JP6687240B2 - 新規化合物、化学センサー、センシング装置及びセンシング方法 - Google Patents
新規化合物、化学センサー、センシング装置及びセンシング方法 Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims description 82
- 238000000034 method Methods 0.000 title claims description 17
- 239000000126 substance Substances 0.000 title claims description 13
- 239000002904 solvent Substances 0.000 claims description 38
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 36
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 14
- 238000001514 detection method Methods 0.000 claims description 13
- -1 R 21 Chemical compound 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 229910052805 deuterium Inorganic materials 0.000 claims description 3
- 125000004431 deuterium atom Chemical group 0.000 claims description 3
- 238000000295 emission spectrum Methods 0.000 description 27
- 239000000243 solution Substances 0.000 description 18
- 230000005284 excitation Effects 0.000 description 16
- 239000000203 mixture Substances 0.000 description 10
- 239000012046 mixed solvent Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 238000006862 quantum yield reaction Methods 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- 238000004020 luminiscence type Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000009849 deactivation Effects 0.000 description 3
- 230000005281 excited state Effects 0.000 description 3
- 230000001747 exhibiting effect Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- WYECURVXVYPVAT-UHFFFAOYSA-N 1-(4-bromophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Br)C=C1 WYECURVXVYPVAT-UHFFFAOYSA-N 0.000 description 2
- GATVIKZLVQHOMN-UHFFFAOYSA-N Chlorodibromomethane Chemical compound ClC(Br)Br GATVIKZLVQHOMN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
- 238000011088 calibration curve Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- XZIAFENWXIQIKR-UHFFFAOYSA-N ethyl 4-bromobenzoate Chemical compound CCOC(=O)C1=CC=C(Br)C=C1 XZIAFENWXIQIKR-UHFFFAOYSA-N 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- MROKJEYKOKZQEK-UHFFFAOYSA-N 1-(4-carbazol-9-ylphenyl)ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 MROKJEYKOKZQEK-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 238000003326 Quality management system Methods 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- FMWLUWPQPKEARP-UHFFFAOYSA-N bromodichloromethane Chemical compound ClC(Cl)Br FMWLUWPQPKEARP-UHFFFAOYSA-N 0.000 description 1
- 229950005228 bromoform Drugs 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- LQEJKDNALLXRCT-UHFFFAOYSA-N chloroform;toluene Chemical compound ClC(Cl)Cl.CC1=CC=CC=C1 LQEJKDNALLXRCT-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 230000001443 photoexcitation Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
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- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
- Indole Compounds (AREA)
Description
フレームドライした300mlの三口フラスコに、1−(p−ブロモフェニル)エタノン(1.52g、7.67mmol)とカルバゾール(1.12g、6.70mmol)、無水炭酸カリウム(2.96g、21.4mmol)及び酢酸パラジウム(スパチュラ一杯分)を加え、脱気し、系内をアルゴン置換した。得られた溶液に、トリ−t−ブチルホスフィン(スパチュラ三杯分)を脱水キシレン(20ml)に溶かしたものを、シリンジを用いて加え、120℃で40時間加熱還流した。得られた溶液に水を加えて簡易ろ過した後、ジクロロメタンと水で抽出した。得られた有機層に硫酸マグネシウムを加え、更にろ過した後、エバポレーター(オイルバス)で溶媒を除去した。得られた化合物をシリカゲルカラムクロマトグラフィー(ヘキサン:ジクロロメタン=1:1、Rf=0.45)を用いて精製し、黄色い粉体を得た。収率は0.78g(35.6%)であった。
1H-NMR(400 MHz, CDCl3, TMS): δ/ppm= 2.70(3H, s),7.30-7.35 (2H, m), 7.41-7.52 (4H, m), 7.70-7.74 (2H, d), 8.14-8.16 (2H, d),8.20-8.23 (2H, d).
