IP Library Granted Patent US 12,252,584
Granted Patent B2
US 12,252,584 · App. 17/560,983 · Granted Mar 18, 2025

Poly(aryl ether) based polymers and associated methods

Inventors: Timothy Manning Swager (Newton, MA); Richard Liu (Cambridge, MA); Sheng Guo (Brookline, MA)
Assignee: Massachusetts Institute of Technology
C08G65/48B01J23/44B01J31/06B01J35/615B01J35/617B01J37/12B01J37/16B01J37/341C08G65/40B01D71/522
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,252,584
App. No.
17/560,983
Granted
Mar 18, 2025
Kind
B2
Abstract

Compositions and methods related to the synthesis and application of poly(aryl ether)s are generally described.

Claims (13)

1. A photoredox catalyst, comprising:

a poly(aryl ether) of the formula [(—Ar′—O—Ar—O—Ar″—O-) n ] or [(—Ar″—O—Ar—O—Ar′—O-) n ], wherein Ar comprises at least one aryl or heteroaryl group, Ar′ comprises at least one aryl or heteroaryl group, Ar″ comprises a chromophore, n is greater than 1, and the poly(aryl ether) has a BET surface area greater than 200 m 2 /g.

2. The photoredox catalyst of claim 1 , wherein the poly(aryl ether) has a BET surface area less than or equal to 1000 m 2 /g.

3. The photoredox catalyst of claim 1 , wherein Ar′ comprises a spirobifluorene or an iptycene.

4. A method of photocatalysis, comprising:

exposing a photoredox catalyst to a substrate, wherein the photoredox catalyst comprises a poly(aryl ether) of the formula [(—Ar′—O—Ar—O—Ar″—O-) n ] or [(—Ar″—O—Ar—O—Ar′—O-) n ], wherein Ar comprises at least one aryl or heteroaryl group, Ar′ comprises at least one aryl or heteroaryl group, Ar″ comprises a chromophore, n is greater than 1, and the poly(aryl ether) has a BET surface area greater than 200 m 2 /g;

activating the photoredox catalyst; and

catalyzing a reaction of the substrate.

5. The method of claim 4 , wherein activating the photoredox catalyst comprises exposing the photoredox catalyst to light.

