N-sulfonyldicarboximide containing tethering compounds

An article comprising:

• a substrate;
• and
• a substrate-attached tethering group comprising a reaction product of a complementary functional group G on a surface of the substrate with a compound of Formula I
• X1 is a substrate-reactive functional group selected from a carboxy, halocarbonyl, halocarbonyloxy, cyano, hydroxy, mercapto, isocyanato, halosilyl, alkoxysilyl, acyloxysilyl, azido, aziridinyl, haloalkyl, tertiary amino, primary aromatic amino, secondary aromatic amino, disulfide, alkyl disulfide, benzotriazolyl, phosphono, phosphoroamido, phosphato, or ethylenically unsaturated group;
• Y1 is a single bond or a divalent group selected from an alkylene, heteroalkylene, arylene, carbonyl, carbonyloxy, carbonylimino, oxy, thio, or —NRd— where Rd is hydrogen or alkyl, or combinations thereof;
• R1 and R2 together with a dicarboximide group to which they are attached form a four to eight membered heterocyclic or heterobicyclic group that can be fused to an optional aromatic group, optional saturated or unsaturated cyclic group, or optional saturated or unsaturated bicyclic group;
• r is 1 when X2 is a monovalent group or equal to 2 when X2 is a divalent group;
• G is the complementary functional group capable of reacting with X1;
• and
• said tethering group is unsubstituted or substituted with a halo, alkyl, alkoxy, or combinations thereof.

An article comprising:

• a substrate;
• a substrate-attached tethering group comprising a reaction product of a complementary functional group G on a surface of the substrate with a compound of Formula II
• wherein
• X2 is a substrate-reactive functional group selected from a carboxy, halocarbonyl, halocarbonyloxy, cyano, hydroxy, mercapto, isocyanato, halosilyl, alkoxysilyl, acyloxysilyl, azido, aziridinyl, haloalkyl, tertiary amino, primary aromatic amino, secondary aromatic amino, disulfide, alkyl disulfide, benzotriazolyl, phosphono, phosphoroamido, phosphato, or ethylenically unsaturated group;
• R4 and R5 together with a dicarboximide group to which they are attached form a four to eight heterocyclic or heterobicyclic group that can be fused to an optional aromatic group, optional saturated or unsaturated cyclic, group, or optional saturated or unsaturated bicyclic group;
• Y2 is a single bond or a divalent group selected from alkylene, heteroalkylene, arylene, carbonyl, carbonyloxy, carbonylimino, oxy, thio, —NRd— where Rd is hydrogen or alkyl, or combinations thereof;
• R3 is an alkyl, aryl, aralkyl, or —NRbRc wherein Rb and Rc are each an alkyl group or taken together with the nitrogen atom to which they are attached form a four to eight membered heterocyclic group;
• r is equal to 1 when X2 is monovalent or equal to 2 when X2 is a divalent group;
• G is the complementary functional group capable of reacting with X2;
• and
• said tethering group is unsubstituted or substituted with a halo, alkyl, alkoxy, or combinations thereof.

A method of immobilizing an amine-containing material, said method comprising:

• selecting a compound of Formula I
• wherein
• X1 is a substrate-reactive functional group selected from a carboxy, halocarbonyl, halocarbonyloxy, cyano, hydroxy, mercapto, isocyanato, halosilyl, alkoxysilyl, acyloxysilyl, azido, aziridinyl, haloalkyl, tertiary amino, primary aromatic amino, secondary aromatic amino, disulfide, alkyldisulfide, benzotriazolyl, phosphono, phosphoroamido, phosphato, or ethylenically unsaturated group;
• Y1 is a single bond or a divalent group selected from an alkylene, heteroalkylene, arylene, carbonyl, carbonyloxy, carbonylimino, oxy, thio, —NRd— where Rd is hydrogen or alkyl, or combinations thereof;
• R1 and R2 together with a dicarboximide group to which they are attached form a four to eight membered heterocyclic or heterobicyclic group that can be fused to an optional aromatic group, optional saturated or unsaturated cyclic group, or optional saturated or unsaturated bicyclic group;
• r is 1 when X1 is a monovalent group or equal to 2 when X1 is a divalent group;
• and
• said compound is unsubstituted or substituted with a halo, alkyl, alkoxy, or combinations thereof;
• providing a substrate having a complementary functional group capable of reacting with X1
• preparing a substrate-attached tethering group by reacting X1 with the complementary functional group on the substrate resulting in an ionic bond, covalent bond, or combination thereof;
• reacting a N-sulfonyldicarboximide group of the substrate-attached tethering group with an amine-containing material to form a connector group between the substrate and the amine-containing material.

A method of immobilizing an amine-containing material comprising:

• selecting a compound of Formula II
• that is unsubstituted or substituted with a halo, alkyl, carboxy, alkoxycarbonyl, nitrile, or combinations thereof where
• X2 is a substrate-reactive functional group selected from a carboxy, halocarbonyl, halocarbonyloxy, cyano, hydroxy, mercapto, isocyanato, halosilyl, alkoxysilyl, acyloxysilyl, azido, aziridinyl, haloalkyl, tertiary amino, primary aromatic amino, secondary aromatic amino, disulfide, alkyl disulfide, benzotriazolyl, phosphono, phosphoroamido, phosphato, or ethylenically unsaturated group;
• R4 and R5 together with a dicarboximide group to which they are attached form a four to eight membered heterocyclic or heterobicyclic group that can be fused to an optional aromatic group, optional saturated or unsaturated cyclic group, or optional saturated or unsaturated bicyclic group;
• Y2 is a single bond or a divalent group selected from alkylene, heteroalkylene, arylene, carbonyl, carbonyloxy, carbonylimino, oxy, thio, —NRd— where Rd is hydrogen or alkyl, or combinations thereof;
• R3 is an alkyl, aryl, aralkyl, or —NRbRc wherein Rb and Rc are each an alkyl group or taken together form a four to eight membered heterocyclic group;
• r is equal to 1 when X3 is monovalent or equal to 2 when X3 is a divalent group;
• and
• said compound is unsubstituted or substituted with a halo, alkyl, alkoxy, or combinations thereof;
• providing a substrate having a complementary functional group capable of reacting with X2;
• preparing a substrate-attached tethering group by reacting X2 with the complementary functional group on the substrate resulting in an ionic bond, covalent bond, or combination thereof;
• and
• reacting a N-sulfonyldicarboximide group of the substrate-attached tethering group with an amine-containing material to form a connector group between the substrate and the amine-containing material.