JP7491601B2 - カルボキシル基含有ジピリドフェナジン有機化合物、合成方法及び用途 - Google Patents
カルボキシル基含有ジピリドフェナジン有機化合物、合成方法及び用途 Download PDFInfo
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- dipyridophenazine
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 title claims description 34
- -1 dipyridophenazine organic compounds Chemical class 0.000 title claims description 30
- 238000001308 synthesis method Methods 0.000 title claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- KCALAFIVPCAXJI-UHFFFAOYSA-N 1,10-phenanthroline-5,6-dione Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CN=C3C2=N1 KCALAFIVPCAXJI-UHFFFAOYSA-N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 10
- 238000005406 washing Methods 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- HEMGYNNCNNODNX-UHFFFAOYSA-N 3,4-diaminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1N HEMGYNNCNNODNX-UHFFFAOYSA-N 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- 230000002194 synthesizing effect Effects 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 4
- 229910017604 nitric acid Inorganic materials 0.000 claims description 4
- KKTUQAYCCLMNOA-UHFFFAOYSA-N 2,3-diaminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1N KKTUQAYCCLMNOA-UHFFFAOYSA-N 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 239000012265 solid product Substances 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims 1
- 239000007772 electrode material Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 7
- 229910001415 sodium ion Inorganic materials 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000002033 PVDF binder Substances 0.000 description 5
- 239000006230 acetylene black Substances 0.000 description 5
- BVQAWSJMUYMNQN-UHFFFAOYSA-N dipyridophenazine Chemical compound C1=CC=C2C3=NC4=CC=CC=C4N=C3C3=CC=CN=C3C2=N1 BVQAWSJMUYMNQN-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 238000002484 cyclic voltammetry Methods 0.000 description 4
- 238000009830 intercalation Methods 0.000 description 4
- 230000002687 intercalation Effects 0.000 description 4
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000000026 X-ray photoelectron spectrum Methods 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000002482 conductive additive Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000011056 performance test Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- DTQVDTLACAAQTR-DYCDLGHISA-N trifluoroacetic acid-d1 Chemical compound [2H]OC(=O)C(F)(F)F DTQVDTLACAAQTR-DYCDLGHISA-N 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910020293 Na2Ti3O7 Inorganic materials 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000004146 energy storage Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910052976 metal sulfide Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000001791 phenazinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- NJFXLNYKQULWQF-UHFFFAOYSA-N quinoxalino[2,3-f][1,7]phenanthroline Chemical compound C1=CC=C2C3=NC4=CC=CC=C4N=C3C3=NC=CC=C3C2=N1 NJFXLNYKQULWQF-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/36—Accumulators not provided for in groups H01M10/05-H01M10/34
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M4/00—Electrodes
- H01M4/02—Electrodes composed of, or comprising, active material
- H01M4/04—Processes of manufacture in general
- H01M4/0402—Methods of deposition of the material
- H01M4/0404—Methods of deposition of the material by coating on electrode collectors
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M4/00—Electrodes
- H01M4/02—Electrodes composed of, or comprising, active material
- H01M4/36—Selection of substances as active materials, active masses, active liquids
