Pioneering click chemistry to craft innovative peptoids with enhanced functionalities is of interest. Poly-N-substituted glycines (peptoids) are polymers designed to emulate biological molecules, providing a more stable mimetic of peptides. Peptoids are polymer chains resembling α-peptides, amino acids linked together by peptide bonds. The key distinction lies in the side chain's attachment, where peptoids have it connected to the nitrogen atom instead of the α-carbon in α- peptides. Click chemistry reactions, known for their simplicity, high yield, stereospecificity, and minimal byproduct formation, offer a practical synthetic approach. Peptoids can be further functionalized by incorporating a click handle, like cyclopentadiene or norbornadiene in the side chain (R-group). This click handle enables Diels-Alder (DA) click reactions with molecules like maleimide, leading to peptoids containing small-molecule drugs or photoacid generators (PAGs). We developed synthetic routes for two click handles, spiro-cyclopentadiene amine, and norbornadiene amine. We utilized commercially available and clickable amines to synthesize our peptoids. Herein, we indicated two "clickable monomers" for integration into sequence-defined peptoid block copolymers and investigated the functionality of these polypeptides for diverse applications.