# US 8,541,583 B2 · Monofunctionalized perylenetetracarboxylic acid bismides > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,541,583 B2 - Document ID: US8541583B2 - Status: Granted - Kind: B2 - Application number: 12/852,687 - Filed: 2010-08-09 - Published: 2010-12-23 - Granted: 2013-09-24 - Earliest claimed: 2003-02-28 - Assignees: Max-Planck-Gesellschaft zur Forderung der Wissenschaften e.V. - Applicants: Christopher Kohl; Jianqiang Qu; Klaus Mullen - Inventors: Christopher Kohl; Jianqiang Qu; Klaus Mullen - Web page: https://patentgrep.com/patent/US8541583B2 ## CPC - C07H 21/00: Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids - C09B 5/62: Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series - C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13) - C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P) ## Abstract The invention relates to novel perylenetetracarboxylic acid bisimide derivatives with improved performance properties. ## Claims ### Claim 1 A perylenetetracarboxylic acid bisimide of the structural formula (I) and wherein R3, R4, R5 or/and R6 comprise aromatic or heteroaromatic radicals, wherein R1 and R2 are different organic radicals selected independently from secondary or tertiary aliphatic radicals or, substituted or unsubstituted, mono- or bicyclic, aromatic, or heteroaromatic radicals having 3-30 carbon atoms, one of the radicals having a group for coupling to a binding partner selected from the group consisting of active esters, maleimides, isocyanates, sulfonyl halides, carbonyl halides, iodoacetamides, aziridines, epoxides, acyl azides, acyl nitriles, sulfonic acid groups, and carboxylic acid groups, and at least two of R3, R4, R5 and R6 are each independently aromatic or heteroaromatic radicals which contain at least one uncharged, positively charged, or negatively charged hydrophilic group, and the uncharged hydrophilic groups are selected from hydroxyl groups or polyoxy -C2-C4-alkylene groups, the positively charged hydrophilic groups are selected from amino groups or ammonium groups, and the negatively charged hydrophilic groups are selected from SO3H, COOH, SO3M, or COOM, wherein M is a cation, and at least one of R3, R4, R5 and R6 has the general structural formula (III): wherein n is an integer of 1-3. ### Claim 2 (depends on 1) A compound as claimed in claim 1, wherein the coupling group is a reactive functionality for binding to amino, thiol or carboxyl groups or a precursor thereof. ### Claim 3 (depends on 1) A compound as claimed in claim 1, wherein the coupling group is an active ester, maleimide, isocyanate, sulfonyl halide, carbonyl halide, iodoacetamide, aziridine, epoxide, acvl azide, acvl nitrile or a precursor thereof. ### Claim 4 (depends on 1) A compound as claimed in claim 1, wherein R1 or/and R2 are aromatic or heteroaromatic radicals, which optionally contain one or more substituents. ### Claim 5 (depends on 1) A compound as claimed in claim 1, wherein at least two of R3, R4, R5 and R6 are an organic radical which bears an uncharged hydrophilic group. ### Claim 6 (depends on 1) A compound as claimed in claim 1, wherein at least two of R3, R4, R5 and R6 are each independently an organic radical which bears a positively charged (in neutral media) group. ### Claim 7 (depends on 1) A compound as claimed in claim 1, wherein at least two of R3, R4, R5 and R6 are each independently an organic radical which bears a group selected from quaternary ammonium and N-alkylated heteroaromatic N groups such as N-alkylpyridinium, N-alkylquinolinium or N-alkylisoquinolinium groups. ### Claim 8 (depends on 1) A compound as claimed in claim 1, wherein R3, R4, R5 and R6 are each independently an organic radical which bears a negatively charged (in neutral media) group. ### Claim 9 (depends on 1) A compound as claimed in claim 1, wherein at least two of R3, R4, R5 and R6 are each independently an organic radical which bears a group selected from SO3H, COOH, SO3M and COOM, wherein M is a cation. ### Claim 10 (depends on 1) A compound as claimed in claim 1, wherein at least three of R3, R4, R5 or/and R6 are an organic radical which carries a charged group. ### Claim 11 (depends on 1) A compound as claimed in claim 1, wherein all four of R3, R4, R5 and R6 are an organic radical which carries a charged group. ### Claim 12 (depends on 1) A compound, as claimed in claim 1, wherein at least one of R3, R4, R5 and R6 has the general structural formula (II): —O—Ar (II) wherein Ar is an aromatic or heteroaromatic radical which contains at least one charged group. ### Claim 13 (depends on 1) A conjugate of compounds as claimed in claim 1 with a binding partner. ### Claim 14 (depends on 13) The conjugate as claimed in claim 13, wherein the binding partner is a biomolecule. ### Claim 15 (depends on 1) A process for preparing perylenetetracarboxylic acid bisimides of the general structural formula (I), of claim 1 comprising the steps of: (a) reacting halogen-substituted perylenedi- or perylenetetracarboxylic anhydrides of the general structural formula (V): wherein at least two of X1, X2, X3 and X4 are halogen and the others are hydrogen with a mixture of two different amines H2NR1 and H2NR2, wherein R1 and R2 are each as defined in claim 1, to give a compound of the general structural formula (VI) (b) reacting the compound (VI) with a compound of the general structural formula (VII): HO—Ar′ (VII) wherein Ar′ is an aromatic or heteroaromatic radical to give tetra-substituted perylenetetracarboxylic acid bisimides of the general structural formula (VIIIa) or to give disubstituted perylenetetracarboxylic acid bisimides of the general structural formula (VIIIb): and (c) introducing hydrophilic groups into the aromatic or heteroaromatic Ar' radicals. ### Claim 16 (depends on 15) The process as claimed in claim 15, wherein step (b) includes the introduction of at least one SO3H or SO3M group into Ar′, where M is a cation. ### Claim 17 (depends on 15) The process as claimed in claim 15, wherein step (b) includes the alkylation of at least one heteroaromatic N atom in Ar'. ### Claim 18 (depends on 1) A compound as claimed in claim 1, wherein R1 and R2 are independently selected from the mono- or bicyclic, aromatic or heteroaromatic radicals that are substituted or unsubstituted. ### Claim 19 (depends on 18) A compound as claimed in claim 18, wherein mono- or bicyclic, aromatic or heteroaromatic radicals are independently selected from, unsubstituted or substituted, phenyl, pyridyl, or naphthyl radicals. ### Claim 20 (depends on 1) A compound as claimed in claim 1, wherein the aromatic or heteroaromatic radicals are selected from phenyl or pyridyl radicals. ### Claim 21 (depends on 4) A compound as claimed in claim 4, wherein the aromatic or heteroaromatic radicals are selected from phenyl, pyridyl, or naphthyl radicals.