Porous compositions and related methods
Porous compositions such as flexible polymers with side chain porosity are generally provided. In some embodiments, the composition comprises a flexible polymer backbone and a plurality of rigid side chains. In some embodiments, the rigid side chains form pores. In some embodiments, the rigid side chains may comprise two or more [2.2.2] bicyclic cores (e.g., formed by a ring opening metathesis polymerization. The compounds and methods described herein may be useful in various applications including, for example, gas separation.
1. A membrane configured for separation,
the membrane comprising a composition, the composition comprising:
a flexible polymer backbone; and
a plurality of rigid side chains associated with the flexible polymer backbone, each rigid side chain comprising a bridged bicyclic-based compound comprising two or more [2.2.2] bicyclic cores,
wherein the composition is porous,
wherein the membrane has a thickness of less than or equal to 180 microns.
2. A membrane as in claim 1 , wherein the membrane exhibits a CO 2 plasticization pressure of greater than or equal to 50 bar.
3. A membrane as in claim 1 , wherein the membrane resists plasticization by CO 2 at pressures up to 51 bar.
4. A membrane as in claim 1 , wherein the membrane has a gas permeability to CO 2 of greater than or equal to 20000 Barrer.
5. A membrane as in claim 1 , wherein the membrane has a gas permeability to H 2 of greater than or equal to 8000 Barrer.
6. A membrane as in claim 1 , wherein the composition has a BET internal surface area of greater than or equal to 100 m 2 g −1 .
7. A membrane as in claim 1 , wherein at least a portion of pores present in the membrane have a pore size of greater than or equal to 40 nm.
8. A membrane as in claim 1 , wherein the flexible polymer backbone comprises poly(norbenzene).
9. A membrane as in claim 1 , wherein at least one of the two or more [2.2.2] bicyclic cores has the following structure:
wherein:
R 1 -R 12 are the same or different and are hydrogen, halo, hydroxyl, amino, alkyl, heteroalkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocyclyl, or a carbonyl group, any of which is optionally substituted, or, any two adjacent groups of R 1 -R 12 are joined together to form an optionally substituted ring.
10. A membrane as in claim 1 , wherein the bridged bicyclic-based compound is an oligoiptycene.
11. A membrane as in claim 1 , wherein the bridged bicyclic-based compound has a structure as in:
wherein:
each R is the same or different and are hydrogen, halo, hydroxyl, amino, alkyl, heteroalkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocyclyl, or a carbonyl group, any of which is optionally substituted, or is joined together to form an optionally substituted ring,
m is an integer and is at least 1, and
n is an integer and is at least 1.
12. A membrane as in claim 11 , wherein each R is CF 3 or OMe.