Soft and Stretchable Thienopyrroledione-Based Polymers via Direct Arylation

Abstract

π-conjugated polymers (CPs) that are concurrently soft and stretchable are needed for deformable electronics. Molecular-level modification of indacenodithiophene (IDT) copolymers, a class of CPs that exhibit high hole mobilities ($\mu$_hole), is an approach that can help realize intrinsically soft and stretchable CPs. Numerous examples of design strategies to adjust the stretchability of CPs exist, but imparting softness is comparatively less studied. In this study, a systematic molecular weight (MW) series is constructed on a promising candidate for soft CPs, poly(indacenodithiophene-co-thienopyrroledione) (p(IDT_C16-TPD_C8)), by optimizing direct arylation polymerization conditions in hopes of improving stretchability and μ_hole without significantly impacting softness. We found p(IDT_C16-TPD_C8) at a degree of polymerization of 32 shows high stretchability (crack onset strain, CoS > 100%) without significantly impacting softness (elastic modulus, E = 32 MPa), which to the best of our knowledge outperforms previously reported stretchable and soft CPs. To further study how molecular-level modifications impact polymer properties, a MW series of a new extended donor unit polymer, poly(indacenodithienothiophene-co-thienopyrroledione) (p(IDTT_C16-TPD_C8)), was synthesized. The IDTT_C16 copolymers did not result in a greater average μ_hole when comparing between p(IDTT_C16-TPD_C8) and p(IDT_C16-TPD_C8) despite their higher crystallinity observed by GIWAXS. While these findings warrant further investigation, this study points toward unique charge transport properties of IDT-based polymers.