[3
n] Cyclophanes ([3
n] CPs : n= 2-6) including the ultimate member of this series, [3
6] CP, and fluorinated [3
3] CPs were synthesized. The fundamental structural properties of these compounds both in solution and in the solid state are described. [3
n] CP shows strong electron-donating ability, which was evaluated by the λ
max of the charge transfer (CT) band of the [3
n] CP-TCNE complex and oxidation potential, and this is attributed to the effective hyperconjugation between the benzyl methylenes and the benzene ring. The solid state structural study of [3
n] CP-TCNQ-F
4 complexes provided the basic knowledge for understanding the CT interaction in the solid state. [3
n] CPs served as good ligands for Ru (II) and Os (II) metals. [3
n] CP (n=2, 4) reacted with dicyanoacetylene to give barrelenophane, which gave various valence isomers on photolysis. Our efforts to the synthesis of hexaprismane derivative via photolysis of [3
n] CP is described.
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