Abstract: A series of derivatives were designed based on the model compound 1,4-divinyphenyl-bridged triphenylene, and the structures were studied using the AM1 method and density functional theory (DFT) at the B3LYP/3-21G level. On the basis of the B3LYP/3-21G optimized geometries, the electronic spectra and 13C NMR spectra of the derivatives were calculated using the INDO/CIS and B3LYP/3-21G methods, respectively. The energy gaps, abilities of accepting holes, and thermal stabilities were affected by the number and electron-donating capability as well as steric effect of the substituents. The red shifts of the first and main absorptions in the electronic spectra of the derivatives relative to those of the parent compound were predicted in the presence of the groups —CN and —OH. The chemical shift of the carbon atom on —CN was transferred to the low field under the effect of the nitrogen atom. The chemical shifts of the carbon atoms associated with —CN were transformed into the high field owing to the high electron density. The chemical shifts of the carbon atoms on the conjugation skeleton were almost unchanged.

Key words: 1,4-divinylphenyl-bridged triphenylenes, Red-shift, LUMO-HOMO energy gap, B3LYP/3-21G