On‐Surface Synthesis of Silole and Disila‐Cyclooctene Derivatives

• Published in: Angewandte Chemie 2024-04, Vol.136 (18), p.n/a
• Main Authors: Sun, Kewei, Kurki, Lauri, Silveira, Orlando J., Nishiuchi, Tomohiko, Kubo, Takashi, Foster, Adam S., Kawai, Shigeki
• Format: Article
• Language: English
• Subjects: Bromination; Chemical synthesis; Density functional theory; nanoribbon structures; Nanoribbons; on-surface synthesis; Organic compounds; Scanning tunneling microscopy; scanning tunneling microscopy/spectroscopy; sila-cyclic rings; Silicon; Spectroscopy
• ISSN: 0044-8249; 1521-3757
• DOI: 10.1002/ange.202401027

The incorporation of Si atoms into organic compounds significantly increases a variety of functionality, facilitating further applications. Recently, on‐surface synthesis was introduced into organosilicon chemistry as 1,4‐disilabenzene bridged nanostructures were obtained via coupling between silicon atoms and brominated phenyl groups at the ortho position on Au(111). Here, we demonstrate a high generality of this strategy via syntheses of silole derivatives and nanoribbon structures with eight‐membered sila‐cyclic rings from dibrominated molecules at the bay and peri positions on Au(111), respectively. Their structures and electronic properties were investigated by a combination of scanning tunneling microscopy/spectroscopy and density functional theory calculations. This work demonstrates a great potential to deal with heavy group 14 elements in on‐surface silicon chemistry. Silole derivatives and nanoribbon structures with eight‐membered sila‐cyclic rings were successfully synthesized on Au(111) through reactions between bromo‐substituted molecules and silicon atoms. Their chemical structures were investigated by bond‐resolved STM and DFT calculations. The band gaps of the silole derivatives and the nanoribbon measured with STS measurements were 3.1 eV and 2.5 eV, respectively.