Structural Properties of Picene–Perfluoropentacene and Picene–Pentacene Blends: Superlattice Formation versus Limited Intermixing
- Johannes Dieterle
- ,
- Katharina Broch
- ,
- Alexander Hinderhofer
- ,
- Heiko Frank
- ,
- Jiří Novák
- ,
- Alexander Gerlach
- ,
- Tobias Breuer
- ,
- Rupak Banerjee
- ,
- Gregor Witte
- , and
- Frank Schreiber
Abstract
The structure and morphology of mixed thin films of picene (C22H14, PIC) and perfluoropentacene (C22F14, PFP) as well as mixed thin films of PIC and pentacene (C22H14, PEN) grown by simultaneous coevaporation is investigated using X-ray diffraction, atomic force microscopy, and near-edge X-ray absorption spectroscopy. For both systems we find mixing on the molecular level and the formation of mixed structures. However, due to the strongly different interactions in both mixtures the ordering is fundamentally different. For the equimolar PFP:PIC mixtures, we observe the formation of two different mixed polymorphs with unit cells containing 2 PIC and 2 PFP molecules depending on the growth temperature. One of these polymorphs is a superlattice with in-plane compound segregation. The other polymorph is less symmetric and results only in a very short ranged in-plane ordering. In contrast, the PEN:PIC mixtures form crystals with unit cell parameters continuously changing with the molar concentrations between those of the pure compounds. The position of molecular species within the crystal lattice is statistical. Surprisingly, for higher concentrations of PIC we observe phase separation of surplus PIC molecules which corresponds to a limited intermixing of the two compounds. Finally, the results are discussed in the context of other organic semiconductor binary mixtures showing that besides chemical composition and steric compatibility the intramolecular arrangement of the atoms important for intermolecular interactions significantly influences the structure formation in organic semiconductor blends.
Cited By
This article is cited by 13 publications.
- Alexander Hinderhofer, Jan Hagenlocher, Alexander Gerlach, Joachim Krug, Martin Oettel, Frank Schreiber. Nonequilibrium Roughness Evolution of Small Molecule Mixed Films Reflecting Equilibrium Phase Behavior. The Journal of Physical Chemistry C 2022, 126 (27) , 11348-11357. https://doi.org/10.1021/acs.jpcc.2c02177
- Valentina Belova, Alexander Hinderhofer, Clemens Zeiser, Timo Storzer, Jakub Rozbořil, Jan Hagenlocher, Jiří Novák, Alexander Gerlach, Reinhard Scholz, Frank Schreiber. Structure-Dependent Charge Transfer in Molecular Perylene-Based Donor/Acceptor Systems and Role of Side Chains. The Journal of Physical Chemistry C 2020, 124 (21) , 11639-11651. https://doi.org/10.1021/acs.jpcc.0c00230
- Johannes Dieterle, Katharina Broch, Alexander Hinderhofer, Heiko Frank, Alexander Gerlach, Frank Schreiber. Revealing Suppressed Intermolecular Coupling Effects in Aggregated Organic Semiconductors by Diluting the Crystal: Model System Perfluoropentacene:Picene. The Journal of Physical Chemistry A 2019, 123 (32) , 7016-7020. https://doi.org/10.1021/acs.jpca.9b03980
- Tullio Toccoli, Paolo Bettotti, Antonio Cassinese, Stefano Gottardi, Yoshihiro Kubozono, Maria A. Loi, Marianna Manca, Roberto Verucchi. Photophysics of Pentacene-Doped Picene Thin Films. The Journal of Physical Chemistry C 2018, 122 (29) , 16879-16886. https://doi.org/10.1021/acs.jpcc.8b02978
- Valentina Belova, Paul Beyer, Eduard Meister, Theresa Linderl, Marc-Uwe Halbich, Marina Gerhard, Stefan Schmidt, Thomas Zechel, Tino Meisel, Alexander V. Generalov, Ana Sofia Anselmo, Reinhard Scholz, Oleg Konovalov, Alexander Gerlach, Martin Koch, Alexander Hinderhofer, Andreas Opitz, Wolfgang Brütting, and Frank Schreiber . Evidence for Anisotropic Electronic Coupling of Charge Transfer States in Weakly Interacting Organic Semiconductor Mixtures. Journal of the American Chemical Society 2017, 139 (25) , 8474-8486. https://doi.org/10.1021/jacs.7b01622
- Fabrizio Moro, Massimo Moret, Alberto Ghirri, Andrés Granados del Águila, Yoshihiro Kubozono, Luca Beverina, Antonio Cassinese. Room-temperature optically detected magnetic resonance of triplet excitons in a pentacene-doped picene single crystal. Journal of Materials Research 2022, 37 (6) , 1269-1279. https://doi.org/10.1557/s43578-022-00536-y
- Prashanth Nayak, Padmanabhan Viswanath. Structural, morphological and photoluminescence studies on annealed Langmuir-Blodgett films of copper and zinc octakis-octyloxy phthalocyanine and their mixture. Optical Materials 2022, 125 , 112069. https://doi.org/10.1016/j.optmat.2022.112069
- Clemens Zeiser, Chad Cruz, David R. Reichman, Michael Seitz, Jan Hagenlocher, Eric L. Chronister, Christopher J. Bardeen, Roel Tempelaar, Katharina Broch. Vacancy control in acene blends links exothermic singlet fission to coherence. Nature Communications 2021, 12 (1) https://doi.org/10.1038/s41467-021-25395-9
- Hiroyuki Matsui, Eiji Takahashi, Seiji Tsuzuki, Kazuo Takimiya, Tatsuo Hasegawa. Field-Induced Electron Spin Resonance of Site-Selective Carrier Accumulation in Field-Effect Transistors Composed of Organic Semiconductor Solid Solutions. Physical Review Applied 2021, 16 (3) https://doi.org/10.1103/PhysRevApplied.16.034019
- Guillaume Schweicher, Guillaume Garbay, Rémy Jouclas, François Vibert, Félix Devaux, Yves H. Geerts. Molecular Semiconductors for Logic Operations: Dead‐End or Bright Future?. Advanced Materials 2020, 32 (10) https://doi.org/10.1002/adma.201905909
- Theyencheri Narayanan, Oleg Konovalov. Synchrotron Scattering Methods for Nanomaterials and Soft Matter Research. Materials 2020, 13 (3) , 752. https://doi.org/10.3390/ma13030752
- K. Broch, J. Dieterle, F. Branchi, N. J. Hestand, Y. Olivier, H. Tamura, C. Cruz, V. M. Nichols, A. Hinderhofer, D. Beljonne, F. C. Spano, G. Cerullo, C. J. Bardeen, F. Schreiber. Robust singlet fission in pentacene thin films with tuned charge transfer interactions. Nature Communications 2018, 9 (1) https://doi.org/10.1038/s41467-018-03300-1
- Johannes Dieterle, Katharina Broch, Heiko Frank, Giuliano Duva, Timo Storzer, Alexander Hinderhofer, Jiří Novák, Alexander Gerlach, Frank Schreiber. Delayed phase separation in growth of organic semiconductor blends with limited intermixing. physica status solidi (RRL) - Rapid Research Letters 2017, 11 (3) , 1600428. https://doi.org/10.1002/pssr.201600428