Edge chlorination of hexa-peri-hexabenzocoronene investigated by density functional theory and vibrational spectroscopy† †Electronic supplementary information (ESI) available: Description and animations of the vibrational normal modes of HBC and HBC-Cl discussed in the text. See DOI: 10.1039/c5cp07755a Click here for additional data file. Click here for additional data file.

We investigate the molecular structure and vibrational properties of perchlorinated hexa-peri-hexabenzocoronene (HBC-Cl) by density functional theory (DFT) calculations and IR and Raman spectroscopy, in comparison to the parent HBC. The theoretical and experimental IR and Raman spectra demonstrated very good agreement, elucidating a number of vibrational modes corresponding to the observed peaks. Compared with the parent HBC, the edge chlorination significantly alters the planarity of the molecule. Nevertheless, the results indicated that such structural distortion does not significantly impair the π-conjugation of such polycyclic aromatic hydrocarbons.