Synthesis of Hexabenzo[a,cd,f,j,lm,o]perylene

Abstract

Hexabenzo[a,cd,f,j,lm,o]perylene (HBP), an undecacyclic condensed polycyclic aromatic hydrocarbon with two severely crowded fjord regions, was synthesized by Clar's method; the starting material 8H-benzo[fg]-naphthacene-8-one was newly prepared by the glycerol condensation of 5,12-dihydro-naphthacene-5,12-dione. ¹H and ¹³C NMR spectra of HBP were measured and the chemical shifts were completely assigned. Absorption and fluorescence spectra of HBP were also measured and the effects of nonplanarity on its spectroscopic properties was discussed.

Keywords:

• condensation
• electronic spectra
• molecular orbital calculation
• nuclear magnetic resonance (NMR) spectra
• polycyclic aromatic hydrocarbon