서강대학교

초록/요약

Our group has designed and synthesized new types of conjugated macrocycles bearing two redox centers that are connected with phenylene-vinylene units in order to investigate the macrocyclic aromaticity. Macrocycles 1, 2, 3 and 4 were designed as a model [18] annulene containing dihydroquinone fragments. Dihydroquinones were introduced as redox centers which can transform the non-aromatic macrocycle into an aromatic one upon oxidation. We first synthesized macrocycles 1 and 2, and then demetylation and oxidation experiments were attempted. However, we were not able to observe macrocyclic aromaticity due to their poor solubilities. In order to increase the solubility, we also synthesized macrocycle 3 with octyl groups on both aromatic rings. Solubility of macrocycle 3 was enhanced enough. However conjugation system was not stable under acidic conditions. To circumvent this problem, allyl groups were chosen for the protecting groups of hydroquinones since allyl phenyl ethers are expected to be removed under mild conditions using a transition metal catalyst. Macrocycle 4 was then synthesized and deallylation experiments were attempted under various conditions but the desired products were not obtained presumably due to their instability. However, some of the photophysical property was investigated to explore the allylation process.