Biofouling resistant coatings and methods of making and using the same

1. A medical device coated with a compound comprising:

a) a repeating unit of Formula (VII):

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;

each A 1 and A 2 is independently selected from —C(═O)—, —S(═O)—, —S(═O) 2 —, and —S(═O)(=NR 3c )—;

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 5c , and R 5d 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 CR 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, 6, 7, and 8; and

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

b) a repeating unit of Formula (VIII):

wherein,

A 3 is —C(═O)—, —S(═O)—, —S(═O) 2 —, or —S(═O)(=NR 3c )—;

B 3 is —O— or —NR 3c —;

D is —S(═O) 2 O − , —S(═O) 2 OR 9a , —C(═O)O − , or —C(═O)OR 9a ;

Z 2 is —(CR 6c R 6d ) t —;

Z 3 is —(CR 6c R 6d ) p —;

each R 3a and R 3b is independently selected from hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted benzyl;

each 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 12a , R 12b , and R 12c is independently selected from hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl;

t is an integer selected from 1, 2, 3, 4, or 5;

p is an integer selected from 1, 2, 3, 4, or 5; and

wherein the repeating unit of Formula (VIII) is charged or zwitterionic; and

c) a repeating unit of Formula (IX):

A 4 is —C(═O)—, —S(═O)—, —S(═O) 2 —, or —S(═O)(=NR 3c )—;

B 4 is —O— or —NR 3c —;

Z 4 is —(CR 6c R 6d ) k —;

E is —CN, —OR 9a , —NR 9a R 9b , —NR 9a R 9b R 9c+ , optionally substituted C 1 -C 4 alkyl, optionally substituted C 1 -C 6 fluoroalkyl, —S(═O) 2 O − , —S(═O) 2 OR 9a , —C(═O)O − , or —C(═O)OR 9a ;

each 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 9b , R 9c , R 13a , R 13b , and R 13c is independently selected from hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; and

k is an integer selected from 1, 2, 3, 4, or 5.

2. The medical device of claim 1 , wherein each of R 1a , R 1b , R 2a , and R 2b is F.

3. The medical device of claim 1 , wherein D is —S(═O) 2 O − or —C(═O)O − .

4. The medical device of claim 1 , wherein A 1 is —S(═O) 2 — and each A 2 , A 3 , and A 4 is —C(═O)—.

5. The medical device of claim 1 , wherein each B 1 , B 2 , and B 3 is independently —O— or —NR 3c —.

6. The medical device of claim 1 , wherein the compound has a number-average molecular weight of between about 10,000 and about 250,000.

7. The medical device of claim 1 , wherein the medical device comprises a silicon-based device or a carbon-based device.

8. The medical device of claim 7 , wherein the silicon-based device comprises a siloxane polymer moiety, a sesquisiloxane polymer moiety, a siloxane-silarylene polymer moiety, a silalkylene polymer moiety, a polysilane moiety, a polysilylene moiety, or a polysilazane moiety.

9. The medical device of claim 7 , wherein the carbon-based device comprises a polyolefin moiety, a polyethylene (PE) moiety, a polypropylene (PP) moiety, a polyamide (PA) moiety, a polytetrafluoroethylene (PTFE) moiety, a polyvinylidene fluoride (PVdF) moiety, or a polyvinyl chloride (PVC) moiety.

10. The medical device of claim 7 , wherein the medical device is a silicon-based device comprising a silicon surface.

11. The medical device of claim 10 , wherein the compound is covalently bound to the silicon surface.

12. The medical device of claim 11 , wherein the medical device comprises an implant, an IV, a prosthesis, suturing material, valve, stent, catheter, rod, shunt, scope, a contact lens, tubing, wiring, electrode, clip, fastener, syringe, container, bandage, patch, or a combination thereof.

13. The medical device of claim 12 , wherein the medical device is a catheter.

14. The medical device of claim 13 , wherein the catheter comprises an indwelling catheter, uretic catheter, permeath, or Foley catheter.

15. The medical device of claim 12 , wherein the medical device is a shunt.

16. The medical device of claim 15 , wherein the shunt comprises a cardiac shunt, a cerebral shunt, a lumbar-peritoneal shunt, a peritoneovenous shunt, a pulmonary shunt, a portosystemic shunt (PSS), a portacaval shunt, or a vesico-amniotic shunt.

17. The medical device of claim 15 , wherein the shunt is a cerebral shunt.

18. The medical device of claim 12 , wherein the medical device is a stent.

19. The medical device of claim 18 , wherein the stent comprises a coronary stent, a vascular stent, or a biliary stent.

20. The medical device of claim 12 , wherein the scope comprises a scope utilized in an image-guided surgery including endoscopy or laparoscopy.

21. The medical device of claim 1 , wherein the medical device comprises an auditory prosthesis, artificial larynx, an artificial bone, an artificial joint, an artificial organ, dental implants, mammary implants, penile implants, cranio/facial tendons, tendons, ligaments, menisci, or disks.

22. The medical device of claim 21 , wherein the medical device is an auditory prostheses.

23. The medical device of claim 21 , wherein the medical device is a mammary implant.

24. The medical device of claim 1 , wherein the medical device is a pacemaker.