Current technological advances and prolific endeavors have entrenched two-dimensional conducting polymers as the rapidly emerging interface across a diversity of functional materials for flexible electronics, sensors, ion-exchange membranes, biotechnology, catalysis, energy storage, and conversion. Rational design and fabrication of polymeric nanostructures enriched with well-ordered geometry are appealing and endorse significant impact on their in-built electrical, optical, and mechanical properties. In particular, recent interest in controlled hierarchical assembly of monomers/oligomers proved the free-standing sheet-like structures with exotic features of high conductivity and flexibility. Yet, the ongoing research to make nanometer-thick polymers suffers from limitations to access large-area, mechanical stability, and high-range internal ordering. In this perspective, we focus on the radical approaches that highlight confinement-entitled features of two-dimensional polymeric materials correlating to their interface or template-assisted synthesis, structure-property relationship, charge transport properties, and future scopes for relevant practical enactments. (c) 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part B: Polym. Phys. 2019, 57, 1169-1176