Poly-cyanostilbene macrocycles

Patent metadata

Field	Value
Publication number	US-9701621-B2
Application number	US-201414767570-A
Country	US
Kind code	B2
Filing date	Feb 13, 2014
Priority date	Feb 13, 2013
Publication date	Jul 11, 2017
Grant date	Jul 11, 2017

Abstract

The present disclosure concerns synthesis and anion binding features of poly-cyanostilbene macrocycles of Formula (I):

First claim

What is claimed is:

1. A poly-cyanostilbene macrocycle of Formula (I):

wherein R 1 , R 2 , R 3 , R 4 , and R 5 are each independently selected from the group consisting of alkenyl, alkyl, alkoxy, alkyl-NH-alkyl, aryl, cycloalkyl, heteroaryl, heterocycle, haloalkyl, hydrogen, iodo, —OR 6 , —N(R 7 R 8 ), —CO 2 R 9 , —C(O)—N(R 10 R 11 ), wherein R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are each independently selected from the group consisting of alkenyl, alkyl, alkoxy, alkyl-NH-alkyl, aryl, arylalkyl, cycloalkyl, heteroaryl, heterocycle, haloalkyl, and hydrogen.

2. The poly-cyanostilbene macrocycle of claim 1 , wherein R 1 , R 2 , R 3 , R 4 , and R 5 comprise identical substituents.

3. The poly-cyanostilbene macrocycle of claim 1 , wherein R 1 , R 2 , R 3 , R 4 , and R 5 comprise tert-butyl groups.

4. The poly-cyanostilbene macrocycle of claim 1 , wherein the poly-cyanostilbene macrocycle having Formula (I) is selected from the following:

5. The poly-cyanostilbene macrocycle of claim 1 , wherein R 1 is iodo and R 2 , R 3 , R 4 , and R 5 comprise substituents other than iodo.

6. The poly-cyanostilbene macrocycle of claim 5 , wherein R 2 , R 3 , R 4 , and R 5 comprise identical substituents.

7. The poly-cyanostilbene macrocycle of claim 6 , wherein R 2 , R 3 , R 4 , and R 5 comprise tert-butyl groups.

8. The poly-cyanostilbene macrocycle of claim 1 , wherein the poly-cyanostilbene macrocycle having Formula (I) is selected from the following:

9. A poly-cyanostilbene macrocycle of Formula (IV):

wherein R 2 , R 3 , R 4 , and R 5 are selected from the group consisting of alkenyl, alkyl, alkoxy, alkyl-NH-alkyl, aryl, cycloalkyl, heteroaryl, heterocycle, haloalkyl, hydrogen, iodo, —OR 6 , —N(R 7 R 8 ), —CO 2 R 9 , —C(O)—N(R 10 R 11 ), wherein R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are selected from the group consisting of alkenyl, alkyl, alkoxy, alkyl-NH-alkyl, aryl, arylalkyl, cycloalkyl, heteroaryl, heterocycle, haloalkyl, and hydrogen, and L comprising an alkyl moiety ranging from C 1-30 , said alkyl moiety comprising a saturated or unsaturated alkyl moiety, and optionally comprises substituents.

10. The poly-cyanostilbene macrocycle of claim 9 , wherein R 2 , R 3 , R 4 , and R 5 comprise tert-butyl groups.

11. The poly-cyanostilbene macrocycle of claim 9 , wherein the poly-cyanostilbene macrocycle of Formula (IV) comprises:

12. A complex comprising:
(a) an anion and
(b) a poly-cyanostilbene macrocycle of Formula (I):

wherein R 1 , R 2 , R 3 , R 4 , and R 5 are selected from the group consisting of alkenyl, alkyl, alkoxy, alkyl-NH-alkyl, aryl, cycloalkyl, heteroaryl, heterocycle, haloalkyl, hydrogen, iodo, —OR 6 , —N(R 7 R 8 ), —CO 2 R 9 , —C(O)—N(R 10 R 11 ), wherein R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are selected from the group consisting of alkenyl, alkyl, alkoxy, alkyl-NH-alkyl, aryl, arylalkyl, cycloalkyl, heteroaryl, heterocycle, haloalkyl, and hydrogen.

