Densely charged catenanes

Patent metadata

Field	Value
Publication number	US-11566014-B2
Application number	US-201917045288-A
Country	US
Kind code	B2
Filing date	Apr 5, 2019
Priority date	Apr 5, 2018
Publication date	Jan 31, 2023
Grant date	Jan 31, 2023

Abstract

Cationic radial catenane comprising a central cationic ring and two or more radial cationic rings mechanically interlocked central cationic ring and methods for making the same are disclosed herein.

First claim

We claim:

1. A cationic catenane comprising a central cationic ring and two or more radial cationic rings mechanically interlocked with the central cationic ring, wherein the central cationic ring comprises two or more viologen subunits and two reactive linkers and wherein the catenane comprises an equal number of radial cationic rings as viologen subunits.

2. The catenane of claim 1 , wherein the central cationic ring comprises

wherein V is a viologen subunit, R 1 and R 2 are reactive linkers formed by a click reaction, and L 1 , L 2 , L 3 , and L 4 are independently selected from an alkyl, an alkenyl, an aryl, an alkylaryl, a triazole, or an alkyltriazole or

wherein V is a viologen subunit, R 1 and R 2 are reactive linkers formed by a click reaction, and L 1 , L 2 , L 3 , and L 4 are independently selected from an alkyl, an alkenyl, an aryl, an alkylaryl, a triazole, or an alkyltriazole.

3. The catenane of claim 2 , wherein the catenane is a dodecacationic catenane (r[3]C 12+ ).

4. The catenane of claim 3 , wherein each of the radial cationic rings comprise cyclobis(paraquat-p-phenylene) tetracation (CBPQT 4+ ).

5. The catenane of claim 2 , wherein the catenane is a hexaradical/hexacationic catenane (r[3]C 6(.+) ).

6. The catenane of claim 5 , wherein each of the radial cationic rings comprise cyclobis(paraquat-p-phenylene) bisradical dication (CBPQT 2(.+) ).

7. The catenane of claim 1 , wherein the central cationic ring comprises

wherein V is a viologen subunit, R 1 and R 2 are reactive linkers formed by a click reaction, and L 1 , L 2 , L 3 , L 4 , and L 5 are independently selected from an alkyl, an alkenyl, an aryl, an alkylaryl, a triazole, or an alkyltriazole.

8. The catenane of claim 7 , wherein the catenane is an octodecacationic catenane (r[4]C 18+ ).

9. The catenane of claim 8 , wherein each of the radial cationic rings comprise cyclobis(paraquat-p-phenylene) tetracation (CBPQT 4+ ).

10. The catenane of claim 7 , wherein the catenane is a nonaradical/nonacationic catenane (r[4]C 9(.+) ).

11. The catenane of claim 10 , wherein each of the radial cationic rings comprise cyclobis(paraquat-p-phenylene) bisradical dication (CBPQT 2(.+) ).

12. The catenane of claim 1 , wherein the central cationic ring comprises

wherein V is a viologen subunit, R 1 and R 2 are reactive linkers formed by a click reaction, and L 1 , L 2 , L 3 , L 4 , L 5 , and L 6 are independently selected from an alkyl, an alkenyl, an aryl, an alkylaryl, a triazole, or an alkyltriazole.

13. The catenane of claim 12 , wherein the catenane is a tetracosacationic catenane (r[5]C 24+ ).

14. The catenane of claim 13 , wherein each of the radial cationic rings comprise cyclobis(paraquat-p-phenylene) tetracation (CBPQT 4+ ).

15. The catenane of claim 12 , wherein the catenane is a dodecaaradical/dodecacationic catenane (r[5]C 12(.+) ).

16. The catenane of claim 15 , wherein each of the radial cationic rings comprise cyclobis(paraquat-p-phenylene) bisradical dication (CBPQT 2(.+) ).

17. A composition comprising the catenane of claim 1 and a counterion.

18. A crystalline composition comprising the catenane of claim 1 .

19. A device comprising the catenane of any one of claim 1 , wherein the device is a switch, transistor, memory device, electrochromic device, or redox-flow battery.

20. A method of forming a cationic catenane, the method comprising:
providing a pseudorotaxane, the pseudorotaxane comprising:
a threading component having a first terminal moiety, a second terminal moiety, and two or more radical/cation viologen subunits between the first terminal moiety and the second terminal moiety and
two or more diradical/dicationic rings threaded by the threading component,
wherein the pseudorotaxane comprises an equal number of diradical/dicationic rings as viologen subunits; and

contacting the first terminal moiety with the second terminal moiety to form a central cationic ring that mechanically interlocks the two or more diradical/dicationic rings, thereby forming the catenane,
wherein each of the radial cationic rings comprise cyclobis(paraquat-p-phenylene) bisradical dication (CBPQT 2(.+) ) and/or wherein the threading component comprises two, three, or four viologen subunits.

Assignees

• Univ Northwestern
• King Abdulaziz City For Science And Tech Kacst

Inventors

• Nguyen Minh T
• Stoddart James Fraser

Classifications

• H01L45/085

  Electricity · mapped topic

• C07D401/14 Primary

  containing three or more hetero rings · CPC title

• C07B2200/13

  Crystalline forms, e.g. polymorphs · CPC title

• H10K85/654

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title

• H10N70/245

  the species being metal cations, e.g. programmable metallization cells · CPC title