JP5288560B2 - 水分検出方法 - Google Patents
水分検出方法 Download PDFInfo
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- JP5288560B2 JP5288560B2 JP2009249485A JP2009249485A JP5288560B2 JP 5288560 B2 JP5288560 B2 JP 5288560B2 JP 2009249485 A JP2009249485 A JP 2009249485A JP 2009249485 A JP2009249485 A JP 2009249485A JP 5288560 B2 JP5288560 B2 JP 5288560B2
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- 238000001514 detection method Methods 0.000 title claims description 13
- 239000007850 fluorescent dye Substances 0.000 claims description 40
- 125000000524 functional group Chemical group 0.000 claims description 23
- 239000011159 matrix material Substances 0.000 claims description 23
- 230000002378 acidificating effect Effects 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000005157 alkyl carboxy group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000005577 anthracene group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000005581 pyrene group Chemical group 0.000 claims description 3
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 69
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 125000003277 amino group Chemical group 0.000 description 15
- 238000004770 highest occupied molecular orbital Methods 0.000 description 15
- 239000000523 sample Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
- -1 hydrogen ions Chemical class 0.000 description 10
- 239000000126 substance Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 230000027756 respiratory electron transport chain Effects 0.000 description 6
- 239000012488 sample solution Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000006850 spacer group Chemical group 0.000 description 4
- 0 **(C=CC=C1*C(*N*)C2)C=C1OC2=O Chemical compound **(C=CC=C1*C(*N*)C2)C=C1OC2=O 0.000 description 3
- LYFYMWWEDCIZPY-UHFFFAOYSA-N 4-[anthracen-9-ylmethyl(methyl)amino]butanoic acid Chemical compound C1=CC=C2C(CN(CCCC(O)=O)C)=C(C=CC=C3)C3=CC2=C1 LYFYMWWEDCIZPY-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- JJIGURGZOYMAJS-UHFFFAOYSA-N ethyl 4-[anthracen-9-ylmethyl(methyl)amino]butanoate Chemical compound C1=CC=C2C(CN(C)CCCC(=O)OCC)=C(C=CC=C3)C3=CC2=C1 JJIGURGZOYMAJS-UHFFFAOYSA-N 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical class [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 238000003908 quality control method Methods 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- WRVHTDZJMNUGQN-UHFFFAOYSA-N 1-anthracen-9-yl-n-methylmethanamine Chemical compound C1=CC=C2C(CNC)=C(C=CC=C3)C3=CC2=C1 WRVHTDZJMNUGQN-UHFFFAOYSA-N 0.000 description 1
- VRLUDYFGYJOSBA-UHFFFAOYSA-N C1=CC=C2C(=C1)C=C3C=CC=CC3=C2CCCCCC(=O)O Chemical compound C1=CC=C2C(=C1)C=C3C=CC=CC3=C2CCCCCC(=O)O VRLUDYFGYJOSBA-UHFFFAOYSA-N 0.000 description 1
- BSSOARBOOVPZSO-UHFFFAOYSA-N CCOC(=O)CCCCCC1=C2C=CC=CC2=CC3=CC=CC=C31 Chemical compound CCOC(=O)CCCCCC1=C2C=CC=CC2=CC3=CC=CC=C31 BSSOARBOOVPZSO-UHFFFAOYSA-N 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000005443 coulometric titration Methods 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- YDVNLQGCLLPHAH-UHFFFAOYSA-N dichloromethane;hydrate Chemical compound O.ClCCl YDVNLQGCLLPHAH-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- XBPOBCXHALHJFP-UHFFFAOYSA-N ethyl 4-bromobutanoate Chemical compound CCOC(=O)CCCBr XBPOBCXHALHJFP-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000003053 immunization Effects 0.000 description 1
- 238000002649 immunization Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 229940127554 medical product Drugs 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
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Description
式1で表される蛍光発光性化合物を試料に添加して紫外線を照射し、
R2N−A−B−R・・・(式1)
(式中、Rは水素、アルキル基、酸性プロトン性官能基または酸性プロトン性官能基を有する基であり、少なくとも1つのRは酸性プロトン性官能基または酸性プロトン性官能基を有する基、Aは酸素またはCH2、Bは蛍光発光母体を表す。)
前記蛍光発光性化合物が双生イオン構造となって発する蛍光の強度を測定して、前記試料中の水分量を検出する、ことを特徴とする。
本実施の形態に係る蛍光発光性化合物は、式1で表される。
R2N−A−B−R・・・(式1)
上述した蛍光発光性化合物を用いて、以下のように有機溶剤や固体材料等の試料中に含まれる微量水分を検出できる。
IR(ATR):ν=1728,cm−1;1H NMR([D6]Acetone,TMS)δ=1.12(t,3H),1.77−1.82(m,2H),2.20−2.23(m,5H),2.59(t,2H),3.92−3.97(m,2H),4.46(s,2H),7.47−7.55(m,4H),8.06(d,2H),8.54(t,3H);EI(+)MSm/z335(M+).
