Photoconductive Core–Shell Liquid-Crystals of a Perylene Bisimide J-Aggregate Donor–Acceptor Dyad
Markus Hecht
Institut für Organische Chemie, Center for Nanosystems Chemistry & Bavarian Polymer Institute, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
Search for more papers by this authorTim Schlossarek
Institut für Organische Chemie, Center for Nanosystems Chemistry & Bavarian Polymer Institute, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
Search for more papers by this authorDr. Matthias Stolte
Institut für Organische Chemie, Center for Nanosystems Chemistry & Bavarian Polymer Institute, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
Search for more papers by this authorCorresponding Author
Prof. Dr. Matthias Lehmann
Institut für Organische Chemie, Center for Nanosystems Chemistry & Bavarian Polymer Institute, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
Search for more papers by this authorCorresponding Author
Prof. Dr. Frank Würthner
Institut für Organische Chemie, Center for Nanosystems Chemistry & Bavarian Polymer Institute, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
Search for more papers by this authorMarkus Hecht
Institut für Organische Chemie, Center for Nanosystems Chemistry & Bavarian Polymer Institute, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
Search for more papers by this authorTim Schlossarek
Institut für Organische Chemie, Center for Nanosystems Chemistry & Bavarian Polymer Institute, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
Search for more papers by this authorDr. Matthias Stolte
Institut für Organische Chemie, Center for Nanosystems Chemistry & Bavarian Polymer Institute, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
Search for more papers by this authorCorresponding Author
Prof. Dr. Matthias Lehmann
Institut für Organische Chemie, Center for Nanosystems Chemistry & Bavarian Polymer Institute, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
Search for more papers by this authorCorresponding Author
Prof. Dr. Frank Würthner
Institut für Organische Chemie, Center for Nanosystems Chemistry & Bavarian Polymer Institute, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
Search for more papers by this authorAbstract
A novel core–shell structured columnar liquid crystal composed of a donor-acceptor dyad of tetraphenoxy perylene bisimide (PBI), decorated with four bithiophene units on the periphery, was synthesized. This molecule self-assembles in solution into helical J-aggregates guided by π–π interactions and hydrogen bonds which organize into a liquid-crystalline (LC) columnar hexagonal domain in the solid state. Donor and acceptor moieties exhibit contrasting exciton coupling behavior with the PBIs’ (J-type) transition dipole moment parallel and the bithiophene side arms’ (H-type) perpendicular to the columnar axis. The dyad shows efficient energy and electron transfer in solution as well as in the solid state. The synergy of photoinduced electron transfer (PET) and charge transport along the narcissistically self-assembled core–shell structure enables the implementation of the dye in two-contact photoconductivity devices giving rise to a 20-fold increased photoresponse compared to a reference dye without bithiophene donor moieties.
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