Intramolecular hydrogen bonds play a pivotal role in shaping the molecular conformation and therefore governing the macroscopic properties of many biomacromolecules and synthetic polymers. It is, however, still challenging to accurately incorporate these noncovalent dynamic bonds into artificial polymers in order to actively control their macromolecular properties. Herein, we report the manipulation of intramolecular hydrogen bonds by labile protecting groups, for efficient synthesis and solution processing of a model polymer that features continuous intramolecular hydrogen bonds along the backbone. A non-coplanar polymer precursor with thermally cleavable Boc groups was synthesized (Mn = 32.4 kg/mol) and well solubilized in organic solvents. After processing this precursor into thin films, in situ thermal treatment regenerated the latent intramolecular hydrogen bonds and led to a much more rigid polymer that adopts a ladder-type conformation. The strong interchain interactions between these rigid backbones of HP rendered strong solvent resistance, allowing for multi-layer deposition of this polymer into thin films.

Active manipulation of intramolecular hydrogen bonds enables synthesis and solution processing of a solvent-resistant rigid polymer

256th National Meeting (2018)

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