CN103059270A - 1,3,5-triazinyl nanopore organic aromatic heterocyclic polymer and preparation method thereof - Google Patents

1,3,5-triazinyl nanopore organic aromatic heterocyclic polymer and preparation method thereof Download PDF

Info

Publication number
CN103059270A
CN103059270A CN2012105395234A CN201210539523A CN103059270A CN 103059270 A CN103059270 A CN 103059270A CN 2012105395234 A CN2012105395234 A CN 2012105395234A CN 201210539523 A CN201210539523 A CN 201210539523A CN 103059270 A CN103059270 A CN 103059270A
Authority
CN
China
Prior art keywords
triazines
preparation
aromatic heterocyclic
polymer
organic aromatic
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN2012105395234A
Other languages
Chinese (zh)
Other versions
CN103059270B (en
Inventor
喻桂朋
潘春跃
熊绍辉
向璐
顾帅
王雪源
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Central South University
Original Assignee
Central South University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Central South University filed Critical Central South University
Priority to CN201210539523.4A priority Critical patent/CN103059270B/en
Publication of CN103059270A publication Critical patent/CN103059270A/en
Application granted granted Critical
Publication of CN103059270B publication Critical patent/CN103059270B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02C—CAPTURE, STORAGE, SEQUESTRATION OR DISPOSAL OF GREENHOUSE GASES [GHG]
    • Y02C20/00—Capture or disposal of greenhouse gases
    • Y02C20/40—Capture or disposal of greenhouse gases of CO2
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/151—Reduction of greenhouse gas [GHG] emissions, e.g. CO2

Landscapes

  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

The invention discloses a 1,3,5-triazinyl nanopore organic aromatic heterocyclic polymer and a preparation method thereof. The 1,3,5-triazinyl nanopore organic aromatic heterocyclic polymer is prepared from 2,4,6- trichlorine-1,3,5-triazine andaromatic compounds through Friedel-Crafts reaction in the presence of catalyst of lewis acid. The prepared polymer has controllable pore size and high specific surface area as well as CO2 capturing ability, good heat stability and chemical stability. The polymer has an important application value in gas storing, especially in CO2 capturing and has a wide application prospect in many fields such as field of catalytic supports and selective separation of ion.

