Wearable and flexible electronics attract a lot of attention in the scientific community since these new technologies have the potential to drastically modify the way that humans interact with everyday electronics. With the goal of producing flexible and wearable electronics, π-conjugated polymers are promising candidates given their synthetic versatility and functionality. In addition, polymers can be easily tuned and processed by previously published methods such as solution-based deposition and possess the ability to carry charge effectively. π-conjugated polymers interact via a π- π stacking mechanism forming a fairly rigid material. Incorporating hydrogen bonding into the polymer backbone will cause a disruption in the π- π stacking resulting in a more fluid material. However, due to the innovative research in this field, there needs to be a consideration of the reciprocal properties and thus the competition between the electronic charge and the mechanical properties of the polymers. The relationship between these features will, in turn, affect the degree of the dynamic bonds available for self-healing analysis. This presentation will focus on our recent effort toward the design and preparation of intrinsically stretchable conjugated polymers. In specific, these properties were investigated through a series of soft contact lamination techniques, allowing for the determination of the mechanical properties of the materials. A direct investigation of the elasticity, crack-on-set-strain, nanoscale morphology, molecular alignment and other important mechanical properties of the new conjugated polymers will be presented. The molecular design rules determined in this research will also be applicable to other important class of rigid materials, such as polyaromatics, and will have multiple impacts in many fields of polymer chemistry as well as provide a template for the next generation of electronics and technologies