CA2425105C - Composes fluorescents - Google Patents

Composes fluorescents Download PDF

Info

Publication number: CA2425105C
Authority: CA; Canada
Prior art keywords: chelate; polymer; tritium; organic polymer; light
Prior art date: 1992-02-14
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 - Fee Related

Application number

CA002425105A

Other languages

English (en)

Other versions

CA2425105A1 (fr

Inventor

Colin David Bell

John Hewer C. Howse

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Eckert and Ziegler Nuclitec GmbH

Original Assignee

QSA UK Ltd

Priority date (The priority date 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 date listed.)

1992-02-14

Filing date

1993-02-10

Publication date

2006-06-20

1993-02-10 Application filed by QSA UK Ltd filed Critical QSA UK Ltd

1993-02-10 Priority claimed from CA002089198A external-priority patent/CA2089198C/fr

1993-08-15 Publication of CA2425105A1 publication Critical patent/CA2425105A1/fr

2006-06-20 Application granted granted Critical

2006-06-20 Publication of CA2425105C publication Critical patent/CA2425105C/fr

2013-02-10 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title abstract description 46
239000013522 chelant Substances 0.000 claims abstract description 40
239000000178 monomer Substances 0.000 claims abstract description 35
YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims abstract description 29
229910052722 tritium Inorganic materials 0.000 claims abstract description 29
229910052751 metal Inorganic materials 0.000 claims abstract description 27
239000002184 metal Substances 0.000 claims abstract description 27
239000007787 solid Substances 0.000 claims abstract description 23
230000005855 radiation Effects 0.000 claims abstract description 19
229910052747 lanthanoid Inorganic materials 0.000 claims abstract description 13
150000002602 lanthanoids Chemical class 0.000 claims abstract description 12
230000007704 transition Effects 0.000 claims abstract description 11
229910052768 actinide Inorganic materials 0.000 claims abstract description 10
150000001255 actinides Chemical class 0.000 claims abstract description 9
239000000203 mixture Substances 0.000 claims description 32
239000011541 reaction mixture Substances 0.000 claims description 21
125000003118 aryl group Chemical group 0.000 claims description 11
229920000620 organic polymer Polymers 0.000 claims description 11
230000000694 effects Effects 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 5
150000002430 hydrocarbons Chemical class 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 4
239000004215 Carbon black (E152) Substances 0.000 claims description 4
229930195733 hydrocarbon Natural products 0.000 claims description 4
230000005258 radioactive decay Effects 0.000 claims description 4
HKCRVXUAKWXBLE-UHFFFAOYSA-N terbium(3+) Chemical group [Tb+3] HKCRVXUAKWXBLE-UHFFFAOYSA-N 0.000 claims description 4
BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 claims description 3
LNBHUCHAFZUEGJ-UHFFFAOYSA-N europium(3+) Chemical group [Eu+3] LNBHUCHAFZUEGJ-UHFFFAOYSA-N 0.000 claims description 3
NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 3
229920000592 inorganic polymer Polymers 0.000 claims description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 3
229920001169 thermoplastic Polymers 0.000 claims description 2
239000004416 thermosoftening plastic Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims 2
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims 1
125000004431 deuterium atom Chemical group 0.000 claims 1
229920000642 polymer Polymers 0.000 abstract description 50
239000007983 Tris buffer Substances 0.000 abstract description 23
229910052693 Europium Inorganic materials 0.000 abstract description 13
239000004793 Polystyrene Substances 0.000 abstract description 13
229920002223 polystyrene Polymers 0.000 abstract description 13
-1 actinide metals Chemical class 0.000 abstract description 12
OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 abstract description 12
BXXYQIADDPAMGV-UHFFFAOYSA-N diphenylphosphorylimino(triphenyl)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)N=P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BXXYQIADDPAMGV-UHFFFAOYSA-N 0.000 abstract description 8
239000003153 chemical reaction reagent Substances 0.000 abstract description 7
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 38
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
239000000243 solution Substances 0.000 description 29
239000000047 product Substances 0.000 description 21
229910052771 Terbium Inorganic materials 0.000 description 19
GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 19
229910021645 metal ion Inorganic materials 0.000 description 16
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
238000002360 preparation method Methods 0.000 description 15
239000003054 catalyst Substances 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
239000002904 solvent Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
230000002285 radioactive effect Effects 0.000 description 9
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 8
UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 8
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
FLTJDUOFAQWHDF-UHFFFAOYSA-N trimethyl pentane Natural products CCCCC(C)(C)C FLTJDUOFAQWHDF-UHFFFAOYSA-N 0.000 description 8
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000007789 gas Substances 0.000 description 7
