DE69710584T2 - Kovalent immobilisierte fluoroionophoren für optische ionen-sensoren - Google Patents
Kovalent immobilisierte fluoroionophoren für optische ionen-sensorenInfo
- Publication number
- DE69710584T2 DE69710584T2 DE69710584T DE69710584T DE69710584T2 DE 69710584 T2 DE69710584 T2 DE 69710584T2 DE 69710584 T DE69710584 T DE 69710584T DE 69710584 T DE69710584 T DE 69710584T DE 69710584 T2 DE69710584 T2 DE 69710584T2
- Authority
- DE
- Germany
- Prior art keywords
- formula
- group
- alkyl
- compound according
- fluoroionophore
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 230000003287 optical effect Effects 0.000 title claims description 16
- -1 sulfonic acid halide Chemical class 0.000 claims description 102
- 229920000642 polymer Polymers 0.000 claims description 66
- 150000001875 compounds Chemical class 0.000 claims description 55
- 125000000524 functional group Chemical group 0.000 claims description 55
- 239000000203 mixture Substances 0.000 claims description 47
- 239000002555 ionophore Substances 0.000 claims description 35
- 230000000236 ionophoric effect Effects 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 239000012876 carrier material Substances 0.000 claims description 30
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 29
- 150000002500 ions Chemical class 0.000 claims description 25
- 239000000463 material Substances 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 18
- 239000000178 monomer Substances 0.000 claims description 17
- 239000002253 acid Chemical class 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 12
- 150000001768 cations Chemical class 0.000 claims description 12
- 230000008859 change Effects 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 238000012360 testing method Methods 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 150000001450 anions Chemical class 0.000 claims description 7
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 6
- 239000012948 isocyanate Substances 0.000 claims description 6
- 150000002513 isocyanates Chemical class 0.000 claims description 6
- 238000001506 fluorescence spectroscopy Methods 0.000 claims description 5
- 239000002245 particle Substances 0.000 claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- GQPLZGRPYWLBPW-UHFFFAOYSA-N calix[4]arene Chemical compound C1C(C=2)=CC=CC=2CC(C=2)=CC=CC=2CC(C=2)=CC=CC=2CC2=CC=CC1=C2 GQPLZGRPYWLBPW-UHFFFAOYSA-N 0.000 claims description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 3
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 2
- 125000003860 C1-C20 alkoxy group Chemical class 0.000 claims description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 150000002923 oximes Chemical class 0.000 claims description 2
- 150000003459 sulfonic acid esters Chemical class 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims 2
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 238000004611 spectroscopical analysis Methods 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 106
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 239000000243 solution Substances 0.000 description 50
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 38
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- 229920001577 copolymer Polymers 0.000 description 33
- 238000001704 evaporation Methods 0.000 description 31
- 230000008020 evaporation Effects 0.000 description 31
- 150000001336 alkenes Chemical class 0.000 description 30
- 150000003254 radicals Chemical class 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 238000005160 1H NMR spectroscopy Methods 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000012074 organic phase Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 18
- 239000000741 silica gel Substances 0.000 description 18
- 229910002027 silica gel Inorganic materials 0.000 description 18
- 229910052938 sodium sulfate Inorganic materials 0.000 description 18
- 235000011152 sodium sulphate Nutrition 0.000 description 18
- 239000007832 Na2SO4 Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 230000008569 process Effects 0.000 description 12
- 229920001059 synthetic polymer Polymers 0.000 description 12
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 10
- 125000004429 atom Chemical group 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000004587 chromatography analysis Methods 0.000 description 10
- 238000005259 measurement Methods 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 150000001298 alcohols Chemical class 0.000 description 9
- 229910052731 fluorine Inorganic materials 0.000 description 9
