The electronic delocalization between chromophores in the solid is an important parameter to optimize when designing organic materials for optoelectronic applications. The [2,2]paracyclophane framework allows for the synthesis of well-defined, nonfluxional molecules that bring together two chromophores into close proximity. From the photophysical properties of these molecules we can examine how the chromophore conjugation length, their relative orientation, and the regiochemistry of contact affects the electronic delocalization between the two subunits.