Dynamic behavior, electrochromism, and two-photon absorption of dicyanomethylenated quinacridone

Takashi Takeda, Hiroyuki Sugihara, Yasutaka Suzuki, Jun Kawamata, Tomoyuki Akutagawa

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)


Molecular structures of dicyanomethylenated quinacridone (1) as a solid and in solution were examined on the basis of single-crystal X-ray structural analysis, temperature-dependent 1H NMR in CD2Cl2, and theoretical calculations. Crystal 1 had a curved, butterfly-shaped molecular structure. Thermally activated flipping between the curved, butterfly-shaped structure and an armchair structure occurred in solution. Electrochemical reduction triggered a dynamic change from the curved, butterfly-shaped conformation in the neutral state to a planar conformation in the dianion state, which represented electrochromic behavior with electrochemical bistability. A large two-photon absorption cross section of compound 1 was observed in the resonance-enhancement region of 423 GM (1 GM = 1 × 10-50 cm4 s photon-1 molecule-1) at 710 nm. Multiple donor-acceptor charge-transfer pathways of molecule 1 enhanced two-photon absorption. (Chemical Equation Presented).

Original languageEnglish
Pages (from-to)9669-9677
Number of pages9
JournalJournal of Organic Chemistry
Issue number20
Publication statusPublished - 2014 Oct 17


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