Dyes undergoing changes in color and fluorescence upon binding of organic oxo compounds
AssigneeBundesrepublik Deutschland, vertreten durch den Bundesminister für Wirtschaft und Energie, dieser vertreten durch den Präsidenten der Bundesanstalt für Materialforschung und -prüfung, (BAM)
InventorsKnut Rurack, Kornelia Gawlitza, Virginia Valderrey Berciano, Victor Pérez Padilla
Life of this patent
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Abstract
A dye for fluorescence detection of an organic oxo compound, oxo acid or their anion, having a donor-acceptor-donor motif according to formulae (1) with terms as defined herein for use as molecular probe, in an analyte sensitive layer or molecularly imprinted polymer.
Claims14
A dye comprising an electron donor-electron acceptor-electron donor motif, wherein the electron donor-electron acceptor-electron donor motif comprises a structure according to formula 1:
- wherein, independently from each other,
- R1=H, CnF2n+1, C5NH4, C4N2H3,
- (CH2)nQ, (C6H5-m)Qm or (OCH2CH2)nQ, wherein m=1,2, 3 or 4, and Q is selected from:
- H,
- C(H)═CH2,
- OC(O)C(H)═CH2, OC(O)C(CH3)═CH2,
- N(H)CC(H)═CH2, N(H)CC(CH3)═CH2,
- Si(OH)3, Si(OCH3)3, Si(OC2H5)3,
- OH, SH, NH2, NO2, CN, CF3, C≡CH, N═N+═N−, F, Cl, Br, I, C2H3O, C6H5,
- C(O)F, C(O)Cl, C(O)Br, C(O)I, CF3SO3,
- B(OZ)2, OZ, C(O)Z, C(O)OZ, C(O)NHZ, C(O)NZ2, and SSZ, wherein
- Z═H, CnH2n+1, CnF2n+1, CnH2nC(H)═CH2, CnH2nC≡CH,
- C6H4C(H)═CH2, C6H5, CH2C6H5, C5NH4 or C4N2H3,
- wherein n=1 to 20;
- R2═H, CnF2n+1, C5NH4, C4N2H3,
- (CH2)nQ or (C6H5-m)Qm, wherein m=1, 2, 3 or 4, and Q is selected from:
- H,
- C(H)═CH2,
- OC(O)C(H)═CH2, OC(O)C(CH3)═CH2,
- N(H)CC(H)═CH2, N(H)CC(CH3)═CH2,
- Si(OH)3, Si(OCH3)3, Si(OC2H5)3,
- OH, SH, NH2, NO2, CN, CF3, C≡CH, N═N+═N−, F, Cl, Br, I, C2H30, C6H5,
- C(O)F, C(O)Cl, C(O)Br, C(O)I, CF3SO3,
- B(OZ)2, OZ, C(O)Z, C(O)OZ, C(O)NHZ, C(O)NZ2, and SSZ, wherein
- Z═H, CnH2n+1, CnF2n+1, CnH2nC(H)═CH2, CnH2nC≡CH,
- C6H4C(H)═CH2, C6H5, CH2C6H5, C5NH4 or C4N2H3,
- wherein n=1 to 20;
- R3═H, CnF2n+1, C5NH4, C4N2H3, C(O)C6H5, C(S)C6H5,
- (CH2)nQ or (C6H5-m)Qm, wherein m=1, 2, 3 or 4, and Q is selected from:
- H,
- C(H)═CH2,
- OC(O)C(H)═CH2, OC(O)C(CH3)═CH2,
- N(H)CC(H)═CH2, N(H)CC(CH3)═CH2,
- Si(OH)3, Si(OCH3)3, Si(OC2H5)3,
- OH, SH, NH2, NO2, CN, CF3, C≡CH, N═N+═N−, F, Cl, Br, I, C2H3O, C6H5,
- C(O)F, C(O)Cl, C(O)Br, C(O)I, CF3SO3,
- B(OZ)2, OZ, C(O)Z, C(O)OZ, C(O)NHZ, C(O)NZ2, and SSZ, wherein
- Z═H, CnH2n+1, CnF2n+1, CnH2nC(H)═CH2, CnH2nC≡CH,
- C6H4C(H)═CH2, C6H5, CH2C6H5, C5NH4 or C4N2H3,
- wherein n=1 to 20;
- X1═N, C(CN), C(COOEt) or C(NO2);
- X2=C(CH3)2, Si (CH3)2, O, S, Se or Te;
- and
- X3=O, S, NH or NH2+X−, wherein X− is selected from:
- F−, Cl−, Br−, I−, NO3−, PF6−, ClO4, BF4−, B4−, B[3,5-(CF3)2C6H3]4−, B(C6H5)4−, Al[OC(CF3)3]4−, H2BO3−, BrO3−, HCO3−, H2NCO2−, C6H5CO2−, C6H5CH2−, and RCOO−, wherein R=saturated alkyl or unsaturated alkyl or aryl.
Dependencies are inferred from the claim text.