Cross-cyclophane twin donors, in which long axes of TTF units are fixed in a cross orientation by four ethylenedithio (x-CPTD (II)) and four trimethylenedithio (x-CPTD (III)) chains, were designed and prepared. Although the donor ability of x-CPTD (II) was low due to a heavy bending of the donor units, that of x-CPTD (III) was the same as BEDT-TTF. The crystal structures of a charge transfer complex, x-CPTD (III).TCNQ, and an ion radical salt,x-CPTD (III).Br (1,1,2-TCE)(2), revealed that x-CPTD (III) has an ability to construct characteristic self-assembled structures, recognizing a size and a shape of accepters or counter ions. The almost isotropic conducting property (sigma(r.t.)(//a) = 1.0 x 10(-2) S.cm(-1), sigma(r.t.)(//c) = 5.5 x 10(3) S.cm(-1)) of the ion radical salt was interpreted based on the unique molecular structure of x-CPTD (III).