| Summary: | Sila[1]ferrocenophane bearing a 9-silafluorenylidene moiety (<b>1</b>) as a bridging unit was synthesized and isolated as a stable crystalline compound. Sila[1]ferrocenophane <b>1</b>, which was newly obtained in this study, was characterized by spectroscopic analyses, a single-crystal X-ray diffraction (SC-XRD) analysis, and electrochemical measurements. Due to the characteristic 9-silafluorenyl moiety, <b>1</b> exhibited large electron affinity and a slightly higher oxidation potential relative to that of ferrocene. In addition, <b>1</b> was found to undergo ring-opening polymerization (ROP) triggered by thermolysis at a lower temperature relative to that of Ph<sub>2</sub>Sifc (<b>1′</b>, fc = 1,1′-ferrocenylidene). It also underwent ROP through reduction by KC<sub>8</sub> to give the corresponding polymeric compound. The DFT calculations suggested that one-electron reduction of <b>1</b> would promote ring-opening polymerization, as shown in the experimental results.
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