Nanohoop compound embodiments comprising meta-substitution and molecular systems comprising the same

Patent metadata

Field	Value
Publication number	US-11142500-B2
Application number	US-201916505252-A
Country	US
Kind code	B2
Filing date	Jul 8, 2019
Priority date	Jul 9, 2018
Publication date	Oct 12, 2021
Grant date	Oct 12, 2021

Abstract

Disclosed herein are embodiments of nanohoop compounds, methods of making, and methods of using the same. The nanohoop compounds disclosed herein have discrete ring system(s) that comprise a unique meta-substituted motif that affords a strained cavity in which myriad reaction chemistries can take place. The unique structures and properties of the nanohoop compounds disclosed herein also lend to their use in a variety of biological applications, and as interlocked structures in molecular machines.

First claim

We claim:

1. A nanohoop compound, having a structure satisfying Formula 1

wherein
each RS ring independently has a structure satisfying Formula II

wherein at least one X is N, P, or C-CFG, wherein CFG is a coordinating functional group;
each other X independently is C or C(R 1 ) where R 1 is selected from an electron-accepting group or an electron-donating group; and
r and t independently are 0 or 1;

each A and A′ ring independently is an aromatic ring;
each R independently is selected from hydrogen, an electron-donating group, an electron-accepting group, or any combinations thereof;
m is an integer selected from 1 to 4;
m′ is an integer selected from 0 to 4;
each s and s′ independently is an integer selected from 0 to 4;
each n and n′ independently is an integer selected from 0 to 24; and
p is an integer selected from 1 to 20.

2. The nanohoop compound of claim 1 , wherein each RS ring independently has a structure satisfying one or more of Formulas IIA-IIC

3. The nanohoop compound of claim 1 , wherein ring B is a heteroaryl ring and r and t are 0.

4. The nanohoop compound of claim 1 , wherein ring B and ring C bind together to provide a hetero-biaryl ring group and r is 0.

5. The nanohoop compound of claim 1 , wherein ring B, ring C, and ring D bind together to provide a three-ring heteroaryl ring system and r is 0.

6. The nanohoop compound of claim 1 , wherein ring B, ring C, ring D, and ring E bind together to provide a four-ring fused heteroaryl ring system, and r is 0.

7. The nanohoop compound of claim 1 , wherein r is 1 and t is 1 and ring B, ring C, and ring F bind together to provide a heterotriaryl ring system.

8. The nanohoop compound of claim 1 , wherein the nanohoop compound has a structure satisfying any one or more of Formulas IIIA-IIIF

9. The nanohoop compound of claim 8 , wherein for Formulas IIIA, IIIB, IIIC, IIIE, and IIIF, each X is N and for Formula IIID, at least one X is C(R 1 ) where R 1 is selected from an electron-accepting group or an electron-donating group and each other X independently is C or C(R 1 ) where R 1 is selected from an electron-accepting group or an electron-donating group.

10. The nanohoop compound of claim 1 , wherein the nanohoop compound has a structure satisfying any one or more of Formulas IVA-IVC

wherein n is 1, or 3-5.

11. The nanohoop compound of claim 1 , wherein the nanohoop compound is

12. The nanohoop compound of claim 1 , further comprising an interlocked molecule that is confined by a cavity defined by the nanohoop compound.

13. The nanohoop compound of claim 12 , wherein the interlocked molecule is a triazole-containing compound or an alkyne-containing compound.

14. The nanohoop compound of claim 12 , wherein the nanohoop compound is selected from

Assignees

• Univ Oregon

Inventors

• Jasti Ramesh
• Van Raden Jeff

Classifications

• C07D471/18

  Bridged systems · CPC title

• C07C15/14

  all phenyl groups being directly linked · CPC title

• C07D471/08

  Bridged systems · CPC title

• Y10T436/11

  Automated chemical analysis · CPC title

• C07D471/22

  in which the condensed systems contains four or more hetero rings · CPC title