Silver- and copper-chelating ionic liquids, polymers, and gels, and uses thereof

A method of antimicrobial treatment, comprising:

• providing a sample comprising a plurality of microorganisms, wherein said microorganisms comprise a metal cation;
• adding to the sample an ionic liquid, thereby killing or inhibiting the growth of at least a portion of the plurality of microorganisms in the sample,
• wherein the ionic liquid comprises a cation and an anion;
• and
• the cation is represented by the following structural formula I:
• wherein, independently for each occurrence:
• R1 is —(C(R)2)n—;
• n is 2, or 3;
• R2 is —(C(R′)2)m—R″;
• m is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10;
• and
• R is H, F, C1-C3 alkyl, or C1-C3 fluoroalkyl;
• R′ is H, F, C1-C8 alkyl, or C1-C8 fluoroalkyl;
• and
• R″ is H, F, C1-C3 alkyl, C1-C3 fluoroalkyl, C1-C3 alkyloxy, C1-C3 fluoroalkyloxy, C6-C10 aryl, C2-C8 alkenyl or C2-C8 fluoroalkenyl;
• wherein each instance of C6-C10 aryl is optionally substituted with one, two, three, four or five substituents independently selected from the group consisting of F, C1-C3 alkyl, C1-C3 fluoroalkyl, C1-C3 alkyloxy, and C1-C3 fluoroalkyloxy, or
• the cation is represented by the following structural formula II:
• wherein, independently for each occurrence:
• R1 is —(C(R)2)n—;
• n is 2, or 3;
• R2 is —(C(R′)2)m—R″;
• m is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10;
• and
• R is H, F, C1-C3 alkyl, or C1-C3 fluoroalkyl;
• R′ is H, F, C1-C8 alkyl, or C1-C8 fluoroalkyl;
• and
• R″ is H, F, C1-C3 alkyl, C1-C3 fluoroalkyl, C1-C3 alkyloxy, C1-C3 fluoroalkyloxy, C6-C10 aryl, C2-C8 alkenyl or C2-C8 fluoroalkenyl;
• wherein each instance of C6-C10 aryl is optionally substituted with one, two, three, four or five substituents independently selected from the group consisting of F, C1-C3 alkyl, C1-C3 fluoroalkyl, C1-C3 alkyloxy, and C1-C3 fluoroalkyloxy.

A method of preventing or suppressing microbial growth on a surface, comprising:

• applying to the surface an ionic liquid mixture comprising an ionic liquid complex comprising an ionic liquid chelated to a metal cation;
• thereby preventing or suppressing microbial growth on the surface,
• wherein the ionic liquid comprises a cation and an anion;
• and
• the cation is represented by the following structural formula I:
• wherein, independently for each occurrence:
• R1 is —(C(R)2)n—;
• n is 2, or 3;
• R2 is —(C(R′)2)m—R″;
• m is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10;
• and
• R is H, F, C1-C3 alkyl, or C1-C3 fluoroalkyl;
• R′ is H, F, C1-C8 alkyl, or C1-C8 fluoroalkyl;
• and
• R″ is H, F, C1-C3 alkyl, C1-C3 fluoroalkyl, C1-C3 alkyloxy, C1-C3 fluoroalkyloxy, C6-C10 aryl, C2-C8 alkenyl or C2-C8 fluoroalkenyl;
• wherein each instance of C6-C10 aryl is optionally substituted with one, two, three, four or five substituents independently selected from the group consisting of F, C1-C3 alkyl, C1-C3 fluoroalkyl, C1-C3 alkyloxy, and C1-C3 fluoroalkyloxy, or
• the cation is represented by the following structural formula II:
• wherein, independently for each occurrence:
• R1 is —(C(R)2)n—;
• n is 2, or 3;
• R2 is —(C(R′)2)m—R″;
• m is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10;
• and
• R is H, F, C1-C3 alkyl, or C1-C3 fluoroalkyl;
• R′ is H, F, C1-C8 alkyl, or C1-C8 fluoroalkyl;
• and
• R″ is H, F, C1-C3 alkyl, C1-C3 fluoroalkyl, C1-C3 alkyloxy, C1-C3 fluoroalkyloxy, C6-C10 aryl, C2-C8 alkenyl or C2-C8 fluoroalkenyl;
• wherein each instance of C6-C10 aryl is optionally substituted with one, two, three, four or five substituents independently selected from the group consisting of F, C1-C3 alkyl, C1-C3 fluoroalkyl, C1-C3 alkyloxy, and C1-C3 fluoroalkyloxy.

A method of preventing or suppressing microbial growth on a surface, comprising:

• applying to the surface an ionic liquid, thereby preventing or suppressing microbial growth on the surface,
• wherein the ionic liquid comprises a cation and an anion;
• and
• the cation is represented by the following structural formula I:
• wherein, independently for each occurrence:
• R1 is —(C(R)2)n—;
• n is 2, or 3;
• R2 is —(C(R′)2)m—R″;
• m is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10;
• and
• R is H, F, C1-C3 alkyl, or C1-C3 fluoroalkyl;
• R′ is H, F, C1-C8 alkyl, or C1-C8 fluoroalkyl;
• and
• R″ is H, F, C1-C3 alkyl, C1-C3 fluoroalkyl, C1-C3 alkyloxy, C1-C3 fluoroalkyloxy, C6-C10 aryl, C2-C8 alkenyl or C2-C8 fluoroalkenyl;
• wherein each instance of C6-C10 aryl is optionally substituted with one, two, three, four or five substituents independently selected from the group consisting of F, C1-C3 alkyl, C1-C3 fluoroalkyl, C1-C3 alkyloxy, and C1-C3 fluoroalkyloxy, or
• the cation is represented by the following structural formula II:
• wherein, independently for each occurrence:
• R1 is —(C(R)2)n—;
• n is 2, or 3;
• R2 is —(C(R′)2)m—R″;
• m is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10;
• and
• R is H, F, C1-C3 alkyl, or C1-C3 fluoroalkyl;
• R′ is H, F, C1-C8 alkyl, or C1-C8 fluoroalkyl;
• and
• R″ is H, F, C1-C3 alkyl, C1-C3 fluoroalkyl, C1-C3 alkyloxy, C1-C3 fluoroalkyloxy, C6-C10 aryl, C2-C8 alkenyl or C2-C8 fluoroalkenyl;
• wherein each instance of C6-C10 aryl is optionally substituted with one, two, three, four or five substituents independently selected from the group consisting of F, C1-C3 alkyl, C1-C3 fluoroalkyl, C1-C3 alkyloxy, and C1-C3 fluoroalkyloxy.