C09B62/523

DYES UNDERGOING CHANGES IN COLOR AND FLUORESCENCE UPON BINDING OF ORGANIC OXO COMPOUNDS

A dye encompassing a donor-acceptor-donor motif having a structure according to formulae (1), (2), (3), (4), (5), (6), (7) or (8):

##STR00001## ##STR00002## wherein, independently from each other, R.sup.1=H, C.sub.nF.sub.2n+1, C.sub.5NH.sub.4, C.sub.4N.sub.2H.sub.3, (CH.sub.2).sub.nQ, (C.sub.6H.sub.5?m)Q.sub.m or (OCH.sub.2CH.sub.2).sub.nQ, wherein m=1, 2, 3 or 4, and Q is selected from: H, C(H)=CH.sub.2, OC(O)C(H)?CH.sub.2, OC(O)C(CH.sub.3)?CH.sub.2, N(H)CC(H)?CH.sub.2, N(H)CC(CH.sub.3)?CH.sub.2, Si(OH).sub.3, Si(OCH.sub.3).sub.3, Si(OC.sub.2H.sub.5).sub.3, OH, SH, NH.sub.2, NO.sub.2, CN, CF.sub.3, C?CH, N?N.sup.+?N.sup.?, F, Cl, Br, I, C.sub.2H.sub.3O, C.sub.6H.sub.5, C(O)F, C(O)Cl, C(O)Br, C(O)I, CF.sub.3SO.sub.3, B(OZ).sub.2, OZ, C(O)Z, C(O)OZ, C(O)NHZ, C(O)NZ.sub.2, and SSZ, wherein Z=H, C.sub.nH.sub.2n+1, C.sub.nF.sub.2n+1, C.sub.nH.sub.2nC(H)?CH.sub.2, C.sub.nH.sub.2nC?CH, C.sub.6H.sub.4C(H)?CH.sub.2, C.sub.6H.sub.5, CH.sub.2C.sub.6H.sub.5, C.sub.5NH.sub.4 or C.sub.4N.sub.2H.sub.3, wherein n=1 to 20; R.sup.2=H, C.sub.nF.sub.2n+1, C.sub.5NH.sub.4, C.sub.4N.sub.2H.sub.3, (CH.sub.2).sub.nQ or (C.sub.6H.sub.5?m)Q.sub.m wherein m=1, 2, 3 or 4, and Q is selected from: H, C(H)?CH.sub.2, OC(O)C(H)?CH.sub.2, OC(O)C(CH.sub.3)?CH.sub.2, N(H)CC(H)?CH.sub.2, N(H)CC(CH.sub.3)?CH.sub.2, Si(OH).sub.3, Si(OCH.sub.3).sub.3, Si(OC.sub.2H.sub.5).sub.3, OH, SH, NH.sub.2, NO.sub.2, CN, CF.sub.3, C?CH, N?N.sup.+?N.sup.?, F, Cl, Br, I, C.sub.2H.sub.3O, C.sub.6H.sub.5, C(O)F, C(O)Cl, C(O)Br, C(O)I, CF.sub.3SO.sub.3, B(OZ).sub.2, OZ, C(O)Z, C(O)OZ, C(O)NHZ, C(O)NZ.sub.2, and SSZ, wherein Z=H, C.sub.nH.sub.2n+1, C.sub.nF.sub.2n+1, C.sub.nH.sub.2nC(H)?CH.sub.2, C.sub.nH.sub.2nC?CH, C.sub.6H.sub.4C(H)?CH.sub.2, C.sub.6H.sub.5, CH.sub.2C.sub.6H.sub.5, C.sub.5NH.sub.4 or C.sub.4N.sub.2H.sub.3, wherein n=1 to 20; R.sup.3=H, C.sub.nF.sub.2n+1, C.sub.5NH.sub.4, C.sub.4N.sub.2H.sub.3, C(O)C.sub.6H.sub.5, C(S)C.sub.6H.sub.5, (CH.sub.2).sub.nQ or (C.sub.6H.sub.5?m)Q.sub.m, wherein m=1, 2, 3 or 4, and Q is selected from: H, C(H)?CH.sub.2, OC(O)C(H)?CH.sub.2, OC(O)C(CH.sub.3)?CH.sub.2, N(H)CC(H)?CH.sub.2, N(H)CC(CH.sub.3)?CH.sub.2, Si(OH).sub.3, Si(OCH.sub.3).sub.3, Si(OC.sub.2H.sub.5).sub.3, OH, SH, NH.sub.2, NO.sub.2, CN, CF.sub.3, C?CH, N?N.sup.+?N.sup.?, F, Cl, Br, I, C.sub.2H.sub.3O, C.sub.6H.sub.5, C(O)F, C(O)Cl, C(O)Br, C(O)I, CF.sub.3SO.sub.3, B(OZ).sub.2, OZ, C(O)Z, C(O)OZ, C(O)NHZ, C(O)NZ.sub.2, and SSZ, wherein Z=H, C.sub.nH.sub.2n+1, C.sub.nF.sub.2n+1, C.sub.nH.sub.2nC(H)?CH.sub.2, C.sub.nH.sub.2nC?CH, C.sub.6H.sub.4C(H)?CH.sub.2, C.sub.6H.sub.5, CH.sub.2C.sub.6H.sub.5, C.sub.5NH.sub.4 or C.sub.4N.sub.2H.sub.3, wherein n=1 to 20; X.sup.1=N, C(CN), C(COOEt) or C(NO.sub.2)

