritiated iodoethane grignard reagent is added dropwise in reaction mixture.Room temperature, Zhi Houjia are restored to after being added dropwise Hot 30-35 DEG C, then by TLC tracking reaction until completing.Stirring is lower, and ammonium chloride saturated solution is added dropwise into reaction mixture Reaction is terminated, then processing obtains target product.
The present invention also protects application of the above-mentioned tritiated Parylene dimer in photoelectric field.
Using gas-phase deposition, by above-mentioned tritiated Parylene dimer elder generation vacuum gasifying, then cracked under high temperature, Ran Hou Deposit cavity cohesion synthesising macromolecule copolymer, is grown on sample surfaces, forms film.
Particularly, tritiated Parylene dimer forms a film in semiconducting nanotubes/line seamless surface densification, long continuous for making Navigate tritium base isotope battery.
Or, after tritiated Parylene dimer film forming, on tritiated Parylene film obtained, cover last layer micron or receive The fluorescent powder film of meter level, for making long-acting spontaneous emission light source.
Or, fire smog detector ionization source is used to prepare after tritiated Parylene dimer film forming, instead of what is used at present It is high-risk, expensive241Am radioactive sources.
Beneficial effects of the present invention are as follows：
By the use of Parylene dimer as the carrier of radioactivity tritium, while utilize Parylene compact structure stabilization, radioresistance By force, the characteristics of molecular level gaseous state forms a film by the seamless fine and close film forming that is vapor-deposited, is widely used in photoelectric field.
1st, by the use of Parylene dimer as the carrier of radioactivity tritium, while using Parylene compact structure is stable, anti-spoke The characteristics of strong, molecular level gaseous state forms a film is penetrated, is directly formed a film by being vapor-deposited in semiconducting nanotubes/line seamless surface densification, For making long continuation of the journey tritium base isotope battery.Due to being molecular level gaseous state film forming, radioactive source substance is made to be received into nano level Mitron inner wall or nano wire gap are possibly realized, and the energetic beta particle of all directions ball-type transmitting is utilized, while β particles arrive Up to semiconductor junction offset from greatly shortening, the total conversion of tritium based nanotube/line isotope battery is made to be greatly improved.
2nd, on obtained tritiated Parylene film, last layer micron or nano level fluorescent powder film are covered, is generated Long-acting spontaneous emission fluorescence.The radiation tritium light source used at present be inner wall scribble closing ballotini that tritium gas is filled in fluorescent powder or Glass tube, tritiated Parylene film are soft solid high molecular polymers, and it is firm that manufactured tritium light source overcomes glass tritium light source Property frangible, the shortcomings that tritium gas self-absorption is serious, improve the transfer efficiency that radiant is converted into luminous energy, soft flexible nature Make tritium light source applications more extensive.
3rd, current fire smog detector ionization source uses241Am radioactive sources,241Am is that high-risk, high poison, ɑ, r of costliness are put Nucleic is penetrated, even if 1 micromicrocurie activity all belongs to the V class radioactive sources of control.Tritium is the low less toxic active kernel-beta element of danger, as ionization source tritium β Radioactive source content is only 1 millicurie, but still belongs to and exempt use scope.Since the free path of tritium β particles is about241Am ɑ particles from By 1/10th of journey, tritium fire smog detector ionisation chamber may be designed to monopole and bipolar twoth area, greatly improve fire hazard aerosol fog Detector sensitivity can also make the thinner smaller of fire smog detector.In short, tritium fire smog detector is safer, cleverer It is quick, less expensive.
Specific embodiment：
It is the further explanation to the present invention rather than limitation of the present invention below.
Embodiment 1：Catalytic tritiation method synthesizes tritiated tetraethyl to ring benzene alkyl compound
Similar to addition reaction of hydrogen, in the presence of the catalyst such as Pd, Pt, Ni, side chain contains four acetenyls of unsaturated bond To ring benzene alkane can catalytic tritiation obtain tritiated tetraethyl to ring benzene alkane.
Specific method is：
Method 1：It puts magnetic stir bar into 25mL round-bottomed flasks, then adds in tetra- acetenyls of 0.1mmol to ring benzene alkane, 2mg Pd/C (5%) catalyst, 5mL tetrahydrofuran solvents, liquid nitrogen frozen about 5 minutes, fine pumping about 5 minutes, Ran Houyin Tritium gas under 1 atmospheric pressure of about 25mL, removes liquid nitrogen, reply room temperature and continue stir about 24 it is small when, then with liquid nitrogen frozen round bottom Flask about 5 minutes, vacuum transfer absorption method recycle unreacted tritium gas, and the residue in flask replys room temperature, is filtered to remove solid Body substance, vacuum rotary steam remove solvent, obtain corresponding tritiated Parylene target product, yield 95%.
