Biofouling resistant coatings and methods of making and using the same

A compound that has the structure of Formula (III):

• wherein
• each R1a and R1b is independently selected from hydrogen and halogen;
• each R2a and R2b is independently selected from halogen, —CN, and optionally substituted C1-C6fluoroalkyl;
• each A1, A2, and A3 is independently selected from —C(═O)—, —S(═O)—, —S(═O)2—, and —S(═O)(═NR3c)—;
• each B1, B2, and B3 is independently selected from —O— and —NR3c—;
• Z1 is —(CR6cR6d)s—;
• Z2 is —(CR6cR6d)t—;
• E is —CN, —OR9a, —NR9aR9b, —NR9aR9bR9c+, optionally substituted C1-C4 alkyl, optionally substituted C1-C6fluoroalkyl, —S(═O)2O−, —S(═O)2OR9a, —C(═O)O−, or —C(═O)OR9a;
• each R4c, R4d, R5d, R5c, R6c, and R6d is independently selected from hydrogen, halogen, —CN, —OR9a, optionally substituted C1-C4 alkyl, optionally substituted C1-C4 fluoroalkyl, optionally substituted C2-C6 alkenyl, —NR3cR3d, —S(═O)2O−, —S(═O)2OR9a, —C(═O)O−, and —C(═O)OR9a;
• each R3c and R3d is independently selected from hydrogen, optionally substituted C1-C4 alkyl, —X-optionally substituted C1-C4 alkyl, optionally substituted C2-C6 alkenyl, and optionally substituted aryl;
• X is —C(═O)—, —S(═O)—, or —S(═O)2—;
• each R9a, R11a, R11b, R11c, R12a, R12b, and R12c is independently selected from hydrogen, optionally substituted C1-C4 alkyl, and optionally substituted aryl;
• n is an integer selected from 0, 1, 2, 3, 4, 5, and 6;
• s is an integer selected from 1, 2, 3, 4, or 5;
• t is an integer selected from 1, 2, 3, 4, or 5;
• q is an integer selected from 40-60;
• and
• r is an integer selected from 1-10.

A medical device coated with a compound that has the structure of Formula (II):

• wherein
• each R1a and R1b is independently selected from hydrogen and halogen;
• each R2a and R2b is independently selected from halogen, —CN, and optionally substituted C1-C6fluoroalkyl;
• each A1, A2, and A3 is independently selected from —C(═O)—, —S(═O)—, —S(═O)2—, and —S(═O)(═NR3c)—;
• each B1, B2, and B3 is independently selected from —O— and —NR3c—;
• D is —S(═O)2O−, —S(═O)2OR9a, —C(═O)O−, or —C(═O)OR9a;
• Z1 is —(CR6cR6d)s—;
• Z2 is —(CR6cR6d)t—;
• Z3 is —(CR6cR6d)p—;
• each R3a and R3c is independently selected from hydrogen, optionally substituted C1-C4 alkyl, and optionally substituted benzyl;
• each R3c and R3d is independently selected from hydrogen, optionally substituted C1-C4 alkyl, —X-optionally substituted C1-C4 alkyl, optionally substituted C2-C6 alkenyl, and optionally substituted aryl;
• X is —C(═O)—, —S(═O)—, or —S(═O)2—;
• each R4c, R4d, R5d, R5e, R6c, and R6d is independently selected from hydrogen, halogen, —CN, —OH, optionally substituted C1-C4 alkyl, optionally substituted C1-C4 fluoroalkyl, optionally substituted C2-C6 alkenyl, —NR3cR3d, —S(═O)2O−, —S(═O)2OR9a, —C(═O)O−, and —C(═O)OR9a;
• each R9a, R11a, R11b, R11c, R12a, R12b, and R12c is independently selected from hydrogen, optionally substituted C1-C4 alkyl, and optionally substituted aryl;
• n is an integer selected from 0, 1, 2, 3, 4, 5, and 6;
• s is an integer selected from 1, 2, 3, 4, or 5;
• t is an integer selected from 1, 2, 3, 4, or 5;
• p is an integer selected from 1, 2, 3, 4, or 5;
• q is an integer selected from 40-60;
• r is an integer selected from 1-10;
• and
• wherein the compounds of Formula (II) is charged or zwitterionic.