# US 12,180,401 B2 · Water-soluble fluorescent polymeric dyes > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,180,401 B2 - Document ID: US12180401B2 - Status: Granted - Kind: B2 - Application number: 17/699,845 - Filed: 2022-03-21 - Published: 2022-10-27 - Granted: 2024-12-31 - Earliest claimed: 2021-04-07 - Assignees: Becton, Dickinson and Company - Applicants: Becton, Dickinson and Company - Inventors: Yongchao Liang; Subodh Devendra Sonar - Web page: https://patentgrep.com/patent/US12180401B2 ## CPC - C09K 11/06: containing organic luminescent materials - C08G 61/12: Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule - C08G 61/122: {derived from five- or six-membered heterocyclic compounds, other than imides} - C08L 65/00: Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C08L7/00 - C08L57/00, C08L61/00 take precedence); Compositions of derivatives of such polymers - C09B 69/10: Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds - C09B 69/109: {containing other specific dyes} - H10K 85/10: Organic polymers or oligomers - H10K 85/115: {Polyfluorene; Derivatives thereof} - C08G 2261/122: statistical - C08G 2261/124: alternating - C08G 2261/1424: containing ether groups, including alkoxy - C08G 2261/148: Side-chains having aromatic units - C08G 2261/1644: comprising other functional groups, e.g. OH groups, NH groups, COOH groups or boronic acid - C08G 2261/1646: comprising aromatic or heteroaromatic end groups - C08G 2261/3142: fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene - C08G 2261/3223: containing one or more sulfur atoms as the only heteroatom, e.g. thiophene - C08G 2261/3241: containing one or more nitrogen atoms as the only heteroatom, e.g. carbazole - C08G 2261/411: Suzuki reactions - C08G 2261/412: Yamamoto reactions - C08G 2261/414: Stille reactions - C08G 2261/522: fluorescent - C09K 2211/1466: containing nitrogen as the only heteroatom - H10K 50/11: characterised by the electroluminescent [EL] layers - H10K 71/15: characterised by the solvent used - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - 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) - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES ## Abstract Water-soluble fluorescent polymeric dyes and polymeric tandem dyes are provided. The polymeric dyes include a water solvated light harvesting multi-chromophore having a conjugated segment of aryl and/or heteroaryl co-monomers. The molar ratio of the co-monomers can be adjusted to provide beneficial technical properties, such as increased water solubility and improved absorption and emission spectra. For instance, the conjugated segment can have a first co-monomer substituted with a water-soluble group (WSG) and a second co-monomer, wherein the first co-monomer is in an amount that is equal or greater than the amount of the second co-monomer, multi-chromophore. The polymeric tandem dyes further include a signaling chromophore covalently linked to the multi-chromophore in energy-receiving proximity therewith. Also provided are aggregation-resistant labeled specific binding members that include the subject water-soluble polymeric dyes. Methods of evaluating a sample for the presence of a target analyte and methods of labeling a target molecule in which the subject polymeric dyes find use are also provided. Systems and kits for practicing the subject methods are also provided. ## Claims ### Claim 1 A water-soluble light harvesting multi-chromophore comprising a conjugated segment having the structure of formula (I): wherein: M1 and M2 are each independently an aryl or heteroaryl co-monomer; R1 and R2 are each independently a non-ionic water-soluble group; R3 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkoxy, substituted alkoxy, aryl, substituted aryl, heteroaryl, substituted heteroaryl, halo, cyano, and hydroxyl; a and b define the mol % of each unit within the conjugated segment, wherein a is greater than or equal to b; and excitation of the multi-chromophore leads to emission of light from M2. ### Claim 2 (depends on 1) The water-soluble light harvesting multi-chromophore according to claim 1, wherein M1 is a 5-membered aromatic group, a 6-membered aromatic group, a fused bicyclic aromatic group, a fused tricyclic aromatic group, or