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How strong are van der Waals interactions in determining the final outcome of self-assembled structures of small molecular systems? Herein we report isolable phthalocyanine (Pc) dimers bound by π-π interactions between monomeric Pcs which can be handled as single entities. Pc dimers have been continuously investigated as one of the simplest models of Pc aggregates. Pcs were substituted with eight dihydrodiazapentacene (DHDAP) moieties on the periphery, which act as pillar-like π-planes and these molecules form H-type dimers with the help o