150000002500 ions Chemical class 0.000 description 7
238000000034 method Methods 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
229910052772 Samarium Inorganic materials 0.000 description 6
230000005284 excitation Effects 0.000 description 6
238000009472 formulation Methods 0.000 description 6
239000000463 material Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
230000009467 reduction Effects 0.000 description 6
238000010992 reflux Methods 0.000 description 6
KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 6
239000000126 substance Substances 0.000 description 6
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
206010056740 Genital discharge Diseases 0.000 description 5
238000001816 cooling Methods 0.000 description 5
230000005670 electromagnetic radiation Effects 0.000 description 5
238000000295 emission spectrum Methods 0.000 description 5
239000011521 glass Substances 0.000 description 5
239000003999 initiator Substances 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
101000738734 Drosophila melanogaster Tyrosine-protein phosphatase 69D Proteins 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
238000010521 absorption reaction Methods 0.000 description 4
238000000695 excitation spectrum Methods 0.000 description 4
238000002372 labelling Methods 0.000 description 4
238000005259 measurement Methods 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
150000003053 piperidines Chemical class 0.000 description 4
229910052761 rare earth metal Inorganic materials 0.000 description 4
239000000376 reactant Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
238000000576 coating method Methods 0.000 description 3
LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
229910052698 phosphorus Inorganic materials 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
150000002910 rare earth metals Chemical class 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
DOMPAWFABHDXFM-UHFFFAOYSA-N terbium;2,2,6,6-tetramethylheptane-3,5-dione Chemical compound [Tb].CC(C)(C)C(=O)CC(=O)C(C)(C)C.CC(C)(C)C(=O)CC(=O)C(C)(C)C.CC(C)(C)C(=O)CC(=O)C(C)(C)C DOMPAWFABHDXFM-UHFFFAOYSA-N 0.000 description 3
238000012546 transfer Methods 0.000 description 3
229910052723 transition metal Inorganic materials 0.000 description 3
150000003624 transition metals Chemical class 0.000 description 3
FCTBKIHDJGHPPO-UHFFFAOYSA-N uranium dioxide Inorganic materials O=[U]=O FCTBKIHDJGHPPO-UHFFFAOYSA-N 0.000 description 3
125000005289 uranyl group Chemical group 0.000 description 3
229920002554 vinyl polymer Polymers 0.000 description 3
PPBRXRYQALVLMV-GDALLCCDSA-N 1,2,3,4,5-pentadeuterio-6-(1,2,2-trideuterioethenyl)benzene Chemical compound [2H]C([2H])=C([2H])C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] PPBRXRYQALVLMV-GDALLCCDSA-N 0.000 description 2
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
229910052692 Dysprosium Inorganic materials 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
239000002879 Lewis base Substances 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
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JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
239000005083 Zinc sulfide Substances 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
229910052787 antimony Inorganic materials 0.000 description 2
229910052785 arsenic Inorganic materials 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
XZCJVWCMJYNSQO-UHFFFAOYSA-N butyl pbd Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)O1 XZCJVWCMJYNSQO-UHFFFAOYSA-N 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
239000000356 contaminant Substances 0.000 description 2
239000003431 cross linking reagent Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
229910052805 deuterium Inorganic materials 0.000 description 2
MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 description 2
JZFGFESISFGKQO-LWTKGLMZSA-K dysprosium(3+);(z)-2,2,6,6-tetramethyl-5-oxohept-3-en-3-olate Chemical compound [Dy+3].CC(C)(C)C(\[O-])=C\C(=O)C(C)(C)C.CC(C)(C)C(\[O-])=C\C(=O)C(C)(C)C.CC(C)(C)C(\[O-])=C\C(=O)C(C)(C)C JZFGFESISFGKQO-LWTKGLMZSA-K 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
230000004907 flux Effects 0.000 description 2
238000007429 general method Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
150000007527 lewis bases Chemical class 0.000 description 2
239000003446 ligand Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000011068 loading method Methods 0.000 description 2
239000011159 matrix material Substances 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 2
150000004682 monohydrates Chemical class 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
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DOSGOCSVHPUUIA-UHFFFAOYSA-N samarium(3+) Chemical compound [Sm+3] DOSGOCSVHPUUIA-UHFFFAOYSA-N 0.000 description 2
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238000007493 shaping process Methods 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
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ZMBHCYHQLYEYDV-UHFFFAOYSA-N trioctylphosphine oxide Chemical compound CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC ZMBHCYHQLYEYDV-UHFFFAOYSA-N 0.000 description 2
FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 2
ZRAOLHHYMQLCAW-UHFFFAOYSA-N tris(1h-pyrazol-5-yl) borate Chemical compound C1=CNN=C1OB(OC1=NNC=C1)OC=1C=CNN=1 ZRAOLHHYMQLCAW-UHFFFAOYSA-N 0.000 description 2
238000009281 ultraviolet germicidal irradiation Methods 0.000 description 2
