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Benzo[e]pyrene Skeleton Dipyrylium Dication with a Strong Donor-Acceptor-Donor Interaction, and Its Two-Electron Reduced Molecule

  作者 RAO KOYA PRABHAKARA; KONDO MIO; SAKAMOTO RYOTA; KUSAMOTO TETSURO; NISHIKAWA MICHIHIRO; KUME SHOKO; NIHEI MASAYUKI; OSHIO HIROKI; NISHIHARA HIROSHI  
  选自 期刊  Chemistry-A European Journal;  卷期  2011年17-50;  页码  14010-14019  
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[摘要]The donor-acceptor-donor (D-A-D) conjugated molecules 1,4-bis(diarylaminophenylethynyl)anthraquinone (1,4-Am(2)Aq) and 1,4-bis(ferrocenylethynyl)anthraquinone (1,4-Fc(2)Aq), undergo a double proton cyclization reaction with bis(trifluoromethanesulfone) imide acid (TFSIH) to yield 1,4-bis(diarylaminophenyl or ferrocenyl) dipyrylium salts [1,4-R(2)Pyl(2)](TFSI)(2) (R = Am or Fc) with novel planar pentacyclic structures similar to the aromatic benzo[e]pyrene-type skeleton. [1,4-Am(2)Pyl(2)](TFSI)(2) could be reduced to give the neutral molecule [1,4-Am(2)Pyl(2)](0), which is stable and maintains the benzo[e]pyrene-type skeleton. To the best of our knowledge, this is the first oxygen-atom-containing polycyclic aromatic hydrocarbon with 22 (4n+2) pi-electrons. The obtained condensed-ring benzo[e]pyrene-type skeleton compounds show physical and chemical properties that are significantly different from those of [1,5-Am(2)Pyl(2)](TFSI)(2), which has a perylene-type skeleton.

 
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