- H01M4/60—Selection of substances as active materials, active masses, active liquids of organic compounds
-
- 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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Battery Electrode And Active Subsutance (AREA)
Description
本発明のカルボキシル基含有ジピリドフェナジン有機化合物の合成方法は、以下のステップを含む。
カルボキシル基含有o-フェニレンジアミン化合物が3,4-ジアミノ安息香酸である場合、反応式が式(IV)である。
好ましくは、前記カルボキシル基含有o-フェニレンジアミン化合物と1,10-フェナントロリン-5,6-ジオンとのモル比は、0.5~2:1である。
実施例3:実施例1との違いは、3,4-ジアミノ安息香酸及び1,10-フェナントロリン-5,6-ジオンのモル比が1:1.5であり、反応時間が24 hである。
実施例4:実施例1との違いは、3,4-ジアミノ安息香酸及び1,10-フェナントロリン-5,6-ジオンのモル比が2:1であり、反応時間が36 hである。
実施例5:実施例1との違いは、3,4-ジアミノ安息香酸及び1,10-フェナントロリン-5,6-ジオンのモル比が1:2であり、反応時間が48 hである。
実施例6:本発明のジピリドフェナジン-1-カルボン酸の合成方法は以下のとおりである。
比較例2:実施例1との違いは、前記カルボキシル基含有o-フェニレンジアミン化合物が4-ジアミノベンゾニトリルに変更され、且つ1,10-フェナントロリン-5,6-ジオンとのモル比が1:1であり、2-シアノメチル-ジピリジノフェナジンを合成したことである。
Claims (5)
- カルボキシル基含有ジピリドフェナジン有機化合物の合成方法であって、
不活性気体の雰囲気下で、反応器に、カルボキシル基含有o-フェニレンジアミン化合物と、1,10-フェナントロリン-5,6-ジオンと、有機溶媒とを添加し、還流状態及び加熱条件下で、反応混合物を攪拌しながら反応させ、十分に反応した後、加熱を停止し、室温に冷却した後、取り出して、遠心分離し、洗浄し、精製して、固体生成物であるカルボキシル基含有ジピリドフェナジン有機化合物を得るステップを含み、前記精製のステップにおいて、洗浄後の生成物を、120~140℃の硝酸溶液に攪拌した後、溶媒で洗浄して、乾燥し、
前記カルボキシル基含有ジピリドフェナジン有機化合物は、化学式(I)のジピリドフェナジン-2-カルボン酸、又は化学式(II)のジピリドフェナジン-1-カルボン酸である、ことを特徴とするカルボキシル基含有ジピリドフェナジン有機化合物の合成方法。
- 前記カルボキシル基含有o-フェニレンジアミン化合物は、3,4-ジアミノ安息香酸又は2,3-ジアミノ安息香酸である、ことを特徴とする請求項1に記載の合成方法。
- 前記カルボキシル基含有o-フェニレンジアミン化合物と1,10-フェナントロリン-5,6-ジオンとのモル比が0.5~2:1である、ことを特徴とする請求項1に記載の合成方法。
- 前記加熱温度は、110~120℃である、ことを特徴とする請求項1に記載の合成方法。
- 前記洗浄のステップにおいて使用される洗浄液は、30~40℃のエタノール、アセトン、エタノール、及び水の順に使用される、ことを特徴とする請求項1に記載の合成方法。
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CN202210641912.1 | 2022-06-08 | ||
CN202210641912.1A CN115260196B (zh) | 2022-06-08 | 2022-06-08 | 含羧基的二吡啶并吩嗪有机化合物及其制备方法和应用 |
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JP7491601B2 true JP7491601B2 (ja) | 2024-05-28 |
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2009078823A1 (en) | 2007-12-17 | 2009-06-25 | Turkiye Sise Ve Cam Fabrikalari A.S. | Novel ruthenium complex photo-sensitizers for dye sensitized solar cells |
CN103896986A (zh) | 2012-12-28 | 2014-07-02 | 江南大学 | 一种含苯并噻唑的钌配合物的制备方法及其抗癌活性 |
JP2016115584A (ja) | 2014-12-16 | 2016-06-23 | 東洋インキScホールディングス株式会社 | 蓄電材料、蓄電デバイス用電極、及び蓄電デバイス |
JP2016122640A (ja) | 2014-12-25 | 2016-07-07 | 東洋インキScホールディングス株式会社 | 蓄電材料、蓄電デバイス用電極、及び蓄電デバイス |
JP2017127863A (ja) | 2016-01-20 | 2017-07-27 | 国立大学法人 筑波大学 | 酸素還元触媒とその活性化方法、および燃料電池触媒 |
-
2022
- 2022-06-08 CN CN202210641912.1A patent/CN115260196B/zh active Active
- 2022-07-14 JP JP2022113109A patent/JP7491601B2/ja active Active
Patent Citations (5)
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WO2009078823A1 (en) | 2007-12-17 | 2009-06-25 | Turkiye Sise Ve Cam Fabrikalari A.S. | Novel ruthenium complex photo-sensitizers for dye sensitized solar cells |
CN103896986A (zh) | 2012-12-28 | 2014-07-02 | 江南大学 | 一种含苯并噻唑的钌配合物的制备方法及其抗癌活性 |
JP2016115584A (ja) | 2014-12-16 | 2016-06-23 | 東洋インキScホールディングス株式会社 | 蓄電材料、蓄電デバイス用電極、及び蓄電デバイス |
JP2016122640A (ja) | 2014-12-25 | 2016-07-07 | 東洋インキScホールディングス株式会社 | 蓄電材料、蓄電デバイス用電極、及び蓄電デバイス |
JP2017127863A (ja) | 2016-01-20 | 2017-07-27 | 国立大学法人 筑波大学 | 酸素還元触媒とその活性化方法、および燃料電池触媒 |
Non-Patent Citations (1)
Title |
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MIAO, L. et al.,Molecular Design Strategy for High-Redox-Potential and Poorly Soluble n-Type Phenazine Derivatives as Cathode Materials for Lithium Batteries,ChemSusCheme,2020年01月22日,Vol. 13, No. 9,pp. 2337-2344 |
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JP2023180194A (ja) | 2023-12-20 |
CN115260196B (zh) | 2023-07-21 |
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