Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Tuning of Molecular Electrostatic Potential Enables Efficient Charge Transport in Crystalline Azaacenes: A Computational Study

Version 1 : Received: 6 July 2020 / Approved: 8 July 2020 / Online: 8 July 2020 (11:23:32 CEST)

A peer-reviewed article of this Preprint also exists.

Sosorev, A.; Dominskiy, D.; Chernyshov, I.; Efremov, R. Tuning of Molecular Electrostatic Potential Enables Efficient Charge Transport in Crystalline Azaacenes: A Computational Study. Int. J. Mol. Sci. 2020, 21, 5654. Sosorev, A.; Dominskiy, D.; Chernyshov, I.; Efremov, R. Tuning of Molecular Electrostatic Potential Enables Efficient Charge Transport in Crystalline Azaacenes: A Computational Study. Int. J. Mol. Sci. 2020, 21, 5654.

Journal reference: Int. J. Mol. Sci. 2020, 21, 5654
DOI: 10.3390/ijms21165654

Abstract

Chemical versatility of organic semiconductors provides nearly unlimited opportunities for tuning their electronic properties. However, despite decades of research, relationship between molecular structure, molecular packing and charge mobility in these materials remains poorly understood. This reduces the search for high-mobility organic semiconductors to the inefficient trial-and-error approach. For clarifying the abovementioned relationship, investigations of the effect of small changes in the chemical structure on OSs properties are particularly important. In this study, we address computationally the impact of substitution of C-H atom pairs by nitrogen atoms (N-substitution) on molecular properties, molecular packing and charge mobility of crystalline oligoacenes. Besides of decreasing frontier molecular orbital levels, N-substitution dramatically alters molecular electrostatic potential yielding pronounced electron-rich and electron-deficient areas. These changes in the molecular electrostatic potential strengthen face-to-face and edge-to-edge interactions in the corresponding crystals and result in the crossover from the herringbone packing motif to π-stacking. When the electron-rich and electron-deficient areas are large, sharply defined and, probably, have certain symmetry, charge mobility increases up to 3-4 cm2V-1s-1. The results obtained highlight the potential of azaacenes for application in organic electronic devices and are expected to facilitate rational design of organic semiconductors for steady improvement of organic electronics.

Subject Areas

organic electronics; organic semiconductors; molecular design; crystal design; π-stacking; charge mobility

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