# Synthesis and redox behavior of Si–Si dimeric 9-methylsilafluorene

## TL;DR

This paper reports the synthesis and redox properties of a silicon-linked dimeric compound, revealing its structural and electronic behavior.

## Contribution

The direct synthesis and redox characterization of a Si–Si dimeric 9-methylsilafluorene with DFT analysis is presented.

## Key findings

- The compound was synthesized in 62% yield and characterized via single crystal X-ray diffraction.
- Redox studies showed irreversible oxidation and reduction features, supported by DFT analysis.
- Bond dissociation energies decreased upon reduction, indicating Si–Si bond homolysis.

## Abstract

Lithium-halogen exchange on 2,2′-dibromo-1,1′-biphenyl followed by salt metathesis with 1,1,2,2-tetrachloro-1,2-dimethyldisilane produced the Si–Si linked dimeric 9-methylsilafluorene (1) in 62% yield. Compound 1 was characterized in the solid state via single crystal X-ray diffraction, which revealed a highly symmetric structure. The redox behavior of 1 was studied experimentally via cyclic voltammetry, where irreversible oxidation and reduction features were observed. Density functional theory was used to further study the electronic structure of 1 as well as its reduced (1˙−) and oxidized (1˙+) forms. A decrease in bond dissociation energies from the neutral species (+75 kcal mol−1) to the reduced species (+43 kcal mol−1) supports Si–Si bond homolysis upon reduction, which is consistent with our observed electrochemical irreversibility.

The direct synthesis of Si–Si dimeric 9-dimethylsilafluorene, structural characterization via single crystal X-ray diffraction studies, and electrochemical redox chemistry with DFT electronic structural analysis is reported herein.