163685-90-3Relevant academic research and scientific papers
Design and synthesis of near-infrared absorbing pigments. II. Structure determination of aceanthrene green and derivatives
Desilets, Denis,Kazmaier, Peter M.,Burt, Richard A.,Hamer, Gordon K.
, p. 325 - 335 (2007/10/03)
The reported structure of aceanthrene green, a pigment prepared by potassium hydroxide fusion of 1,9-anthracenedicarboxylic imide, was found to be incorrect.The structure of the pigment is reassigned to 7,8,15,16-dibenzoperylenetetracarboxylic diimide on the basis of COSY, NOESY, and inversion-recovery 1H NMR experiments.N-Alkyl- or N-phenyl-1,9-anthracenedicarboxylic imides, aceanthrylenoquinoxaline, and a benzimidazole derivative of 1,9-anthracenedicarboxylic anhydride were found to give the same dibenzoperylene structure when reacted in potassium hydroxide.The electronic spectra of these derivatives is reported and it is shown that, as predicted by Pariser-Parr-Pople calculations, they absorb in the near-infrared.Finally, a mechanistic outline for the fusion is proposed on the basis of AM1 and frontier molecular orbital calculations.Key words: photoconductor, near-infrared, aceanthrene green, alkalifusion, polycyclic aromatic hydrocarbon.
