Abstract
Dithiafulvenyl (DTF) end groups were linked to the 1 and 8 positions of a pyrene core directly or via phenylene bridges to afford redox-active pyrene derivatives. Upon oxidation, the 1,8-bis(DTF)pyrene underwent stepwise electron transfers to form radical cation and dication species, whereas the phenylene-extended bis(DTF)pyrene derivative was cyclized into a macrocyclic trimer through sequential DTF oxidative coupling reactions in solution and in the solid state. The structural, electronic, and supramolecular properties of the pyrene-based macrocycle were investigated using various spectroscopic techniques and molecular modeling studies.
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