JP2010209044A - 二核金属錯体及びそれを含む光触媒 - Google Patents
二核金属錯体及びそれを含む光触媒 Download PDFInfo
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- 150000004696 coordination complex Chemical class 0.000 title claims abstract description 56
- 239000011941 photocatalyst Substances 0.000 title claims abstract description 29
- 239000003446 ligand Substances 0.000 claims abstract description 33
- -1 hexafluorophosphate Chemical compound 0.000 claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 21
- 150000003624 transition metals Chemical class 0.000 claims abstract description 21
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 229910052703 rhodium Inorganic materials 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- 150000002500 ions Chemical class 0.000 claims description 4
- 101150003085 Pdcl gene Proteins 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052741 iridium Inorganic materials 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 abstract description 46
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 17
- 239000003054 catalyst Substances 0.000 abstract description 12
- OKQKDCXVLPGWPO-UHFFFAOYSA-N sulfanylidenephosphane Chemical compound S=P OKQKDCXVLPGWPO-UHFFFAOYSA-N 0.000 abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract description 8
- MQZFZDIZKWNWFX-UHFFFAOYSA-N osmium(2+) Chemical compound [Os+2] MQZFZDIZKWNWFX-UHFFFAOYSA-N 0.000 abstract description 6
- KKLCYBZPQDOFQK-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=CC=C1 KKLCYBZPQDOFQK-UHFFFAOYSA-N 0.000 abstract description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract description 4
- 239000007868 Raney catalyst Substances 0.000 abstract description 4
- 229910000564 Raney nickel Inorganic materials 0.000 abstract description 4
- LXQPBCHJNIOMQU-UHFFFAOYSA-N 2,4-dimethylpent-1-ene Chemical compound CC(C)CC(C)=C LXQPBCHJNIOMQU-UHFFFAOYSA-N 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 2
- GLKDQQSGPJKBDB-UHFFFAOYSA-N [Rh].P.P.N1=C(C=CC=C1)[Os](C1=NC=CC=C1)(C1=NC=CC=C1)(C1=NC=CC=C1)(C1=NC=CC=C1)C1=NC=CC=C1 Chemical compound [Rh].P.P.N1=C(C=CC=C1)[Os](C1=NC=CC=C1)(C1=NC=CC=C1)(C1=NC=CC=C1)(C1=NC=CC=C1)C1=NC=CC=C1 GLKDQQSGPJKBDB-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 12
- 229910052762 osmium Inorganic materials 0.000 description 12
- 239000010948 rhodium Substances 0.000 description 12
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 10
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 230000027756 respiratory electron transport chain Effects 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 5
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000013032 photocatalytic reaction Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 239000002803 fossil fuel Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 235000010378 sodium ascorbate Nutrition 0.000 description 3
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 3
- 229960005055 sodium ascorbate Drugs 0.000 description 3
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 230000007306 turnover Effects 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- 238000006161 Suzuki-Miyaura coupling reaction Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000003504 photosensitizing agent Substances 0.000 description 2
- 238000000607 proton-decoupled 31P nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 229910002367 SrTiO Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000032900 absorption of visible light Effects 0.000 description 1
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000010265 fast atom bombardment Methods 0.000 description 1
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 1
