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Sumanenemonoone Imines Bridged by Redox‐Active π‐Conjugated Unit: Synthesis, Stepwise Coordination to Palladium(II), and Laser‐Induced Formation of Nitrogen‐Doped Graphitic Carbon
Author(s) -
Amaya Toru,
Inada Yuhi,
Shimizu Yasutomo,
Saeki Akinori,
Tsuji Ryotaro,
Seki Shu,
Hirao Toshikazu
Publication year - 2014
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201402242
Subject(s) - imine , chemistry , conjugated system , raman spectroscopy , carbon fibers , redox , nitrogen , palladium , inorganic chemistry , photochemistry , organic chemistry , materials science , catalysis , polymer , physics , composite material , composite number , optics
Sumanenemonoone imine compounds bridged by a redox‐active π‐conjugated unit on the basis of the conversion between 1,4‐phenylenediamine and 1,4‐benzoquinonediimine were synthesized and characterized. The stepwise coordination of the imino groups to Pd II in the sumanenemonoone imine compound bridged by 1,4‐benzoquinonediimine was indicated by the titration experiment. Laser irradiation of a film of the metal‐free quionediimine gave nitrogen‐doped graphitic carbon, which was supported by an increase in conductivity and by Raman spectroscopy. The obtained graphitic carbon corresponds to carbonous compounds thermally treated at approximately 700–1000 °C. The ratio of nitrogen and carbon relative to that in the starting compound was nearly completely retained (5.4 % decrease).