Arene-Inserted Extended Germa[n]pericyclynes: Synthesis, Structure, and Phosphorescence Properties

Hiroki Tanimoto*, Junta Mori, Shunichiro Ito, Yasuhiro Nishiyama, Tsumoru Morimoto, Kazuo Tanaka, Yoshiki Chujo, Kiyomi Kakiuchi

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

This report describes the synthesis and characterization of arene-inserted extended (ArEx) germa[n]pericyclynes composed of germanium and 1,4-diethynylbenzene units. These novel cyclic germanium-π unit materials were synthesized with diethynylbenzene and germanium dichloride. X-ray crystallographic analysis revealed their structures, and the planar conformation of ArEx germa[4]pericyclyne along with the regular aromatic rings. UV/Vis absorption spectra and fluorescence emission spectra showed considerably unique and highly improved character compared to previously reported germa[n]pericyclynes. Even in the absence of transition metal components, phosphorescence emissions were observed, and the emission lifetimes were dramatically improved. ArEx germa[n]pericyclynes showed high photoluminescence quantum yields, whereas low photoluminescence quantum yields were observed for acyclic compounds. Density functional theory calculations show delocalized orbitals between skipped alkyne units through a germanium tether, and an increase in the HOMO energy level, leading to a small HOMO–LUMO energy gap.

Original languageEnglish
Pages (from-to)10080-10086
Number of pages7
JournalChemistry - A European Journal
Volume23
Issue number42
DOIs
StatePublished - 2017/07/26

Keywords

  • X-ray crystallography
  • fluorescence emission
  • germanium
  • pericyclynes
  • phosphorescence emission

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Organic Chemistry

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