The Combination of Cross-Hyperconjugation and σ-Conjugation in 2,5-Oligosilanyl Substituted Siloles

Alexander Pöcheim, Gül Altınbaș Özpınar, Thomas Müller*, Judith Baumgartner*, Christoph Marschner*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


Reaction of a 2,5-dilithiated silole with excess dichlorodimethylsilane gives the respective 2,5-bis(chlorodimethylsilyl) substituted silole. This compound can be converted to 2,5-bis(oligosilanyl) substituted siloles by addition of a suitable oligosilanide. In the UV spectra of the thus obtained compounds the lowest energy absorptions are bathochromically shifted compared to the absorptions of the two constituents, namely the 2,5-disilyl substituted silole and a trisilane. The bathochromic shift is interpreted as being caused by a mixed σ-conjugation/cross-hyperconjugation. This assumption is supported by TD-DFT calculations, which show a significant contribution from Si−Si bonds to the HOMO of the molecule.

Original languageEnglish
Pages (from-to)17252-17260
Number of pages9
JournalChemistry - a European Journal
Issue number71
Early online date27 Jul 2020
Publication statusPublished - 18 Dec 2020


  • cross hyperconjugation
  • oligosilanes
  • siloles
  • σ-conjugation

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Fields of Expertise

  • Advanced Materials Science

Cite this