Synthesis and Photodynamics of Tetragermatetrathia[8]circulene

Shuhei Akahori, Hayato Sakai, Taku Hasobe, Hiroshi Shinokubo, Yoshihiro Miyake

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Tetragermatetrathia[8]circulene has successfully been synthesized from tetraiodotetrathienylene through palladium-catalyzed germylation and rhodium-catalyzed intramolecular dehydrogenative cyclization. A single-crystal X-ray diffraction analysis elucidated that tetragermatetrathia[8]circulene has a highly symmetric, planar, and rigid structure. DFT calculations suggested that LUMO of tetragermatetrathia[8]circulene is stabilized due to σâÏ€∗ interactions between σ∗ orbitals of the Ge-C bonds and Ï€∗ orbitals of the thiophene rings. The excited dynamics of tetragermatetrathia[8]circulene have also been found to be significantly affected by the heavy-atom effect of the germanium atom.

Original languageEnglish
Pages (from-to)304-307
Number of pages4
JournalOrganic Letters
Volume20
Issue number1
DOIs
Publication statusPublished - 2018 Jan 5

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Germanium
Thiophenes
Rhodium
Palladium
Cyclization
X-Ray Diffraction
Rigid structures
orbitals
Atoms
planar structures
synthesis
rigid structures
thiophenes
rhodium
Discrete Fourier transforms
X ray diffraction analysis
atoms
palladium
germanium
Single crystals

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Synthesis and Photodynamics of Tetragermatetrathia[8]circulene. / Akahori, Shuhei; Sakai, Hayato; Hasobe, Taku; Shinokubo, Hiroshi; Miyake, Yoshihiro.

In: Organic Letters, Vol. 20, No. 1, 05.01.2018, p. 304-307.

Research output: Contribution to journalArticle

Akahori, Shuhei ; Sakai, Hayato ; Hasobe, Taku ; Shinokubo, Hiroshi ; Miyake, Yoshihiro. / Synthesis and Photodynamics of Tetragermatetrathia[8]circulene. In: Organic Letters. 2018 ; Vol. 20, No. 1. pp. 304-307.
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