Biofouling resistant coatings and methods of making and using the same

1. A phenyl azide-based copolymer comprising a compound of formula (IV):

wherein

each R 1a and R 1b is independently selected from hydrogen and halogen;

each R 2a and R 2b is independently selected from halogen, —CN, and optionally substituted C 1 -C 6 fluoroalkyl;

A 1 is —S(═O) 2 —;

A 2 is —C(═O)—;

each B 1 and B 2 is independently selected from —O— and —NR 3c —;

Z 1 is —(CR 6c R 6d ) s —); each R 4c , R 4d , R 5d , R 5e , R 6c and R 6d is independently selected from hydrogen, halogen, —CN, —OR 9a , optionally substituted C 1 -C 4 alkyl, optionally substituted C 1 -C 4 fluoroalkyl, optionally substituted C 2 -C 6 alkenyl, —NR 3c R 3d , —S(═O) 2 O − , —S(═O) 2 OR 9a , —C(═O)O − , and —C(═O)OR 9a ;

each R 3c and R 3d is independently selected from hydrogen, optionally substituted C 1 -C 4 alkyl, —X-, optionally substituted C 1 -C 4 alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl;

X is —C(═O)—, —S(═O)—, or —S(═O) 2 —;

each R 9a , R 11a , R 11b , and R 11c is independently selected from hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl;

n is an integer selected from 0, 1, 2, 3, 4, 5, and 6; and

s is an integer selected from 1, 2, 3, 4, and 5.

2. The phenyl azide-based copolymer of claim 1 , wherein R 1a and R 1b are each F.

3. The phenyl azide-based copolymer of claim 1 , wherein R 2a and R 2b are each F.

4. The phenyl azide-based copolymer of claim 1 , wherein B 1 and B 2 are each —NR 3c —; and wherein R 3c in —NR 3c — is hydrogen or —CH 3 .

5. The phenyl azide-based copolymer of claim 4 , wherein R 3c in —NR 3c — is hydrogen.

6. The phenyl azide-based copolymer of claim 1 , wherein each R 6c and R 6d is independently selected from hydrogen and -CH 3 .

7. The phenyl azide-based copolymer of claim 1 , wherein each R 5d and R 5e is hydrogen and n is 0.

8. The phenyl azide-based copolymer of claim 1 , wherein R 11a is hydrogen or —CH 3 .

9. The phenyl azide-based copolymer of claim 1 , wherein each R 11b and R 11c is hydrogen.

10. The phenyl azide-based copolymer of claim 1 , wherein the phenyl azide-based copolymer comprises a monomer comprising sulfobetaine.

11. The phenyl azide-based copolymer of claim 10 , wherein the monomer is sulfobetaine methacrylate.

12. The phenyl azide-based copolymer of claim 11 , wherein the phenyl azide-based copolymer is formed from a reaction of the sulfobetaine methacrylate and the compound of formula (IV).

13. The phenyl azide-based copolymer of claim 1 , wherein the phenyl azide-based copolymer comprises sulfobetaine methacrylate-co-perfluorophenylazide methacrylate.

14. The phenyl azide-based copolymer of claim 1 , wherein the phenyl azide-based copolymer consists of sulfobetaine methacrylate-co-perfluorophenylazide methacrylate.

15. A biofouling resistant coating comprising the phenyl azide-based copolymer of claim 1 .

16. The biofouling resistant coating of claim 15 , wherein the biofouling resistant coating is configured to be coated onto a medical device.

17. A medical device coated with a compound that has the structure of the phenyl azide-based copolymer of claim 1 .

18. The medical device of claim 17 , wherein the medical device comprises an implant, an IV, a prosthesis, a suturing material, a valve, a stent, a catheter, a rod, a shunt, a scope, a contact lens, a tubing, a wiring, an electrode, a clip, a fastener, a syringe, a container for storage of one or more other medical devices, or a combination thereof.

19. The medical device of claim 18 , wherein the medical device comprises the tubing.