Description

Organic aromatic heterocyclic polymer of a kind of 1,3,5-triazines base nano pore and preparation method thereof
Technical field
The present invention relates to a kind of high CO 2Organic nano pore polymer of capture ability and preparation method thereof, particularly a kind of 1,3,5-triazines base nano pore polymkeric substance and preparation method thereof.
Background technology
The nanoporous organic polymer is because of intrinsic excellent properties such as it has that special bigger serface, pore size distribution are narrow, high chemical stability and low skeletal densities, therefore the important application in the numerous areas such as its selective separation at support of the catalyst, gas, gas storage and become [(1) the Davis ME.Nature 2002 of study hotspot outside the Present Domestic, 417:813 – 821. (2) Budd P M.Science 2007,316:210-211. (3) Kuhn P, Kruger K, Thomas A et al.Chem.Commun.2008,44:5815-5817].Contain 1,3, the polymkeric substance of 5-triazine skeleton has high temperature resistant, high stability because of it, good flame retardant resistance and excellent optics and chemical property, therefore play a significant role at high performance engineering plastics, electron transport material and separation function material, especially have tempting application prospect at separation field.The 1,3,5-triazines skeleton polymer of the people such as present Ji Young Chang report is at low pressure area (P/P 0=10 -5~ 10 -2), under the 298K condition to CO 2Adsorptive capacity the highest also only be 4.0cm 3/ g, yet the CO of this polymkeric substance 2Adsorptive capacity lower [Ho Lim, Min Chul Cha, Ji Young Chang.Macromolecular Chemistry and Physics.2012,13,1385] is difficult to reach practical application.Up to now, the structure of the 1,3,5-triazines base nano pore organic polymer of this report there is not yet any public publication report.
Summary of the invention
First purpose of the present invention is to provide a kind of controlled, bigger serface in aperture that has, and has good thermostability and chemical stability and reaches CO 2The organic aromatic heterocyclic polymer of 1,3,5-triazines base nano pore with high capture ability.
Second purpose of the present invention is to provide that a kind of reaction conditions is gentle, with low cost, easy, the preparation method of the organic aromatic heterocyclic polymer of 1,3,5-triazines base nano pore that is easy to control.
The 3rd purpose of the present invention is to provide the application of the organic aromatic heterocyclic polymer of above-mentioned 1,3,5-triazines base nano pore, is applied to preparation to CO 2Sorbing material with selectivity absorption and over capacity reserve function.
The invention provides the organic aromatic heterocyclic polymer of a kind of 1,3,5-triazines base nano pore, have formula I structure:
Figure BDA00002581327800021
Formula I
Wherein, Ar is selected from the following structural formula any one:
Figure BDA00002581327800022
Figure BDA00002581327800031
Wherein, n is 0 ~ 4 integer;
Described polymkeric substance is Powdered or particulate state.
Described polymkeric substance mean pore size scope is 0.5～100nm.
The present invention also provides a kind of preparation method of aforesaid 1,3,5-triazines base nano pore polymkeric substance, and Fu-Ke reaction occurs under Louis acid catalysis for 2,4,6-, three chloro-1,3,5-triazines and aromatics, and get final product;
Wherein, described aromatics has any one in the following structural formula:
Figure BDA00002581327800032
Figure BDA00002581327800041
Wherein, n is 0 ~ 4 integer.
In the aforesaid method 2,4,6-three chloro-1,3,5-triazines and aromatics with etc. the ratio of mole functional group add and carry out polyreaction.
Described Fu-Ke reacts under protection of inert gas, at 25 ~ 120 ℃ of lower reaction 1 ~ 36h.
Described Lewis acid at room temperature drips or is added in batches in the reaction system of 2,4,6-, three chloro-1,3,5-triazines and aromatics, and dropping or the time that in batches adds are 10 ~ 60min.
The mol ratio of described Lewis acid: 2,4,6-three chloro-1,3,5-triazines is 5.0 ~ 30.0:1.
Described Lewis acid comprises: one or more in Anhydrous Ferric Chloride, Aluminum chloride anhydrous, tosic acid, methanesulfonic, trifluoromethanesulfonic acid or the boron trifluoride.
Described Fu-used solvent of Ke reaction comprises: one or more in chlorobenzene, dichlorobenzene, bromobenzene or the oil of mirbane.
The preparation method of 1,3,5-triazines base nano pore polymkeric substance of the present invention may further comprise the steps:
(1) add 2,4 of functional group's ratio mixing such as pressing, 6-three chloro-1,3,5-triazines and aromatics add substituted benzene as solvent under atmosphere of inert gases.
