Photoacid compositions having extended lifetime of proton dissociation state

Patent metadata

Field	Value
Publication number	US-10208029-B2
Application number	US-201615057856-A
Country	US
Kind code	B2
Filing date	Mar 1, 2016
Priority date	Jan 30, 2012
Publication date	Feb 19, 2019
Grant date	Feb 19, 2019

Abstract

A photoacid includes a nucleophilic (NuH) moiety having a photodissociable proton, an electron accepting (EA) moiety, and a bridge structure (X) bonded to both the NuH moiety and EA moiety positioned between the NuH and EA moieties. The NuH and EA moieties each include respective structure so that the EA moiety bonds to a proton photodissociated form of the NuH moiety during a reversible photoinduced intramolecular reaction to form a ring, which has been found to significantly increase the lifetime of the proton dissociation state.

First claim

The invention claimed is:

1. A photoacid composition, comprising:
a nucleophilic (NuH) moiety selected from the group consisting of a phenol, a napthol, a pyrazole, an indazole, a triazole and a benzotriazole and having a photodissociable proton;
an electron accepting (EA) moiety selected from the group consisting of an indolinium, a furan having a trifluoromethyl group, a benzothiophene, an indene and a dicyanoethene; and
a bridge structure (X) comprising a double-bond selected from the group consisting of a C═N bond and a C═C bond, wherein said bridge structure is bonded to both said NuH moiety and said EA moiety positioned between said NuH moiety and said EA moiety,
wherein the EA moiety is neutral, and
wherein said NuH moiety and said EA moiety include respective structure so that said EA moiety bonds to a proton photodissociated form of said NuH moiety during a reversible photoinduced intramolecular ring closing reaction to form a ringed structure and generate a proton H+.

2. The photoacid composition of claim 1 , wherein said EA moiety comprises a zwitterion.

3. The photoacid composition of claim 1 , wherein said reversible photoinduced intramolecular ring closing reaction results from irradiation.

4. The photoacid composition of claim 1 , wherein double-bond comprises a C═N bond.

5. The photoacid composition of claim 1 , wherein said double-bond comprises a C═C bond.

6. The photoacid composition of claim 1 , wherein said composition comprises a structure selected from the group consisting of a phenol, a napthol, an indazole, a pyrazole, a benzotriazole, a triazole, an indolinium, an indoline, a furan having a trifluoromethyl group, a benzothiophene, an indene and a dicyanomethane.

7. A photoacid of the formula:

wherein:
R 3 is H, OH, Me, or OMe;
R 4 is H, OH, Me, or OMe;
R 5 is H, OH, NO 2 , Me, OMe, COOH, OCOCH═CH 2 , CH 2 OCOCH═CH 2 , or CH 2 Cl;
R 5 ′ is H, Me, or OMe; and
R 6 is H or OMe.

8. A photoacid of the formula:

9. A photoacid of the formula:

10. A photoacid of the formula:

wherein:
R is H, Me, or OMe.

11. The photoacid of claim 10 wherein R is H.

12. A photoacid of the formula:

wherein:
R is H or OMe.

13. A photoacid of the formula:

14. A photoacid of the formula:

wherein:
R is NO 2 , COOH, CH 2 OCOCH═CH 2 , or CH 2 Cl.

15. The photoacid of claim 14 wherein R is CH 2 Cl.

16. A photoacid of the formula:

wherein:
R is H or OMe.

17. The photoacid of claim 16 wherein R is H.

18. A photoacid of the formula:

19. A photoacid of the formula:

20. A photoacid composition, comprising:
a nucleophilic (NuH) moiety selected from the group consisting of a phenol, a napthol, a pyrazole, an indazole, a triazole and a benzotriazole and having a photodissociable proton;
an electron accepting (EA) moiety selected from the group consisting of an indolinium, a furan, a benzothiophene, an indene and a dicyanoethene; and
a bridge structure (X) comprising a C═N bond, wherein said bridge structure is bonded to both said NuH moiety and said EA moiety positioned between said NuH moiety and said EA moiety,
wherein the EA moiety is neutral, and
wherein said NuH moiety and said EA moiety include respective structure so that said EA moiety bonds to a proton photodissociated form of said NuH moiety during a reversible photoinduced intramolecular ring closing reaction to form a ringed structure and generate a proton H+.

Assignees

• Univ Central Florida Res Found Inc

Inventors

• Liao Yi

Classifications

• C07D405/08

  linked by a carbon chain containing alicyclic rings · CPC title

• C07D403/06

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• C07D417/06 Primary

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• C07D209/12

  Radicals substituted by oxygen atoms · CPC title

• C07D307/68

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen · CPC title