Viologen-based rotaxanes

Patent metadata

Field	Value
Publication number	US-10259913-B2
Application number	US-201715419030-A
Country	US
Kind code	B2
Filing date	Jan 30, 2017
Priority date	Jan 29, 2016
Publication date	Apr 16, 2019
Grant date	Apr 16, 2019

Abstract

Disclosed herein are nanoactuating rotaxanes comprising a threading component, the threading component comprising a oligoviologen, and at least two macrocylic components, wherein the oligoviologen is threaded through each of the macrocylic components. Also disclosed are methods for making and using the rotaxanes.

First claim

We claim:

1. An nanoaccuator comprising a rotaxane,
wherein the rotaxane comprises a threading component and at least two macrocylic components;
wherein the threading component comprises a oligoviologen;
wherein the threading component is threaded through each of the macrocylic components and
wherein the at least two macrocylic components are CBPQT macrocylic components.

2. The nanoaccuator of claim 1 , wherein the threading component further comprises a first linking subunit, L, and/or a second linking subunit, L′.

3. The nanoaccuator of claim 1 ,
wherein the threading component further comprises a first stopper, S, and/or a second stopper, S′.

4. The nanoaccuator of claim 2 ,
wherein the threading component further comprises a first stopper, S, and/or a second stopper, S′ and
wherein the L links a first end of the oligoviologen to S and the L′ links a second end of the oligoviologen to the S′.

5. The nanoaccuator of claim 1 , wherein the oligoviologen comprises n+1 viologen subunits, V, and wherein n is an integer.

6. The nanoaccuator of claim 5 , wherein V is a BIPY subunits.

7. The nanoaccuator of claim 1 , wherein the oligoviolgen further comprises n bridging subunits, B, linking the viologen subunits.

8. The nanoaccuator of claim 7 , wherein B is a paraxylene subunit.

9. The nanoaccuator of claim 5 , wherein n is 3 or 4.

10. The nanoaccuator of claim 2 , wherein the first linking subunit, L, the second linking subunit, L′, or both the first linking subunit and the second linking subunit comprise an alkyl subunit.

11. The nanoaccuator of claim 2 , wherein L is a polyethylene oxide, L′ is a polyethylene oxide, or both L and L′ are polyethylene oxides.

12. The nanoaccuator of claim 3 ,
wherein S is a triazole stopper moiety having a formula of R—C 2 N 3 —R′, S′ is a triazole stopper moiety having a formula of R—C 2 N 3 —R′, or both of S and S′ are triazole stopper moieties having the formula R—C 2 N 3 —R′, and
wherein R and R′ are bulky moieties capable of preventing dethreading of the macrocyclic components.

13. The nanoaccuator of claim 1 , wherein the rotaxane is complexed with an anion.

14. The nanoaccuator of claim 13 , wherein the anion is PF 6 − or CF 3 C(═O)O − .

15. The nanoaccuator of claim 1 , wherein the reducing the rotaxane contracts the nanoreactor and/or oxidizing the rotaxane extends the nanoactuator.

16. The nanoaccuator of claim 1 , wherein the nanoactuator is capable of reversible contraction and extension.

17. A nanoaccuator comprising a rotaxane,
wherein the rotaxane comprises a threading component;
wherein the threading component comprising a linear subchain having a formula L-V-[B-V] n -L′, and at least two macrocycle components;
wherein each of the at least two macrocycle components are threaded onto the threading component;
wherein V is a viologen subunit;
wherein B is a bridging subunit;
wherein L and L′ are linking subunits;
wherein n is an integer, and
wherein the at least two macrocylic components are CBPQT macrocylic components.

18. The nanoaccuator of claim 17 ,
wherein the threading component further comprises a first stopper subunit, S, and a second stopper subunit, S′, and
wherein the threading component has a formula of S-L-V-[B-V] n -L′-S′.

19. A method of accuating a nanoactuator, the method comprising oxidating or reducing a nanoreactor as in claim 1 ,
wherein oxidizing the nanoactuator extends the nanoactuator and reducing the nanoactuator contracts the nanoactuator.

Assignees

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

Inventors

• Stoddart James Fraser
• Wang Yuping
• Frasconi Marco
• Sun Junling

Classifications

• C07D471/22

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

• C08G83/007 Primary

  Polyrotaxanes; Polycatenanes · CPC title

• C07D401/14

  containing three or more hetero rings · CPC title

• C07D213/57

  Nitriles · CPC title