JP6675771B2 - 有機金属複合体用多方向性リガンド - Google Patents
有機金属複合体用多方向性リガンド Download PDFInfo
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- JP6675771B2 JP6675771B2 JP2018545604A JP2018545604A JP6675771B2 JP 6675771 B2 JP6675771 B2 JP 6675771B2 JP 2018545604 A JP2018545604 A JP 2018545604A JP 2018545604 A JP2018545604 A JP 2018545604A JP 6675771 B2 JP6675771 B2 JP 6675771B2
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- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012621 metal-organic framework Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004001 molecular interaction Effects 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- VMUZVGRNTPFTKE-UHFFFAOYSA-N octanehydrazide Chemical compound CCCCCCCC(=O)NN VMUZVGRNTPFTKE-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- SXBRULKJHUOQCD-UHFFFAOYSA-N propanoic acid Chemical compound CCC(O)=O.CCC(O)=O SXBRULKJHUOQCD-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- KFUSANSHCADHNJ-UHFFFAOYSA-N pyridine-3-carbohydrazide Chemical compound NNC(=O)C1=CC=CN=C1 KFUSANSHCADHNJ-UHFFFAOYSA-N 0.000 description 1
- NGVDGCNFYWLIFO-UHFFFAOYSA-N pyridoxal 5'-phosphate Chemical compound CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O NGVDGCNFYWLIFO-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002207 retinal effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- HKCRVXUAKWXBLE-UHFFFAOYSA-N terbium(3+) Chemical compound [Tb+3] HKCRVXUAKWXBLE-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
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- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
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- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/86—Hydrazides; Thio or imino analogues thereof
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- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/48—Two nitrogen atoms
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- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/001—General concepts, e.g. reviews, relating to catalyst systems and methods of making them, the concept being defined by a common material or method/theory
- B01J2531/002—Materials
- B01J2531/004—Ligands
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- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
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- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/30—Complexes comprising metals of Group III (IIIA or IIIB) as the central metal
- B01J2531/38—Lanthanides other than lanthanum
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- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/50—Complexes comprising metals of Group V (VA or VB) as the central metal
- B01J2531/56—Vanadium
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- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
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Description
本出願は、2016年7月29日付韓国特許出願第10−2016−0096904号に基づく優先権の利益を主張し、当該韓国特許出願の文献に開示されたすべての内容は本明細書の一部として含まれる。
Rは、それぞれ独立して−R1、−NH−CO−R2、または−NH−R2であり、
R1は、それぞれ独立して−OH、C6−60アリール、C1−10アルキル、またはアミノ酸残基であり、
R2は、C1−10アルキル、C6−60アリール、またはN、O及びSのうちいずれか一つを含むC4−60ヘテロアリールである。
