JP6358680B2 - 共有結合性有機構造体を含む導電性ハイブリッド材料 - Google Patents
共有結合性有機構造体を含む導電性ハイブリッド材料 Download PDFInfo
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- JP6358680B2 JP6358680B2 JP2016546317A JP2016546317A JP6358680B2 JP 6358680 B2 JP6358680 B2 JP 6358680B2 JP 2016546317 A JP2016546317 A JP 2016546317A JP 2016546317 A JP2016546317 A JP 2016546317A JP 6358680 B2 JP6358680 B2 JP 6358680B2
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- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
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- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 2
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- 238000001514 detection method Methods 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
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- 238000005755 formation reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
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- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
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- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
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- 239000004816 latex Substances 0.000 description 1
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
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- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- CFQCIHVMOFOCGH-UHFFFAOYSA-N platinum ruthenium Chemical compound [Ru].[Pt] CFQCIHVMOFOCGH-UHFFFAOYSA-N 0.000 description 1
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- 239000005518 polymer electrolyte Substances 0.000 description 1
- -1 polytetrafluoroethylene Polymers 0.000 description 1
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- 230000000717 retained effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
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- 238000001878 scanning electron micrograph Methods 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
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- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
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- 238000003756 stirring Methods 0.000 description 1
- PTISTKLWEJDJID-UHFFFAOYSA-N sulfanylidenemolybdenum Chemical class [Mo]=S PTISTKLWEJDJID-UHFFFAOYSA-N 0.000 description 1
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- 238000012546 transfer Methods 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
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Classifications
-
- 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
- H01M4/86—Inert electrodes with catalytic activity, e.g. for fuel cells
- H01M4/96—Carbon-based electrodes
-