13. The complex of claim 12 , wherein R 1 , R 2 , R 3 , R 4 , and R 5 comprise tert-butyl groups.

14. The complex of claim 12 , wherein the poly-cyanostilbene macrocycle having Formula (I) is selected from the following:

15. The complex of claim 12 , wherein the anion is selected from a group consisting of BF 4 − , ClO 4 − , PF 6 − , N(SO 2 CF 3 ) 2 − , N(SO 2 C 2 F 5 ) 2 − , CH 3 SO 3 − , CF 3 SO 3 − , AsO 4 3− , AsF 6 − , AlCl 4 − , PO 4 3− , HPO 4 2− , H 2 PO 4 − , SO 4 2− , HSO 4 − , B(CN) 4 − , Cl − , Br − , I − , cyanide, BrO 4 − , IO 4 − , F − , HF 2 − , TcO 4 − , RPO 4 2− , R 2 PO 4 − , RSO 3 − , SCN − , N 3 − , I 3 − , CO 3 2− , HCO 3 − , FeCl 4 − , and PtCl 6 2− , wherein R comprises a substituent.

16. A complex comprising:
(a) an anion and
(b) a poly-cyanostilbene macrocycle of Formula (IV):

wherein R 2 , R 3 , R 4 , and R 5 are selected from the group consisting of alkenyl, alkyl, alkoxy, alkyl-NH-alkyl, aryl, cycloalkyl, heteroaryl, heterocycle, haloalkyl, hydrogen, iodo, —OR 6 , —N(R 7 R 8 ), —CO 2 R 9 , —C(O)—N(R 10 R 11 ), wherein R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are selected from the group consisting of alkenyl, alkyl, alkoxy, alkyl-NH-alkyl, aryl, arylalkyl, cycloalkyl, heteroaryl, heterocycle, haloalkyl, and hydrogen, and L comprising an alkyl moiety ranging from C 1-30 , said alkyl moiety comprising a saturated or unsaturated alkyl moiety, and optionally comprises substituents.

17. The complex of claim 16 , wherein R 2 , R 3 , R 4 , and R 5 comprise tert-butyl groups.

18. The complex of claim 16 , wherein the poly-cyanostilbene macrocycle of Formula (IV) comprises:

19. The complex of claim 16 , wherein the anion is selected from a group consisting of BF 4 − , ClO 4 − , PF 6 − , N(SO 2 CF 3 ) 2 − , N(SO 2 C 2 F 5 ) 2 − , CH 3 SO 3 − , CF 3 SO 3 − , AsO 4 3− , AsF 6 − , AlCl 4 − , PO 4 3− , HPO 4 2− , H 2 PO 4 − , SO 4 2− , HSO 4 − , B(CN) 4 − , Cl − , Br − , I − , cyanide, BrO 4 − , IO 4 − , F − , HF 2 − , TcO 4 − , RPO 4 2− , R 2 PO 4 − , RSO 3 − , SCN − , N 3 − , I 3 − , CO 3 2− , HCO 3 − , FeCl 4 − , and PtCl 6 2− , wherein R comprises a substituent.

Assignees

• Univ Indiana Res & Tech Corp
• Univ Indiana Res & Tech Corp

Inventors

• Flood Amar H
• Lee Semin
• Mcdonald Kevin

Classifications

• C07D249/04

  1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles · CPC title

• C07D213/57

  Nitriles · CPC title

• C07C255/47 Primary

  to carbon atoms of rings being part of condensed ring systems · CPC title

• C07F7/1804

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title

• C07F7/081

  comprising at least one atom selected from the elements N, O, halogen, S, Se or Te · CPC title