Poly-cyanostilbene macrocycles

Patent metadata

Field	Value
Publication number	US-10077233-B2
Application number	US-201715645721-A
Country	US
Kind code	B2
Filing date	Jul 10, 2017
Priority date	Feb 13, 2013
Publication date	Sep 18, 2018
Grant date	Sep 18, 2018

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 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,
wherein the anion is selected from 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 − , PtCl 6 2− , S n x− where n=1-8, and x=1 or 2, P 2 O 7 4− , HP 2 O 7 3− , H 2 P 2 O 7 2− H 3 P 2 O 7 − , a polyphosphate polyanion, a tetrazine anion, a dithiadiazolide anion, RBF 3 − , Ar—O − , wherein R comprises a substituent.

2. The complex of claim 1 , wherein R 1 , R 2 , R 3 , R 4 , and R 5 comprise identical substituents.

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

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

5. 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,
wherein the anion is selected from 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 31 , AsO 4 3− , AsF 6 − , AlCl 4 − , PO 4 3− , HPO 4 2− , H 2 PO 4 − , SO 4 2− , HSO 3 − , B(CN) 4 − , Cl − , Br − , I − , cyanide, BrO 4 31 , 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 − , PtCl 6 2− , S n x− where n=1-8, and x=1 or 2, P 2 O 7 4− , HP 2 O 7 3− , H 2 P 2 O 7 2− , H 3 P 2 O 7 − , a polyphosphate polyanion, a tetrazine anion, a dithiadiazolide anion, RBF 3 − , Ar—O − , wherein R comprises a substituent.

6. The complex of claim 5 , wherein R 2 , R 3 , R 4 , and R 5 comprise identical substituents.

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

8. The complex of claim 5 , wherein the poly-cyanostilbene macrocycle of Formula (IV) comprises:

Assignees

• Univ Indiana Res & Tech Corp

Inventors

• Flood Amar H
• Lee Semin
• Mcdonald Kevin

Classifications

• C07C255/47 Primary

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

• C07C2603/90

  containing more than four rings · CPC title

• C07F7/1852

  Chemistry & Metallurgy · mapped topic

• C07D249/06

  with aryl radicals directly attached to ring atoms · CPC title

• C07D213/57

  Nitriles · CPC title