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 150000002170 ethers Chemical class 0.000 description 8
- 239000012528 membrane Substances 0.000 description 8
- 150000002894 organic compounds Chemical class 0.000 description 8
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 7
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 7
- 150000001408 amides Chemical class 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 150000002009 diols Chemical class 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 229920005615 natural polymer Polymers 0.000 description 7
- 229910052700 potassium Inorganic materials 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 6
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 6
- 239000011859 microparticle Substances 0.000 description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- 229920001444 polymaleic acid Polymers 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 229920002451 polyvinyl alcohol Polymers 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- GNWBLLYJQXKPIP-ZOGIJGBBSA-N (1s,3as,3bs,5ar,9ar,9bs,11as)-n,n-diethyl-6,9a,11a-trimethyl-7-oxo-2,3,3a,3b,4,5,5a,8,9,9b,10,11-dodecahydro-1h-indeno[5,4-f]quinoline-1-carboxamide Chemical compound CN([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)N(CC)CC)[C@@]2(C)CC1 GNWBLLYJQXKPIP-ZOGIJGBBSA-N 0.000 description 5
- ZYVYEJXMYBUCMN-UHFFFAOYSA-N 1-methoxy-2-methylpropane Chemical compound COCC(C)C ZYVYEJXMYBUCMN-UHFFFAOYSA-N 0.000 description 5
- 239000004908 Emulsion polymer Substances 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 150000004985 diamines Chemical class 0.000 description 5
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 4
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 125000000732 arylene group Chemical group 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 125000002704 decyl group Chemical class [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 125000003187 heptyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 125000001400 nonyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000001147 pentyl group Chemical class C(CCCC)* 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000001436 propyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 3
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 229920001661 Chitosan Polymers 0.000 description 3
- 101000983970 Conus catus Alpha-conotoxin CIB Proteins 0.000 description 3
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 101100311330 Schizosaccharomyces pombe (strain 972 / ATCC 24843) uap56 gene Proteins 0.000 description 3
- 229920002125 Sokalan® Polymers 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 125000005396 acrylic acid ester group Chemical group 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229920001525 carrageenan Polymers 0.000 description 3
- 239000000679 carrageenan Substances 0.000 description 3
- 235000010418 carrageenan Nutrition 0.000 description 3
- 229940113118 carrageenan Drugs 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 235000010980 cellulose Nutrition 0.000 description 3
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 239000008199 coating composition Substances 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
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- 235000010445 lecithin Nutrition 0.000 description 1
- QTWZICCBKBYHDM-UHFFFAOYSA-N leucomethylene blue Chemical compound C1=C(N(C)C)C=C2SC3=CC(N(C)C)=CC=C3NC2=C1 QTWZICCBKBYHDM-UHFFFAOYSA-N 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 150000002634 lipophilic molecules Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 150000002668 lysine derivatives Chemical class 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 229940041033 macrolides Drugs 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 150000001247 metal acetylides Chemical class 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- UEBNVLLIWJWEKV-VIFPVBQESA-N methyl (2s)-6-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate Chemical class NCCCC[C@@H](C(=O)OC)NC(=O)OC(C)(C)C UEBNVLLIWJWEKV-VIFPVBQESA-N 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- JESXATFQYMPTNL-UHFFFAOYSA-N mono-hydroxyphenyl-ethylene Natural products OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- KOWHWGGCIXBOKF-UHFFFAOYSA-N n-(1-hydroxyethyl)acetamide Chemical compound CC(O)NC(C)=O KOWHWGGCIXBOKF-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 239000008239 natural water Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 229920002601 oligoester Polymers 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- PBLZLIFKVPJDCO-UHFFFAOYSA-N omega-Aminododecanoic acid Natural products NCCCCCCCCCCCC(O)=O PBLZLIFKVPJDCO-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- NWLSIXHRLQYIAE-UHFFFAOYSA-N oxiran-2-ylmethoxysilicon Chemical compound [Si]OCC1CO1 NWLSIXHRLQYIAE-UHFFFAOYSA-N 0.000 description 1
