4.5 Review

π-Electron systems containing Si=Si double bonds

Journal

SCIENCE AND TECHNOLOGY OF ADVANCED MATERIALS
Volume 19, Issue 1, Pages 108-129

Publisher

TAYLOR & FRANCIS LTD
DOI: 10.1080/14686996.2017.1414552

Keywords

Silicon; pi-electron systems; disilenes; conjugation; bulky protecting groups

Funding

  1. Precursory Research for Embryonic Science and Technology (PRESTO) from Japan Science and Technology Agency (JST)
  2. Ministry of Education, Culture, Sports, Science and Technology (MEXT) of Japan [24109003, 2408]
  3. MEXT
  4. Japan Society for the Promotion of Science (JSPS) [JP16J01036]
  5. Kindai University
  6. [24350031]
  7. [15H03788]
  8. Grants-in-Aid for Scientific Research [15H03788, 16J01036, 24109003] Funding Source: KAKEN

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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 pi-bonds consisting of the 3p pi 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 pi-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 pi-conjugated disilene compounds are described. [GRAPHICS]

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