Surface independent, surface-modifying, multifunctional coatings and applications thereof
The invention provides surface treatments that reduce or eliminate marine biofouling of various surfaces. A surface that is to be subjected to a marine environment can be treated with a mPEG-DOPA. The treated surface is thus rendered less susceptible to fouling of the surface.
1. A method of spontaneously modifying a substrate surface, the method comprising contacting at least a portion of the substrate with an alkaline solution comprising an oxidant selected from the group consisting of dissolved oxygen, triethylamine, hydrogen peroxide, sodium periodate, tertiary butylhydroperoxide, organic peroxides, quinines, nitroaryl compounds, Cu 2+ , Fe 3+ , Co 3+ , Mn 3+ , phenols, indoles, and aminobenzenes; the solution further comprising a surface-modifying agent according to Formula I:
wherein each of R 1 , R 2 , R 3 , R 4 and R 5 is independently selected from the group consisting of a thiol, a primary amine, a secondary amine, a nitrile, an aldehyde, an imidazole, an azide, a halide, a polyhexamethylene dithiocarbonate, a hydrogen, a hydroxyl, a carboxylic acid, an aldehyde, a carboxylic ester or a carboxamide, provided at least one of R 1 , R 2 , R 3 , R 4 and R 5 is not a hydrogen atom;
wherein x ranges from 0 to 10 and wherein y ranges from 0 to 10, provided that x or y is at least 1;
wherein the substrate surface is spontaneously modified.
2. The method of claim 1 wherein x and y are both 1, and wherein R 1 and R 4 form a double bond when eliminated.
3. The method of claim 1 wherein R 2 is NH 2 or NHR, wherein R is an alkyl or aromatic group.
4. The method of claim 1 wherein one of R 1 or R 4 is a halide, a hydroxyl or a thiol, and wherein one of R 3 or R 5 is a hydrogen atom.
5. The method of claim 1 wherein x is 1, y is 1, R 1 is a hydroxyl, and wherein each of R 3 , R 4 and R 5 are hydrogen atoms.
6. The method of claim 5 wherein R 2 is a NH 2 .
7. The method of claim 1 wherein x and y are each 1 and wherein each of R 1 , R 3 , R 4 and R 5 are hydrogen atoms.
8. The method of claim 7 wherein R 2 is NH 2 .
9. The method of claim 1 wherein R 2 is NH 2 or NHR, wherein R is an alkyl or aromatic group.
10. The method of claim 9 wherein one of R 1 or R 4 is a halide, a hydroxyl, or a thiol and wherein one of R 3 or R 5 is a hydrogen atom.
11. The method of claim 9 wherein R 2 is an amine.
12. The method of claim 1 wherein x+y is at least 2.
13. The method of claim 1 wherein x+y is at least 3.
14. The method of claim 1 wherein the hydroxyls of the phenyl moiety are positioned at the 3 and 4 positions of the phenyl group relative to the side chain.
15. The method of claim 1 wherein the surface-modifying agent forms a polymeric coat on the substrate surface.
16. The method of claim 1 wherein the surface-modifying agent is selected from the group consisting of 3,4-dihydroxy-L-phenylalanine (DOPA), 3,4-dihydroxyphenylalanine methyl ester dopamine, norepinephrine and epinephrine.
17. The method of claim 1 wherein the solution is aqueous.
18. The method of claim 1 wherein x+y ranges from 1 to 6.
19. A method of spontaneously modifying a substrate surface to provide a desired functionality, the method comprising:
a) contacting at least a portion of the substrate surface with an alkaline, aqueous solution comprising an oxidant selected from the group consisting of dissolved oxygen, triethylamine, hydrogen peroxide, sodium periodate, tertiary butylhydroperoxide, organic peroxides, quinines, nitroarl compounds, Cu 2+ , Fe 3+ , Co 3+ , Mn 3+ , phenols, indoles, and aminobenzenes; the solution further comprising a surface-modifying agent according to Formula I:
wherein each of R 1 , R 2 , R 3 , R 4 and R 5 is independently selected from the group consisting of a thiol, a primary amine, a secondary amine, a nitrile, an aldehyde, an imidazole, an azide, a halide, a polyhexamethylene dithiocarbonate, a hydrogen, a hydroxyl, a carboxylic acid, an aldehyde, a carboxylic ester or a carboxamide, provided at least one of R 1 , R 2 , R 3 , R 4 and R 5 is not a hydrogen atom;
wherein x ranges from 0 to 10 and wherein y ranges from 0 to 10, provided that x or y is at least 1; and
wherein the substrate surface is spontaneously modified; and
b) contacting the surface-modified substrate with a reactive moiety, wherein the reactive moiety reacts with and is bound to the modified surface.
20. The method of claim 19 wherein the reactive moiety comprises a nucleophile.
21. The method of claim 19 wherein the reactive moiety comprises a metal.