@article{BoldStolteShoyamaetal.2022, author = {Bold, Kevin and Stolte, Matthias and Shoyama, Kazutaka and Krause, Ana-Maria and Schmiedel, Alexander and Holzapfel, Marco and Lambert, Christoph and W{\"u}rthner, Frank}, title = {Macrocyclic Donor-Acceptor Dyads Composed of Oligothiophene Half-Cycles and Perylene Bisimides}, series = {Chemistry - A European Journal}, volume = {28}, journal = {Chemistry - A European Journal}, number = {30}, doi = {10.1002/chem.202200355}, url = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-276435}, year = {2022}, abstract = {A series of donor-acceptor (D-A) macrocyclic dyads consisting of an electron-poor perylene bisimide (PBI) π-scaffold bridged with electron-rich α-oligothiophenes bearing four, five, six and seven thiophene units between the two phenyl-imide substituents has been synthesized and characterized by steady-state UV/Vis absorption and fluorescence spectroscopy, cyclic and differential pulse voltammetry as well as transient absorption spectroscopy. Tying the oligothiophene strands in a conformationally fixed macrocyclic arrangement leads to a more rigid π-scaffold with vibronic fine structure in the respective absorption spectra. Electrochemical analysis disclosed charged state properties in solution which are strongly dependent on the degree of rigidification within the individual macrocycle. Investigation of the excited state dynamics revealed an oligothiophene bridge size-dependent fast charge transfer process for the macrocyclic dyads upon PBI subunit excitation.}, language = {en} } @article{MenekseMahlAlbertetal.2023, author = {Menekse, Kaan and Mahl, Magnus and Albert, Julius and Niyas, M. A. and Shoyama, Kazutaka and Stolte, Matthias and W{\"u}rthner, Frank}, title = {Supramolecularly Engineered Bulk-Heterojunction Solar Cells with Self-Assembled Non-Fullerene Nanographene Tetraimide Acceptors}, series = {Solar RRL}, volume = {7}, journal = {Solar RRL}, number = {2}, doi = {10.1002/solr.202200895}, url = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-312099}, year = {2023}, abstract = {A series of novel imide-functionalized C\(_{64}\) nanographenes is investigated as acceptor components in organic solar cells (OSCs) in combination with donor polymer PM6. These electron-poor molecules either prevail as a monomer or self-assemble into dimers in the OSC active layer depending on the chosen imide substituents. This allows for the controlled stacking of electron-poor and electron-rich π-scaffolds to establish a novel class of non-fullerene acceptor materials to tailor the bulk-heterojunction morphology of the OSCs. The best performance is observed for derivatives that are able to self-assemble into dimers, reaching power conversion efficiencies of up to 7.1\%.}, language = {en} } @article{BoldStolteShoyamaetal.2022, author = {Bold, Kevin and Stolte, Matthias and Shoyama, Kazutaka and Holzapfel, Marco and Schmiedel, Alexander and Lambert, Christoph and W{\"u}rthner, Frank}, title = {Macrocyclic donor-acceptor dyads composed of a perylene bisimide dye surrounded by oligothiophene bridges}, series = {Angewandte Chemie Internationale Edition}, volume = {61}, journal = {Angewandte Chemie Internationale Edition}, number = {1}, doi = {10.1002/anie.202113598}, url = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-256569}, year = {2022}, 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 F{\"o}rster Resonance Energy Transfer and photoinduced electron transfer, thereby leading to extremely low fluorescence quantum yields even in the lowest polarity cyclohexane solvent.}, language = {en} } @article{BrustNaglerShoyamaetal.2023, author = {Brust, Felix and Nagler, Oliver and Shoyama, Kazutaka and Stolte, Matthias and W{\"u}rthner, Frank}, title = {Organic Light-Emitting Diodes Based on Silandiol-Bay-Bridged Perylene Bisimides}, series = {Advanced Optical Materials}, volume = {11}, journal = {Advanced Optical Materials}, number = {5}, doi = {10.1002/adom.202202676}, url = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-312599}, year = {2023}, abstract = {Perylene bisimides (PBIs) are among the best fluorophores but have to be enwrapped for optoelectronic applications by large and heavy substituents to prevent their ππ-stacking, which is known to accelerate non-radiative decay processes in the solid state. Here, light-weight di-tert-butylsilyl groups are introduced to bridge 1,12-dihydroxy and 1,6,7,12-tetrahydroxy PBIs to afford sublimable dyes for vacuum-processed optoelectronic devices. For both new compounds, this substitution provides a twisted and shielded perylene π-core whose, via OSiObridges, rigid structure affords well-resolved absorption and emission spectra with strong fluorescence in solution, as well as in the solid state. The usefulness of these dyes for vacuum-processed optoelectronic devices is demonstrated in organic light-emitting diodes (OLEDs) that show monomer-like emission spectra and high maximum external quantum efficiency (EQEmax) values of up to 3.1\% for the doubly silicon-bridged PBI.}, language = {en} }