Macrocyclic Donor-Acceptor Dyads Composed of a Perylene Bisimide Dye Surrounded by Oligothiophene Bridges

Two macrocyclic architectures comprising oligothiophene strands that connect the imide positions of a perylene bisimide (PBI) dye have been synthesized via a platinum-mediated cross-coupling strategy. The crystal structure of the double bridged PBI reveals all syn-arranged thiophene units that completely enclose the planar PBI chromophore via a 12-membered macrocycle. The target structures were characterized by steady-state UV/Vis absorption, fluorescence and transient absorption spectroscopy, as well as cyclic and differential pulse voltammetry. Both donor-acceptor dyads show ultrafast Forster Resonance Energy Transfer and photoinduced electron transfer, thereby leading to extremely low fluorescence quantum yields even in the lowest polarity cyclohexane solvent.

Automated summary

Two macrocyclic architectures comprising oligothiophene strands that connect the imide positions of a perylene biscimide (PBI) dye have been synthesized via a platinum-mediated cross-coupling strategy. The crystal structure of the double bridged PBI reveals all syn-arranged thiophene units enclosed a planar PBI chromophore via a 12-membered macrocycle. The target structures exhibit ultrafast Forster Resonance Energy Transfer and photoinduced electron transfer, resulting in extremely low fluorescence quantum yields even in the lowest polarity cyclohexane solvent.