The design and synthesis of a novel type of bisphthalocyanines, anti-[2.2](1,4)phthalocyaninophanes, were reported. The phthalocyanine dimer exhibited significantly split and red-shifted absorption in the near-IR region and maintained the fluorescence properties of phthalocyanines. The origin of the electronic communication between the two phthalocyanines was rationalized on the basis of the MO model analysis.