(2) under the protection of rare gas element, the Lewis acid that adds under the stirring at room is as the catalyst reaction system, and the mol ratio of 2,4,6-, three chloro-1,3,5-triazines and Lewis acid is 1:5.0 ~ 30.0.
(3) reaction system is carried out solution reaction under 25 ~ 120 ℃, and behind reaction 1～36h, system is down to room temperature, and washing copolymer material and vacuum-drying make mano-porous material after removing solvent.
The present invention also provides above-mentioned polymkeric substance preparing CO 2Have that selectivity absorbs and the sorbing material of over capacity reserve function on application.
Effect of the present invention and benefit are: contain simultaneously the novel nano hole material of 1,3,5-triazines ring and rigidity phenyl structure in the 1,3,5-triazines base nano pore polymer molecule skeleton of the present invention, aromatic ring is rich in the heteroatomss such as N, O, S, can be to gas CO particularly 2Have better absorption property and selective adsorption performance.And skeleton is the 1,3,5-triazines structure, and the polymkeric substance of this skeleton structure has high chemically stable and thermal stability, can better resist the environment of harshness behind absorption and the divided gas flow.The 1,3,5-triazines structure nano pore polymer that the present invention relates to can be used for the fields such as the selective separation, gas storage of support of the catalyst, gas, is with a wide range of applications.
Description of drawings
[Fig. 1] is the infrared spectra of example 1 nano-pore polymer material.
[Fig. 2] is the solid state nmr carbon spectrum of example 1 nano-pore polymer material.
[Fig. 3] is the infrared spectra of example 4 nano-pore polymer materials.
Embodiment
Following examples are to further specify of the present invention, rather than restriction the present invention.
Contain 1,3,5-triazines skeleton structure nano-pore polymer in the specific embodiment of the invention and carry out the FT-IR confirmation at Nicolet-S0640234 type infrared spectrometer, with the sample preparation of KBr compressing tablet.The polymer thermostable test: the decomposition temperature test of thermogravimetic analysis (TGA) (TGA) polymkeric substance is carried out at Mettler TGA/SDTA851e, under nitrogen atmosphere, 15 ℃/min of temperature rise rate, Range of measuring temp is 100 ~ 700 ℃, gets 5% thermal weight loss temperature as the polymer unwinds temperature.The performance test of polymer gas absorption property: polymer specific surface area and pore size distribution are measured the CO of ultra-high purity grade at Monosorb Autosorb type U.S. Kang Ta company static capacity method specific surface and pore analysis instrument 2In the absorption test experiments, Nonlocal D FT (NL-DFT) Stomatal model that pore size distribution and pore volume derive from the adsorption isothermal curve of gas calculates.
Embodiment 1
Add and to mix in molar ratio 0.2 part of 0.2 part of 2,4,6-, three chloro-1,3,5-triazines and triphenylamine, as mixed solvent, whole reaction system adopts argon shield with chlorinated benzene and oil of mirbane in reaction.Under agitation condition, under the room temperature methylsulfonic acid in the constant pressure funnel is added drop-wise in the reaction system, time for adding is 10 minutes, is warming up to 100 ℃, lasts reaction 10h, then is down to room temperature, the amount that wherein adds methylsulfonic acid is 15 parts.Above-mentioned mixed system direct filtration is obtained polymer crude product, and water, ethanol, tetrahydrofuran (THF), acetone, chloroform, washing with acetone obtain polymkeric substance successively again; At 100 ℃ of lower vacuum-drying 3d, can obtain the polymer powder product.
5% thermal weight loss decomposition temperature of polymkeric substance is 450 ℃, and specific surface area reaches 862m 2/ g, mean pore size is distributed in 2.2nm, at low pressure area (P/P 0=10 -5~ 10 -2), under the 298K condition to CO 2Adsorptive capacity reach 55cm 3/ g.
Through infrared analysis (such as Fig. 1): 3071cm -1C-H stretching vibration absorption band on the aromatic ring; 1596cm -1Aromatic ring C=N stretching vibration absorption band; 1484cm -1Aromatic ring C-N stretching vibration absorption band; 850cm -1The C-Cl stretching vibration of 2,4,6-, three chloro-1,3,5-triazines disappears; 810cm -1Aromatic ring CH stretching vibration absorption band; 725 ~ 680cm -1Bands of a spectrum disappear, and further proof obtains target product.
Through solid state nmr carbon spectrum analysis (such as Fig. 2): on the 171ppm phenyl ring with directly the link to each other chemical shift of carbon of triazine ring; Directly the link to each other chemical shift of the carbon on the phenyl ring of 147ppm and triazine ring; The chemical shift of unsubstituted carbon on the 138ppm phenyl ring; The chemical shift of carbon links to each other with N on the 127ppm phenyl ring.