Method 2：5mL tetrahydrofurans in method 1 are replaced with 5mL ethyl alcohol, remaining operating method is identical with post processing, obtains Same target product.
Method 3：The 5mL tetrahydrofurans in method 1, remaining operation side are replaced with 3mL tetrahydrofurans and 2mL alcohol mixtures Method is identical with post processing, obtains same target product.
Method 4：With 2 milligrams of Raney Raney nickels replace method 1 in 2 milligrams of palladium-carbon catalysts, remaining operating method and It post-processes identical, obtains same target product.
Method 5：With 2 milligrams of Raney Raney nickels replace method 2 in 2 milligrams of palladium-carbon catalysts, remaining operating method and It post-processes identical, obtains same target product.
Method 6：2 milligrams of palladium-carbon catalysts in method 1 are replaced with 2 milligrams of platinum carbon catalyst, remaining operating method is with after It handles identical, obtains same target product.
Method 7：2 milligrams of palladium-carbon catalysts in method 2 are replaced with 2 milligrams of platinum carbon catalyst, remaining operating method is with after It handles identical, obtains same target product.
Wherein four acetenyls comprise the following steps the synthetic method of ring benzene alkane：
First, bromo-reaction is carried out to ring benzene alkane, obtains tetrabromo to ring benzene alkane：It is installed in 250mL three neck round bottom Then the conduit being connected with hydrogen bromide gas absorbing device adds in 30mL (589mmol, 94.2g) bromines and 150mg (0.6mmol) Iodine, the lower magnetic agitation of ice water cooling after closing, and reaction is positioned over dark place as far as possible.When temperature is below 10 DEG C, at 12 Point 10 addition 10.0g (48mmol) are to ring benzene alkane in hour.The quick effusion of bromination hydrogen is paid attention at this time.It treats to ring benzene alkane After adding, reply room temperature and continue stirring 3 days, and by TLC tracking reaction until completing.After the completion of reaction, 300mL20% is used Sodium hydrate aqueous solution decomposition reaction, solid product is collected by filtration, then with 3X 50mL hot ethanol washed products.Vacuum is done Four bromo of 22g products is obtained after dry to ring benzene alkane, yield 87.5%.1H NMR(400MHz,CD3Cl)σ:7.02(s,4H), 3.42-3.32(m,4H),3.16-3.08(m,4H)。
2nd, four bromos carry out Sonogashira coupling reactions to ring benzene alkane and trimethylsilyl acetylene：Justify in tri- necks of 100mL 50mL tetrahydrofurans, four bromos of 10mmol (5.24g) are added in the flask of bottom to ring benzene alkane and 50mL diisopropylamines, is passed through nitrogen 30 minutes to remove air.0.8mmol (0.92g) tetraphenyl phosphine palladium and 1.6mmol (0.3g) cuprous iodide are then added in, is being stirred It mixes and lower mixture is heated to 40-50 DEG C.8.8mL (6mmol) three is injected in the interior upward mixture by syringe when 10 is small Methyl silico acetylene and the tetrahydrofuran compound of 50mL deoxidations.Reaction mixture passes through TLC when 40-50 DEG C of reactions 48 are small Tracking reaction is until complete.After vacuum rotary steam removes solvent, residue purifies to obtain four (trimethyl silicane second by column chromatography for separation Alkynyl) to ring benzene alkane 2.67g, yield 45%.1H NMR(400MHz,CD3Cl)σ:7.23-7.02(m,4H),3.34-3.22(m, 4H),3.06-2.94(m,4H),0.21(s,36H).3rd, hydrolysis of four (the trimethylsilyl acetylene bases) to ring benzene alkane：Four (trimethyls Silico acetylene base) trimethyl silicon substrate is taken off in alkaline conditions to ring benzene alkane, four acetenyls are obtained to ring benzene alkane.Concrete operation method For：Product four (trimethylsilyl acetylene base) is walked on being added in 250mL round-bottomed flasks to ring benzene alkane 2.93g (5.0mmol), finely ground Anhydrous potassium carbonate 9.01g (66.0mmol), dry dichloromethane 30mL and absolute methanol 30mL.Mixture stirs at room temperature 24 it is small when after add in dichloromethane 50mL, saturated aqueous ammonium chloride 50mL is then slowly added dropwise, organic layer satisfied respectively with 50mL With aqueous ammonium chloride solution and water washing once.After organic layer is dried with anhydrous sodium sulfate, vacuum rotary steam removes solvent, obtains sticky Four acetenyl of shape product is to ring benzene alkane 1.46g, yield 96%.1H NMR(400MHz,CD3Cl)σ:7.08(s,4H),3.50- 3.42(m,4H),3.40(s,4H),3.38-3.3.32(m,4H)。
Embodiment 2：Tritium halogen exchanges under catalytic condition
Put magnetic stir bar into 10mL round-bottomed flasks, then add in 0.1mmol benzene ring halogenateds to ring benzene alkane, 1mg Pd/C (5%) catalyst, 3mL tetrahydrofuran solvents, liquid nitrogen frozen about 5 minutes, fine pumping about 5 minutes, Ran Houyin Tritium gas under 1 atmospheric pressure of about 10mL, removes liquid nitrogen, reply room temperature and continue stir about 2 it is small when, then with liquid nitrogen frozen round bottom Flask about 5 minutes, vacuum transfer absorption method recycle unreacted tritium gas, and the residue in flask replys room temperature, is filtered to remove solid Body substance, vacuum rotary steam remove solvent, obtain corresponding tritiated Parylene target product, yield 95%.
