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Communication | Special issue | Vol 80, No. 1, 2010, pp.149-155
Published online, 21st July, 2009
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, and Kenshu Fujiwara

*Division of Chemistry, Graduate School of Science, Hokkaido University, Kita 10 Nishi 8, Kita-ku, Sapporo, Hokkaido 060-0810, Japan


The title dication (12+) 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 12+ 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 (32+).