- BTZNPZMHENLISZ-UHFFFAOYSA-N fluoromethanesulfonic acid Chemical compound OS(=O)(=O)CF BTZNPZMHENLISZ-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000002907 osmium Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
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
- 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
- Y02E60/30—Hydrogen technology
- Y02E60/36—Hydrogen production from non-carbon containing sources, e.g. by water electrolysis
Abstract
【解決手段】以下の製法により特定のヘキサピリジルオスミウムジホスフィンロジウムを含む二核金属錯体。ビス(5−ブロモ−2,2’:6’,2”−テルピリジル)オスミウム(II)のヘキサフルオロリン酸塩と、ホスフィノチオイル基を有するフェニルボロン酸ピナコールエステルとをパラジウム触媒の存在下でクロスカップリングさせ、対応するホスフィンスルフィドを得る。次いで、ラネーニッケルと反応させることにより、Os(tpy)2部分を有するジホスフィン配位子が得られる。次に、得られたジホスフィン配位子と、遷移金属錯体、例えば、クロロジカルボニルロジウム(I)ダイマー[RhCl(CO)2]2とを、適切な溶媒中において室温で混合することにより、目的の二核金属錯体を得ることができる。
【選択図】なし
Description
(1)以下の一般式(1)、すなわち、
(2)Rが水素である、上記(1)に記載の二核金属錯体。
(3)R’がフェニル基、イソプロピル基、エチル基、tert−ブチル基、シクロヘキシル基、プロピル基、及びナフチル基からなる群より選択される少なくとも1種である、上記(1)又は(2)に記載の二核金属錯体。
(4)MがRh、Pd、Pt、Ir又はRuである、上記(1)〜(3)のいずれか1つに記載の二核金属錯体。
(5)MLmがRhCl(CO)、RhCl3、PtCl2、PdCl2、又はIrCl3である、上記(1)〜(4)のいずれか1つに記載の二核金属錯体。
(6)Xがヘキサフルオロリン酸イオン、テトラフルオロホウ酸イオン、トリフルオロメタンスルホン酸イオン、テトラフェニルホウ酸イオン、又はパラトルエンスルホン酸イオンである、上記(1)〜(5)のいずれか1つに記載の二核金属錯体。
(7)上記(1)〜(6)のいずれか1つに記載の二核金属錯体を含む光触媒。
[Os(tpy)2 2+部分を有するジホスフィン配位子(1a)の合成]
まず、ビス(5−ブロモ−2,2’:6’,2”−テルピリジル)オスミウム(II)のヘキサフルオロリン酸塩と、ジフェニルホスフィノチオイル基を有するフェニルボロン酸ピナコールエステル(先に記載した反応式(3)において置換基R’がフェニル基であるものに相当)とをそれぞれ所定の量で混合し、パラジウム触媒の存在下で鈴木−宮浦カップリング反応によりクロスカップリングさせ、対応するホスフィンスルフィド(2a)を得た(収率93%)。次いで、得られたホスフィンスルフィド(2a)をラネーニッケルと反応させることにより、Os(tpy)2 2+部分を有するジホスフィン配位子(1a)を得た(収率84%)。
上で得られたジホスフィン配位子(1a)を、室温でアセトン−d6中0.5当量のクロロジカルボニルロジウム(I)ダイマー[RhCl(CO)2]2と混合して二核金属錯体(3a)を得た。この二核金属錯体(3a)は、2つの異性体の混合物として得られ、それらの比は5:2であった。主異性体の31P{1H}NMRスペクトル(δ29.4(d,JRh-P=127Hz),29.6(d,JRh-P=128Hz))は、2つのリン原子のトランス配列を示していた。したがって、副異性体は、31P{1H}NMRスペクトル(δ29.5(brd,JRh-P=128Hz),46.3(brd,JRh-P=177Hz))からシス配列を有していると推定した。加えて、高速原子衝撃質量分析(FAB MS)(1344[M−2PF6])及びIR(1974cm-1(VCO))スペクトルの結果も同様に、本発明の二核金属錯体(3a)の構造を支持するものであった。これらの結果は、ジホスフィン配位子(1a)がロジウムに対して二座で配位していることを示すものである。
[Os(tpy)2 2+部分を有するジホスフィン配位子(1b)の合成]
ジイソプロピルホスフィノチオイル基を有するフェニルボロン酸ピナコールエステル(先に記載した反応式(3)において置換基R’がイソプロピル基であるものに相当)を用いたこと以外は実施例1と同様にして、対応するホスフィンスルフィド(2b)を得(収率78%)、次いで、得られたホスフィンスルフィド(2b)をラネーニッケルと反応させることにより、Os(tpy)2 2+部分を有するジホスフィン配位子(1b)を得た(収率87%)。
実施例1と同様にして、上で得られたジホスフィン配位子(1b)から、対応する二核金属錯体(3b)を得ることができた。
本実施例では、本発明の二核金属錯体を光触媒として使用し、その活性について調べた。結果を表1に示す。
次に、本発明による二核金属錯体の光物理的性質を表2にまとめる。なお、ビス(2,2’:6’,2”−テルピリジル)オスミウム(II)のヘキサフルオロリン酸塩[Os(tpy)2][PF6]2と、先に記載した反応式(4)の生成物であるジホスフィン配位子1aの光物理的性質についても併せて示している。
Claims (7)
- Rが水素である、請求項1に記載の二核金属錯体。
- R’がフェニル基、イソプロピル基、エチル基、tert−ブチル基、シクロヘキシル基、プロピル基、及びナフチル基からなる群より選択される少なくとも1種である、請求項1又は2に記載の二核金属錯体。
- MがRh、Pd、Pt、Ir又はRuである、請求項1〜3のいずれか1項に記載の二核金属錯体。
- MLmがRhCl(CO)、RhCl3、PtCl2、PdCl2、又はIrCl3である、請求項1〜4のいずれか1項に記載の二核金属錯体。
- Xがヘキサフルオロリン酸イオン、テトラフルオロホウ酸イオン、トリフルオロメタンスルホン酸イオン、テトラフェニルホウ酸イオン、又はパラトルエンスルホン酸イオンである、請求項1〜5のいずれか1項に記載の二核金属錯体。
- 請求項1〜6のいずれか1項に記載の二核金属錯体を含む光触媒。
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103554183A (zh) * | 2013-09-11 | 2014-02-05 | 南开大学 | 一种新型多芳基桥联的长链二膦配体合成方法和应用 |
CN111269268A (zh) * | 2020-02-13 | 2020-06-12 | 湘潭大学 | 具有双发射性质的Ru配合物、具有双发射性质含空白配位点的Ru配合物及双发射配合物 |
CN113387986A (zh) * | 2021-04-02 | 2021-09-14 | 四川轻化工大学 | 一种含双膦配体的双核[镍]金属化合物的制备及其应用 |
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CN103554183A (zh) * | 2013-09-11 | 2014-02-05 | 南开大学 | 一种新型多芳基桥联的长链二膦配体合成方法和应用 |
CN111269268A (zh) * | 2020-02-13 | 2020-06-12 | 湘潭大学 | 具有双发射性质的Ru配合物、具有双发射性质含空白配位点的Ru配合物及双发射配合物 |
CN113387986A (zh) * | 2021-04-02 | 2021-09-14 | 四川轻化工大学 | 一种含双膦配体的双核[镍]金属化合物的制备及其应用 |
CN113387986B (zh) * | 2021-04-02 | 2022-06-24 | 四川轻化工大学 | 一种含双膦配体的双核[镍]金属化合物的制备及其应用 |
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