Embodiment 2
Add and to mix in molar ratio 0.3 part of 0.3 part of 2,4,6-, three chloro-1,3,5-triazines and three-(5-linked phenyl-four-) amine, reaction with oil of mirbane as solvent, whole reaction system employing nitrogen protection.Under agitation condition, under the room temperature Aluminum chloride anhydrous is joined in the reaction system, aluminum chloride adds in three batches.System is warming up to 50 ℃, lasts reaction 6h, then be down to room temperature, the Aluminum chloride anhydrous amount that wherein adds is 8 parts.Above-mentioned mixed system direct filtration is obtained polymer crude product, and water, acetone, chloroform, washing with acetone obtain polymkeric substance successively again; At 130 ℃ of lower vacuum-drying 1d, can obtain the polymer powder product.
5% thermal weight loss decomposition temperature of polymkeric substance is 490 ℃, and specific surface area reaches 1010m 2/ g, mean pore size is distributed in 18nm, at low pressure area (P/P 0=10 -5~ 10 -2), under the 298K to CO 2Adsorptive capacity reach 49cm 3/ g.
Through infrared analysis, 3071cm -1C-H stretching vibration absorption band on the aromatic ring; 1600,1580,1450cm -1Skeleton stretching vibration for phenyl ring; 1596cm -1Aromatic ring C=N stretching vibration absorption band; 1484cm -1Aromatic ring C-N stretching vibration absorption band; 850cm -1The C of 2,4,6-, three chloro-1,3,5-triazines-Cl stretching vibration disappears; 810cm -1Aromatic ring C-H stretching vibration absorption band;
Embodiment 3
Add and to mix in molar ratio 0.3 part of 0.4 part of 2,4,6-, three chloro-1,3,5-triazines and Tetrabenzene methane, as solvent, whole reaction system adopts argon shield with bromobenzene in reaction.Under agitation condition, under the room temperature trifluoromethanesulfonic acid is added drop-wise in the reaction system, 0 ℃ of lower trifluoromethanesulfonic acid that drips, time for adding is 30 minutes, is warming up to 25 ℃, lasts reaction 24h, the amount that wherein adds methylsulfonic acid is 5 parts.Above-mentioned mixed system direct filtration is obtained polymer crude product, and water, tetrahydrofuran (THF), chloroform, washing with acetone obtain polymkeric substance successively again; At 100 ℃ of lower vacuum-drying 2d, can obtain the polymer powder product.
5% thermal weight loss decomposition temperature of polymkeric substance is 280 ℃, and specific surface area reaches 750m 2/ g, mean pore size is distributed in 3nm, at low pressure area (P/P 0=10 -5~ 10 -2), under the 298K to CO 2Adsorptive capacity reach 39cm 3/ g.
Infared spectrum 3071cm -1C-H stretching vibration absorption band on the aromatic ring; 2163 ~ 2100Si-H stretching vibration absorption band; 1596cm -1Aromatic ring C=N stretching vibration absorption band; 1484cm -1Aromatic ring C-N stretching vibration absorption band; 1253cm -1, 860cm -1C-Si stretching vibration absorption band; 850cm -1The C-Cl stretching vibration of 2,4,6-, three chloro-1,3,5-triazines disappears; 810cm -1Aromatic ring C-H stretching vibration absorption band.
Embodiment 4
Add and to mix in molar ratio 0.3 part of 0.2 part of 2,4,6-, three chloro-1,3,5-triazines and phenyl ether, reaction is take phenyl ether as solvent, and whole reaction system adopts nitrogen protection.Under agitation condition, under the room temperature Anhydrous Ferric Chloride is joined in the reaction system, iron(ic) chloride adds in three batches.System is warming up to 80 ℃, lasts reaction 9h, then be down to room temperature, the Anhydrous Ferric Chloride that wherein adds is 8 parts.Above-mentioned mixed system direct filtration is obtained polymer crude product, and water, acetone, chloroform washing obtain polymkeric substance successively again; At 130 ℃ of lower vacuum-drying 1d, can obtain the granular product of polymer particles.
5% thermal weight loss decomposition temperature of polymkeric substance is 300 ℃, and specific surface area reaches 532m 2/ g, mean pore size is distributed in 4.6nm, at low pressure area (P/P 0=10 -5~ 10 -2), under the 298K to CO 2Adsorptive capacity reach 36cm 3/ g.
Through infrared analysis (such as Fig. 2), 3071cm -1C-H stretching vibration absorption band on the aromatic ring; 1710cm -1, 1210cm -1Carbon-oxygen bond C-O stretching vibration absorption band; 1596cm -1Aromatic ring C=N stretching vibration absorption band; 1484cm -1Aromatic ring C-N stretching vibration absorption band; 850cm -1The C of 2,4,6-, three chloro-1,3,5-triazines-Cl stretching vibration disappears; 810cm -1Aromatic ring C-H stretching vibration absorption band.

