1,7-diaryl-1,6-heptadiene-3,5-dione derivatives, methods for the production and use thereof

A compound with formula (1):

• or formula (2)
• wherein the residue Q1 represents an aromatic residue with the general formula (11a), (12a) or (13a)
• and the residue Q2 represents an aromatic residue with the general formula (11b), (12b) or (13b),
• wherein respectively, at least 1 residue R6a to R10a, R11a to R17a, R18a to R24a, R6b to R10b, R11b to R17b or R18b to R24b, respectively independently of each other, is an organic residue W1a or an organic residue W1b, and
• wherein the residues R6a to R10a, R11a to R17a, R18a to R24a, R6b to R10b, R11b to R17b and R18b to R24b, which are not an organic residue W1a or an organic residue W1b, respectively independently of each other, are identical or different and represent hydrogen, halogen, thiol, nitro, carboxylate, aldehyde containing 1 to 8 C atoms, ketone containing 2 to 8 C atoms, O-alkyl containing 1 to 12 C atoms, S-alkyl containing 1 to 12 C atoms, O-alkenyl containing 2 to 12 C atoms, S-alkenyl containing 2 to 12 C atoms, O-aryl containing 5 to 20 C atoms, S-aryl containing 5 to 20 C atoms, ether containing 2 to 12 C atoms, thioether containing 2 to 12 C atoms, carboxylic acid ester containing 1 to 12 C atoms, carboxylic acid amide containing 1 to 12 C atoms, thioester containing 1 to 12 C atoms, alkyl containing 1 to 12 C atoms, alkenyl containing 2 to 12 C atoms, cycloalkyl containing 3 to 12 C atoms, cycloalkenyl containing 3 to 12 C atoms, alkylaryl containing 1 to 12 C atoms, aryl containing 5 to 20 C atoms, or heteroaryl, which does not contain a nitrogen atom, containing 4 to 20 C atoms, and
• wherein the compound with formula (1) and the compound with formula (2) does not contain an OH group which is bonded directly to the organic residue Q1 or Q2, and
• wherein in formula (1) K represents hydrogen or a cation, and wherein in formula (2) K represents a cation Mz+ of a metal M or boron, wherein z is the formal oxidation number of the metal M or boron and is a whole number from 1 to 7, and
• wherein L1 and L2, respectively independently of each other, represent water, halide, cyanide, thiocyanate, phosphate, hydrogen phosphate, or a carboxylate ion of a carboxylic acid containing 1 to 10 carbon atoms and wherein
• (a) at least one of the residues Q1 and Q2, respectively independently of each other, is substituted with at least one organic residue W1a, wherein
• the at least one organic residue W1a has the general formula (5a), (6a), (7a), (8a), or (9a):
• -A-(C(D)(E))h-Xa, (5a)
• —(C(D)(E))k-aryl-(C(D)(E))l-Xa, (6a)
• -A-(C(D)(E))k-aryl-(C(D)(E))l-Xa, (7a)
• —((C(D)(E))m-A)p-(C(D)(E))n-Xa, (8a)
• -A-((C(D)(E))m-A)p-(C(D)(E))n-Xa, (9a)
• wherein h represents a whole number from 1 to 20, wherein k represents a whole number from 0 to 10, wherein 1 represents a whole number from 0 to 10, and wherein m, n and p, respectively independently of each other, represent a whole number from 1 to 6, and
• wherein A, respectively independently of each other, represents oxygen or sulphur,
• wherein D and E, respectively independently of each other, represent hydrogen, halogen, G-R(I), or G-C(=G)-R(II), wherein G, respectively independently of each other, represents oxygen or sulphur, and wherein the residues R(I) and R(II), respectively independently of each other, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, wherein phenyl and benzyl may be unsubstituted or substituted,
• wherein aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group which does not contain a nitrogen atom,
• wherein Xa, respectively independently of each other, represents a residue with formula (20c), (20d), or (21):
