Development of aromatic/antiaromatic dehydroannulenes aiming at the rational tuning of the electronic properties

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In this study, dehydroannulenes annulated at the 9,10-positions of tetraalkoxyphenanthrene have been designed and synthesized, and their various properties have been investigated in detail. Various spectroscopic studies and theoretical calculations clearly indicated that the annulation at the 9,10-positions of phenanthrene into a dehydroannulene ring enhances the tropicities and decreases the HOMO-LUMO gaps as compared to the benzannulation. Dehydro[12]- and [18]annulenes produced1D self-assembling clusters with high aspect ratios, which differed in the morphology and crystallinity depending on the topology of the annulene ring and the length of appended chains. Moreover, [12]- and [18]annulenes formed liquid crystals due to the phase separation facilitated by the flexible decyloxy side chains.