Supramolecular assembly of rigid macrocycles through cooperative hydrogen bond interactions

Patent metadata

Field	Value
Publication number	US-10745418-B2
Application number	US-201716069940-A
Country	US
Kind code	B2
Filing date	Jan 13, 2017
Priority date	Jan 13, 2016
Publication date	Aug 18, 2020
Grant date	Aug 18, 2020

Abstract

Provided herein are supramolecular assemblies, the supramolecular assemblies comprising a racemic mixture of rigid macrocycles capable of interacting through [C—H . . . O] hydrogen bonds. Also provided herein are methods for preparing supramolecular assemblies, the method comprising providing a mixture of rigid macrocycles capable of interacting through [C—H . . . O] hydrogen bonds, the mixture of rigid macrocycles comprising a first rigid macrocycle enantiomer and a second rigid macrocycle enantiomer, and providing a solvent.

First claim

What is claimed:

1. A supramolecular assembly comprising a mixture of rigid macrocycles capable of interacting through [C—H . . . O] hydrogen bonds, wherein the mixture of rigid macrocycles comprises a first rigid napthalenediimide-based macrocycle entantiomer and a second rigid napthalenediimide-based macrocycle enantiomer.

2. The supramolecular assembly of claim 1 , wherein the mixture is a racemic mixture of the first rigid macrocycle enantiomer and the second rigid macrocycle enantiomer.

3. The supramolecular assembly of claim 1 , wherein the first rigid macrocycle enantiomer is a first rigid triangular macrocycle enantiomer and the second rigid macrocycle enantiomer is a second rigid triangular macrocycle enantiomer.

4. The supramolecular assembly of claim 1 , wherein the first rigid napthalenediimide-based macrocycle enantiomer is the compound of:

and the second rigid napthalenediimide-based macrocycle enantiomer is a compound of:

5. The supramolecular assembly of claim 1 , wherein the first rigid macrocycle enantiomer cooperatively interacts with the second rigid macrocycle enantiomer through [C—H . . . O] hydrogen bonds.

6. The supramolecular assembly of claim 1 , wherein the supramolecular assembly is a gel.

7. The supramolecular assembly of claim 1 , wherein the supramolecular assembly is a precipitate.

8. The supramolecular assembly of claim 1 wherein the supramolecular assembly has a fibrillar morphology or a needle morphology.

9. The supramolecular assembly of claim 1 , wherein the supramolecular assembly has a high-aspect ratio.

10. The supramolecular assembly of claim 1 , wherein the supramolecular assembly has a first dimension of less than about 3 nm and a second dimension of greater than about 100 nm.

11. The supramolecular assembly of claim 1 , wherein the first rigid macrocycle enantiomer and the second rigid macrocycle enantiomer coaxially stack in an alternating fashion.

12. A method for preparing a supramolecular assembly, the method comprising providing a mixture of rigid macrocycles capable of interacting through [C—H . . . O] hydrogen bonds, the mixture of rigid macrocycles comprising a first rigid napthalenediimide-based macrocycle enantiomer and a second rigid napthalenediimide-based macrocycle enantiomer, and providing a solvent.

13. The method of claim 12 , wherein the mixture of rigid macrocycles is an equimolar mixture of the first rigid macrocycle and the second rigid macrocycle.

14. The method of claim 12 , wherein providing the mixture of rigid macrocycles comprises mixing a first solution, the first solution comprising the first rigid macrocycle, and a second solution, the second solution comprising the second rigid macrocycle.

15. The method of claim 12 , wherein providing the mixture of rigid macrocycles comprises dissolving the first rigid macrocycle and/or the second rigid macrocycle.

16. The method of claim 12 , wherein the solvent is a halogenated alkane.

17. A battery comprising the supramolecular assembly as in claim 1 .

18. The battery of claim 17 , wherein the battery is a lithium battery.

19. The method of claim 12 , wherein the first rigid napthalenediimide-based macrocycle enantiomer is the compound of:

and the second rigid napthalenediimide-based macrocycle enantiomer is a compound of:

20. The battery of claim 17 , wherein the first rigid napthalenediimide-based macrocycle enantiomer is the compound of:

and the second rigid napthalenediimide-based macrocycle enantiomer is a compound of:

Assignees

• Univ Northwestern

Inventors

• Stoddart James Fraser
• Liu Zhichang

Classifications

• Y02E60/10

  Energy storage using batteries · CPC title

• C07D471/06

  Peri-condensed systems · CPC title

• C07D519/00 Primary

  Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00 · CPC title

• H01M10/052

  Li-accumulators · CPC title