US 12,384,964 B2
Conjugated polymers and methods of use
Xinshe Xu, San Diego, CA (US); Jing Wang, San Diego, CA (US); and Matthew Yerou, San Diego, CA (US)
Assigned to BioLegend, Inc., San Diego, CA (US)
Filed by BioLegend, Inc., San Diego, CA (US)
Filed on Nov. 30, 2022, as Appl. No. 18/072,304.
Application 18/072,304 is a division of application No. 16/702,146, filed on Dec. 3, 2019, granted, now 11,584,883.
Application 16/702,146 is a continuation of application No. PCT/US2018/043911, filed on Jul. 26, 2018.
Claims priority of provisional application 62/538,583, filed on Jul. 28, 2017.
Prior Publication US 2023/0109663 A1, Apr. 6, 2023
Int. Cl. C09K 11/06 (2006.01); C08G 61/10 (2006.01); G01N 33/58 (2006.01)
CPC C09K 11/06 (2013.01) [C08G 61/10 (2013.01); G01N 33/582 (2013.01); C08G 2261/12 (2013.01); C08G 2261/1424 (2013.01); C08G 2261/1432 (2013.01); C08G 2261/1644 (2013.01); C08G 2261/1646 (2013.01); C08G 2261/312 (2013.01); C08G 2261/3142 (2013.01); C08G 2261/522 (2013.01); C08G 2261/94 (2013.01); C09K 2211/1416 (2013.01); C09K 2211/1425 (2013.01)] 15 Claims
 
1. A macromer of formula I:

OG Complex Work Unit Chemistry
wherein each of R1, R2, R3 and R4 are each independently a member selected from the group consisting of hydrogen, an optionally substituted C1-C10 alkyl, an optionally substituted C1-C18 alkoxy, optionally substituted C6-C18 aryl, optionally substituted C4-C18 acyl, optionally substituted C4-C18 acyloxy, NRaRb, wherein Ra and Rb are each independently hydrogen or lower alkyl, a water soluble group, ethylene oxide oligomers and an ethylene oxide oligomer methyl ether;
wherein at least one of R1 and R2 or R3 and R4 together with the carbons to which they are attached, join to form a cyclobutyl, a cyclopentyl or a cyclohexyl ring;
each R5 is independently a member selected from the group consisting of halo, alkyl, alkoxy, amino, ethylene oxide oligomers and an ethylene oxide oligomer methyl ether;
each p is a value from 0-3;
m is a value selected from the group consisting of 1-10,000;
each of A and B, can be present or absent and can each be the same or different, and each is selected from the group consisting of an aromatic group or heteroaromatic group, which group completes a π-conjugated backbone;
each of 1, 2 and 3 can be present or absent and can each be the same or different, and each is selected from the group consisting of an aromatic group or heteroaromatic group, which group completes a π-conjugated backbone;
n and o are each independently a value selected from the group consisting of 0-10,000, wherein the monomers within m, n, and o may be the same or different;
E1 and E2 are each independently a member selected from the group consisting of hydrogen, halogen, alkynyl, optionally substituted aryl, optionally substituted heteroaryl, halo, substituted aryl, boronic acid substituted aryl, boronic ester substituted aryl, boronic ester, boronic acid, optionally substituted fluorene and aryl or heteroaryl substituted with one or more pendant chains terminated with: i) a functional group selected from amine, carbamate, carboxylic acid, carboxylate, maleimide, activated esters, N-hydroxysuccinimidyl, hydrazines, hydrazids, hydrazones, azide, alkyne, aldehydes, thiols, and protected groups thereof for conjugation to a molecule or biomolecule; or ii) a conjugated organic dye or biomolecule; and
wherein the macromer of Formula I can be an alternating copolymer, a block copolymer, a random copolymer or a graph copolymer between E1 and E2.