Here we introduce a new family of surface modification materials based on bioinspired, sequencedefined polypeptoid brushes, which offer an ideal means to bridge the gap between synthetic and bio materials. There is also a need to bridge the gap between small molecule SAMs that have precise molecular structures and higher molecular weight yet dispersed polymers. Polypeptoids, or poly(N-substituted glycine)s, share similarities with polypeptides, but offer better solubility and processability in a range of organic solvents, increased resistance to thermal and protease degradation. They can be precisely synthesized with defined sequences for tailored molecular structures and functionalities. Furthermore, polypeptoids feature highly versatile and diverse side chains, which can range from enabling compatibility with inorganic materials and processes to ensuring compatibility and stability with biomaterials. We designed and synthesized polypeptoids with a terminal hydroxyl (-OH) group that reacts with the activated surface with silanol groups to graft the polymer onto Si substrates and form ~1 nm thick tethered brush monolayers, which enable efficient modification of the surface properties. This manuscript is organized as follows: In the first section, we detail the design and structure of five polypeptoids of different composition and sequence, along with the process for creating uniform brush monolayers grafted on Si substrates. The second section focuses on the versatility of the polypeptoid brush platform, highlighting its capability to customize and fine-tune a wide range of interfacial interactions. This includes 1) modulating surface energy, demonstrated by achieving a range of water contact angles; 2) achieving passivation and selective immobilization of biomolecules through various short-range interactions, particularly in relation to DNA origami nanostructures;