- 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
- H01M4/86—Inert electrodes with catalytic activity, e.g. for fuel cells
- H01M4/8663—Selection of inactive substances as ingredients for catalytic active masses, e.g. binders, fillers
- H01M4/8673—Electrically conductive fillers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
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Description
H2→2H++2e− (水素酸化反応)
2H2O+2e−→H2+2OH− (水素発生反応)
本実施形態において、「共有結合性有機構造体」は、水素、炭素、窒素、酸素、ホウ素、硫黄などの原子が共有結合のみによって連結して形成された分子である。より具体的には、共有結合性有機構造体は、同一又は異なる複数の芳香族環基が共有結合によって環状の繰返しユニットを形成した構造を有する高分子を意味する。また、共有結合性有機構造体は、当該繰返しユニットが他の1つ以上の繰返しユニットと共有結合により連続して連結された、二次元又は三次元のネットワーク構造を有する高分子も意味する。このような共有結合性有機構造体は、メゾやマイクロサイズの細孔を有する多孔質構造を有するとともに、低密度かつ優れた熱安定性を有する。
本実施形態の導電性ハイブリッド材料において、共有結合性有機構造体とともに用いられる導体材料は、当該技術分野において二次電池の電極用導電性材料として一般に用いられ得るものである。導体材料は、共有結合性有機構造体を担持することによって、当該共有結合性有機構造体に電子伝導性を付与できるものであれば特に限定されない。ただ、導体材料は炭素材料であることが好ましい。
上述のように、本実施形態の導電性ハイブリッド材料は、共有結合性有機構造体を炭素材料等の導体材料上に担持させることによって、電子伝導性を付与でき、さらに金属を原子レベルで高分散させることができる。そのため、導電性ハイブリッド材料は、当該技術分野において公知の二次電池や燃料電池における電極触媒、あるいは、その他電子移動を伴う系における触媒や電極として用いることができる。
1.導電性ハイブリッド材料の合成
化学式10に示すスキームに従って、ケッチェンブラック(KB)上に、共有結合性トリアジン構造体(CTF−1)の白金錯体を担持したハイブリッド材料を合成した。
まず、実施例1と同様に、1.363gのZnCl2、0.129gの2,6−ジシアノピリジン、及び0.129gのケッチェンブラックをグローブボックス中で混合した。
2,6−ジシアノピリジンに替えて、化学式12に示すジシアノベンゼン誘導体を用いた以外は実施例1−1と同様にして、以下の構造を有するCTF−2、CTF−4及びCTF−5をそれぞれケッチェンブラックで保持したハイブリッド材料を合成した。なお、化学式12の上段が用いたモノマーの構造を示し、下段がCTFの構造を示す。
トリアジン環を硫黄原子により連結させた、化学式13に示すCTF−7を合成した。具体的には、まず、0.235gのトリチオシアヌル酸(和光純薬工業株式会社製)を30mlの1,4−ジオキサン(和光純薬工業株式会社製)中に溶解し、0.625mlのN,N−ジイソプロピルエチルアミン(東京化成工業株式会社製)を加えた。この溶液を15℃に保持しながら、7.5mlの1,4−ジオキサン中に0.125gの2,4,6−トリクロロ−1,3,5−トリアジン(東京化成工業株式会社製)を溶解した溶液を加えた。さらにこの溶液に、0.360gのケッチェンブラック(EC600JD)を加えて、15℃で1時間、25℃で2時間、85℃で4時間還流した。得られた固体をろ過し、1,4−ジオキサン、エタノールで洗浄した後、減圧乾燥した。
市販の、20質量%の白金を炭素粉末に担持した20質量%Pt/C、及びPt−Vulcan XC−72を用いた。
1.走査型電子顕微鏡観察等
実施例1−1で調製した、白金/CTF:ケッチェンブラックの質量比が100:5、100:20、100:100となるようにしたハイブリッド材料の走査型電子顕微鏡画像を図1に示す。また、共有結合性トリアジン構造体(pure CTF)及びケッチェンブラック(pure KB)の走査型電子顕微鏡画像も図1に示す。当該SEM画像から、共有結合性トリアジン構造体とケッチェンブラックが良好に混合した導電性ハイブリッド材料が得られたことが分かる。
実施例1−1〜1−4で合成したハイブリッド材料を含む回転ディスク電極(RDE)を作製し、その電気化学的特性の評価を行った。
本実施例では、X線光電子分光によって定量される共有結合性有機構造体と導体材料の元素組成比が2.39である導電性ハイブリッド材料を調製した。
本実施例のハイブリッド材料をXPS測定することにより、ハイブリッド材料を構成する窒素と炭素の組成比(N/C)を測定した。XPS測定は、XPS装置(AXIS Ultra HAS、Kratos Analytical社製)を用いた。また、励起X線として、monochromatic Al X線(10kV)を用いた。そして、各元素についてのナロースキャン測定を行い、各ピークの面積から組成比を求めた。
本実施例では、X線光電子分光によって定量される共有結合性有機構造体と導体材料の元素組成比が0.74である、導電性ハイブリッド材料を調製した。具体的には、ケッチェンブラックの添加量を0.0258gとした以外は、実施例2−1と同様にしてハイブリッド材料を合成した。
本実施例では、X線光電子分光によって定量される共有結合性有機構造体と導体材料の元素組成比が0.30である、導電性ハイブリッド材料を調製した。具体的には、ケッチェンブラックの添加量を0.129gとした以外は、実施例2−1と同様にしてハイブリッド材料を合成した。
