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A self-healing dielectric elastomer is achieved by the incorporation of metal–ligand coordination as cross-linking sites in nonpolar polydimethylsiloxane (PDMS) polymers. The ligand is 2,2′-bipyridine-5,5′-dicarboxylic amide, while the metal salts investigated here are Fe²⁺ and Zn²⁺ with various counteranions. The kinetically labile coordination between Zn²⁺ and bipyridine endows the polymer fast self-healing ability at ambient condition. When integrated into organic field-effect transistors (OFETs) as gate dielectrics, transistors with FeCl₂ and ZnCl₂ salts cross-linked PDMS exhibited increased dielectric constants compared to PDMS and demonstrated hysteresis-free transfer characteristics, owing to the low ion conductivity in PDMS and the strong columbic interaction between metal cations and the small Cl^– anions which can prevent mobile anions drifting under gate bias. Fully stretchable transistors with FeCl …