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

本论文设计并合成了四烷氧基菲9，10-位上的脱氢轮烯，并对其各种性质进行了详细的研究。各种光谱研究和理论计算清楚地表明，在9，10-位的菲成环到脱氢轮烯环增强的向性和减少的HOMO-LUMO间隙相比，benzannulation。脱氢[12]-和[18]轮烯产生了具有高纵横比的一维自组装簇，其形态和结晶度取决于轮烯环的拓扑结构和附加链的长度。此外，[12]-和[18]轮烯形成液晶，由于相分离的柔性癸氧基侧链促进。

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.