• wherein each of the residues R(VII), R(VIII), and R(IX), respectively independently of each other, represents hydrogen, an aryl residue containing 5 to 12 C atoms, an alkylaryl residue containing 5 to 12 C atoms, an alkyl residue, which may be linear or branched, containing 1 to 8 C atoms, or an ether residue, which may be linear or branched, containing 1 to 8 C atoms, and
• wherein organic residues with formula (20d) and (21) have independently a fluoride, chloride, bromide, iodide, sulphate, hydrogen sulphate, phosphate, hydrogen phosphate, dihydrogen phosphate, tosylate, mesylate, or at least one carboxylation of a carboxylic acid containing 1 to 15 carbon atoms and/or mixtures thereof as a counter-ion, and
• wherein the residues R1, R2, R3, R4 and R5, respectively independently of each other, represent hydrogen, halogen, alkyl containing 1 to 12 C atoms, cycloalkyl containing 1 to 12 C atoms, alkylaryl containing 1 to 12 C atoms, aryl containing 5 to 20 C atoms, ether containing 2 to 12 C atoms or glycol containing 2 to 12 C atoms,
• or wherein
• (b) the residue R3 is an organic residue W2a which contains at least one neutral nitrogen atom which can be protonated, and/or at least one positively charged nitrogen atom and/or at least one positively charged phosphorus atom, which has a fluoride, chloride, bromide, iodide, sulphate, hydrogen sulphate, phosphate, hydrogen phosphate, dihydrogen phosphate, tosylate, mesylate, or at least one carboxylation of a carboxylic acid containing 1 to 15 carbon atoms and/or mixtures thereof as a counter-ion, wherein
• the one organic residue W2a has the general formula (4b), (5b), (6b), (7b), (8b), or (9b):
• —(C(D)(E))h-Xb, (4b)
• -A-(C(D)(E))h-Xb, (5b)
• —(C(D)(E))k-aryl-(C(D)(E))l-Xb, (6b)
• -A-(C(D)(E))k-aryl-(C(D)(E))l-Xb, (7b)
• —[(C(D)(E))m-A]p—(C(D)(E))n-Xb, (8b)
• -A-[(C(D)(E))m-A]p—(C(D)(E))n-Xb, (9b)
• and
• wherein, optionally, at least one of the residues Q1 and Q2, respectively independently of each other, is substituted with at least one organic residue W1b which has the general formula (4b), (5b), (6b), (7b), (8b), or (9b),
• wherein h represents a whole number from 1 to 20, wherein k represents a whole number from 0 to 10, wherein 1 represents a whole number from 0 to 10, and wherein m, n and p, respectively independently of each other, represent a whole number from 1 to 6, and
• wherein A, respectively independently of each other, represents oxygen or sulphur,
• wherein D and E, respectively independently of each other, represent hydrogen, halogen, G-R(I), or G-C(=G)-R(II), wherein G, respectively independently of each other, represents oxygen or sulphur, and wherein the residues R(I) and R(II), respectively independently of each other, represent hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, phenyl or benzyl, wherein phenyl and benzyl may be unsubstituted or substituted,
• wherein aryl represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group which does not contain a nitrogen atom,
• wherein Xb, respectively independently of each other, is an organic residue which (i) contains at least one neutral nitrogen atom which can be protonated, or (ii) contains at least one positively charged nitrogen atom, or (iii) contains at least one positively charged phosphorus atom, which has a fluoride, chloride, bromide, iodide, sulphate, hydrogen sulphate, phosphate, hydrogen phosphate, dihydrogen phosphate, tosylate, mesylate, or at least one carboxylation of a carboxylic acid containing 1 to 15 carbon atoms and/or mixtures thereof as a counter-ion, and
• wherein the residues R1, R2, R4 and R5, respectively independently of each other, represent hydrogen, halogen, alkyl containing 1 to 12 C atoms, alkylaryl containing 1 to 12 C atoms, aryl containing 5 to 20 C atoms, ether containing 2 to 12 C atoms or glycol containing 2 to 12 C atoms.