Mimicking the structure of proteins using synthetic polymers
requires
building blocks with structural similarity and the use of various
noncovalent and dynamic covalent interactions. We report the synthesis
of helical poly(isocyanide)s bearing diaminopyridine and pyridine
side-chains and the multistep functionalization of the polymers’
side-chains using hydrogen bonding and metal coordination. The orthogonality
of the hydrogen bonding and metal coordination was proved by varying
the sequence of the multistep assembly. The two side-chain functionalizations
are reversible through the use of competitive solvents and/or competing
ligands. Throughout the assembly and disassembly, the helical conformation
of the polymer backbone is sustained as proved by circular dichroism
spectroscopy. These results open the possibility to incorporate helical
domains into complex polymer architectures and create a helical scaffold
for smart materials.