DYES UNDERGOING CHANGES IN COLOR AND FLUORESCENCE UPON BINDING OF ORGANIC OXO COMPOUNDS

A dye encompassing a donor-acceptor-donor motif having a structure according to formulae (1), (2), (3), (4), (5), (6), (7) or (8):

##STR00001## ##STR00002## wherein, independently from each other, R.sup.1=H, C.sub.nF.sub.2n+1, C.sub.5NH.sub.4, C.sub.4N.sub.2H.sub.3, (CH.sub.2).sub.nQ, (C.sub.6H.sub.5?m)Q.sub.m or (OCH.sub.2CH.sub.2).sub.nQ, wherein m=1, 2, 3 or 4, and Q is selected from: H, C(H)=CH.sub.2, OC(O)C(H)?CH.sub.2, OC(O)C(CH.sub.3)?CH.sub.2, N(H)CC(H)?CH.sub.2, N(H)CC(CH.sub.3)?CH.sub.2, Si(OH).sub.3, Si(OCH.sub.3).sub.3, Si(OC.sub.2H.sub.5).sub.3, OH, SH, NH.sub.2, NO.sub.2, CN, CF.sub.3, C?CH, N?N.sup.+?N.sup.?, F, Cl, Br, I, C.sub.2H.sub.3O, C.sub.6H.sub.5, C(O)F, C(O)Cl, C(O)Br, C(O)I, CF.sub.3SO.sub.3, B(OZ).sub.2, OZ, C(O)Z, C(O)OZ, C(O)NHZ, C(O)NZ.sub.2, and SSZ, wherein Z=H, C.sub.nH.sub.2n+1, C.sub.nF.sub.2n+1, C.sub.nH.sub.2nC(H)?CH.sub.2, C.sub.nH.sub.2nC?CH, C.sub.6H.sub.4C(H)?CH.sub.2, C.sub.6H.sub.5, CH.sub.2C.sub.6H.sub.5, C.sub.5NH.sub.4 or C.sub.4N.sub.2H.sub.3, wherein n=1 to 20; R.sup.2=H, C.sub.nF.sub.2n+1, C.sub.5NH.sub.4, C.sub.4N.sub.2H.sub.3, (CH.sub.2).sub.nQ or (C.sub.6H.sub.5?m)Q.sub.m wherein m=1, 2, 3 or 4, and Q is selected from: H, C(H)?CH.sub.2, OC(O)C(H)?CH.sub.2, OC(O)C(CH.sub.3)?CH.sub.2, N(H)CC(H)?CH.sub.2, N(H)CC(CH.sub.3)?CH.sub.2, Si(OH).sub.3, Si(OCH.sub.3).sub.3, Si(OC.sub.2H.sub.5).sub.3, OH, SH, NH.sub.2, NO.sub.2, CN, CF.sub.3, C?CH, N?N.sup.+?N.sup.?, F, Cl, Br, I, C.sub.2H.sub.3O, C.sub.6H.sub.5, C(O)F, C(O)Cl, C(O)Br, C(O)I, CF.sub.3SO.sub.3, B(OZ).sub.2, OZ, C(O)Z, C(O)OZ, C(O)NHZ, C(O)NZ.sub.2, and SSZ, wherein Z=H, C.sub.nH.sub.2n+1, C.sub.nF.sub.2n+1, C.sub.nH.sub.2nC(H)?CH.sub.2, C.sub.nH.sub.2nC?CH, C.sub.6H.sub.4C(H)?CH.sub.2, C.sub.6H.sub.5, CH.sub.2C.sub.6H.sub.5, C.sub.5NH.sub.4 or C.sub.4N.sub.2H.sub.3, wherein n=1 to 20; R.sup.3=H, C.sub.nF.sub.2n+1, C.sub.5NH.sub.4, C.sub.4N.sub.2H.sub.3, C(O)C.sub.6H.sub.5, C(S)C.sub.6H.sub.5, (CH.sub.2).sub.nQ or (C.sub.6H.sub.5?m)Q.sub.m, wherein m=1, 2, 3 or 4, and Q is selected from: H, C(H)?CH.sub.2, OC(O)C(H)?CH.sub.2, OC(O)C(CH.sub.3)?CH.sub.2, N(H)CC(H)?CH.sub.2, N(H)CC(CH.sub.3)?CH.sub.2, Si(OH).sub.3, Si(OCH.sub.3).sub.3, Si(OC.sub.2H.sub.5).sub.3, OH, SH, NH.sub.2, NO.sub.2, CN, CF.sub.3, C?CH, N?N.sup.+?N.sup.?, F, Cl, Br, I, C.sub.2H.sub.3O, C.sub.6H.sub.5, C(O)F, C(O)Cl, C(O)Br, C(O)I, CF.sub.3SO.sub.3, B(OZ).sub.2, OZ, C(O)Z, C(O)OZ, C(O)NHZ, C(O)NZ.sub.2, and SSZ, wherein Z=H, C.sub.nH.sub.2n+1, C.sub.nF.sub.2n+1, C.sub.nH.sub.2nC(H)?CH.sub.2, C.sub.nH.sub.2nC?CH, C.sub.6H.sub.4C(H)?CH.sub.2, C.sub.6H.sub.5, CH.sub.2C.sub.6H.sub.5, C.sub.5NH.sub.4 or C.sub.4N.sub.2H.sub.3, wherein n=1 to 20; X.sup.1=N, C(CN), C(COOEt) or C(NO.sub.2)