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Benzo[ e ]pyrene Skeleton Dipyrylium Dication with a Strong Donor–Acceptor–Donor Interaction, and Its Two‐Electron Reduced Molecule
Author(s) -
Rao Koya Prabhakara,
Kondo Mio,
Sakamoto Ryota,
Kusamoto Tetsuro,
Nishikawa Michihiro,
Kume Shoko,
Nihei Masayuki,
Oshio Hiroki,
Nishihara Hiroshi
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201101708
Subject(s) - chemistry , dication , pyrene , molecule , anthraquinone , conjugated system , perylene , electron acceptor , ring (chemistry) , imide , medicinal chemistry , photochemistry , acceptor , electron donor , stereochemistry , polymer chemistry , organic chemistry , catalysis , physics , condensed matter physics , polymer
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 (4 n +2) π‐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.