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Physical blending conjugated polymers (CPs) with elastomers has been established as an effective method for enhancing the stretchability of semiconductors. However, predictable control of the morphology for incompatible polymer rubber blends remains a challenge. In this work, we demonstrated the control of phase separation size of CP/elastomer composites by strategically controlling the location sites of H-bonding functional groups in CPs and elastomers, while investigating their effects on mechanical and electrical properties. We incorporated amide functional groups into a DPP-based semiconducting polymer (DPPTVT-A) and polyisobutylene-based elastomer (PIB-A) to enable inter- and intraphase hydrogen bonding (H-bonding) cross-links within CP/elastomer composites. Along with their nonamide counterparts, we fabricated four different CP/elastomer composites, DPPTVT-A/PIB-A, DPPTVT-A/PIB …