フレームドライした300mlの三口フラスコに、エチル−p−ブロモベンゾエート(3.02g、13.6mmol)とカルバゾール(2.20g、12.5mmol)、無水炭酸カリウム(5.07g、36.7mmol)、酢酸パラジウム(スパチュラ二杯分)を加え、脱気し、系内をアルゴン置換した。得られた溶液に、トリ−t−ブチルホスフィン10wt%ヘキサン溶液(1ml)と脱水キシレン(40ml)を、シリンジを用いて加え、120℃で48時間加熱還流した。得られた溶液に水を加えて簡易ろ過した後、ジクロロメタンと水で抽出した。得られた有機層に硫酸マグネシウムを加え、更にろ過した後、エバポレーター(オイルバス)で溶媒を除去した。得られた化合物に少量のエタノールを加えると白濁した。これを吸引ろ過することにより、白色の粉体が得られた。収率は0.76g(17.6%)であった。
1H-NMR(400 MHz, CDCl3, TMS):δ/ppm= 1.44-1.47 (3H,t), 4.43-4.48 (2H, q), 7.30-7.34 (2H, m), 7.40-7.49 (4H, m), 7.67-7.70 (2H, d),8.14-8.16 (2H, d), 8.28-8.31 (2H, d).
フレームドライした300mlの三口フラスコに、エチル−4−(9H−カルバゾール−9−イル)ベンゾエート(0.76g、1.90mmol)及び水素化ナトリウム(0.40g、10.0mmol)を加え、脱気し、系内をアルゴン置換した。得られた溶液に脱水THF(40ml)を加え、室温で30分攪拌させた。得られた溶液に、4−(9−カルバゾリル)フェニルエタノン(0.54g、1.90mmol)を脱水THF(20 ml)に溶かしたものを加え、65℃で24時間加熱還流した。溶液に水を加え、約2mol/L塩酸を加え中和した後、ジクロロメタンと水で抽出した。得られた有機層に硫酸マグネシウムを加え、ろ過した後、エバポレーターで溶媒を除去した。得られた化合物をジクロロメタンとヘキサンで再沈殿した後、ジクロロメタン及びヘキサンで再結晶し、茶色い粉体を得た。収率は0.47g(44.8%)であった。得られた化合物は、NMR及び質量分析によってジ(4−カルバゾール−ベンゾイル)メタン(DCBM)と同定された。
1H-NMR(400 MHz, CD2Cl2): δ/ppm= 7.08(1H, s), 7.30-7.35 (4H, d,d), 7.43-7.48 (4H, d,d), 7.52-7.56 (4H, d), 7.77-7.80(4H, d), 8.15-8.18 (4H, d), 8.29-8.31 (4H, d), 17.1 (1H, s), HRMS(ESI): found :m / z =555.20, calcd for C39H26O2N2: [M+H]+ = 555.20.
Claims (8)
- R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、R18、R19、R20、R21、R22、R23及びR24が水素原子である、請求項1に記載の化合物。
- 請求項1又は2に記載の化合物を含む化学センサー。
- 溶媒をセンシングするために用いられる、請求項3に記載のセンサー。
- 前記溶媒が有機溶媒である、請求項4に記載のセンサー。
- 前記有機溶媒が、ヘキサン、トルエン、クロロホルム、ジクロロメタン及びN,N−ジメチルホルムアミドからなる群から選ばれる1種以上である、請求項5に記載のセンサー。
- 請求項1又は2に記載の化合物を含む検出部を備える、センシング装置。
- 請求項1又は2に記載の化合物によって対象物をセンシングすることを含む、センシング方法。
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JP6687240B2 true JP6687240B2 (ja) | 2020-04-22 |
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JP5400448B2 (ja) * | 2009-03-31 | 2014-01-29 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子 |
US8673458B2 (en) * | 2010-06-11 | 2014-03-18 | Universal Display Corporation | Delayed fluorescence OLED |
JP6311093B2 (ja) * | 2013-03-07 | 2018-04-18 | 国立大学法人九州大学 | 超分子複合体、発光体、および有機化合物検出用のセンサー素子 |
US9324949B2 (en) * | 2013-07-16 | 2016-04-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10461260B2 (en) * | 2014-06-03 | 2019-10-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
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