Embodiment 3：Halides and tritiated grignard reagent coupling reaction
Take [double (diphenylphosphine) propane of the 1,3-]-chlorination of 0.10mmol tetrabromos to ring benzene alkane (0.053g) and 5%mmol Nickel (II) (Ni (dppp) Cl2) be added in 25mL round-bottomed flasks, adding in 5mL anhydrous ethers makes its dissolving.Under ice cooling, 4, The grignard reagent diethyl ether solution of the tritiated iodoethane of 0.40mmol is added dropwise in reaction mixture under stiring.It is added dropwise rear extensive Room temperature is arrived again, heats 30-35 DEG C afterwards, then by TLC tracking reaction until completing.Stirring is lower to be added dropwise into reaction mixture Ammonium chloride saturated solution terminates reaction.Organic layer is isolated, water layer is extracted secondary with ether.Merge organic layer, organic layer difference It is washed with saturated salt solution and sodium acid carbonate, vacuum distillation removing solvent, obtains crude product after being dried with sodium sulphate.Crude product is used Ethyl alcohol recrystallization obtains target product, yield 80%.
Tetrabromo is as follows to the synthetic method of ring benzene alkane：It installs in 250mL three neck round bottom and is inhaled with bromination hydrogen Then the conduit that receiving apparatus is connected adds in 30mL (589mmol, 94.2g) bromines and 150mg (0.6mmol) iodine, ice water is cold after closing But magnetic agitation is descended, and reaction is positioned over dark place as far as possible.When temperature is below 10 DEG C, point 10 additions within 12 hours 10.0g (48mmol) is to ring benzene alkane.The quick effusion of bromination hydrogen is paid attention at this time.It treats after adding to ring benzene alkane, replys room Temperature continues stirring 3 days, and by TLC tracking reaction until completing.It is water-soluble with the sodium hydroxide of 300mL20% after the completion of reaction Solid product is collected by filtration in liquid decomposition reaction, then with 3X 50mL hot ethanol washed products.22g products are obtained after vacuum drying Four bromos are to ring benzene alkane, yield 87.5%.1H NMR(400MHz,CD3Cl)σ:7.02(s,4H),3.42-3.32(m,4H), 3.16-3.08(m,4H)。
Tritium is for the preparation method of the Grignard Reagent diethyl ether solution of iodoethane：Be separately added into 10mL round-bottomed flasks 3mL without Water ether, 0.44mmol (0.01g) magnesium rod are mixed being made of 3mL anhydrous ethers and 0.4mmol (0.063g) tritiums for iodoethane Object drop 5 is closed to instill in round-bottomed flask.After reaction starts, solution of iodine oxide is added dropwise in reaction bulb in batches and is reacted with magnesium rod. It is added dropwise that rear the reaction was continued obtains the Grignard Reagent of iodoethane after a certain period of time.

Claims (10)

1. a kind of tritiated Parylene dimer, which is characterized in that on the phenyl ring of Parylene dimer of the structural formula as shown in formula I Or at least one hydrogen of the substituent group on phenyl ring is replaced by tritium：
Wherein, A, B, C, D are arbitrary substituent group, and E is selected from hydrogen or halogen.
2. tritiated Parylene dimer according to claim 1, which is characterized in that A, B, C, D are selected from hydrogen or ethyl.