- 239000006174 pH buffer Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- QWYZFXLSWMXLDM-UHFFFAOYSA-M pinacyanol iodide Chemical class [I-].C1=CC2=CC=CC=C2N(CC)C1=CC=CC1=CC=C(C=CC=C2)C2=[N+]1CC QWYZFXLSWMXLDM-UHFFFAOYSA-M 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 125000002577 pseudohalo group Chemical group 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001055 reflectance spectroscopy Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- OSQUFVVXNRMSHL-LTHRDKTGSA-M sodium;3-[(2z)-2-[(e)-4-(1,3-dibutyl-4,6-dioxo-2-sulfanylidene-1,3-diazinan-5-ylidene)but-2-enylidene]-1,3-benzoxazol-3-yl]propane-1-sulfonate Chemical compound [Na+].O=C1N(CCCC)C(=S)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 OSQUFVVXNRMSHL-LTHRDKTGSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000004416 surface enhanced Raman spectroscopy Methods 0.000 description 1
- 238000002198 surface plasmon resonance spectroscopy Methods 0.000 description 1
- 238000006557 surface reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- FCFMKFHUNDYKEG-UHFFFAOYSA-N thietane 1,1-dioxide Chemical compound O=S1(=O)CCC1 FCFMKFHUNDYKEG-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 125000001814 trioxo-lambda(7)-chloranyloxy group Chemical group *OCl(=O)(=O)=O 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- FCFNRCROJUBPLU-DNDCDFAISA-N valinomycin Chemical compound CC(C)[C@@H]1NC(=O)[C@H](C)OC(=O)[C@@H](C(C)C)NC(=O)[C@@H](C(C)C)OC(=O)[C@H](C(C)C)NC(=O)[C@H](C)OC(=O)[C@@H](C(C)C)NC(=O)[C@@H](C(C)C)OC(=O)[C@H](C(C)C)NC(=O)[C@H](C)OC(=O)[C@@H](C(C)C)NC(=O)[C@@H](C(C)C)OC1=O FCFNRCROJUBPLU-DNDCDFAISA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 carbon atoms of the ring system
- C07D219/08—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/90—Xanthenes with hydrocarbon radicals, substituted by amino radicals, directly attached in position 9
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/52—Use of compounds or compositions for colorimetric, spectrophotometric or fluorometric investigation, e.g. use of reagent paper and including single- and multilayer analytical elements
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/84—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving inorganic compounds or pH
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S436/00—Chemistry: analytical and immunological testing
- Y10S436/80—Fluorescent dyes, e.g. rhodamine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Physics & Mathematics (AREA)
- Pathology (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Cell Biology (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Inorganic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Claims (27)
1. Verbindung der Formel (I)
worin
I den einwertigen Rest eines Ionophors darstellt,
F den einwertigen Rest eines Fluorophors darstellt,
G eine funktionelle Gruppe darstellt,
T einen dreiwertigen organischen Rest darstellt und
R&sub0;&sub1;, R&sub0;&sub2; und R&sub0;&sub3; jeweils unabhängig voneinander eine
direkte Bindung oder eine Brückengruppe darstellen.
2. Verbindung nach Anspruch 1, worin R&sub0;&sub1;, R&sub0;&sub2; und R&sub0;&sub3;
jeweils unabhängig voneinander eine Brückengruppe darstellen.
3. Verbindung nach Anspruch 1, worin die funktionelle
Gruppe G eine Carbon- oder Sulfonsäure-, ein Carbon- oder
Sulfonsäurehalogenid-, Carbon- oder Sulfonsäureamid-, Carbon-
oder Sulfonsäureester-, Thiol-, Amin-, Hydroxyl-, Cyanat-,
Isocyanat-, Oxim-, Aldehyd- oder Ketongruppe oder eine
polymerisierbare Gruppe darstellt.
4. Verbindung nach Anspruch 3, worin die
polymerisierbare Gruppe ausgewählt ist aus der Gruppe -O-R&sub8;, -S-R&sub8;, -NR&sub7;R&sub8;,
-NR&sub7;C(O)R&sub8;, -OC(O)R&sub8;, -C(O)OR&sub8;, -C(O)NR&sub7;R&sub8;, -CH=N-O-R&sub8; und -NH-
C(O)-NR&sub7;R&sub8;, worin R&sub7; H oder C&sub1;-C&sub4;-Alkyl darstellt und R&sub8; eine
olefinische Gruppe mit 1 bis 12 Kohlenstoffatomen darstellt,
wobei die Gruppe an den dreiwertigen Rest T direkt oder über
eine Brückengruppe R&sub0;&sub3; gebunden ist.
5. Verbindung nach Anspruch 1, worin der dreiwertige
Rest C&sub1;-C&sub2;&sub0;-Alkantriyl darstellt, der linear oder verzweigt ist
und durch ein oder mehrere Heteroatom(e), ausgewählt aus der
Gruppe, O, S und N, unterbrochen ist.