238000005292 vacuum distillation Methods 0.000 description 2
DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 2
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CORMBJOFDGICKF-UHFFFAOYSA-N 1,3,5-trimethoxy 2-vinyl benzene Natural products COC1=CC(OC)=C(C=C)C(OC)=C1 CORMBJOFDGICKF-UHFFFAOYSA-N 0.000 description 1
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OEVVKKAVYQFQNV-UHFFFAOYSA-N 1-ethenyl-2,4-dimethylbenzene Chemical compound CC1=CC=C(C=C)C(C)=C1 OEVVKKAVYQFQNV-UHFFFAOYSA-N 0.000 description 1
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125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
QEDJMOONZLUIMC-UHFFFAOYSA-N 1-tert-butyl-4-ethenylbenzene Chemical compound CC(C)(C)C1=CC=C(C=C)C=C1 QEDJMOONZLUIMC-UHFFFAOYSA-N 0.000 description 1
BYSUYBCCLCSGPR-UHFFFAOYSA-N 1h-pyrazol-5-yloxyboronic acid Chemical compound OB(O)OC1=CC=NN1 BYSUYBCCLCSGPR-UHFFFAOYSA-N 0.000 description 1
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FZZACAFXVBODJN-UHFFFAOYSA-N 2,2-dichloro-5-(2-phenylethyl)-4-trimethylsilylfuran-3-one Chemical compound O1C(Cl)(Cl)C(=O)C([Si](C)(C)C)=C1CCC1=CC=CC=C1 FZZACAFXVBODJN-UHFFFAOYSA-N 0.000 description 1
PDELBHCVXBSVPJ-UHFFFAOYSA-N 2-ethenyl-1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=C(C=C)C(C)=C1 PDELBHCVXBSVPJ-UHFFFAOYSA-N 0.000 description 1
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125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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241000720974 Protium Species 0.000 description 1
240000001987 Pyrus communis Species 0.000 description 1
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COQLPRJCUIATTQ-UHFFFAOYSA-N Uranyl acetate Chemical compound O.O.O=[U]=O.CC(O)=O.CC(O)=O COQLPRJCUIATTQ-UHFFFAOYSA-N 0.000 description 1
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SZYDIWSZWMYIPR-UHFFFAOYSA-N [PH2](=O)Cl.C1(=CC=CC=C1)C1=CC=CC=C1 Chemical compound [PH2](=O)Cl.C1(=CC=CC=C1)C1=CC=CC=C1 SZYDIWSZWMYIPR-UHFFFAOYSA-N 0.000 description 1
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WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical group C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
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RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
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230000003197 catalytic effect Effects 0.000 description 1
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NNMXSTWQJRPBJZ-UHFFFAOYSA-K europium(iii) chloride Chemical compound Cl[Eu](Cl)Cl NNMXSTWQJRPBJZ-UHFFFAOYSA-K 0.000 description 1
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230000005283 ground state Effects 0.000 description 1
VOAPTKOANCCNFV-UHFFFAOYSA-N hexahydrate;hydrochloride Chemical compound O.O.O.O.O.O.Cl VOAPTKOANCCNFV-UHFFFAOYSA-N 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
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238000011835 investigation Methods 0.000 description 1
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DNNSSWSSYDEUBZ-OUBTZVSYSA-N krypton-85 Chemical compound [85Kr] DNNSSWSSYDEUBZ-OUBTZVSYSA-N 0.000 description 1
229910021644 lanthanide ion Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
YERRTOUSFSZICJ-UHFFFAOYSA-N methyl 2-amino-2-(4-bromophenyl)acetate Chemical compound COC(=O)C(N)C1=CC=C(Br)C=C1 YERRTOUSFSZICJ-UHFFFAOYSA-N 0.000 description 1
239000011325 microbead Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
HDBWAWNLGGMZRQ-UHFFFAOYSA-N p-Vinylbiphenyl Chemical group C1=CC(C=C)=CC=C1C1=CC=CC=C1 HDBWAWNLGGMZRQ-UHFFFAOYSA-N 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
VBQCHPIMZGQLAZ-UHFFFAOYSA-N phosphorane Chemical class [PH5] VBQCHPIMZGQLAZ-UHFFFAOYSA-N 0.000 description 1
239000002985 plastic film Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
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238000001953 recrystallisation Methods 0.000 description 1
230000011514 reflex Effects 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
BHXBZLPMVFUQBQ-UHFFFAOYSA-K samarium(iii) chloride Chemical compound Cl[Sm](Cl)Cl BHXBZLPMVFUQBQ-UHFFFAOYSA-K 0.000 description 1
230000007017 scission Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
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230000003595 spectral effect Effects 0.000 description 1
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BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
GFISHBQNVWAVFU-UHFFFAOYSA-K terbium(iii) chloride Chemical compound Cl[Tb](Cl)Cl GFISHBQNVWAVFU-UHFFFAOYSA-K 0.000 description 1
MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
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229910001428 transition metal ion Inorganic materials 0.000 description 1
STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
ULJUVCOAZNLCJZ-UHFFFAOYSA-K trichloroterbium;hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Cl-].[Tb+3] ULJUVCOAZNLCJZ-UHFFFAOYSA-K 0.000 description 1
XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
AXVOAMVQOCBPQT-UHFFFAOYSA-N triphos Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 AXVOAMVQOCBPQT-UHFFFAOYSA-N 0.000 description 1
238000005533 tritiation Methods 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
238000012800 visualization Methods 0.000 description 1
238000002424 x-ray crystallography Methods 0.000 description 1
229940106670 xenon-133 Drugs 0.000 description 1
239000008096 xylene Substances 0.000 description 1

