Nanohoop-functionalized polymer embodiments and methods of making and using the same

Patent metadata

Field	Value
Publication number	US-2023323019-A1
Application number	US-202318208671-A
Country	US
Kind code	A1
Filing date	Jun 12, 2023
Priority date	Sep 27, 2019
Publication date	Oct 12, 2023
Grant date	—

Abstract

Disclosed herein are embodiments of a nanohoop-functionalized polymer and methods of making and using the same. In particular embodiments, polymer comprises one or more nanohoops that extend from the polymer backbone. Also disclosed herein are polymerizable nanohoop monomer embodiments that can be used to make the polymer embodiments disclosed herein.

First claim

We claim:

1 . A compound having a structure according to Formula I

wherein:
each PFG independently is a polymerizable functional group comprising a bicyclic structure comprising at least one double bond;
the optional linker is selected from aliphatic, heteroaliphatic, haloaliphatic, haloheteroaliphatic, aromatic, or an organic functional group;
the nanohoop comprises six or more aromatic ring systems and wherein each aromatic ring is directly bound to at least two other rings of the nanohoop by two separate single covalent bonds positioned para, ortho, or meta relative to one another; and
q is 1 or 2.

2 . The compound of claim 1 , wherein the bicyclic structure is norbornene.

3 . The compound of claim 1 , wherein each aromatic ring is directly bound to at least two other rings of the nanohoop by two separate single covalent bonds positioned para relative to one another.

4 . The compound of claim 1 , wherein q is 2 and each PFG is the same.

5 . The compound of claim 1 , wherein q is 2 and each PFG is different.

6 . The compound of claim 1 , having a structure according to Formula II or III

wherein each R′ independently is a substituent other than hydrogen; each s independently is an integer selected from 0 to 10; and p is an integer selected from 1 to 1000.

7 . The compound of claim 1 , wherein the compound is

8 . A method of making the compound of claim 1 , comprising:
coupling together two coupling partners using a transition metal-mediated cross-coupling reaction to provide a polymerizable nanohoop monomer precursor; and performing a reductive aromatization step with the polymerizable nanohoop monomer precursor to provide the compound of claim 1 .

9 . The method of claim 8 , wherein at least one of the two coupling partners comprises the PFG.

10 . The method of claim 8 , wherein the PFG is norbornene.

11 . A compound having a structure according to Formula I

wherein:
each PFG independently is a polymerizable functional group selected from a bicyclic structure comprising at least one double bond, an acrylate, a methacrylate, a methyacrylamide, a styrene, a diene, vinyl acetate, n-vinylpyrrolidone, an epoxide, an acrylonitrile, a cyanoacrylate, or an ether;
the optional linker is selected from aliphatic, heteroaliphatic, haloaliphatic, haloheteroaliphatic, aromatic, or an organic functional group;
the nanohoop comprises six or more aromatic ring systems and wherein each aromatic ring is bound to at least two other rings of the nanohoop by two separate single covalent bonds positioned para, ortho, or meta relative to one another; and
q is 1 or 2.

12 . The compound of claim 11 , wherein the PFG is norbornene.

13 . The compound of claim 11 , wherein each aromatic ring is directly bound to at least two other rings of the nanohoop by two separate single covalent bonds positioned para relative to one another.

14 . The compound of claim 11 , wherein q is 2 and each PFG is the same.

15 . The compound of claim 11 , wherein q is 2 and each PFG is different.

16 . A method of making the compound of claim 11 , comprising:
coupling together two coupling partners using a transition metal-mediated cross-coupling reaction to provide a polymerizable nanohoop monomer precursor; and performing a reductive aromatization step with the polymerizable nanohoop monomer precursor to provide the compound of claim 11 .

17 . The method of claim 16 , wherein at least one of the two coupling partners comprises the PFG.

18 . The method of claim 16 , wherein the PFG is norbornene.

Assignees

• Univ Oregon

Inventors

• Jasti Ramesh
• Maust Ruth
• Li Penghao

Classifications

• C08G61/10 Primary

  only aromatic carbon atoms, e.g. polyphenylenes · CPC title

• C08J3/24

  Crosslinking, e.g. vulcanising, of macromolecules (mechanical aspects B29C35/00; crosslinking agents C08K) · CPC title

• C08J2365/02

  Polyphenylenes · CPC title

• C08G61/08 Primary

  of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring · CPC title

• C08G2261/11

  Homopolymers · CPC title