a combination thereof. ### Claim 3 (depends on 2) The water-soluble light harvesting multi-chromophore according to claim 2, wherein M1 is a phenyl group, pyridyl group, napthyl group, binapthyl group, a fused tricyclic aromatic group, or a combination thereof. ### Claim 4 (depends on 3) The water-soluble light harvesting multi-chromophore according to claim 3, wherein M1 is a fused tricyclic aromatic group. ### Claim 5 (depends on 4) The water-soluble light harvesting multi-chromophore according to claim 4, wherein M1 is a fused tricyclic aromatic group described by the following structure: wherein: each R4 is independently H or one or more alkyl, substituted alkyl, aryl or heteroaryl substituents and wherein any two convenient R4 groups are optionally cyclically linked; Y is C(R5)2, —C(R5)2C(R5)2—, —C(R5)2Si(R5)2—, NR5, Si(R5)2 or Se; each R5 is independently selected from H, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, acyl, substituted acyl, alkoxy, substituted alkoxy, amido, substituted amido, an aralkyl, a substituted aralkyl, a poly(ethylene glycol) moiety, -L1-Z1, where L1 is a linker and Z1 is a chemoselective tag and a water-soluble group; and each Z is independently CH, CR4 or N, wherein at least two of Z in each ring is CH or CR4; each * indicates a location for attachment to an M2 group or another M1 group; and at least one R4 or R5 is a water-soluble group. ### Claim 6 (depends on 5) The water-soluble light harvesting multi-chromophore according to claim 5, wherein Y is C(R5)2. ### Claim 7 (depends on 5) The water-soluble light harvesting multi-chromophore according to claim 5, wherein Y is —C(R5)2C(R5)2—. ### Claim 8 (depends on 5) The water-soluble light harvesting multi-chromophore according to claim 5, wherein each Z is CH or CR4. ### Claim 9 (depends on 4) The water-soluble light harvesting multi-chromophore according to claim 4, wherein M1 is a fused tricyclic group is described by one of the following structures: ### Claim 10 (depends on 3) The water-soluble light harvesting multi-chromophore according to claim 3, wherein M1 is a group described by one of the following structures: wherein each R6 is independently H or one or more alkyl, substituted alkyl, aryl or heteroaryl substituents and wherein any two convenient R6 groups are optionally cyclically linked, wherein the structure has at least one R6 that is a water-soluble group. ### Claim 11 (depends on 1) The water-soluble light harvesting multi-chromophore according to claim 1, wherein R1 and R2 each independently comprise a poly(alkylene oxide) group. ### Claim 12 (depends on 1) The water-soluble light harvesting multi-chromophore according to claim 1, wherein M1 and M2 are different groups. ### Claim 13 (depends on 1) The water-soluble light harvesting multi-chromophore according to claim 1, wherein R1 and R2 are different groups. ### Claim 14 (depends on 1) The water-soluble light harvesting multi-chromophore according to claim 1, wherein R3 does not comprise a poly(ethylene glycol) group. ### Claim 15 (depends on 1) The water-soluble light harvesting multi-chromophore according to claim 1, wherein a ranges from 0.50 to 0.80 and b ranges from 0.50 to 0.20. ### Claim 16 (depends on 15) The water-soluble light harvesting multi-chromophore according to claim 15, wherein a ranges from 0.60 to 0.70 and b ranges from 0.40 to 0.30. ### Claim 17 (depends on 1) The water-soluble light harvesting multi-chromophore according to claim 1, wherein the multi-chromophore is π conjugated. ### Claim 18 (depends on 1) The water-soluble light harvesting multi-chromophore according to claim 1, wherein the multi-chromophore comprises 10 or more M1 groups. ### Claim 19 A water-soluble light harvesting multi-chromophore comprising a conjugated segment of formula (II): wherein: M1 and M2 are each independently an aryl or heteroaryl co-monomer; R1 is a non-ionic water-soluble group; R3 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkoxy, substituted alkoxy, aryl, substituted aryl, heteroaryl, substituted heteroaryl, halo, cyano, and hydroxyl; c and d define the mol % of each unit within the conjugated segment, wherein c is greater than or equal to d; and excitation of the multi-chromophore leads to emission of light from M2.