乾燥された丸底フラスコにHMTA(hexamethylenetetramine、7.530g、53.70mmol)を入れた。前記フラスコをアルゴンでパージングし、TFA(trifluoroacetic acid、50mL)を入れた。HMTAを完全に溶解した後、ビフェニル−4,4’−ジオール(1.000g、5.370mmol)を急速に入れた。前記混合物がオレンジ色になったことを確認した後、120℃で7日間加熱した。生成物は赤黒い色であり、これを4N HCl(100mL)に注ぎ、黄色沈殿物をろ過した。沈殿物を熱いDMSOで再結晶して黄色の微細結晶2.460g(収率:65.1%)を得た。
反応器に前記段階1で製造した化合物(0.296g、1.000mmol)及びNH2OH−HCl(0.420g、6.0mmol)を入れた。水(7mL)を添加した後、80℃で加熱した。前記混合物が透明になる時までメタノールを滴加した。反応器を固く密封した後100℃で1時間加熱した。常温に冷却した後に水を添加して沈殿物を誘導し、これをろ過及び水で洗浄して明るい黄色の生成物(powder、0.360g)を得た。
1H NMR (300 MHz,DMSO−d)δ11.60(s,4H),10.88(s,2H),8.45(s,4H),7.83(s,4H)
1H NMR(300 MHz,D2O)δ3.31(s,8H),7.91(s,4H)
LC−MS:calculated for C40H34N8O2[M]+658.28,found 659.4
MALDI−TOF:calculated for C40H30N12O6[M]+ 774.24、found 775.5
LC−MS:calculated for C48H74N8O6[M]+858.57、found 859.7
1)実験例1−1
ガラス瓶に前記実施例1で製造した化合物(50.0mg、0.140mmol)を入れ、DMF(1.0mL)を入れてこれを溶解した。トリエチルアミン(0.12mL、0.840mmol)を滴加して溶液がオレンジ色になったことを確認した後、下記表1の物質を急速に添加した。5秒間前記混合物を攪拌した後、ゲルを形成するために100℃で加熱し、この過程で漸進的にゲルが形成された。
ガラス瓶に前記実施例1で製造した化合物(50.0mg、0.140mmol)を入れ、DMF(1.0mL)を入れてこれを溶解した。完全に溶解した後、下記表2の物質を添加した。その後、急速にトリエチルアミン(0.12mL、0.840mmol)を滴加し、滴加直後に黒いゲルが形成された。5秒間前記混合物を攪拌した後、ゲルの均質化及び強度増加のために100℃で加熱した。約1時間後にゲルが完成した。
ガラス瓶に前記実施例1で製造した化合物(50.0mg、0.140mmol)を入れ、DMF(1.0mL)を入れてこれを溶解した。トリエチルアミン(0.12mL、0.840mmol)を滴加して溶液がオレンジ色になったことを確認した後、下記表3の物質を急速に添加した。添加直後にゲルの形成が始まった。5秒間前記混合物を攪拌した後、ゲルの均質化及び強度増加のために100℃で加熱し、約1時間後にゲルが完成した。
ガラス瓶に前記実施例1で製造した化合物(50.0mg、0.140mmol)を入れ、DMF(1.0mL)を入れてこれを溶解した。ナトリウムメトキシド(22.5mg、0.420mmol)を1.0mLのエタノールに溶かした溶液を滴加して溶液がオレンジ色になったことを確認した後、下記表4の物質を急速に添加した。添加直後にゲルの形成が始まった。5秒間前記混合物を攪拌した後、ゲルの均質化及び強度増加のために100℃で加熱した。約1時間後にゲルが完成した。
前記実験例1−9で製造したゲルをスライドグラスに塗った後、80℃の真空オーブンで2時間乾燥した。このように乾燥したゲルの蛍光性を測定し、吸収波長は450nmであり、図3に示すように最大放出波長は629nmであった。
1)実験例3−1
前記実験例1−3で製造したコバルトゲルを真空で12時間乾燥した結果物を用いて、SEMイメージを得た。具体的には、乾燥したゲルをカーボン両面テープを貼ったスタブ(stub)に分散させて白金コーティングをし、15kV電圧条件で観察した。その結果を図4に示した。
前記実験例1−4で製造したニッケルゲルを真空で12時間乾燥した結果物を用いて、SEMイメージを得た。具体的には、乾燥したゲルをカーボン両面テープを貼ったスタブ(stub)に分散させて白金コーティングをし、5−15kV電圧条件で観察した。その結果を図5に示した。
前記実験例1−2〜1−10で製造したゲルを超臨界二酸化炭素で処理して溶媒を乾燥させる過程によりキセロゲル(xerogel)を作った。具体的には、ステンレス鋼で作ったシリンダーに前記で製造したゲルを入れた後、超臨界二酸化炭素機器に設置した。40℃温度で200気圧の超臨界二酸化炭素を0.1mL/分速度で流れるようにして溶媒を除去して粉形態の結果物を得た。そのうち一部を肉眼で観察した結果を図6に示した。
前記実験例4で製造されたキセロゲルを用いて、SEMイメージを得た。具体的には、キセロゲルをカーボン両面テープを貼ったスタブ(Stub)に分散させて白金コーティングをし、5−15kV電圧条件で観察してその結果を図7〜15に示した。同時に、キセロゲル表面の元素分布を確認するためにEDS(energydispersive X−ray spectroscopy;エネルギー分散X線分光分析)を測定し、その結果を図16〜図23に示した。各図面の内容は、下記表5のとおりである。
Claims (4)
- 下記化学式1で表される化合物、またはその塩:
Rは、それぞれ独立して−R1、−NH−CO−R2、または−NH−R2であり、
R1は、それぞれ独立して−OHまたはアミノ酸残基であり、
R2は、C1−10アルキル、C6−60アリール、またはN、O及びSのうちいずれか一つを含むC4−60ヘテロアリールであり、
前記アミノ酸残基が、それぞれ独立して、アラニン、システイン、アスパラギン酸、グルタミン酸、フェニルアラニン、ヒスチジン、イソロイシン、リシン、ロイシン、メチオニン、アスパラギン、ピロリシン、グルタミン、アルギニン、セリン、スレオニン、セレノシステイン、バリン、トリプトファン、チロシンからなる群より選ばれるいずれか一つのアミノ酸の残基である。 - R2は、メチル、エチル、プロピル、イソプロピル、ブチル、イソブチル、tert−ブチル、ペンチル、tert−ペンチル、ネオペンチル、イソペンチル、sec−ペンチル、3−ペンチル、ヘキシル、オクチル、フェニル、ナフチル、またはピリジニルであることを特徴とする、請求項1に記載の化合物。
- 前記化学式1で表される化合物は、下記化学式1−1〜1−5で表される化合物であることを特徴とする、請求項1に記載の化合物:
- 1)下記化学式1’で表される化合物、下記化学式2’で表される化合物及びトリフルオロ酢酸を反応させて、下記化学式3’で表される化合物を製造する段階と、
2)下記化学式3’で表される化合物を下記化学式4’で表される化合物と反応させる段階とを含む、下記化学式1で表される化合物の製造方法:
Rの定義は請求項1〜3のうちいずれか一項に定義されたとおりである。
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