Phenanthrene-4,5-diylbis(10-methylacridinium) with a short C + - - C + contact: Preparation, molecular structure, redox properties, and electrochromic interconversion with dihydropyrene derivative

Takanori Suzuki, Yasuyo Yoshimoto, Kazuhisa Wada, Takashi Takeda, Hidetoshi Kawai, Kenshu Fujiwara

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

The title dication (1 2+) was generated by oxidative bond cleavage of a 4,5-dihydoropyrene derivative (2) with two spiro(10-methylacridan) units. Despite the skewed deformation of the arylene spacer, two cationic chromophores in 1 2+ are forced to face in a proximity with a very short interatomic separation of 2.98(1) Å between carbenium centers (X-ray), which makes the LUMO level of 1 much lower than that of biphenyl-2,2′-diyl-type dication (3 2+).

Original languageEnglish
Pages (from-to)149-155
Number of pages7
JournalHeterocycles
Volume80
Issue number1
DOIs
Publication statusPublished - 2010 Jan 1
Externally publishedYes

Keywords

  • Carbocation
  • Electrochromism
  • Helicity
  • Redox System
  • Strained Molecule

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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