6. The method of claim 4 , wherein the reaction of the substrate is reduction of the substrate.

7. The method of claim 4 , wherein the reaction of the substrate is oxidation of the substrate.

8. The method of claim 4 , wherein the reaction of the substrate is a reaction between the substrate and a reactant.

9. The method of claim 4 , wherein the poly(aryl ether) has a surface area less than or equal to 1000 m 2 /g.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 3, 2022
From: SWAGER, TIMOTHY MANNING; LIU, RICHARD; GUO, SHENG
To: MASSACHUSETTS INSTITUTE OF TECHNOLOGY
Reel/Frame 061290/0944 →
Continuity (3)
Provisional Application 63214501 · Jun 24, 2021
Provisional Application 63155697 · Mar 2, 2021
Related Publication 20220282042A1 · Sep 8, 2022
References Cited (43)
US 1932688A · Brubaker · 1933 [cited by applicant]
US 5030252A · Sanders, Jr. et al. · 1991 [cited by applicant]
US 5034034A · Sanders, Jr. et al. · 1991 [cited by applicant]
US 5082921A · Parker · 1992 [cited by applicant]
US 6913696B1 · Korngold et al. · 2005 [cited by applicant]
US 9676906B1 · Huang et al. · 2017 [cited by applicant]
US 11891481B2 · Swager et al. · 2024 [cited by applicant]
US 20050191841A1 · Aoyama et al. · 2005 [cited by applicant]
US 20060155097A1 · Weber et al. · 2006 [cited by applicant]
US 20070117954A1 · Swager et al. · 2007 [cited by applicant]
US 20120223010A1 · Mickols et al. · 2012 [cited by applicant]
US 20150322210A1 · Sriram et al. · 2015 [cited by applicant]
US 20190054429A1 · Di Nicolo'et al. · 2019 [cited by applicant]
US 20190060835A1 · Ding et al. · 2019 [cited by applicant]
US 20200131436A1 · Fossum · 2020 [cited by examiner]
US 20200282363A1 · Harrigan · 2020 [cited by applicant]
US 20220040647A1 · Di Nicolo'et al. · 2022 [cited by applicant]
US 20220282041A1 · Swager et al. · 2022 [cited by applicant]
WO WO2017015336A1 · 2017 [cited by applicant]
WO WO2017195068A1 · 2017 [cited by applicant]
Invitation to Pay Additional Fees mailed Apr. 22, 2022, for Application No. PCT/US2021/065083. [cited by applicant]
International Search Report and Written Opinion mailed Jun. 17, 2022, for Application No. PCT/US2021/065083. [cited by applicant]
International Preliminary Report on Patentability mailed Sep. 14, 2023, for Application No. PCT/US2021/065083. [cited by applicant]
Bezzu et al., A spirobifluorene-based polymer of intrinsic microporosity with improved performance for gas separation. Adv Mater. Nov. 20, 2012;24(44):5930-3. doi: 10.1002/adma.201202393. Epub Sep. 7, 2012. [cited by applicant]
Budd et al., Solution-processed, organophilic membrane derived from a polymer of intrinsic microporosity. Adv Mater. Mar. 2004; 16(5): 456-9. [cited by applicant]
Carta et al., An efficient polymer molecular sieve for membrane gas separations. Science. Jan. 18, 2013;339(6117):303-7. [cited by applicant]
Dhara et al., Fluorinated high-performance polymers: poly(arylene ether)s and aromatic polyimides containing trifluoromethyl groups. Prog Poly Sci. Aug. 2010; 35(8): 1022-77. [cited by applicant]
Gao et al., Controlling fluoride-forming reactions for improved rate capability in lithium-perfluorinated gas conversion batteries. Adv Energy Mater 2019; 1900393. [cited by applicant]
Gao et al., Advances in the chemistry and applications of alkali-metal-gas batteries. Nat Rev Chem. Oct. 2020; 4:566-83. [cited by applicant]
He et al., Polymers with Side Chain Porosity for Ultrapermeable and Plasticization Resistant Materials for Gas Separations. Adv Mater. May 2019;31(21):e1807871. doi: 10.1002/adma.201807871. Epub Apr. 9, 2019. [cited by applicant]
He et al., Electrochemical Conversion of Nitrogen Trifluoride as a Gas-to-Solid Cathode in Li Batteries. J Phys Chem Lett. Aug. 16, 2018;9(16):4700-4706. doi: 10.1021/acs.jpclett.8b01897. Epub Aug. 3, 2018. [cited by applicant]
Huang et al. Sterically encumbered poly(arylene ether)s containing spiro-annulated substituents: Synthesis and thermal properties. J Poly Sci A; Poly Chem. Dec. 2010; 48(24): 5872-84. [cited by applicant]
Li et al., A high-capacity lithium-gas battery based on sulfur fluoride conversion. J Phys Chem C. 2018; 122(13): 7128-38. [cited by applicant]
Moghadam et al., Development of a Cambridge Structural Database Subset: A Collection of Metal-Organic Frameworks for Past, Present, and Future. Chemistry Materials 2017 29 (7), 2618-2625. [cited by applicant]
Percec et al., Termination by reductive elimination in the polyetherification of bis(aryl chlorides) activated by carbonyl groups, with bisphenolates. Macromol. 1991; 24(21): 5889-92. [cited by applicant]
Rose et al., Polymer ultrapermeability from the inefficient packing of 2D chains. Nat Mater. Sep. 2017;16(9):932-937. doi: 10.1038/nmat4939. Epub Jul. 31, 2017. [cited by applicant]
Shamsabadi et al., A New Pentiptycene-Based Dianhydride and Its High-Free-vol. Polymer for Carbon Dioxide Removal. ChemSusChem. Jan. 23, 2018;11(2):472-482. doi: 10.1002/cssc.201701491. Epub Jan. 4, 2018. [cited by applicant]
Shibasaki et al., Synthesis of Poly(aryl ether) by Pd-catalyzed polycondensation. Chem Lett. Aug. 2002; 31(8): 794-5. [cited by applicant]
Slater et al., Porous materials. Function-led design of new porous materials. Science. May 29, 2015;348(6238):aaa8075. doi: 10.1126/science.aaa8075. PMID: 26023142. [cited by applicant]
Tian et al., Porous Aromatic Frameworks (PAFs). Chem Rev. Aug. 2, 20206;120(16):8934-8986. doi: 10.1021/acs.chemrev.9b00687. Epub Feb. 26, 2020. PMID: 32101403. [cited by applicant]
Wang et al., Synthesis of new fluorene-based poly(aryl ether) containing pendant tert-butyl groups for low dielectric materials. Coll Poly Sci. Oct. 2014; 293: 313-8. [cited by applicant]
Yu et al., Role of amine type of CO2 separation performance within amine functionalized silica/organosilica membranes: a review. Appl Sci. Jun. 2018; 8(7): 1032. [cited by applicant]
Zou et al., Synthesis of cardo poly(arylene ether ketone amide)s by heterogeneous palladium-catalyzed polycondensation of aromatic diiodides, aromatic diamines containing cardo groups and CO. Poly Bull. Jun. 2019; 77(4)… [cited by applicant]