Optical Characteristics of Hybrid Macrocycles with Dithienogermole and Tricoordinate Boron Units

Yohei Adachi, Taishi Nabeya, Keigo Kawakami, Kosuke Yamaji, Frieder Jäkle, Joji Ohshita

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

The introduction of unconventional elements into π-conjugated systems has been studied to manipulate the electronic states and properties of compounds. Herein, boron- and germanium-containing hybrid macrocycles, as a new class of element-hybrid conjugated systems, have been synthesized. The palladium-catalyzed Stille cross coupling of bis(bromothienyl)borane and bis(trimethylstannylthienyl)- or bis(trimethylstannylphenyl)-substituted dithienogermoles as the boron- and germanium-containing building blocks, respectively, produced a mixture of several macrocyclic compounds. Single-crystal X-ray analysis of the 2:2 coupling product revealed a planar structure with a cavity inside the macrocycle. The optical properties of the macrocyclic products indicated rather small electronic interactions between the building units. However, intramolecular photoenergy transfer from the dithienogermole unit to the boron unit was clearly observed with respect to the fluorescence spectra.

Original languageEnglish (US)
Pages (from-to)3306-3314
Number of pages9
JournalChemistry - A European Journal
Volume27
Issue number10
DOIs
StatePublished - Feb 15 2021

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Keywords

  • boron
  • energy transfer
  • germoles
  • hybrid materials
  • macrocycles

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