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| Naji, M. |
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| Motta, Antonella |
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| Aletan, Dirar |
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| Mohamed, Tarek |
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| Ertürk, Emre |
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| Taccardi, Nicola |
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| Kononenko, Denys |
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| Petrov, R. H. | Madrid |
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| Alshaaer, Mazen | Brussels |
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| Bih, L. |
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| Casati, R. |
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| Muller, Hermance |
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| Kočí, Jan | Prague |
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| Šuljagić, Marija |
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| Kalteremidou, Kalliopi-Artemi | Brussels |
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| Azam, Siraj |
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| Ospanova, Alyiya |
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| Blanpain, Bart |
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| Ali, M. A. |
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| Popa, V. |
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| Rančić, M. |
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| Ollier, Nadège |
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| Azevedo, Nuno Monteiro |
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| Landes, Michael |
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| Rignanese, Gian-Marco |
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Bredas, Jean-Luc
in Cooperation with on an Cooperation-Score of 37%
Topics
Publications (16/16 displayed)
- 2023Additive-free molecular acceptor organic solar cells processed from a biorenewable solvent approaching 15% efficiencycitations
- 2022Controlled n‐Doping of Naphthalene‐Diimide‐Based 2D Polymerscitations
- 2018Characterization of the Valence and Conduction Band Levels of n = 1 2D Perovskites: A Combined Experimental and Theoretical Investigationcitations
- 2017Singlet Fission in Rubrene Derivatives: Impact of Molecular Packingcitations
- 2017High operational and environmental stability of high-mobility conjugated polymer field-effect transistors achieved through the use of molecular additivescitations
- 2017High operational and environmental stability of high-mobility conjugated polymer field-effect transistors through the use of molecular additives.
- 2017Open-Circuit Voltage in Organic Solar Cells: The Impacts of Donor Semicrystallinity and Coexistence of Multiple Interfacial Charge-Transfer Bandscitations
- 2016High operational and environmental stability of high-mobility conjugated polymer field-effect transistors through the use of molecular additivescitations
- 2016Improving the Stability of Organic Semiconductors: Distortion Energy versus Aromaticity in Substituted Bistetracenecitations
- 2016Passivation of Molecular n-Doping: Exploring the Limits of Air Stabilitycitations
- 2016Ionization Energies, Electron Affinities, and Polarization Energies of Organic Molecular Crystals: Quantitative Estimations from a Polarizable Continuum Model (PCM)-Tuned Range-Separated Density Functional Approachcitations
- 2016Spectroscopy and control of near-surface defects in conductive thin film ZnOcitations
- 2016Phosphonic Acids for Interfacial Engineering of Transparent Conductive Oxidescitations
- 2015Magnetite Fe3O4 (111) Surfaces: Impact of Defects on Structure, Stability, and Electronic Propertiescitations
- 2015Effect of Solvent Additives on the Solution Aggregation of Phenyl-C61-Butyl Acid Methyl Ester (PCBM)citations
- 2012Controlled Conjugated Backbone Twisting for an Increased Open-Circuit Voltage while Having a High Short-Circuit Current in Poly(hexylthiophene) Derivativescitations
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article
Improving the Stability of Organic Semiconductors: Distortion Energy versus Aromaticity in Substituted Bistetracene
Abstract
Polycyclic aromatic hydrocarbons (PAHs) have been widely explored as molecular semiconductors in organic electronic devices such as field-effect transistors or solar cells. However, their tendency to undergo photooxidation is a primary limitation to their practical applications. Bistetracene derivatives have recently been demonstrated to possess much larger photo oxidation stability than the widely investigated pentacene and rubrene, while maintaining high charge-carrier mobilities. Here, using several levels of density functional theory, we identify the origin of the increased stability of bistetracene with respect to molecular oxygen by systematically investigating the [4 + 2] cycloaddition (Diels Alder) photooxidation reaction mechanism. Importantly, our computational results indicate that endoperoxide formation in bis(2-(trimethylsilyl)ethynyl) bistetracene (BT) occurs not on the ring with least aromaticity, but rather on the ring with smallest distortion energy. This feature was subsequently confirmed by experimental NMR analyses. The oxidation activation barriers of bistetracene, pentacene, and rubrene are found to be 17.7, 13.6, and 14.4 kcal/mol, respectively, in agreement with the observed order of stability of these molecules with respect to oxidation reactions in solution. In the cases of BT and pentacene, the rates of electron transfer to create charged species (PAH(+) and O-2) are at least two orders of magnitude lower than that of the charge recombination process (back to PAH and O-2); for rubrene, both of these processes are calculated to be of the same order of magnitude, in agreement with experimental electron paramagnetic resonance spectroscopy observations.