Visible light induced photogeneration of ground state atomic oxygen

Patent metadata

Field	Value
Publication number	US-11602724-B2
Application number	US-202016863109-A
Country	US
Kind code	B2
Filing date	Apr 30, 2020
Priority date	Apr 30, 2019
Publication date	Mar 14, 2023
Grant date	Mar 14, 2023

Abstract

The present invention generally relates to various polycyclic aromatic selenoxide compounds, methods for preparing these compounds, and methods of us these and other compounds to generate ground state atomic oxygen.

First claim

What is claimed is:

1. A method for producing ground state atomic oxygen [O( 3 P)] and an oxidation product, the method comprising illuminating a mixture comprising a polycyclic aromatic selenoxide and an oxygen accepting substrate with light to produce ground state atomic oxygen and an oxidation product, wherein the light has a wavelength of from about 370 nm to about 900 nm, wherein the polycyclic aromatic selenoxide has a structure of Formula (Ia), (Ib), (IIa), (IIb), (IIIa), (IIIb), (IVa), or (IVb):

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are each independently hydrogen, hydroxy, substituted or unsubstituted hydrocarbyl, or substituted or unsubstituted amino and n is 1 or 2.

2. The method of claim 1 wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are each independently hydrogen, hydroxy, C 1 -C 20 alkyl, C 1 -C 20 alkoxy, C 1 -C 20 haloalkyl, C 1 -C 20 haloalkoxy, substituted or unsubstituted C 2 -C 20 alkenyl, substituted or unsubstituted C 2 -C 20 alkynyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

3. The method of claim 1 wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are each independently hydrogen, hydroxy, C 1 -C 10 alkyl, C 1 -C 10 alkoxy, C 1 -C 10 haloalkyl, C 1 -C 10 haloalkoxy, halo-substituted C 1 -C 10 alkenyl, halo-substituted C 2 -C 10 alkynyl, aryl, alkyl-substituted aryl, halo-substituted aryl, or hydroxy-substituted aryl.

4. The method of claim 1 wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are each independently hydrogen, hydroxy, methyl, ethyl, butyl, methoxy, ethoxy, propoxy, trifluoromethyl, phenyl, hydroxyphenyl, ethylphenyl, carboxyphenyl, napthyl, anthracenyl, biphenyl, tolyl, cumyl, styryl, ortho-xylyl, meta-xylyl, para-xylyl, fluorophenyl, chlorophenyl, bromophenyl, or iodobenzyl.

5. The method of claim 1 wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are each hydrogen.

6. The method of claim 1 wherein n is 1.

7. The method of claim 1 wherein the polycyclic aromatic selenoxide is:

8. The method of claim 1 wherein the mixture is illuminated with light having a wavelength of from about 390 nm to about 740 nm.

9. The method of claim 1 wherein the oxygen accepting substrate comprises a biological specimen, nucleic acid, DNA, RNA, or a protein.

10. The method of claim 1 wherein the oxygen accepting substrate comprises an unsaturated hydrocarbon, an aromatic compound, or a thiol.

11. The method of claim 1 , further comprising contacting the mixture with a cell, tissue, or other living system prior to illumination.

12. A compound of Formula (Ia) or (Ib):

wherein R 1 and R 2 are each independently hydrogen, hydroxyl, substituted or unsubstituted hydrocarbyl, or substituted or unsubstituted amino and n is 1 or 2.

13. The compound of claim 12 wherein each R 1 and R 2 are independently hydrogen, hydroxy, C 1 -C 20 alkyl, C 1 -C 20 alkoxy, C 1 -C 20 haloalkyl, C 1 -C 20 haloalkoxy, substituted or unsubstituted C 2 -C 20 alkenyl, or substituted or unsubstituted C 2 -C 20 alkynyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

14. The compound of claim 12 wherein R 1 and R 2 are each hydrogen.

15. A compound of Formula (IIa) or (IIb):

wherein R 3 and R 4 are each independently hydrogen, hydroxyl, substituted or unsubstituted hydrocarbyl, or substituted or unsubstituted amino and n is 1 or 2.

16. The compound of claim 15 wherein each R 3 and R 4 are independently hydrogen, hydroxy, C 1 -C 20 alkyl, C 1 -C 20 alkoxy, C 1 -C 20 haloalkyl, C 1 -C 20 haloalkoxy, substituted or unsubstituted C 2 -C 20 alkenyl, or substituted or unsubstituted C 2 -C 20 alkynyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

17. The compound of claim 16 wherein R 3 and R 4 are each hydrogen.

18. The compound of claim 16 wherein n is 1.

Assignees

• Univ Saint Louis

Inventors

• Chintala Satyanarayana M
• Mcculla Ryan D

Classifications

• C07D345/00 Primary

  Heterocyclic compounds containing rings having selenium or tellurium atoms as the only ring hetero atoms · CPC title

• C01B13/0222

  from organic compounds · CPC title

• B01J19/123 Primary

  Ultraviolet light · CPC title