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| Type |
Symposium |
| Area |
[Korea-Poland Joint Organic Chemistry Symposium] Recent Advances in Organic Chemistry in Cognate Areas of Biology and Materials |
| Room No. |
Room 325A+B |
| Time |
FRI 14:30-: |
| Code |
ORGN3-1 |
| Subject |
Conformationally rigid, β,β′-fused antiaromatic hexaphyrins[1.0.1.0.1.0]: structure and redox properties |
| Authors |
Chang Hee Lee
Department of Chemistry, Kangwon National University, Korea |
| Abstract |
A β,β′-fused, (1.0.1.0.1.0)hexaphyrin derivatives are Huckel’s 4nπ anti-aromatic system. The compounds are known to form stable (4n+1)π dication radical species upon exposure to acids. Naphthorosarin derivatives especially bearing substituents on the periphery were not reported due to the limited accessibility to the key building blocks. We have been interested in developing a generic synthetic pathway to the key building blocks that can lead to the peripherally substituted, new naphthorosarins. As the results, we successfully synthesized several new naphthorosarins building blocks and corresponding naphthorosarins. The structural and spectroscopic properties, redox properties and protonation behavior was studied. The results revealed interesting chemistry. The redox properties and protonation behavior of the newly synthesized naphthorosarins was studied. The absorption spectral changes after addition of acids indicates that the single electron reduction rates vary depending on the peripheral substituents. Slightly increased reduction potential of substituted rosarin and the electron withdrawing nature of fluoride exhibited dramatically different redox properties. The findings clearly indicate that the fine-tuning of the redox properties is possible by introduction of various peripheral substituents. |
| E-mail |
chhlee@kangwon.ac.kr |
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122nd General Meeting of the KCS