Substituted thiophene oligomers and polymers
The present disclosure provides an antimicrobial substrate including a substrate and a polythiophene polymer. The polythiophene polymer has a number of repeated monomer units from n is 5-14 or 30 to 120, a number average molecular weight (Mn) from 1,000 to 4,000 or 10,000 to 40,000; and a polydispersity index (PDI) from 1 to 1.3. The present disclosure also provides the polythiophene polymer and uses thereof.
1. An antimicrobial substrate, comprising a substrate and a polythiophene having the structure
wherein
R 1 is
each of R 2 and R 3 is independently C 1 -C 3 alkyl;
R 4 is C 1 -C 3 alkyl;
A is a counterion;
L is a divalent C1-C6 alkyl linker;
T is a terminal group;
m is 1;
n is 5 to 14, or 30 to 120;
the polythiophene has a number average molecular weight (Mn) from 1,000 to 4,000, or from 10,000 to 40,000; and
the polythiophene has a polydispersity index (PDI) of from 1 to 1.25.
2. The antimicrobial substrate of claim 1 , wherein n is 50 to 110.
3. The antimicrobial substrate of claim 1 , wherein n is at least 60.
4. The antimicrobial substrate of claim 1 , wherein about 1 μg/cm 3 to about 10 μg/cm 3 of the antimicrobial substrate is the polythiophene.
5. The antimicrobial substrate of claim 1 , wherein R 1 is
and R 2 and R 3 are each ethyl.
6. The antimicrobial substrate of claim 1 , wherein R 1 is
and R 4 is methyl.
7. The antimicrobial substrate of claim 1 , wherein L is hexyl.
8. The antimicrobial substrate of claim 1 , wherein the substrate is a wipe, a tissue, a bandage, a medical device, surgical instrument, tubing, a catheter, warfighter machinery, a sponge, a textile, a diaper, a counter-top, a food preparation surface, a wound dressing, a dressing for surgical incisions, a keyboard surface, a packing for wounds, a packing for surgical incisions, a nasal packing or a feminine care product, or a combination thereof.
9. The antimicrobial substrate of claim 1 , wherein the substrate is a wipe.
10. The antimicrobial substrate of claim 1 , wherein the polythiophene provides a temporary antimicrobial coating on the substrate which is removable by treatment with one or more of water, organic solvent, base and detergent.
11. The antimicrobial substrate of claim 1 , wherein the polythiophene is embedded in the substrate and remains at a concentration of about from about 0.1 μg/cm 3 to about 10 μg/cm 3 after washing the antimicrobial substrate.
12. The antimicrobial substrate of claim 1 , wherein the polythiophene absorbs visible light.
13. The antimicrobial substrate of claim 1 , wherein the substrate comprises a polysaccharide.
14. The antimicrobial substrate of claim 13 , wherein the polysaccharide is alginate, carboxymethyl amylose or carboxymethyl cellulose.
15. The antimicrobial substrate of claim 13 , wherein a hydrogel comprises the polythiophene polymer.
16. The antimicrobial substrate of claim 1 , further comprising at least one of a detergent, a calcium salt and a copper salt.
17. The antimicrobial substrate of claim 1 , wherein the polythiophene comprises the structure: