Structure, synthesis, and applications for oligo phenylene ethynylenes (OPEs)

Patent metadata

Field	Value
Publication number	US-10092000-B2
Application number	US-201113809573-A
Country	US
Kind code	B2
Filing date	Jul 13, 2011
Priority date	Jul 13, 2010
Publication date	Oct 9, 2018
Grant date	Oct 9, 2018

Abstract

The present disclosure provides novel oligo phenylene ethynylene (OPE) compounds, methods for synthesizing these compounds, and materials and substances incorporating these compounds. The various OPEs show antibacterial, antiviral and antifungal activity.

First claim

What is claimed is:

1. A material incorporating an oligo-(phenylene ethynylene), wherein the oligo-(phenylene ethynylene) is grafted thereto by chemisorption or wherein the positively charged polymer attaches to a negatively charged surface by physisorption, wherein the oligo-(phenylene ethynylene) has the structure:

wherein:
n is selected from the group consisting of 1, 2, 3 and 4;
A is selected from the group consisting of C 2 C 6 H 2 and C 2 C 4 S;
B=C 2 C 6 H 2 ;
C=is either C 6 H 4 or not present;
X is selected from the group consisting of: COOCH 2 CH 3 , O(CH 2 ) k N(CH 3 ) 3 + , O(CH 2 ) k SO 3 − , and O(CH 2 ) k (C 6 H 12 N 2 )C 6 H 13 ;
Y is selected from the group consisting of: COOCH 2 CH 3 , O(CH 2 ) k N(CH 3 ) 3 + , O(CH 2 ) k SO 3 − , C 6 H 2 (OCH 3 ) 3 , and O(CH 2 ) k (C 6 H 12 N 2 )C 6 H 13 2+ ;
k is selected from the group of whole numbers from 1 to 10;
Z A is selected from the group consisting of H and O(CH 2 ) j (C 6 H 12 N 2 )C 6 H 13 2+ ; where j is selected from the group of whole numbers from 1 to 10; and
Z B =H;

wherein:
if X=COOCH 2 CH 3 and Y=COOCH 2 CH 3 , then A=B=C 2 C 6 H 2 , C is C 6 H 4 , and Z A is O(CH 2 ) k (C 5 H 12 N 2 )C 6 H 13 2+ ;
if Z A is H, A is C 2 C 6 H 2 , X=O(CH 2 ) k N(CH 3 ) 3 + , and C=C 6 H 4 , then Y is selected from the group consisting of COOCH 2 CH 3 , O(CH 2 ) k SO 3 − , C 6 H 2 (OCH 3 ) 3 , and O(CH 2 ) k (C 6 H 12 N 2 )C 6 H 13 2+ ;
if Z A is H, A is C 2 C 6 H 2 , X=O(CH 2 ) k N(CH 3 ) 3 + , C=C 6 H 4 , and B=C 2 C 6 H 2 , then k is selected from the group consisting of 1, 2, 4, 5, 6, 7, 8, 9, and 10;
if Z A is H, A is C 2 C 6 H 2 , X=O(CH 2 ) k N(CH 3 ) 3 + , and C is not present, then Y=C 6 H 2 (OCH 3 ) 3 ;
if Z A is H, A is C 2 C 6 H 2 and X=O(CH 2 ) k SO 3 − , then C=C 6 H 4 and Y=O(CH 2 ) k SO 3 − ;
if Z A is H, A is C 2 C 6 H 2 , and X=O(CH 2 ) k (C 5 H 12 N 2 )C 6 H 13 2+ , then C=C 6 H 4 and Y=O(CH 2 ) k (C 6 H 12 N 2 )C 6 H 13 2+ ;
if A is C 2 C 4 S, then C=C 6 H 4 and X is selected from the group consisting of O(CH 2 ) k N(CH 3 ) 3 + and O(CH 2 ) k (C 6 H 12 N 2 )C 6 H 13 2+ ;
if X is O(CH 2 ) k (C 6 H 12 N 2 )C 6 H 13 2+ , then Y=O(CH 2 ) k (C 6 H 12 N 2 )C 6 H 13 2+ ;

wherein both the oligo-(phenylene ethynylene) and the material incorporating the same have biocidal, antiviral, and antifungal properties.

2. The material of claim 1 wherein Z A =O(CH 2 ) j (C 6 H 12 N 2 )C 6 H 13 2+ ; A and B=C 2 C 6 H 2 , C=C 6 H 4 , and X and Y=COOCH 2 CH 3 .

