US 12,084,554 B2
Polyphenylenes, methods, and uses thereof
Steven Holdcroft, Pitt Meadows (CA); Thomas J. G. Skalski, Vaulx-Vraucourt (FR); Michael Adamski, Vancouver (CA); Benjamin Britton, Vancouver (CA); and Timothy J. Peckham, Vancouver (CA)
Assigned to Simon Fraser University, Burnaby (CA)
Filed by Simon Fraser University, Burnaby (CA)
Filed on Sep. 11, 2023, as Appl. No. 18/464,836.
Application 18/464,836 is a continuation of application No. 16/603,785, granted, now 11,802,187, previously published as PCT/CA2018/050436, filed on Apr. 10, 2018.
Claims priority of provisional application 62/483,668, filed on Apr. 10, 2017.
Prior Publication US 2024/0117132 A1, Apr. 11, 2024
Int. Cl. C08J 5/22 (2006.01); B01D 69/02 (2006.01); B01D 71/82 (2006.01); C07C 211/63 (2006.01); C07C 309/44 (2006.01); C08G 61/10 (2006.01); H01M 8/10 (2016.01); H01M 8/1023 (2016.01)
CPC C08J 5/2256 (2013.01) [B01D 69/02 (2013.01); B01D 71/82 (2013.01); C07C 211/63 (2013.01); C07C 309/44 (2013.01); C08G 61/10 (2013.01); H01M 8/1023 (2013.01); B01D 2325/42 (2013.01); C08G 2261/11 (2013.01); C08G 2261/1452 (2013.01); C08G 2261/148 (2013.01); C08G 2261/228 (2013.01); C08G 2261/312 (2013.01); C08J 2365/02 (2013.01); H01M 2008/1095 (2013.01)] 23 Claims
OG exemplary drawing
 
1. An ionic membrane comprising a copolymer having a first repeating unit of Formula (I):

OG Complex Work Unit Chemistry
and
a second repeating unit of Formula (II):

OG Complex Work Unit Chemistry
wherein:
R1A, R1B, R1C, R1D, R1E, and R1F are independently aryl or heteroaryl, each optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from C1-6 alkyl, halo, nitro, cyano, SO3−X+, PO32−X2+, and COO−X+, wherein X+ is H+ or a cation, and provided that at least two of R1A, R1B, R1C, R1D, R1E, and R1F are independently aryl or heteroaryl substituted with 1, 2, 3, 4, or 5 substituents independently selected from SO3−X+, PO32−X2+, and COO−X+, wherein X is H+ or a cation;
R1G and R1H are independently H, aryl, or heteroaryl, wherein said aryl and heteroaryl are each optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from C1-6 alkyl, halo, nitro, cyano, SO3−X+, PO32−X2+, and COO−X+, wherein X+ H+ or a cation;
R3A, R3B, R3C, R3D, R3E, and R3F are independently aryl or heteroaryl, each optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from C1-6 alkyl, halo, nitro, and cyano;
R3G and R3H are independently H, aryl, or heteroaryl, wherein said aryl and heteroaryl are each optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from C1-6 alkyl, halo, nitro, and cyano;
A1 and B1 are independently arylene, heteroarylene, aralkylene, or heteroaralkylene, each optionally substituted with 1, 2, 3, or 4 substituents independently selected from halo, nitro, cyano, aryl, and heteroaryl;
A2 and B2 are independently absent, arylene, or heteroarylene, wherein said arylene and heteroarylene are each optionally substituted with 1, 2, 3, or 4 substituents independently selected from halo, nitro, cyano, aryl, and heteroaryl;
L1 and K1 are independently an optionally substituted linking heteroatom, arylene, heteroarylene, aralkylene, or heteroaralkylene, wherein said arylene, heteroarylene, aralkylene, and heteroaralkylene are each optionally substituted with 1, 2, 3, or 4 substituents independently selected from C1-6 alkyl, halo, nitro, cyano, aryl, and heteroaryl;
L2 and K2 are independently absent, arylene, or heteroarylene, wherein said arylene and heteroarylene are each optionally substituted with 1, 2, 3, or 4 substituents independently selected from C1-6 alkyl, halo, nitro, cyano, aryl, and heteroaryl; and
L3 and K3 are independently absent, arylene, or heteroarylene, wherein said arylene and heteroarylene are each optionally substituted with 1, 2, 3, or 4 substituents independently selected from C1-6 alkyl, halo, nitro, cyano, aryl, and heteroaryl;
provided that the repeating unit of Formula (I) is not

OG Complex Work Unit Chemistry