US 12,084,544 B2
Diversity-oriented polymers of intrinsic microporosity and uses thereof
Brett A. Helms, Oakland, CA (US); Swagat Sahu, La Jolla, CA (US); Miranda J. Baran, Onartio (CA); Miles N. Braten, San Francisco, CA (US); Mark E. Carrington, Port of Spain (TT); and Stephen M. Meckler, Redwood City, CA (US)
Assigned to The Regents of the University of California, Oakland, CA (US)
Appl. No. 17/269,228
Filed by The Regents of the University of California, Oakland, CA (US)
PCT Filed Aug. 16, 2019, PCT No. PCT/US2019/046886
§ 371(c)(1), (2) Date Feb. 17, 2021,
PCT Pub. No. WO2020/037246, PCT Pub. Date Feb. 20, 2020.
Claims priority of provisional application 62/719,498, filed on Aug. 17, 2018.
Prior Publication US 2021/0309802 A1, Oct. 7, 2021
Int. Cl. C08G 65/48 (2006.01); B01D 67/00 (2006.01); B01D 69/02 (2006.01); B01D 71/52 (2006.01); B01J 39/07 (2017.01); B01J 39/19 (2017.01); C07C 215/64 (2006.01); C07D 211/46 (2006.01); C07D 295/135 (2006.01); C07D 295/205 (2006.01); C08G 65/40 (2006.01); H01M 10/24 (2006.01); H01M 50/403 (2021.01); H01M 50/414 (2021.01); H01M 50/491 (2021.01)
CPC C08G 65/48 (2013.01) [B01D 67/00091 (2022.08); B01D 69/02 (2013.01); B01D 71/5211 (2022.08); B01J 39/07 (2017.01); B01J 39/19 (2017.01); C07C 215/64 (2013.01); C07D 211/46 (2013.01); C07D 295/135 (2013.01); C07D 295/205 (2013.01); C08G 65/4006 (2013.01); H01M 10/24 (2013.01); H01M 50/403 (2021.01); H01M 50/414 (2021.01); H01M 50/491 (2021.01); B01D 2325/02831 (2022.08); H01M 2300/0014 (2013.01)] 28 Claims
OG exemplary drawing
 
1. A microporous polymer according to the formula:
-[A-AB-B]n—,
or a salt thereof,
wherein:
n is an integer ranging from 10 to 10,000;
each monomer segment A-A is independently a monomer segment according to Formula (A), (B), (C), (D), (E), (F), (G) or (H):

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
each monomer segment B-B is independently a monomer segment according to Formula (a), (b), (c), (d), (e), or (f):

OG Complex Work Unit Chemistry
each R11 is independently selected from the group consisting of —CH2NR1R2 and H;
each R12 is independently selected from the group consisting of —C(NOR13)N(R14)2 and —CN;
at least one R11 in at least one monomer segment A-A is —CH2NR1R2, or at least one R12 in at least one monomer segment B-B is —C(NOR13)N(R14)2;
each R1 and R2 is independently selected from the group consisting of (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, (C3-8)cycloalkyl(C1-20)alkyl, hetero(C1-20)alkyl, 3- to 8-membered heterocyclyl, 3- to 8-membered heterocyclyl-(C1-20)alkyl, 5- to 8-membered heteroaryl, heteroaryl(C1-20)alkyl,
wherein each R1 and R2 is optionally and independently substituted with one or more Z1,
wherein each (C1-20)alkyl, (C2-20)alkenyl, and (C2-20)alkynyl in R1 and R2 optionally and independently comprises one or more heteroatoms independently selected from silicon, a chalcogenide, and a pnictide, and
wherein one or more atoms in R1 and R2 are optionally and independently present in oxidized form as C═O, C═S, N═O, N═S, S═O or S(O)2; or
alternatively, each R1 is optionally and independently taken together with R2, and the nitrogen atom to which both are attached, to form 3- to 8-membered heterocyclyl or 5- to 8-membered heteroaryl, each of which is optionally substituted with one or more Z2;
each Z1 and Z2 is independently selected from the group consisting of halogen, —OH, —NO2, —CN, (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8) cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl, 3- to 8-membered heterocyclyl, 5- to 8-membered heteroaryl, (C3-8)cycloalkyl-(C1-20)alkyl, 3- to 8-membered heterocyclyl-(C1-20)alkyl, 5- to 8-membered heteroaryl-(C1-20)alkyl, halo(C1-20)alkyl, halo(C1-20)alkyloxy, —OR6, —SR6, —S(O)R6, —S(O)2R6, —SO2NR6R7, —NR6C(O)R7, —NR6S(O)2R7, —NR6C(O)NR7R8, —NR6R7, —CO2R6, —C(O)NR6R7, and —C(O)R6;
each R3, R4, R5, R6, R7, and R8 is independently selected from the group consisting of (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8)cycloalkyl, (C6-12)aryl(C1-20)alkyl, (C3-8)cycloalkyl(C1-20)alkyl, hetero(C1-20)alkyl, 3- to 8-membered heterocyclyl, 3- to 8-membered heterocyclyl-(C1-20)alkyl, 5- to 8-membered heteroaryl, 5- to 8-membered heteroaryl-(C1-20)alkyl; or
alternatively, R4 and R5 are taken together to form (C4-8)cycloalkyl, (C6-12)aryl, 4- to 8-membered heterocyclyl, or 5- to 8-membered heteroaryl; or
alternatively, R6 and R7 are taken together to form 4- to 8-membered heterocyclyl or 5- to 8-membered heteroaryl; or
alternatively, R7 and R8 are taken together to form 4- to 8-membered heterocyclyl or 5- to 8-membered heteroaryl;
each R13 is selected from the group consisting of H, (C1-20)alkyl, and (C3-8)cycloalkyl, wherein (C1-20)alkyl and (C3-8)cycloalkyl are optionally and independently substituted with one or more Z3,
provided that R13 is (C1-20)alkyl or (C3-8)cycloalkyl, each of which is optionally and independently substituted with one or more Z3, when all R11 groups in monomer segments according to Formula (A) are H;
each R14 is independently selected from the group consisting of H, (C1-20)alkyl, and (C3-8)cycloalkyl; and
each Z3 is independently selected from the group consisting of halogen, —NO2, —CN, —OH, —SO3H, —NH2, (C1-20)alkyl, (C2-20)alkenyl, (C2-20)alkynyl, (C6-12)aryl, (C3-8) cycloalkyl, (C6-12)aryl(C1-20)alkyl, hetero(C1-20)alkyl, 3- to 8-membered heterocyclyl, 5- to 8-membered heteroaryl, (C3-8)cycloalkyl-(C1-20)alkyl, 3- to 8-membered heterocyclyl-(C1-20)alkyl, 5- to 8-membered heteroaryl-(C1-20)alkyl, halo(C1-20)alkyl, halo(C1-20)alkyloxy, —OR6, —SR6, —S(O)R6, —S(O)2R6, —SO2NR6R7, —NR6C(O)R7, —NR6S(O)2R7, —NR6C(O)NR7R8, —NR6R7, —CO2R6, —C(O)NR6R7, and —C(O)R6.