Abstract: Aminopropyl terminated polydimethylsiloxane (APT-PDMS) was synthesized by the ring-opening equilibrium reaction of octamethylcyclotetrasiloxane (D₄) using 1,3-bis(3-aminopropyl)tetramethyldisiloxane as a blocking agent. The silicone elastomer (PDMS-PU) was synthesized by forming a prepolymer of diisocyanate and APT-PDMS, followed by the addition of 2,6-diaminopyridine (2,6-DAP) as a chain extender. Finally, a series of self-healing silicone elastomers (PDMS-PU/M) were obtained through the formation of coordination bonds between PDMS-PU and iron ions. The structures of products were characterized by nuclear magnetic resonance (NMR), Fourier transform infrared spectroscopy (FT-IR) and ultraviolet-visible spectrophotometer (UV-Vis). Water contact angle measurement and universal testing machine were used to characterize the surface properties and mechanical properties of the materials. The self-healing performance of PDMS-PU/M was studied by laser confocal microscopy, and the mechanical properties of the healed samples were tested by universal testing machine. The results showed that the PDMS-PU/M were successfully synthesized. The hydrophobicity of the material was less affected by the modification of PDMS, and the water contact angle was higher than 90°. It had good waterproof performance. The prepared PDMS-PU/M had excellent mechanical properties and satisfactory self-healing ability. The effects of different ratios of pyridine group to iron ion contents contents on the elastomer properties were investigated. With the increasing of iron ion contents, the tensile stress of PDMS-PU/M was increased from 0.95 MPa to 1.96 MPa due to the increase in the crosslinking density between the pyridine groups and iron ions. Meanwhile, the self-healing efficiency of PDMS-PU/M with the highest tensile stress could reach 82.7% for only 6 h. These results indicated that the self-healing silicone elastomer was an ideal candidate for the self-healable flexible substrates which could be used in flexible electronics and other applications involving resources saving and environment protection. In addition, the self-healing efficiency of PDMS-PU/M could be improved by increasing the temperature, by which the repairing time decreased.