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Paper | Special issue | Vol 76, No. 1, 2008, pp.541-550
Published online, 21st April, 2008
DOI: 10.3987/COM-08-S(N)41
Synthesis, Molecular Structure, and Oxidation Behavior of Exhaustively Methylated Azacalix[6]arene

Koichi Ishibashi, Hirohito Tsue,* Hiroki Takahashi, Satoshi Tokita, Kazuhiro Matsui, and Rui Tamura

*Graduate School of Human and Environmental Studies, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan


The molecular structure and oxidation behavior of an exhaustively methylated azacalix[6]arene have been investigated with the intention of developing high-spin materials. The azacalix[6]arene adopted a distorted 1,3-alternate conformation in the solid state, whereas the conformation was highly flexible in solution at ambient temperature. As a result of the flexible structure in solution, the decreased stability of the corresponding cation radicals was observed, as compared to that of the smaller inflexible homologue yielding stable cation radicals. Both the conformational inflexibility and the steric protection of reactive sites were found to be crucial for stabilizing the oxidized species of this molecular system.