3. the synthetic method of the tritiated Parylene dimer described in claim 2, which is characterized in that including following：
When at least one hydrogen of the phenyl ring of Parylene dimer is replaced by tritium, existed by corresponding halogenated Parylene dimer Tritium halogen, which exchanges, under Pd, Pt, Ni catalytic condition realizes：When at least one hydrogen of the substituent group on the phenyl ring of Parylene dimer is by tritium During replacement, by side chain unsaturated bond tritium addition under catalytic condition or pass through halides and tritiated grignard reagent coupling reaction.
4. the synthetic method of tritiated Parylene dimer according to claim 3, which is characterized in that when Parylene dimer At least one hydrogen of phenyl ring when being replaced by tritium, exchanged and realized by tritium halogen under Pd, Pt, Ni catalytic condition, specifically included following Step：Added in round-bottomed flask benzene ring halogenated to ring benzene alkane, catalyst, tetrahydrofuran solvent, liquid nitrogen frozen 5 minutes, Fine pumping 5 minutes, then introduces the tritium gas under 1 atmospheric pressure, removes liquid nitrogen, be stirred at room temperature 2 it is small when, then justified with liquid nitrogen frozen Bottom flask 5 minutes, vacuum transfer absorption method recycle unreacted tritium gas, and the residue in flask replys room temperature, is filtered to remove solid Body substance, vacuum rotary steam remove solvent, obtain corresponding tritiated Parylene target product.
5. the synthetic method of tritiated Parylene dimer according to claim 3, which is characterized in that side chain under catalytic condition Unsaturated bond tritium addition specifically includes following steps：In round-bottomed flask add in side chain contain unsaturated bond to ring benzene alkane, Pd/ Then C catalyst, tetrahydrofuran solvent, liquid nitrogen frozen 5 minutes, fine pumping 5 minutes introduce the tritium gas under 1 atmospheric pressure, move Open liquid nitrogen, reply room temperature and continue stir about 24 it is small when, then with liquid nitrogen frozen round-bottomed flask 5 minutes, vacuum transfer absorption method was returned Receive unreacted tritium gas, the residue in flask replys room temperature, is filtered to remove solid matter, and vacuum rotary steam removes solvent, obtains Corresponding tritiated Parylene target product.
6. the synthetic method of tritiated Parylene dimer according to claim 3, which is characterized in that halogenated Parylene dimerization Body and tritiated grignard reagent coupling reaction comprise the following steps：Bromo is to ring benzene alkane and [double (diphenylphosphine) propane of 1,3-]-chlorine Change nickel (II) to be added in round-bottomed flask, adding in anhydrous ether makes its dissolving, under ice cooling, 4, under stiring tritiated iodine second The diethyl ether solution of alkane grignard reagent is added dropwise in reaction mixture, and room temperature is restored to after being added dropwise, and heats 30-35 DEG C afterwards, Until reaction is completed, the lower ammonium chloride saturated solution that is added dropwise into reaction mixture of stirring terminates reaction, post-treated to obtain target Product.
7. tritiated Parylene dimer is in the application of photoelectric field described in claim 1, which is characterized in that uses vapor deposition work Skill by tritiated Parylene dimer elder generation vacuum gasifying, then cracks under high temperature, high molecular polymerization is then aggregated into deposit cavity Object is grown on sample surfaces, forms film.
8. tritiated Parylene dimer is in the application of photoelectric field according to claim 7, which is characterized in that tritiated Parylene Dimer forms a film in semiconducting nanotubes/line seamless surface densification, for making long continuation of the journey tritium base isotope battery.
9. tritiated Parylene dimer is in the application of photoelectric field according to claim 7, which is characterized in that tritiated Parylene After dimer film forming, on tritiated Parylene film obtained, last layer micron or nano level fluorescent powder film are covered, is used for Make long-acting spontaneous emission light source.
10. tritiated Parylene dimer is in the application of photoelectric field according to claim 7, which is characterized in that it is tritiated send it is auspicious Fire smog detector ionization source is used to prepare after woods dimer film forming.
CN201711296035.4A 2017-12-08 2017-12-08 Tritiated Parylene dimer and its application Pending CN108046970A (en)

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CN112837840A (en) * 2019-11-25 2021-05-25 深圳鼎邦能源科技有限公司 Method for manufacturing tritium isotope battery

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Publication number Priority date Publication date Assignee Title
CN112837840A (en) * 2019-11-25 2021-05-25 深圳鼎邦能源科技有限公司 Method for manufacturing tritium isotope battery
CN112837840B (en) * 2019-11-25 2024-04-19 深圳鼎邦能源科技有限公司 Tritium isotope battery manufacturing method

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Application publication date: 20180518