1,8-Diphenyl-9,10-Bis(arylethynyl)phenanthrenes: Synthesis, Distorted Structure, and Optical Properties

Akihito Konishi, Atsushi Morinaga, Gaku Fukuhara, Masaki Nishijima, Tadashi Mori, Toshiyuki Kida, Makoto Yasuda

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

The synthesis and optical properties of 1,8-diphenyl-9,10-bis(arylethynyl)phenanthrenes, which are distorted phenanthrenes, are reported. The presence of the two phenyl groups at the 1,8-positions of phenanthrene significantly distorts the molecular geometries, as was evidenced by X-ray crystallography. The congested substitution pattern in the K region results in a distorted aromatic framework, which leads to a redshift in the emission spectrum. These observations are in stark contrast to 9,10-bis(phenylethynyl)phenanthrene with no phenyl groups at the 1,8-positions. A large Stokes shift suggested extensive structural relaxation between the phenyl and arylethynyl units in the excited state, which was supported by theoretical calculations.

Original languageEnglish
Pages (from-to)6625-6631
Number of pages7
JournalChemistry - A European Journal
Volume24
Issue number25
DOIs
Publication statusPublished - 2018 May 2

Keywords

  • density functional calculations
  • phenanthrenes
  • polycycles
  • steric hindrance
  • synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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