IR(ATR):ν=1706cm−1;1H NMR([D6]Acetone,TMS)δ=1.84(t,2H),2.22−2.28(m,5H),2.68(t,2H),4.51(s,2H),7.48−7.57(m,4H),8.07(d,2H),8.56(t,3H);EI(+)MSm/z307(M+).
得られた4−(Anthracen−9−ylmethyl−methyl−amino)−butyric acidを用いて、各種溶液の水分量の検出を行った。
測定装置:HITACHI F−4500 測定条件:励起波長(光照射波長):366nm スキャンスピード:1200nm/min 励起側スリット:5.0nm 蛍光側スリット:5.0nm ホトマル:400V レスポンス:0.004s
Claims (4)
- 式1で表される蛍光発光性化合物を試料に添加して紫外線を照射し、
R2N−A−B−R・・・(式1)
(式中、Rは水素、アルキル基、酸性プロトン性官能基または酸性プロトン性官能基を有する基であり、少なくとも1つのRは酸性プロトン性官能基または酸性プロトン性官能基を有する基、Aは酸素またはCH2、Bは蛍光発光母体を表す。)
前記蛍光発光性化合物が双生イオン構造となって発する蛍光の強度を測定して、前記試料中の水分量を検出する、ことを特徴とする水分検出方法。 - 前記酸性プロトン性官能基はカルボキシル基、スルホン酸基またはリン酸基であることを特徴とする請求項1に記載の水分検出方法。
- 前記酸性プロトン性官能基を有する基はアルキルカルボキシル基、アルキルスルホン酸基またはアルキルリン酸基であることを特徴とする請求項1又は2に記載の水分検出方法。
- 前記蛍光発光母体はアントラセン系骨格、クマリン系骨格またはピレン系骨格であることを特徴とする請求項1乃至3のいずれかに記載の水分検出方法。
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JP5288560B2 true JP5288560B2 (ja) | 2013-09-11 |
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JP3321601B2 (ja) * | 1999-12-10 | 2002-09-03 | 独立行政法人物質・材料研究機構 | 粘土/有機複合体湿度センサー |
US6387672B1 (en) * | 2000-12-04 | 2002-05-14 | Beckman Coulter, Inc. | Photo-induced electron transfer fluorescent sensor molecules |
US20020127626A1 (en) * | 2001-01-05 | 2002-09-12 | Sensors For Medicine And Science, Inc. | Detection of glucose in solutions also containing an alpha-hydroxy acid or a beta-diketone |
JP4691333B2 (ja) * | 2004-07-23 | 2011-06-01 | テルモ株式会社 | 糖類測定用蛍光モノマー化合物、糖類測定用蛍光センサー物質および体内埋め込み用の糖類測定用センサー |
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