Wurster's blue-type cation radicals framed in a 5,10-Dihydrobenzo[a] indolo[2,3-c]carbazole (BIC) Skeleton: Dual electrochromism with drastic changes in UV/Vis/NIR and fluorescence

Takanori Suzuki, Yuto Sakano, Yusuke Tokimizu, Youhei Miura, Ryo Katoono, Kenshu Fujiwara, Naoki Yoshioka, Nobutaka Fujii, Hiroaki Ohno

研究成果: Article査読

26 被引用数 (Scopus)

抄録

Electron-donating dihydrobenzindolocarbazoles (BICs) 1 a-c, which adopt planar disk-shaped geometries, were prepared by gold(I)-catalyzed cyclization as a key step. Due to the presence of a 1,4-phenylenediamine (PD) moiety in the framework, they undergo reversible one-electron oxidation to the corresponding Wurster's Blue (WB)-type species that exhibits NIR absorptions up to λ=1200 nm. In the case of the N,N -dimethyl derivative, cation radical 1 c+. is stable enough to be isolated as a salt and X-ray analysis indicated paraquinoid-type bond alternation in the WB core unit, whereas the bond lengths in the peripheral benzene rings are identical to those in the neutral donor. Upon electrochemical interconversion, the redox pairs of 1 a-c and 1 a-c+. exhibited an electrochromic response in the UV/Vis/NIR region, which was accompanied by a drastic change in the fluorescence spectrum because only neutral donors 1 a-c are highly emissive (ΦF: 0.7-0.8). Potential for change: Both UV/Vis/NIR and fluorescence can be reversibly modified by application of electric potential to the highly fluorescent π-extended p-phenylenediamines with disk-shaped geometries to form stable cation radical species (see figure).

本文言語English
ページ(範囲)1841-1846
ページ数6
ジャーナルChemistry - An Asian Journal
9
7
DOI
出版ステータスPublished - 2014 7

ASJC Scopus subject areas

  • 生化学
  • 有機化学

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