Macrocyclic arrays which are composed of highly organized chromophores play a unique role in chemistry and biology. One of the most exceptional examples in this regard is given by the light-harvesting system of the purple bacteria, in which numerous chlorophyll and bacteriochlorophyll chromophores are arranged in macrocyclic assemblies by non-covalent interactions. As a consequence of the intriguing functional properties of those dye arrays the interest in the development of artificial counterparts has grown tremendously.Here we present the synthesis of a series of covalent bonded perylene bisimide (PBI) macrocycles with ring sizes of two up to nine PBI dyes which exhibit a well-defined electronic coupling among the dye molecules due to the rigidity of the cyclic systems. These supramolecular macrocycles were self-assembled on a highly ordered pyrolytic graphite surface in a two-dimensional manner which could be confirmed by atomic force microscopy. Furthermore these compounds were used to investigate host-guest phenomena by encapsulating fullerene and perylene.

Perylene bisimide macrocycles: From dimer to nonamer

248th National Meeting (2014)

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