Dyes undergoing changes in color and fluorescence upon binding of organic oxo compounds

Abstract

A dye encompassing a donor-acceptor-donor motif having a structure according to formulae (1), (2), (3), (4), (5), (6), (7) or (8): 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, 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; 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; X3=O, S, NH or NH2+X−, wherein X− is selected from: F−, Cl−, Br−, I−, NO3−, PF6−, ClO4−, BF4−, 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. Further, a molecular probe, an analyte sensitive layer, a molecularly imprinted polymer, a sensor arrangement—each having the dye are provided as well as its use for different analytical purposes and imaging.

Dependencies are inferred from the claim text.