Novel polysulfonated fluorescence dyes

Compounds of the general formulae (I)-(IV)

• in which R1, R4, R5, R6, R7, and R10 independently of one another mean hydrogen, halogen, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), NH2, NH(alkyl), NH(aryl), N(alkyl)2, N(aryl)2, NO2, CHO, COOH, COO(alkyl), COO(aryl), PO3H2, SO3H or a hydrocarbon group having 1-20 C atoms, wherein the hydrocarbon group optionally comprises one or more heteroatoms selected from the group consisting of N, O, and S or/and one or more substituents preferably selected from the group consisting of halogen, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), NH2, NH(alkyl), NH(aryl), N(alkyl)2, N(aryl)2, NO2, CHO, COOH, COO(alkyl), COO(aryl), PO3H2 and SO3H,
• R2, R3, R8, and R9 independently of one another mean hydrogen or a hydrocarbon group having 1-20 C atoms, wherein the hydrocarbon group optionally comprises one or more heteroatoms selected from the group consisting of N, O and S or/and one or more substituents preferably selected from the group consisting of halogen, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), NH2, NH(alkyl), NH(aryl), N(alkyl)2, N(aryl)2, NO2, CHO, COOH, COO(alkyl), COO(aryl), PO3H2 and SO3H,
• wherein each of the moieties in the compounds of the general formulae (I)-(IV) can form a ring system with one or more adjacent moieties,
• X in the general formula (I) means a group selected from O, S, SO2, CR11R12 or SiR13R14,
• X in the general formula (II) means a group selected from O, S, CR11R12, SiR13R14 or NR15,
• X in the general formula (III) means a group selected from O, S or CR11R12,
• X in the general formula (IV) means O or NR15,
• and wherein R11, R12, R13, R14 and R15 independently of one another mean hydrogen, CN, COOH, COO(alkyl), COO(aryl), PO3H2, SO3H or a hydrocarbon group having 1-20 C atoms, wherein the hydrocarbon group optionally comprises one or more heteroatoms selected from the group consisting of N, O and S or/and one or more substituents preferably selected from the group consisting of halogen, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), NH2, NH(alkyl), NH(aryl), N(alkyl)2, N(aryl)2, NO2, CHO, COOH, COO(alkyl), COO(aryl), PO3H2 and SO3H,
• or R11 and R12 or R13 and R14 in each case together with the atom to which they are attached, form a 3- to 7-membered ring, wherein the ring can comprise one or more double bonds or/and one or more heteroatoms selected from the group consisting of N, O and S or/and one or more substituents preferably selected from the group consisting of halogen, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), NH2, NH(alkyl), NH(aryl), N(alkyl)2, N(aryl)2, NO2, CHO, COOH, COO(alkyl), COO(aryl), PO3H2, SO3H and a hydrocarbon group having 1-20 C atoms or/and can be annulated with one or more 3- to 7-membered rings, wherein the hydrocarbon group optionally comprises one or more heteroatoms selected from the group consisting of N, O and S or/and one or more substituents preferably selected from the group consisting of halogen, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), NH2, NH(alkyl), NH(aryl), N(alkyl)2, N(aryl)2, NO2, CHO, COOH, COO(alkyl), COO(aryl), PO3H2, and SO3H,
• A in the general formula (I) means an aryl or heteroaryl moiety, which optionally comprises one or more substituents preferably selected from the group consisting of halogen, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), NH2, NH(alkyl), NH(aryl), N(alkyl)2, N(aryl)2, NO2, CHO, COOH, COO(alkyl), COO(aryl), CONH(alkyl), CON(alkyl)2, CONH(aryl), CON(aryl)2, PO3H2, SO3H and a hydrocarbon group, wherein the hydrocarbon group itself optionally comprises one or more heteroatoms selected from the group consisting of N, O and S or/and one or more substituents preferably selected from the group consisting of halogen, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), NH2, NH(alkyl), NH(aryl), N(alkyl)2, N(aryl)2, NO2, CHO, COOH, COO(alkyl), COO(aryl), PO3H2 and SO3H,
• Y in the general formula (II) means hydrogen, CN, COOH, COO(alkyl), COO(aryl), NHR16, NR17R18, PO3H2, SO3H or an aliphatic hydrocarbon group having 1-20 C atoms, wherein the hydrocarbon group optionally comprises one or more heteroatoms selected from the group consisting of N, O and S or/and one or more substituents preferably selected from the group consisting of halogen, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), NH2, NH(alkyl), NH(aryl), N(alkyl)2, N(aryl)2, NO2, CHO, COOH, COO(alkyl), COO(aryl), PO3H2 and SO3H,
