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Published on: October 24, 2017
Macrocyclic Donor-Acceptor Dyads Composed of a Perylene Bisimide Dye Surrounded by Oligothiophene Bridges
Kevin Bold1, Matthias Stolte1,2, Kazutaka Shoyama1
1Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.
Abstract:
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 Förster Resonance Energy Transfer and photoinduced electron transfer, thereby leading to extremely low fluorescence quantum yields even in the lowest polarity cyclohexane solvent.
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