# Two-fold addition reaction of silylene to C60: structural and electronic properties of a bis-adduct

## TL;DR

This paper reports the first crystal structure of a fullerene with two silylene groups attached, and explores its electronic properties.

## Contribution

The first crystallographic characterization of a bis-silylene adduct of C60 and its electronic analysis.

## Key findings

- The bis-adduct 3 was structurally confirmed by single-crystal X-ray analysis.
- Compound 3 shows cathodically shifted redox potentials compared to the mono-adduct.
- DFT calculations supported the electronic properties of the bis-adduct.

## Abstract

The addition reaction of C60 with silylene 1, a silicon analog of carbene, yielded the corresponding bis-adduct 3. The structure of 3 was determined by single-crystal X-ray structure analysis, representing the first example of a crystal structure of a silirane (silacyclopropane) derivative of fullerenes. Electrochemical measurements confirmed that the redox potentials of 3 are shifted cathodically compared to those of the parent mono-adduct 2. Density functional theory (DFT) calculations provided the basis for the electronic properties of compound 3.