A biphenyl-type electron donor 1a with two diarylmethylene chromophores was prepared, which gave a dihydrophenanthrene-type dication 2a2+ upon oxidation. It is shown that the redox pair of 1a and 2a2+ exhibits electrochromism accompanied by reversible C-C bond making/breaking. On the other hand, the binaphthyl derivative of 1a is chiral due to the axial chirality, thus realizing a chiroptical response by electron transfer. The title compounds were shown to be a useful skeleton to obtain the multi-output response system based on chiral redox systems, for which only a limited numbers of successful examples were reported.