Structural and Thermal Effects on the Charge Transport of Core-Twisted Chlorinated Perylene Bisimide Semiconductors

Motta, Simone Di; Siracusa, Melania; Negri, Fabrizia

doi:10.1021/jp207333y

Cited by 35 publications

(46 citation statements)

References 59 publications

(109 reference statements)

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“…68 However, the presence of the ethynylene bridges in (ArCC) 2 Ph derivatives substantially lowers λ i to values comparable to those reported for the above mentioned reference compounds (see Table 1). The decrease of λ i is closely related to the change in the shape of the LUMO, which becomes completely delocalized for (ArCC) 2 Tz (see Figure 1 for (PhCC) 2 Tz).…”

Section: Resultssupporting

confidence: 68%

Bis(arylene-ethynylene)-s-tetrazines: A Promising Family of n-Type Organic Semiconductors?

et al. 2015

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We theoretically describe in this work the n-type semiconducting behavior of a set of bis(arylene-ethynylene)-s-tetrazines ((ArCC) 2 Tz), by comparing their electronic properties with those of their parent diaryl-s-tetrazines (Ar 2 Tz) after the introduction of ethynylene bridges. The significantly reduced internal reorganization energy for electron transfer is ascribed to an extended delocalization of the LUMO for (ArCC) 2 Tz as opposite to that for Ar 2 Tz, which was described mostly localized on the s-tetrazine ring. The largest electronic coupling and the corresponding electron transfer rates found 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 2 for bis(phenyl-ethynylene)-s-tetrazine, as well as for some halogenated derivatives, are comparable to those reported for the best performing n-type organic semiconductors materials such as diimides and perylenes. The theoretical mobilities for the studied compounds turn out to be in the range 0.3 -1.3 cm 2 V −1 s −1 , close to values experimentally determined for common n-type organic semiconductors used in real devices. In addition, ohmic contacts can be expected when these compounds are coupled to metallic cathodes such as Na, Ca and Sm. For these reasons, the future application of semiconducting bis(phenyl-ethynylene)-s-tetrazine and its fluorinated and brominated derivatives in optoelectronic devices is envisioned.

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Section: Resultssupporting

confidence: 68%

Bis(arylene-ethynylene)-s-tetrazines: A Promising Family of n-Type Organic Semiconductors?

et al. 2015

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“…The Monte Carlo method is a stochastic approach to tackle mathematical problems which are analytically or numerically hard to handle. The kinetic Monte Carlo method, which allows for the simulation of the time evolution of a system, is frequently used to study charge and exciton transport in organic solids. Instead of solving the master equation directly in order to obtain the (probability) distribution, one can also solve this equation stochastically.…”

Section: Simulation Of the Dynamicsmentioning

confidence: 99%

Comparison of different rate constant expressions for the prediction of charge and energy transport in oligoacenes

Stehr

Fink

Tafipolski

et al. 2016

WIREs Comput Mol Sci

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Charge and exciton transport in organic semiconductors is crucial for a variety of optoelectronic applications. The prediction of the material-dependent exciton diffusion length and the charge carrier mobility is a prerequisite for tailoring new materials for organic electronics. At room temperature often a hopping process can be assumed. In this work, three hopping models based on Fermi's Golden rule but with different levels of approximation-the spectral overlap approach, the Marcus theory, and the Levich-Jortner theory-are compared for the calculation of charge carrier mobilities and exciton diffusion lengths for oligoacenes, using the master equation approach and Monte Carlo simulations. Efor the donor deexcitation/neutralization and the analogue equation for the acceptor excitation/ionization respectively, the hopping rate, Eq. (1), can be written aswith the Franck-Condon weighted density of states (FCWD) 40,41,43WIREs Computational Molecular Science Prediction of charge and energy transport in oligoacenes using rate constant expressions Volume 6, November/December 2016Here, a linear approximation for e J E AD ð Þ is used, where J 0 : = d e J E AD ð Þ=dE AD j E AD = 0 and J : = e J 0 ð Þ, and thereforeEq. (14), the difference vector Δd ! of the equilibrium structures of the charged/excited state and the neutral/ground state is determined. This vector is transformed from Cartesian coordinates into a vector Δq ! in the normal mode basis viawhere the matrix A contains the normal mode vectors. The molecular vibrations are treated as harmonic oscillators. 50,55 Therefore, the relaxation Advanced Review

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“…1) may easily happen. 50,90,91 But for excitons the coupling decays much slower with the distance and a much larger number of dimers gives significant contributions to the transport and one would expect a much weaker trapping effect. Here it is shown that, nevertheless, the effect is important for exciton diffusion as well.…”

Section: A Naphthalenementioning

confidence: 99%

Anisotropy of singlet exciton diffusion in organic semiconductor crystals from ab initio approaches

Stehr

Engels

Deibel

et al. 2014

The Journal of Chemical Physics

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Due to its importance for the function of organic optoelectronic devices, accurate simulations of the singlet exciton diffusion are crucial to predict the performance of new materials. We present a protocol which allows for the efficient directional analysis of exciton transport with high-level ab initio methods. It is based on an alternative to the frequently employed rate equation since the latter was found to be erroneous in some cases. The new approach can be used in combination with the master equation which is considerably faster than the corresponding Monte Carlo approach. The long-range character of the singlet exciton coupling is taken into account by an extrapolation scheme. The approach is applied to singlet exciton diffusion in those substances where these quantities are experimentally best established: naphthalene and anthracene. The high quality of the crystals, furthermore, diminish uncertainties arising from the geometrical structures used in the computations. For those systems, our new approach provides exciton diffusion lengths L for naphthalene and anthracene crystals which show an excellent agreement with their experimental counterparts. For anthracene, for example, the computed L value in a direction is computed to 58 nm while the experimental value is 60 ± 10 nm.

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Structural and Thermal Effects on the Charge Transport of Core-Twisted Chlorinated Perylene Bisimide Semiconductors

Abstract: We acknowledge grants from MIUR: ex 60% and PRIN Project 2008 JKBBK4 "Tracking ultrafast photoinduced intra-and intermolecular processes in natural and artificial photosensors". Whe are indebted to the referees for their comments and suggestions.

Cited by 35 publications

References 59 publications

Bis(arylene-ethynylene)-s-tetrazines: A Promising Family of n-Type Organic Semiconductors?

Bis(arylene-ethynylene)-s-tetrazines: A Promising Family of n-Type Organic Semiconductors?

Comparison of different rate constant expressions for the prediction of charge and energy transport in oligoacenes

Anisotropy of singlet exciton diffusion in organic semiconductor crystals from ab initio approaches

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