• and R16, R17, and R18 independently of one another mean hydrogen, CN, COOH, COO(alkyl), COO(aryl), PO3H2, SO3H or a hydrocarbon group having 1-20 C atoms, wherein the hydrocarbon group optionally comprises one or more heteroatoms selected from the group consisting of N, O and S or/and one or more substituents preferably selected from the group consisting of halogen, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), NH2, NH(alkyl), NH(aryl), N(alkyl)2, N(aryl)2, NO2, CHO, COOH, COO(alkyl), COO(aryl), PO3H2 and SO3H,
• or R17 and R18 together with the atom to which they are attached, form a 3- to 7-membered ring, wherein the ring can comprise one or more double bonds or/and one or more heteroatoms selected from the group consisting of N, O and S or/and one or more substituents preferably selected from the group consisting of halogen, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), NH2, NH(alkyl), NH(aryl), N(alkyl)2, N(aryl)2, NO2, CHO, COOH, COO(alkyl), COO(aryl), PO3H2, SO3H and a hydrocarbon group having 1-20 C atoms or/and can be annulated with one or more 3- to 7-membered rings, wherein the hydrocarbon group optionally comprises one or more heteroatoms selected from the group consisting of N, O and S or/and one or more substituents preferably selected from the group consisting of halogen, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), NH2, NH(alkyl), NH(aryl), N(alkyl)2, N(aryl)2, NO2, CHO, COOH, COO(alkyl), COO(aryl), PO3H2 and SO3H,
• provided that at least one of the moieties R2, R3, R8 or R9 has the structure B, wherein B means either an aliphatic hydrocarbon group having 1-6 C atoms, preferably 1-2 C atoms, wherein this hydrocarbon group itself optionally comprises one or more heteroatoms selected from the group consisting of N, O and S or/and one or more substituents preferably selected from the group consisting of halogen, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), NH2, NH(alkyl), NH(aryl), N(alkyl)2, N(aryl)2, NO2, CHO, COOH, COO(alkyl), COO(aryl), PO3H2 and SO3H and which carries at least one SO3H substituent or means an aliphatic hydrocarbon group having 1-6 C atoms, preferably 1-3 C atoms, more preferably 1-2 C atoms, wherein this hydrocarbon group itself optionally comprises one or more heteroatoms selected from the group consisting of N, O and S or/and one or more substituents preferably selected from the group consisting of halogen, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), NH2, NH(alkyl), NH(aryl), N(alkyl)2, N(aryl)2, NO2, CHO, COOH, COO(alkyl), COO(aryl), PO3H2 and SO3H and which carries at least one aryl or heteroaryl moiety, which optionally comprises one or more substituents preferably selected from the group consisting of hydrogen, halogen, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), NH2, NH(alkyl), NH(aryl), N(alkyl)2, N(aryl)2, NO2, CHO, COOH, COO(alkyl), COO(aryl), CONH(alkyl), CON(alkyl)2, CONH(aryl), CON(aryl)2, PO3H2, SO3H and a hydrocarbon group, wherein the hydrocarbon group itself optionally comprises one or more heteroatoms selected from the group consisting of N, O and S or/and one or more substituents preferably selected from the group consisting of halogen, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), NH2, NH(alkyl), NH(aryl), N(alkyl)2, N(aryl)2, NO2, CHO, COOH, COO(alkyl), COO(aryl), PO3H2 and SO3H and which carries at least one SO3H substituent
• or means an aryl or heteroaryl moiety, which optionally comprises one or more substituents preferably selected from the group consisting of hydrogen, halogen, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), NH2, NH(alkyl), NH(aryl), N(alkyl)2, N(aryl)2, NO2, CHO, COOH, COO(alkyl), COO(aryl), CONH(alkyl), CON(alkyl)2, CONH(aryl), CON(aryl)2, PO3H2, SO3H and a hydrocarbon group, wherein the hydrocarbon group itself optionally comprises one or more heteroatoms selected from the group consisting of N, O and S or/and one or more substituents preferably selected from the group consisting of halogen, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), NH2, NH(alkyl), NH(aryl), N(alkyl)2, N(aryl)2, NO2, CHO, COOH, COO(alkyl), COO(aryl), PO3H2 and SO3H and which carries at least one SO3H substituent
• or means a moiety, which is derived from cyanuric chloride and instead of one or both available CI atoms is substituted with a moiety —NH(CH2)nSO3H, wherein n is an integer from 1 to 6 and preferably n=2,
• wherein structure B is not integrated within a ring system with one or more adjacent moieties,
• wherein in compounds of the general formula (I) for X═O the moiety B is not —(CH2)mSO3H, wherein m is an integer from 1 to 6, unless at the same time at least one or more of the moieties R1, R4, R5, R6, R7, R10 and/or A comprises at least one further SO3H group,
• wherein in compounds of the general formula (IV) for X═O, moiety B, if it means an aliphatic hydrocarbon group, represents —CH2SO3H or —CH2CH2SO3H.