Sumanenemonoone imines bridged by redox-active π-conjugated unit: synthesis, stepwise coordination to palladium(II), and laser-induced formation of nitrogen-doped graphitic carbon.

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).