Articles and methods comprising persistent carbenes and related compositions

A compound having the structure:

• each X is independently selected from the group consisting of —NR—, —N═, —N+R═, —C—, —CR═, —CR2—, —CR—, —S—, and —O—;
• each R is independently hydrogen, optionally substituted alkyl, alcohol, halo, optionally substituted heteroalkyl, optionally substituted cycloheteroalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkenyloxy, optionally substituted alkoxy, optionally substituted thio, epoxy, optionally substituted acyl, optionally substituted oxyacyloxy, optionally substituted aminoacyl, azide, optionally substituted amino, optionally substituted phosphine, optionally substituted sulfide, isonitrile, cyanate, isocynanate, or nitrile, provided at least one R comprises a functionalizable group;
• optionally, any two R may be joined to form a ring;
• and
• optionally, any R may be substituted with a group forming a bond to a second persistent carbene.

A compound having the structure:

• each X is independently selected from the group consisting of —NR—, —N═, —N+R═, —C—, —CR═, —CR2—, —S—, and —O—;
• each R is independently hydrogen, optionally substituted alkyl, alcohol, halo, optionally substituted heteroalkyl, optionally substituted cycloheteroalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkenyloxy, optionally substituted alkoxy, optionally substituted thio, epoxy, optionally substituted acyl, optionally substituted oxyacyloxy, optionally substituted aminoacyl, azide, optionally substituted amino, optionally substituted phosphine, optionally substituted sulfide, isonitrile, cyanate, isocynanate, or nitrile, provided at least one R comprises a functionalizable group;
• optionally, any two R may be joined to form a ring;
• optionally, any R may be substituted with a group forming a bond to a second persistent carbene;
• and
• Z− is a counter anion.