3. The material of claim 2 wherein j=3.

4. The material of claim 1 wherein A and B=C 2 C 6 H 2 , C=C 6 H 4 , and X and Y=O(CH 2 ) k N(CH 3 ) 3 + .

5. The material of claim 4 where k=2.

6. The material of claim 1 wherein A and B=C 2 C 6 H 2 , C=C 6 H 4 , and X and Y=O(CH 2 ) 3 SO 3 − .

7. The material of claim 1 wherein A=C 2 C 4 S, B=C 2 C 6 H 2 , C=C 6 H 4 , and X and Y=O(CH 2 ) 3 N(CH 3 ) 3 + .

8. The material of claim 1 wherein A and B=C 2 C 6 H 2 , C is not present, X=O(CH 2 ) 3 N(CH 3 ) 3 + and Y=C 6 H 2 (OCH 3 ) 3 .

9. The material of claim 1 wherein A and B=C 2 C 6 H 2 and C=C 6 H 4 .

10. The material of claim 1 wherein A=C 2 C 4 S, B=C 2 C 6 H 2 , and C=C 6 H 4 .

11. The material of claim 1 functionally attached to a material or substance so that the oligo-(phenylene ethynylene) can interfere with the pathogenicity of a pathogen that contacts the oligo-(phenylene ethynylene).

12. The material of claim 1 where k=3.

13. The material of claim 1 wherein the material is a fiber, or a textile formed therefrom.

14. The material of claim 13 wherein the fiber or textile comprises a natural fiber, a synthetic fiber, or both.

15. The material of claim 14 wherein the natural fiber is cotton, silk, or wool, or a blend thereof.

16. The material of claim 14 wherein the synthetic fiber is rayon or nylon.

17. The material of claim 14 wherein the synthetic fiber is produced by electrospinning.

18. The material of claim 13 wherein the fiber or textile is comprised by an object that is potentially contaminated with a microorganism or a virus.

19. The material of claim 18 wherein the object is a wound treatment, a bandage, a swab, a sterile mat, a liner, or a filter for water purification.

20. The material of claim 18 wherein the object is a mattress, a bed linen, a countertop covering, a tablecloth, or a curtain.

21. A material incorporating an oligo-(phenylene ethynylene), wherein the oligo-(phenylene ethynylene) is grafted thereto by chemisorption or wherein the positively charged polymer attaches to a negatively charged surface by physisorption, wherein the oligo-(phenylene ethynylene) has the structure:

wherein:
n is selected from the group consisting of 1, 2, 3 and 4;
A is selected from the group consisting of C 2 C 6 H 2 and C 2 C 4 S;
B=C 2 C 6 H 2 ;
C=is either C 6 H 4 or not present;
X is selected from the group consisting of: COOCH 2 CH 3 , − O(CH 2 ) 2 N(CH 3 ) 3 + , O(CH 2 ) 3 N(CH 3 ) 3 + , and O(CH 2 ) 3 SO 3 − ;
Y is selected from the group consisting of: COOCH 2 CH 3 , − O(CH 2 ) 2 N(CH 3 ) 3 + , O(CH 2 ) 3 N(CH 3 ) 3 + , and O(CH 2 ) 3 SO 3 − ;
Z A is H; and
Z B =H;

wherein:
if A is C 2 C 6 H 2 , X=O(CH 2 ) 3 N(CH 3 ) 3 + , C=C 6 H 4 , and B=C 2 C 6 H 2 , then Y is selected from the group consisting of COOCH 2 CH 3 , and O(CH 2 ) 3 SO 3 − ;
if A is C 2 C 6 H 2 and X=O(CH 2 ) 2 N(CH 3 ) 3 + or O(CH 2 ) 3 N(CH 3 ) 3 + , and C is not present, then Y=C 6 H 2 (OCH 3 ) 3 ; and
if A is C 2 C 6 H 2 and X=O(CH 2 ) 3 SO 3 − then C=C 6 H 4 and Y=O(CH 2 ) 3 SO 3 − ;

wherein
both the oligo-(phenylene ethynylene) and the material incorporating the same have biocidal, antiviral, and antifungal properties, and
the material is a fiber, or a textile formed therefrom.

22. The material of claim 1 , wherein the material is a stimuli responsive material.

Assignees

• Whitten David G
• Schanze Kirk S
• Ji Eunkyung
• Corbitt Thomas S
• Zhou Zhijun
• Dascier Dimitri
• Wang Ying
• Ista Linnea K
• Parthasarathy Anand
• Hill Eric H
• Tang Yanli
• Stc Unm
• Univ Florida

Inventors

• Whitten David G
• Schanze Kirk S
• Ji Eunkyung
• Corbitt Thomas S
• Zhou Zhijun
• Dascier Dimitri
• Wang Ying
• Ista Linnea K
• Parthasarathy Anand
• Hill Eric H
• Tang Yanli

Classifications

• A01N43/10

  with sulfur as the ring hetero atom · CPC title

• C07D409/14

  containing three or more hetero rings · CPC title

• C08G2261/3328

  alkyne-based · CPC title

• C07C217/14

  the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring · CPC title

• C08G2261/93

  Applications in textiles, fabrics and yarns · CPC title