本実施例では、X線光電子分光によって定量される共有結合性有機構造体と導体材料の元素組成比が0.16である、導電性ハイブリッド材料を調製した。具体的には、ケッチェンブラックの添加量を0.129gとし、2,6−ジシアノピリジンを0.0645gとした以外は、実施例2−1と同様にしてハイブリッド材料を合成した。
本実施例では、X線光電子分光によって定量される共有結合性有機構造体と導体材料の元素組成比が0.10である、導電性ハイブリッド材料を調製した。具体的には、ケッチェンブラックの添加量を0.129gとし、2,6−ジシアノピリジンを0.0323gとした以外は、実施例2−1と同様にしてハイブリッド材料を合成した。
本実施例では、X線光電子分光によって定量される共有結合性有機構造体と導体材料の元素組成比が0.030である、導電性ハイブリッド材料を調製した。具体的には、ケッチェンブラックの添加量を0.129gとし、2,6−ジシアノピリジンを0.0161gとした以外は、実施例2−1と同様にしてハイブリッド材料を合成した。
本実施例では、X線光電子分光によって定量される共有結合性有機構造体と導体材料の元素組成比が0.0090である、導電性ハイブリッド材料を調製した。具体的には、ケッチェンブラックの添加量を0.129gとし、2,6−ジシアノピリジンを0.0040gとした以外は、実施例2−1と同様にしてハイブリッド材料を合成した。
20wt%の白金を炭素粉末に担持した20wt%Pt/C(HiSPEC(登録商標)−3000、Johnson Matthey Fuel Cells社製)を用いた。
まず、2.5mgのハイブリッド材料の粉末を750μLのエタノール及び50μLのNafion溶液中に加え、超音波ホモジナイザーにより分散した。Nafion溶液は、低級脂肪族アルコール混合物と水の5質量%溶液で、シグマアルドリッチ社製のものを使用した。そして、当該溶液2.1μLをグラッシーカーボン電極(0.1256cm2)に滴下し、作用電極を作製した。この際、ハイブリッド材料(触媒)のグラッシーカーボン電極上への担持量は、52.2μg/cm2であった。
Claims (17)
- メゾサイズ又はマイクロサイズの細孔を有し、かつ、同一又は異なる複数の芳香族環基が共有結合によって環状の繰返しユニットを形成した構造を有する高分子である共有結合性有機構造体と、ナノ粒子の形態の炭素材料である導体材料と、を含み、
前記共有結合性有機構造体が前記導体材料の表面に膜状に担持されている、導電性ハイブリッド材料。 - 前記共有結合性有機構造体は、分子内に複数のトリアジン環を有する繰返しユニットよりなる高分子である、請求項1に記載の導電性ハイブリッド材料。
- 前記共有結合性有機構造体は、アリーレン、ヘテロアリーレン又はヘテロ原子を介して、複数のトリアジン環が共有結合で連結した構造を有する、請求項1に記載の導電性ハイブリッド材料。
- 前記共有結合性有機構造体は、フェニレン又はピリジレンを介して、複数のトリアジン環が共有結合で連結した構造を有する、請求項1に記載の導電性ハイブリッド材料。
- 前記共有結合性有機構造体は、ジシアノベンゼン又はジシアノピリジンの縮合反応により得られる化合物である、請求項4に記載の導電性ハイブリッド材料。
- 前記共有結合性有機構造体は、前記導体材料上においてモノマーを重合させるin−situ反応により得られる化合物である、請求項1乃至5のいずれか一項に記載の導電性ハイブリッド材料。
- 前記共有結合性有機構造体は、以下の群より選択される少なくとも一つの化合物である、請求項1に記載の導電性ハイブリッド材料。
- 前記炭素材料は、グラファイト、カーボンブラック、ケッチェンブラック、アセチレンブラック、カーボンナノチューブ、グラフェン及びカーボンファイバーからなる群より選ばれる少なくとも一つである、請求項1乃至7のいずれか一項に記載の導電性ハイブリッド材料。
- 前記共有結合性有機構造体に金属が配位する、請求項1乃至8のいずれか一項に記載の導電性ハイブリッド材料。
- 前記金属は、白金族元素又は銅である、請求項9に記載の導電性ハイブリッド材料。
- 請求項1乃至10のいずれか一項に記載の導電性ハイブリッド材料を含む電極。
- 請求項1乃至10のいずれか一項に記載の導電性ハイブリッド材料を含む触媒。
- 請求項12に記載の触媒を含み、前記共有結合性有機構造体に白金族元素が配位する、水素発生触媒。
- 前記導体材料に対する前記共有結合性有機構造体の元素組成比が、0.005〜1である、請求項13に記載の水素発生触媒。
- 請求項12に記載の触媒を含み、前記共有結合性有機構造体に白金族元素が配位する、水素酸化触媒。
- 前記導体材料に対する前記共有結合性有機構造体の元素組成比が、0.005〜1である、請求項15に記載の水素酸化触媒。
- 請求項12に記載の触媒を含み、前記導体材料が炭素材料である酸素還元触媒。
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KR20230030153A (ko) * | 2021-08-25 | 2023-03-06 | 주식회사 엘지에너지솔루션 | 다공성 고체 화합물, 이의 제조방법, 상기 다공성 고체 화합물을 포함하는 리튬 이차전지용 양극 및 리튬 이차전지 |
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CN115181265B (zh) * | 2022-07-29 | 2023-10-31 | 华侨大学 | 一种亚甲基修饰共价三嗪骨架材料及其制备方法和应用 |
US20240055638A1 (en) * | 2022-08-11 | 2024-02-15 | Wisconsin Alumni Research Foundation | Glassy organic framework ion-conductive membranes |
CN117142552B (zh) * | 2023-09-19 | 2024-05-31 | 郑州大学 | 一种自组装双功能光热蒸发柱及其制备方法 |
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