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

doi:10.3987/COM-09-S(S)35

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 journal › Article › peer-review

9 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 language	English
Pages (from-to)	149-155
Number of pages	7
Journal	Heterocycles
Volume	80
Issue number	1
DOIs	https://doi.org/10.3987/COM-09-S(S)35
Publication status	Published - 2010 Jan 1
Externally published	Yes

Keywords

Carbocation
Electrochromism
Helicity
Redox System
Strained Molecule

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

Access to Document

10.3987/COM-09-S(S)35

Cite this

Phenanthrene-4,5-diylbis(10-methylacridinium) with a short C ⁺ - - C ⁺ contact : Preparation, molecular structure, redox properties, and electrochromic interconversion with dihydropyrene derivative. / Suzuki, Takanori; Yoshimoto, Yasuyo; Wada, Kazuhisa; Takeda, Takashi; Kawai, Hidetoshi; Fujiwara, Kenshu.

In: Heterocycles, Vol. 80, No. 1, 01.01.2010, p. 149-155.

Research output: Contribution to journal › Article › peer-review

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