CA002425105A 1992-02-14 1993-02-10 Composes fluorescents Expired - Fee Related CA2425105C (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
EP92301249		1992-02-14
EP92301249.6		1992-02-14
CA002089198A CA2089198C (fr)	1992-02-14	1993-02-10	Composes fluorescents

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CA002089198A Division CA2089198C (fr)	1992-02-14	1993-02-10	Composes fluorescents

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CA2425105A1 CA2425105A1 (fr)	1993-08-15
CA2425105C true CA2425105C (fr)	2006-06-20

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CA002425105A Expired - Fee Related CA2425105C (fr)	1992-02-14	1993-02-10	Composes fluorescents

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- 1993-02-10 CA CA002425105A patent/CA2425105C/fr not_active Expired - Fee Related

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Publication	Publication Date	Title
CA2089198C (fr)	2004-08-31	Composes fluorescents
EP0688849B1 (fr)	2000-01-12	Composés fluorescents
EP0913448B1 (fr)	2003-06-18	Composé fluorescent
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US5658494A (en)	1997-08-19	Fluorescent compounds
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De Silva et al.	2006	Highly luminescent Eu (III) complexes with 2, 4, 6-tri (2-pyridyl)-1, 3, 5-triazine ligand: Synthesis, structural characterization, and photoluminescence studies
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