6. Verbindung nach Anspruch 1, worin der dreiwertige
Rest ein Rest der Formel Ib oder Ic
=T&sub1;-R&sub0;&sub4;- (Ib),
-T&sub2;-R&sub0;&sub5;= (Ic),
ist, worin
T&sub1; einen cycloaliphatischen, heterocycloaliphatischen,
aromatischen oder heteroaromatischen dreiwertigen Rest
darstellt,
T&sub2; einen cycloaliphatischen, heterocycloaliphatischen,
aromatischen oder heteroaromatischen zweiwertigen Rest
darstellt,
R&sub0;&sub4; einen zweiwertigen aliphatischen Rest mit 1 bis 20
Kohlenstoffatomen darstellt und
R&sub0;&sub5; einen dreiwertigen aliphatischen Rest mit 1 bis 20
Kohlenstoffatomen darstellt.
7. Verbindung nach Anspruch 1, worin die Brückengruppe
R&sub0;&sub1; der Formel (IIa) entspricht,
-X&sub1;-(R&sub3;)r-X&sub2;- (IIa),
die Brückengruppe R&sub0;&sub2; der Formel (IIb) entspricht
-X&sub3;-(R&sub4;)s-X&sub4;- (IIb),
und die Brückengruppe R&sub0;&sub3; der Formel (IIc) entspricht,
-X&sub5;-(R&sub2;)t-X&sub7;- (IIc),
worin X&sub1;, X&sub2;, X&sub3;, X&sub4;, X&sub5; und X&sub7; jeweils unabhängig
voneinander eine direkte Bindung darstellen oder X&sub1;, X&sub2;, X&sub3;, X&sub4;, X&sub5;
und X&sub7; jeweils unabhängig voneinander ausgewählt sind aus der
Gruppe -O-, -S-, -NR&sub5;-, -C(O)-O-, -O-C(O)-, -O-C(O)-O-,
-SO&sub2;-O-, -O-SO&sub2;-, -O-SO&sub2;-O-, -NR&sub5;-C(O)-, -C(O)-NR&sub5;-,
-NR&sub5;-C(O)-O-, -O-C(O)-NR&sub5;-, -NRS-C(O)-NR&sub5;-, -NR&sub5;SO&sub2;-, -SO&sub2;-NR&sub5;-,
-NR&sub5;-SO&sub2;-O-, -O-SO&sub2;NR&sub5;- und -NR&sub5;SO&sub2;-NR&sub5;-,
R&sub5; H oder C&sub1;-C&sub3;&sub0;-Alkyl, C&sub5;- oder C&sub6;-Cycloalkyl, C&sub5;- oder
C&sub6;-Cycloalkylmethyl- oder -ethyl, Phenyl, Benzyl oder
1-Phenyleth-2-yl darstellt,
R&sub2;, R&sub3; und R&sub4; jeweils unabhängig voneinander eine
zweiwertige Brückengruppe darstellen,
r, s und t jeweils unabhängig voneinander 0 oder 1
sind, mit der Maßgabe, dass r, s oder t 1 ist, wenn X&sub1; oder X&sub3;
oder X&sub5; eine von diesen Gruppen darstellt.
8. Verbindung nach Anspruch 1, worin das Ionophor von
einer 1,3-alternierenden Calix[4]Krone-5 abgeleitet ist.
9. Verbindung nach Anspruch 1, worin das Ionophor von
einer 1,3-alternierenden Calix[4]Krone-5 der Formel IV
abgeleitet ist,
worin
R&sub0;&sub7; und R&sub0;&sub8; jeweils unabhängig voneinander H, lineares
oder verzweigtes C&sub1;-C&sub2;&sub0;-Alkyl oder lineares oder verzweigtes C&sub1;-
C&sub2;&sub0;-Alkoxy oder ein Säurederivat davon darstellen.
10. Verbindung nach Anspruch 1, worin das Ionophor von
einem Calix[4]aren abgeleitet ist.
