Double-pillaring strategy for silacyclophanes: Synthesis and structures of disilanyl double-pillared bisanthracenes

Waka Nakanishi, Shunpei Hitosugi, Yusuke Shimada, Hiroyuki Isobe

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

A new series of silacyclophanes with two disilanyl pillars has been synthesized using a straightforward method. A silylation reaction of 1,8-dilithioanthracenes allowed the connection of two anthracene rings with two Si-Si bonds to afford disilanyl double-pillared bisanthracenes ( SiDPBAs). The major product had an anti geometry of the anthracene rings, and a unique steplike structure favorable for σ-π conjugations was revealed by X-ray crystallographic analysis. Upon introducing a substituent at the 10-position of anthracene, we obtained a U-shaped isomer with syn geometry that yielded an excimer upon excitation and can decompose without steric protection. Easy access to silacyclophanes: A new series of silacyclophanes, disilanyl double-pillared bisanthracenes (SiDPBAs), was synthesized using a one-pot operation from 1,8-diiodoanthracenes. The major product with anti geometry bears a steplike structure favorable for σ-π conjugation, and the minor product with syn geometry bears a U-shaped structure favorable for excimer formation.

Original languageEnglish
Pages (from-to)554-559
Number of pages6
JournalChemistry - An Asian Journal
Volume6
Issue number2
DOIs
Publication statusPublished - 2011 Feb 1

Keywords

  • arenes
  • cyclophanes
  • macrocycles
  • silanes
  • substituent effects

ASJC Scopus subject areas

  • Chemistry(all)
  • Biochemistry
  • Organic Chemistry

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