Click thiol-X monomers and polymers containing such monomers are disclosed. The clickable sequence controllable monomers include an optionally protected thiol moiety; an optionally protected Michael acceptor moiety; a primary functional side chain and one ore more secondary functional side chains. A clickable sequence controllable monomer, can have the structure: wherein independently Y and Z are atoms having a valence electrons of 3 or more; n is a integer from 0-10; m is a integer from 0-10; x is a integer from 0-10; PFS is a functional group SFSi; SFS2; and SFS3 are independently a combination of hydrogen, hydroxyl, aromatic, amine, carboxyl, and carbonyls, optionally substituted to form hydrophilic, hydrophobic, amphiphilic, or charged (positive or negative or both) side chains; T is an optionally protected thiol; and TCA is an optionally protected thiol-click acceptor. Methods of using such polymers are also disclosed.