π-Electron systems containing Si=Si double bonds

Abstract

Sterically large substituents can provide kinetic stabilization to various types of low-coordinate compounds. For example, regarding the chemistry of the group 14 elements, since West et al. introduced the concept of kinetic protection of the otherwise highly reactive Si=Si double bond by bulky mesityl (2,4,6-trimethylphenyl) groups in 1981, a number of unsaturated compounds of silicon and its group homologs have been successfully isolated by steric effects using the appropriate large substituents. However, the functions and applications of the Si–Si π-bonds consisting of the 3pπ electrons on the formally sp 2-hybridized silicon atoms have rarely been explored until 10 years ago, when Scheschkewitz and Tamao independently reported the model systems of the oligo(p-phenylenedisilenylene)s (Si–OPVs) in 2007. This review focuses on the recent advances in the chemistry of π-electron systems containing Si=Si double bonds, mainly published in the last decade. The synthesis, characterization, and potential application of a variety of donor-free π-conjugated disilene compounds are described.

Keywords

• Silicon
• π-electron systems
• disilenes
• conjugation
• bulky protecting groups