JP5506306B2 - 発光物質 - Google Patents
発光物質 Download PDFInfo
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- JP5506306B2 JP5506306B2 JP2009219400A JP2009219400A JP5506306B2 JP 5506306 B2 JP5506306 B2 JP 5506306B2 JP 2009219400 A JP2009219400 A JP 2009219400A JP 2009219400 A JP2009219400 A JP 2009219400A JP 5506306 B2 JP5506306 B2 JP 5506306B2
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- tzv
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- europium
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- 239000000126 substance Substances 0.000 title claims description 9
- 229910052693 Europium Inorganic materials 0.000 claims description 21
- 239000000463 material Substances 0.000 claims description 19
- 229910052692 Dysprosium Inorganic materials 0.000 claims description 10
- 229910052772 Samarium Inorganic materials 0.000 claims description 10
- 229910052771 Terbium Inorganic materials 0.000 claims description 7
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 58
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 41
- 230000007704 transition Effects 0.000 description 19
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 17
- 239000003446 ligand Substances 0.000 description 17
- 238000001228 spectrum Methods 0.000 description 15
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- 229910052761 rare earth metal Inorganic materials 0.000 description 12
- 238000000295 emission spectrum Methods 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 150000002910 rare earth metals Chemical class 0.000 description 10
- -1 hetero metal complex Chemical class 0.000 description 8
- 238000010586 diagram Methods 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 6
- 230000005284 excitation Effects 0.000 description 5
- 150000002602 lanthanoids Chemical class 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 4
- 229910052747 lanthanoid Inorganic materials 0.000 description 4
- 230000005389 magnetism Effects 0.000 description 4
- 150000003536 tetrazoles Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 229910052688 Gadolinium Inorganic materials 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 3
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical group CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- JJMDCOVWQOJGCB-UHFFFAOYSA-N 5-aminopentanoic acid Chemical compound [NH3+]CCCCC([O-])=O JJMDCOVWQOJGCB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000000918 Europium Chemical class 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- TWNOVENTEPVGEJ-UHFFFAOYSA-K europium(3+);trifluoromethanesulfonate Chemical compound [Eu+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F TWNOVENTEPVGEJ-UHFFFAOYSA-K 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000006862 quantum yield reaction Methods 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000002216 synchrotron radiation X-ray diffraction Methods 0.000 description 2
- DKPSSMOJHLISJI-UHFFFAOYSA-N 1,10-phenanthrolin-5-amine Chemical compound C1=CC=C2C(N)=CC3=CC=CN=C3C2=N1 DKPSSMOJHLISJI-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical group [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- XSVCYDUEICANRJ-UHFFFAOYSA-K dysprosium(3+);trifluoromethanesulfonate Chemical compound [Dy+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F XSVCYDUEICANRJ-UHFFFAOYSA-K 0.000 description 1
- JVYYYCWKSSSCEI-UHFFFAOYSA-N europium(3+);trinitrate;hexahydrate Chemical compound O.O.O.O.O.O.[Eu+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O JVYYYCWKSSSCEI-UHFFFAOYSA-N 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- DYOBTPTUHDTANY-UHFFFAOYSA-K gadolinium(3+);trifluoromethanesulfonate Chemical compound [Gd+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F DYOBTPTUHDTANY-UHFFFAOYSA-K 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 230000001443 photoexcitation Effects 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- DDCWGUIPLGMBPO-UHFFFAOYSA-K samarium(3+);trifluoromethanesulfonate Chemical compound [Sm+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F DDCWGUIPLGMBPO-UHFFFAOYSA-K 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
配位子にテトラゾールのアルキル誘導体tzv及びフェナントロリンphenを有する三元ランタニド錯体[Ln2(tzv)6(phen)2](Lnは、Eu、Dy、Tb、Smを示す)は、以下の手順によって得られる。
5−アミノ吉草酸2.0 g、アジ化ナトリウム1.3 g、オルトギ酸トリエチル3.1 gを熱酢酸中で2時間攪拌した。反応終了後、濃塩酸を用いてpHを2に調整した。混合溶液を酢酸エチルで抽出し、酢酸エチル層を減圧乾固し、得られた粉末を再結晶することにより目的物を得た。収率は20 %であった。
ユーロピウム錯体[Eu2(tzv)6(phen)2]の合成においては、ユーロピウムトリフレート57 mgをメタノールに溶解させ、フェナントロリン33.5 mgを加え攪拌した。さらに、Htzv 43.9 mg、水酸化テトラエチルアンモニウム150 mgをゆっくり加え、2時間攪拌させ錯体を得た。収率は45 %であった。
図1〜3にユーロピウム錯体[Eu2(tzv)6(phen)2]の粉末X線回折スペクトル(Spring-8 BL02B2)を示す。図1は300 Kにおいて測定したスペクトル、図2は250 Kにおいて測定したスペクトル、図3は200 Kにおいて測定したスペクトルである。このスペクトルにより、得られた錯体は単一相であることが確認された。また、図4は2θ = 4°付近におけるXRDスペクトルの拡大図である。
飽和脂肪酸(ステアリン酸)を含む配位子phen-C18を有するユーロピウム錯体[Eu(phen-C18)2(NO3)3]は、以下の手順によって得られる。
5−アミノ−1,10−フェナントロリン100 mg (0.53 mmol)、ステアロイルクロリド241 mg (0.53 mmol)、トリエチルアミン0.1 mL (0.70 mmol)をテトラヒドロフラン(THF)100 mLに溶解し、室温で3時間攪拌した。反応終了後、純水50 mLを加えTHFを減圧留去した。析出した粉末をろ過し、ジエチルエーテルで洗浄することで白色粉末を得た。収率は90 %であった。
硝酸ユーロピウム6水和物28 mg(62 μmol)、phen-C18 57 mg(124 μmol)をエタノール20 mLに溶解し、室温で1時間攪拌した。析出した沈澱をろ過することで白色粉末を得た。収率は71 %であった。
図12は、ユーロピウム錯体[Eu(phen-C18)2(NO3)3]の発光スペクトル(励起波長, 295 nm)である。ユーロピウム錯体は594 nm及び618 nmにそれぞれ5D0→7F1及び5D0→7F2遷移に帰属されるEu(III)由来のff発光を示した。また、650 nm付近及び680 nm付近にそれぞれ5D0→7F3、5D0→7F4遷移に帰属されるEu(III)由来のff発光を示した。なお、400 nm付近にフェナントロリン由来のブロードなピークが観測された。
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JP5506306B2 true JP5506306B2 (ja) | 2014-05-28 |
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Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
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JP6460739B2 (ja) * | 2014-11-18 | 2019-01-30 | 美貴 長谷川 | ランタニド錯体を用いた環境調和型分子膜 |
CN107286350B (zh) * | 2017-06-28 | 2021-06-15 | 江西师范大学 | 具有高热稳定性的稀土配位聚合物及其制备方法 |
CN112368848A (zh) * | 2018-06-21 | 2021-02-12 | 新唐科技日本株式会社 | 白色发光装置 |
CN113880868B (zh) * | 2021-10-12 | 2023-09-08 | 江西师范大学 | 一种双核稀土配合物晶态材料及其制备方法和应用 |
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