This research work explores the development and application of small molecules and oligomers in advanced technologies and focuses on their role in improving structure-property relationships and enhancing performance in various fields. A major part of the research investigates a set of thieno[3,2-b]thiophene (BTTT)-based liquid crystalline (LC) materials. By tuning the structure of the mesogen core, a novel thieno[3,2-b]thiophene-based LC semiconductor with oligomeric ethylene glycol end units (BTTT/dEO4) displays dual-conductivities with promising ionic conductivity at room temperature, surpassing that of benchmark PEO-based polyelectrolytes. The research further reveals that side chain positioning in BTTT-based LCs (BTTT/dEO3 and BTTT/mEO6) affects mesophase stability and charge-transport efficiency, with BTTT/mEO6 exhibiting superior performance due to its asymmetric structure and effective ionic shielding indicated in molecular dynamic simulations. Additionally, the study explores the potential of the real-world application of such LC-based materials through the incorporation of acrylate groups in LCs and the use of UV-initiated solid-state polymerization. This approach not only improves mechanical properties but also maintains long-range order and thermal stability, which is crucial for bioelectronics applications. By slight modification of the LC monomer structure, two LC monomers could be blended together to achieve a balance of the desired parameters. This thesis also addresses challenges in photoresist materials for extreme ultraviolet (EUV) lithography. Current polymeric chemically amplified photoresists (CARs) struggle to reach the necessary benchmark for EUV exposure, driving the urgent development of new materials. This research introduces the idea of sequence-defined peptoid oligomers and non-ionic photoacid generators (PAGs), showing that these advanced materials can be EUV patternable and can potentially reduce stochastic issues related to molecular uniformity. Ongoing work aims to optimize click chemistry reactions and PAG integration, with the goal of creating more effective photoresists for next-generation lithographic patterning.