Claims (10)

1. the organic aromatic heterocyclic polymer of 1,3,5-triazines base nano pore is characterized in that, has formula I structure:
Figure FDA00002581327700011
Formula I
Wherein, Ar is selected from the following structural formula any one:
Wherein, n is 0 ~ 4 integer;
2. polymkeric substance according to claim 1 is characterized in that, described polymkeric substance is Powdered or particulate state.
3. polymkeric substance according to claim 1 is characterized in that, described polymkeric substance mean pore size scope is 0.5～100nm.
4. the preparation method of the organic aromatic heterocyclic polymer of 1,3,5-triazines base nano pore as claimed in claim 1 is characterized in that, Fu-Ke reaction occurs under Louis acid catalysis for 2,4,6-, three chloro-1,3,5-triazines and aromatics, and get final product; Wherein, described aromatics has any one in the following structural formula:
Figure FDA00002581327700022
Figure FDA00002581327700031
Wherein, n is 0 ~ 4 integer.
5. preparation method as claimed in claim 4 is characterized in that, 2,4,6-, three chloro-1,3,5-triazines and aromatics with etc. the ratio of mole functional group add and to carry out polyreaction.
6. preparation method as claimed in claim 4 is characterized in that, described Fu-Ke reacts under protection of inert gas, at 25 ~ 120 ℃ of lower reaction 1 ~ 36h.
7. preparation method as claimed in claim 4 is characterized in that, described Lewis acid at room temperature drips or is added in batches in the reaction system of 2,4,6-, three chloro-1,3,5-triazines and aromatics, and dropping or the time that in batches adds are 10 ~ 60min.
8. such as claim 4 or 7 each described preparation methods, it is characterized in that the mol ratio of described Lewis acid: 2,4,6-three chloro-1,3,5-triazines is 5.0 ~ 30.0:1.
9. preparation method as claimed in claim 8 is characterized in that, described Lewis acid comprises: one or more in Anhydrous Ferric Chloride, Aluminum chloride anhydrous, tosic acid, methanesulfonic, trifluoromethanesulfonic acid or the boron trifluoride.
10. the application such as the organic aromatic heterocyclic polymer of each described 1,3,5-triazines base nano pore of claim 1 ~ 3 is characterized in that, the organic aromatic heterocyclic polymer of described 1,3,5-triazines base nano pore is applied to preparation to CO 2Sorbing material with selectivity absorption and over capacity reserve function.
CN201210539523.4A 2012-12-13 2012-12-13 Organic aromatic heterocyclic polymer of a kind of 1,3,5-triazines base nano pore and preparation method thereof Active CN103059270B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201210539523.4A CN103059270B (en) 2012-12-13 2012-12-13 Organic aromatic heterocyclic polymer of a kind of 1,3,5-triazines base nano pore and preparation method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201210539523.4A CN103059270B (en) 2012-12-13 2012-12-13 Organic aromatic heterocyclic polymer of a kind of 1,3,5-triazines base nano pore and preparation method thereof

Publications (2)

Publication Number Publication Date
CN103059270A true CN103059270A (en) 2013-04-24
CN103059270B CN103059270B (en) 2015-10-28

Family

ID=48102189

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201210539523.4A Active CN103059270B (en) 2012-12-13 2012-12-13 Organic aromatic heterocyclic polymer of a kind of 1,3,5-triazines base nano pore and preparation method thereof

Country Status (1)

