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