Enamine compound and use thereof

Patent metadata

Field	Value
Publication number	US-11773052-B2
Application number	US-201816489563-A
Country	US
Kind code	B2
Filing date	Mar 2, 2018
Priority date	Mar 2, 2017
Publication date	Oct 3, 2023
Grant date	Oct 3, 2023

Abstract

Provided are a donor-acceptor type compound having a novel structure and its use.
An enamine compound represented by general formula (1)

(in the formula:

R 1 represents an electron-withdrawing group;
A represents a divalent aromatic hydrocarbon group which may contain a substituent, a divalent aromatic heterocyclic group which may contain a substituent or a divalent unsaturated aliphatic hydrocarbon group which may contain a substituent;
R 2 represents a hydrogen atom or a hydrocarbon group which may contain a substituent;
R 3 and R 4 are the same or different from each other and represent an aromatic hydrocarbon group which may contain a substituent or an aromatic heterocyclic group which may contain a substituent, or R 3 and R 4 together form an optionally substituted bicyclic aromatic heterocyclic group containing two or more nitrogen atoms or a nitrogen atom and an oxygen atom or a sulfur atom, or a tricyclic aromatic heterocyclic group which may contain a substituent; and
R 2 and A, or R 2 and R 3 may together form a cyclic structure).

First claim

The invention claimed is:

1. An enamine compound of formula (1)

wherein
R 1 is a halogen, a nitro group, an acyl group, a cyano group, a hydrocarbon oxycarhonyl group, an unsubstituted carboxamide group, an aromatic heterocyclic group, or -A 1 -C(R 5 )═CH—N(R 6 )(R 7 ),
A 1 is a single bond. an unsubstituted divalent aromatic hydrocarbon group, an unsubstituted divalent aromatic heterocyclic group, or an unsubstituted divalent unsaturated aliphatic hydrocarbon group.
R 5 is H or an unsubstituted hydrocarbon group,
R 6 and R 7 are independently an unsubstituted aromatic hydrocarbon group, or an unsubstituted aromatic heterocyclic group, or R 6 and R 7 together form a bicyclic aromatic heterocyclic group comprising two or more nitrogen atoms or a nitrogen atom and an oxygen atom or a sulfur atom, or a tricyclic aromatic heterocyclic group, and
A is an unsubstituted phenylene group,
R 2 is H or an unsubstituted hydrocarbon group, and
R 3 and R 4 are each an unsubstituted phenyl group.

2. The enamine compound of claim 1 , wherein R 2 is H, an aliphatic hydrocarbon group, or an aromatic hydrocarbon group.

3. The enamine compound of claim 1 , wherein R 2 is H, an alkyl group having 1 to 6 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms.

4. The enamine compound of claim 1 , wherein R 1 is a halogen atom, a nitro group, an acyl group, a cyano group, a hydrocarbon oxycarbonyl group, a carboxamide group optionally comprising an alkyl group as a substituent, a dicyanoethenyl group, an aromatic heterocyclic group having at least 1 to 4heteroatoms, or -A 1 -C(R 5 )═CH—N(R 6 )(R 7 ),
wherein
A 1 is an aromatic heterocyclic group having 1 to 4 heteroatoms,
R 5 is H or a hydrocarbon group, and
R 6 and R 7 are independently an aromatic hydrocarbon group or an aromatic heterocyclic group, or R 6 and R 7 together form a bicyclic aromatic heterocyclic group comprising two or more nitrogen atoms or a nitrogen atom and an oxygen atom or a sulfur atom, or a tricyclic aromatic heterocyclic group.

5. A method for producing the enamine compound of claim 1 , the method comprising:
reacting an amide compound of formula (a)

with a hydrosilane compound in the presence of an iridium complex.

6. The method of claim 5 , wherein the iridium complex is of formula (3)

wherein X 2 is a halogen atom, and Y and Z each represent a phenyl group, a phenoxy, group, a pyrrolyl group, a perfluorophenoxy group, or a perfluoroalkoxy group.

7. A fluorescent luminescent agent composition, comprising the enamine compound of claim 1 .

8. The composition of claim 7 , further comprising:
an electron acceptor.

9. The composition of claim 8 , wherein the electron acceptor is a cation donor.

10. The composition of claim 9 , wherein the cation donor is a proton or a halogen cation.

11. The composition of claim 10 , wherein the proton is a Bronsted acid.

12. The composition of claim 10 , wherein the halogen cation is a halogen bond donor.

13. The composition of claim 8 , wherein the electron acceptor is a Lewis acid.

14. A photosensitizer composition, comprising:
the enamine compound of claim 1 .

15. The composition of claim 14 , further comprising:
an electron acceptor.

16. The composition of claim 15 , wherein the electron acceptor is a cation donor.

17. The composition of claim 16 , wherein the cation donor is a proton or a halogen cation.

18. The composition of claim 17 , wherein the proton is a Bronsted acid.

19. The composition of claim 17 , wherein the halogen cation is a halogen bond donor.

20. The composition of claim 15 , wherein the electron acceptor is a Lewis acid.

21. The enamine compound of claim 1 , wherein R 1 is -A 1 -C(R 5 )═CH—N(R 6 )(R 7 ).

Assignees

• Japan Science & Tech Agency

Inventors

• Nagashima Hideo
• TAHARA Atsushi
• Kitahara Ikumi
• Kuninobu Yoichiro

Classifications

• C07C211/55 Primary

  Diphenylamines · CPC title

• C07C255/58

  containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton · CPC title

• C07D265/38

  [b, e]-condensed with two six-membered rings · CPC title

• C07D285/14 Primary

  condensed with carbocyclic rings or ring systems · CPC title

• C07F5/02

  Boron compounds · CPC title