Country Link
CN (1) CN103059270B (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103289088A (en) * 2013-05-13 2013-09-11 中南大学 Poly-aryl sym-triazine and poly-aryl sym-triazine porous material as well as preparation methods thereof
TWI554836B (en) * 2014-07-15 2016-10-21 三星Ｓｄｉ股份有限公司 Hardmask composition and method of forming patterns using the hardmask composition
CN106084217A (en) * 2016-05-27 2016-11-09 山西师范大学 A kind of triazine radical porous polymer material, Ag/ triazine radical porous polymer catalyst and be the application of acetylenic acid by carbon dioxide conversion
CN107930606A (en) * 2017-11-17 2018-04-20 中南大学 One kind is containing triazine ring and azo bond functional group porous polymer sorbing material, porous polymer catalysis material and preparation and application
CN109180912A (en) * 2018-09-21 2019-01-11 台州学院 Conjugation microporous polymer and preparation method thereof based on Cyanuric Chloride and dibenzothiophenes
CN109265657A (en) * 2018-09-21 2019-01-25 台州学院 Conjugation microporous polymer and preparation method thereof based on s-indacene -1,3,5,7 (2H, 6H)-tetrone
CN109734906A (en) * 2019-01-07 2019-05-10 中南大学 A kind of triazine radical porous polymer and preparation method and application
CN109762085A (en) * 2018-12-25 2019-05-17 中国科学院合肥物质科学研究院 A kind of poly- aryne nanometer sheet of Novel compressive and preparation method thereof
CN109897169A (en) * 2019-03-20 2019-06-18 中国科学院上海高等研究院 A kind of triazine skeleton polymer and preparation method thereof containing alkynyl

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102585186A (en) * 2012-02-06 2012-07-18 中南大学 Aryl-1,3,5-triazine polyarylester and preparation method thereof

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102585186A (en) * 2012-02-06 2012-07-18 中南大学 Aryl-1,3,5-triazine polyarylester and preparation method thereof

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
喻桂朋: ""含芳基均三嗪环耐高温聚合物的研究"", 《中国博士学位论文全文数据库工程科技I辑》 *
熊绍辉等: ""基于1,3,5-三嗪骨架的纳米孔有机聚合物的合成及性能研究"", 《2012年两岸三地高分子液晶态与超分子有序结构学术研讨会（暨第十二届全国高分子液晶态与超分子有序结构学术论文报告）会议论文集》 *

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103289088A (en) * 2013-05-13 2013-09-11 中南大学 Poly-aryl sym-triazine and poly-aryl sym-triazine porous material as well as preparation methods thereof
CN103289088B (en) * 2013-05-13 2016-01-20 中南大学 A kind of poly-aryl s-triazine and poly-aryl s-triazine Porous materials and their preparation method
TWI554836B (en) * 2014-07-15 2016-10-21 三星Ｓｄｉ股份有限公司 Hardmask composition and method of forming patterns using the hardmask composition
US9568825B2 (en) 2014-07-15 2017-02-14 Samsung Sdi Co., Ltd. Hardmask composition and method of forming patterns using the hardmask composition
CN106084217A (en) * 2016-05-27 2016-11-09 山西师范大学 A kind of triazine radical porous polymer material, Ag/ triazine radical porous polymer catalyst and be the application of acetylenic acid by carbon dioxide conversion
CN106084217B (en) * 2016-05-27 2018-04-06 山西师范大学 A kind of triazine radical porous polymer material, Ag/ triazine radical porous polymer catalyst and its application by carbon dioxide conversion for acetylenic acid
CN107930606A (en) * 2017-11-17 2018-04-20 中南大学 One kind is containing triazine ring and azo bond functional group porous polymer sorbing material, porous polymer catalysis material and preparation and application
CN109180912A (en) * 2018-09-21 2019-01-11 台州学院 Conjugation microporous polymer and preparation method thereof based on Cyanuric Chloride and dibenzothiophenes
CN109265657A (en) * 2018-09-21 2019-01-25 台州学院 Conjugation microporous polymer and preparation method thereof based on s-indacene -1,3,5,7 (2H, 6H)-tetrone
CN109265657B (en) * 2018-09-21 2021-02-05 台州学院 Conjugated microporous polymer based on symmetric indacene-1, 3,5,7(2H,6H) -tetraone and preparation method thereof
CN109762085A (en) * 2018-12-25 2019-05-17 中国科学院合肥物质科学研究院 A kind of poly- aryne nanometer sheet of Novel compressive and preparation method thereof
CN109762085B (en) * 2018-12-25 2021-06-01 中国科学院合肥物质科学研究院 Compression-resistant polyaryne nanosheet and preparation method thereof
CN109734906A (en) * 2019-01-07 2019-05-10 中南大学 A kind of triazine radical porous polymer and preparation method and application
CN109734906B (en) * 2019-01-07 2022-01-25 长沙瑞庭科技有限公司 Triazine-based porous polymer and preparation method and application thereof
CN109897169A (en) * 2019-03-20 2019-06-18 中国科学院上海高等研究院 A kind of triazine skeleton polymer and preparation method thereof containing alkynyl

