Pentacene, a linear fusion of five benzene rings, has been shown to display remarkable photophysical and electronic properties. It has been studied extensively for use in organic field effect transistors (OFETs) due to its high carrier mobility, and it plays a central role in the search for more efficient solar cells due to its ability to undergo fast and efficient singlet fission. Incorporation of pentacene into a macrocyclic framework could enable a number of new phenomena, taking advantage of the propensity for rigid macrocycles to facilitate supramolecular assembly and host-guest chemistry. Utilizing a reversible zirconocene mediated coupling of alkynes, we have developed concise synthetic routes to two pentacene macrocycles on gram scale. Through judicious choice of monomer geometry and rigidity we were able to rationally target both a dimeric and trimeric macrocycle, exercising control over the orientation of individual pentacenes within the macrocyclic scaffold. The dimeric macrocycle displays a unique packing arrangement in the solid state with potential implications for using host-guest chemistry to tune charge transport and singlet fission behavior.

Rational control of geometry in pentacene macrocycles

2019 Fall National Meeting

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