11. Verbindung nach Anspruch 10, worin das Ionophor von
einem Calix[4]aren der Formel (IVa) abgeleitet ist
worin R&sub0;&sub6; H oder substituiertes oder unsubstituiertes
C&sub1;-C&sub2;&sub0;-Alkyl darstellt und
R&sub6; H oder substituiertes oder unsubstituiertes C&sub1;-C&sub3;&sub0;-
Alkyl darstellt.
12. Verbindung nach Anspruch 1, worin das Fluorophor,
von dem F in Formel (I) abgeleitet ist, eine Verbindung der
Formeln A-F darstellt
13. Verbindung nach Anspruch 1, worin das Fluorophor,
von dem F in Formel (I) abgeleitet ist, ein Acridin der Formel
oder ein Derivat davon darstellt, worin R&sub0;&sub1; und R&sub0;&sub2;
jeweils unabhängig voneinander H oder C&sub1;-C&sub2;&sub0;-Alkyl darstellen und
R&sub0;&sub3; H oder C&sub1;-C&sub6;-Alkyl darstellt.
14. Verbindung nach Anspruch 1, worin das
Fluoroionophor eine Verbindung der Formel (Ia) ist
worin
X&sub8;, X&sub9; und X&sub1;&sub0; jeweils unabhängig voneinander
-C(O)O-, -OC(O)-, -C(O)NR&sub5;- oder -NR&sub5;-C(O)- darstellen und I,
R&sub0;&sub1;, R&sub0;&sub2;, R&sub0;&sub3;, G und F wie in Anspruch 1 definiert sind, u eine
ganze Zahl von 1 bis 6 ist und die Reste R&sub5; jeweils unabhängig
voneinander H oder C&sub1;-C&sub4;-Alkyl darstellen.
15. Verbindung nach Anspruch 1, die ein Fluoroionophor
der Formel
darstellt.
16. Verbindung nach Anspruch 1, die ein Fluoroionophor
der Formel
darstellt.
17. Verbindung nach Anspruch 1, die ein Fluoroionophor
der Formel
darstellt.
18. Zusammensetzung, umfassend (a) ein anorganisches
oder organisches Trägermaterial, an das (b), ein
Fluoroionophor der Formel (I), über die funktionelle Gruppe G direkt
oder über eine Brückengruppe gebunden ist.
19. Zusammensetzung nach Anspruch 18, worin das
Trägermaterial ein organisches Trägermaterial darstellt, das ein
Polymer ist, umfassend Monomere mit kovalent gebundenem
Fluoroionophor (Ausführungsform A).
20. Zusammensetzung nach Anspruch 18, worin das
Trägermaterial ein fein verteiltes anorganisches oder organisches
Trägermaterial an dessen Oberfläche das Fluoroionophor
kovalent gebunden ist (Ausführungsform B).
21. Zusammensetzung nach Anspruch 18, die eine
Ausführungsform (B) darstellt, worin das Fluoroionophor kovalent an
die Oberfläche eines fein verteilten Trägermaterials gebunden
ist.
22. Zusammensetzung nach Anspruch 19, worin die Menge
des Fluoroionophors, das kovalent an das Trägermaterial
gebunden ist, 0,0001 bis 99 Gewichtsprozent, bezogen auf das
Trägermaterial, beträgt.
23. Material, umfassend (a) einen Träger und (b) eine
aktive Schicht auf mindestens einer Oberfläche, wobei die
aktive Schicht aus (1) einem Polymer nach Anspruch 19, einzeln
oder in Anmischung mit einem Polymer Z oder (2) einem Polymer
Z, worin Teilchen gemäß Anspruch 20 eingearbeitet sind,
besteht.
24. Zusammensetzung, umfassend (a) eine Verbindung der
Formel I, einzeln, oder (b) zusammen mit mindestens einem
Comonomer und, falls geeignet, ein Lösungsmittel für Komponenten
(a) und (b).
25. Verwendung einer Zusammensetzung nach Anspruch 18
als eine aktive Schicht in optischen Sensoren für die
Bestimmung von Ionen.
26. Verwendung eines Materials nach Anspruch 23 als ein
optischer Sensor für die Bestimmung von Kationen oder Anionen
durch Spektroskopie, insbesondere Fluoreszenzspektroskopie.
27. Verfahren für die optische Bestimmung von Ionen in
wässerigen Testproben, wobei eine aktive Schicht des Materials
nach Anspruch 23 mit einer wässerigen Testprobe in Kontakt
gebracht wird und dann die Änderung der Fluoreszenz gemessen
wird.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH183296 | 1996-07-22 | ||
| PCT/EP1997/003913 WO1998003497A1 (en) | 1996-07-22 | 1997-07-21 | Covalently immobilised fluoroionophores for optical ion sensors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69710584D1 DE69710584D1 (de) | 2002-03-28 |
| DE69710584T2 true DE69710584T2 (de) | 2003-04-24 |
Family
ID=4219649
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69710584T Expired - Lifetime DE69710584T2 (de) | 1996-07-22 | 1997-07-21 | Kovalent immobilisierte fluoroionophoren für optische ionen-sensoren |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6294390B1 (de) |
| EP (1) | EP0915865B1 (de) |
| JP (1) | JP4223555B2 (de) |
| AU (1) | AU3695897A (de) |
| DE (1) | DE69710584T2 (de) |
| WO (1) | WO1998003497A1 (de) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6165796A (en) * | 1997-11-26 | 2000-12-26 | Beckman Coulter, Inc. | Pipettable ion detector and method |
| US6406668B1 (en) * | 1998-08-03 | 2002-06-18 | University Of Iowa Research Foundation | Sensing array and sensor structure |
| WO2001004623A1 (de) * | 1999-07-07 | 2001-01-18 | Fritz Andreae | Optischer sensor für kaliumionen |
| US6660526B2 (en) | 2001-12-21 | 2003-12-09 | Bayer Corporation | Potassium fluoroionophore |
| WO2004022033A1 (en) * | 2002-09-04 | 2004-03-18 | Microchips, Inc. | Method and device for the controlled delivery of parathyroid hormone |
| WO2006081279A2 (en) | 2005-01-25 | 2006-08-03 | Microchips, Inc. | Control of drug release by transient modification of local microenvironments |
| US8242203B2 (en) | 2005-11-10 | 2012-08-14 | Eric Bakker | Covalently attached nile blue derivatives for optical sensors |
| WO2007059449A2 (en) * | 2005-11-10 | 2007-05-24 | Beckman Coulter, Inc. | Covalently attached nile blue derivatives for optical sensors |
| WO2009023287A1 (en) * | 2007-08-16 | 2009-02-19 | Beckman Coulter, Inc. | Polymerized nile blue derivatives for plasticizer-free fluorescent ion optode microsphere sensors |
| CN105175623A (zh) * | 2010-05-06 | 2015-12-23 | 康奈尔大学 | 可调lcst聚合物及其制备方法 |
| RU2449261C1 (ru) * | 2011-02-08 | 2012-04-27 | Открытое акционерное общество "Государственный научный центр Научно-исследовательский институт атомных реакторов" | СПОСОБ ОПРЕДЕЛЕНИЯ МАССОВЫХ КОНЦЕНТРАЦИЙ ОСНОВНЫХ И ПРИМЕСНЫХ ЭЛЕМЕНТОВ В МАТЕРИАЛАХ И ИЗДЕЛИЯХ ИЗ ТИТАНАТА ДИСПРОЗИЯ (Dy2O3·TiO2) ГАФНАТА ДИСПРОЗИЯ (nDy2O3·mHfO2) И ИХ СМЕСЕЙ |
| JP6288669B2 (ja) * | 2014-02-18 | 2018-03-07 | 独立行政法人国立高等専門学校機構 | 環境汚染物質の検出材およびその製造方法、ならびに環境汚染の評価方法 |
| US10407436B2 (en) * | 2015-06-09 | 2019-09-10 | Andrei POLUKHTIN | Carboxamide-substituted xanthene dyes |
| CN106543120A (zh) * | 2016-11-02 | 2017-03-29 | 武汉工程大学 | 化合物偏苯三酸酐正丁酯及其合成方法 |
| CN106543122A (zh) * | 2016-11-02 | 2017-03-29 | 武汉工程大学 | 化合物1,5‑二偏苯三酸酐戊二酯及其合成方法 |
| CN106543121A (zh) * | 2016-11-02 | 2017-03-29 | 武汉工程大学 | 化合物偏苯三酸酐正庚酯及其合成方法 |
| JP7536496B2 (ja) * | 2019-06-10 | 2024-08-20 | 保土谷化学工業株式会社 | キサンテン系色素、該色素を含有する着色組成物、カラーフィルター用着色剤およびカラーフィルター |
| RU2747025C1 (ru) * | 2020-10-23 | 2021-04-23 | ФЕДЕРАЛЬНОЕ ГОСУДАРСТВЕННОЕ УНИТАРНОЕ ПРЕДПРИЯТИЕ "ИНСТИТУТ ХИМИЧЕСКИХ РЕАКТИВОВ И ОСОБО ЧИСТЫХ ХИМИЧЕСКИХ ВЕЩЕСТВ НАЦИОНАЛЬНОГО ИССЛЕДОВАТЕЛЬСКОГО ЦЕНТРА "КУРЧАТОВСКИЙ ИНСТИТУТ" (НИЦ "Курчатовский институт - ИРЕА") | Способ получения 4-(или 5)-аминотетра-C1-C2-алкилродаминов |
| RU2747027C1 (ru) * | 2020-10-23 | 2021-04-23 | ФЕДЕРАЛЬНОЕ ГОСУДАРСТВЕННОЕ УНИТАРНОЕ ПРЕДПРИЯТИЕ "ИНСТИТУТ ХИМИЧЕСКИХ РЕАКТИВОВ И ОСОБО ЧИСТЫХ ХИМИЧЕСКИХ ВЕЩЕСТВ НАЦИОНАЛЬНОГО ИССЛЕДОВАТЕЛЬСКОГО ЦЕНТРА "КУРЧАТОВСКИЙ ИНСТИТУТ" (НИЦ "Курчатовский институт - ИРЕА") | Способ получения смеси 4(или 5)-нитротетраэтилродаминов |
| CN113189262A (zh) * | 2021-05-31 | 2021-07-30 | 广西壮族自治区食品药品检验所 | 一种红葱的质量检测方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1452777A (fr) * | 1964-07-23 | 1966-04-15 | Spofa Vereinigte Pharma Werke | Procédé pour la préparation des dérivés xanthéniques ainsi que les produits conformes à ceux obtenus par le présent procédé ou procédé similaire |
| DE2842862A1 (de) | 1978-10-02 | 1980-04-10 | Boehringer Mannheim Gmbh | Verfahren zur bestimmung von ionen, polaren und/oder lipophilen substanzen in fluessigkeiten |
| US5177221A (en) * | 1987-04-15 | 1993-01-05 | Miles Inc. | Chromogenic hemispherands and their preparation |
| US5162525A (en) | 1987-07-31 | 1992-11-10 | Allied-Signal Inc. | Fluorogenic and chromogenic three-dimensional ionophores as selective reagents for detecting ions in biological fluids |
| GB9126829D0 (en) * | 1991-12-18 | 1992-02-19 | Kodak Ltd | Ion-sensitive dyes |
| EP0623599A1 (de) * | 1993-03-26 | 1994-11-09 | Ciba-Geigy Ag | Optischer Sensor zur Bestimmung von Kationen |
-
1997
- 1997-07-21 JP JP50657098A patent/JP4223555B2/ja not_active Expired - Fee Related
- 1997-07-21 WO PCT/EP1997/003913 patent/WO1998003497A1/en active IP Right Grant
- 1997-07-21 EP EP97933688A patent/EP0915865B1/de not_active Expired - Lifetime
- 1997-07-21 AU AU36958/97A patent/AU3695897A/en not_active Abandoned
- 1997-07-21 DE DE69710584T patent/DE69710584T2/de not_active Expired - Lifetime
- 1997-07-21 US US09/230,217 patent/US6294390B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US6294390B1 (en) | 2001-09-25 |
| JP4223555B2 (ja) | 2009-02-12 |
| JP2000516580A (ja) | 2000-12-12 |
| WO1998003497A1 (en) | 1998-01-29 |
| AU3695897A (en) | 1998-02-10 |
| EP0915865A1 (de) | 1999-05-19 |
| DE69710584D1 (de) | 2002-03-28 |
| WO1998003497A9 (en) | 1999-10-28 |
| EP0915865B1 (de) | 2002-02-20 |
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