Also Published As

Publication number Publication date
CN103059270B (en) 2015-10-28

Similar Documents

Publication Publication Date Title
CN103059270B (en) Organic aromatic heterocyclic polymer of a kind of 1,3,5-triazines base nano pore and preparation method thereof
Cui et al. Design and synthesis of a multifunctional porous N-rich polymer containing s-triazine and Tröger's base for CO 2 adsorption, catalysis and sensing
Dang et al. An azo-linked porous triptycene network as an absorbent for CO 2 and iodine uptake
Saleh et al. Highly stable CO2/N2 and CO2/CH4 selectivity in hyper-cross-linked heterocyclic porous polymers
Kuhn et al. Toward tailorable porous organic polymer networks: a high-temperature dynamic polymerization scheme based on aromatic nitriles
Hug et al. A functional triazine framework based on N-heterocyclic building blocks
Li et al. One-pot synthesis of viologen-based hypercrosslinked polymers for efficient volatile iodine capture
Tilford et al. Tailoring microporosity in covalent organic frameworks
Yuan et al. Promoting and tuning porosity of flexible ether-linked phthalazinone-based covalent triazine frameworks utilizing substitution effect for effective CO2 capture
Shen et al. Synthesis of 1, 3, 5, 7-tetrakis (4-cyanatophenyl) adamantane and its microporous polycyanurate network for adsorption of organic vapors, hydrogen and carbon dioxide
Li et al. Pyrrolidinone-based hypercrosslinked polymers for reversible capture of radioactive iodine
Jia et al. Extremely hydrophobic POPs to access highly porous storage media and capturing agent for organic vapors
Rao et al. Extended phenylene based microporous organic polymers with selective carbon dioxide adsorption
Hassan et al. Hydroxy functionalized triptycene based covalent organic polymers for ultra-high radioactive iodine uptake
Mondal et al. A facile approach for the synthesis of hydroxyl-rich microporous organic networks for efficient CO 2 capture and H 2 storage
Xu et al. Porous cationic covalent triazine‐based frameworks as platforms for efficient CO2 and iodine capture
Shen et al. Synthetic modulation of micro-and mesopores in polycyanurate networks for adsorptions of gases and organic hydrocarbons
Liu et al. One-pot synthesis of nitrogen-rich aminal-and triazine-based hierarchical porous organic polymers with highly efficient iodine adsorption
Wang et al. Synthetic Control and Multifunctional Properties of Fluorescent Covalent Triazine‐Based Frameworks
Weng et al. Tuning the adsorption and fluorescence properties of aminal‐linked porous organic polymers through N‐heterocyclic group decoration
Li et al. A simple and cost-effective synthesis of ionic porous organic polymers with excellent porosity for high iodine capture
Yu et al. Bisindole [3] arenes—indolyl macrocyclic arenes having significant iodine capture capacity
Feng et al. Polytriazine porous networks for effective iodine capture
Geng et al. The spirobifluorene-based fluorescent conjugated microporous polymers for reversible adsorbing iodine, fluorescent sensing iodine and nitroaromatic compounds
Yuan et al. Phthalazinone-based copolymers with intrinsic microporosity (PHPIMs) and their separation performance

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant