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Molecular stacking character and charge transport properties of tetrabenzoheptacenes derivatives: the effects of nitrogen doping and phenyl substitution

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Abstract

The nitrogen doping and phenyl substitution effects on the geometries, molecular stacking character, electronic, and charge transport properties of tetrabenzoheptacene (TTBH) have been investigated by means of density functional theory (DFT) calculation and incoherent charge hopping model. Our results indicate that the nitrogen doping (TTH) at the 6,8,15,17 positions improves its stability in air and the ability of electron injection and in the meantime slightly changes the molecular stacking due to the C-H···N interaction. For both TTBH and TTH, large hole transport mobility (μ h ) and electron transport mobility (μ e ), which are on the same order of magnitude, are given rise by their dense displaced π-stacking in crystal. Comparatively, the phenyl substitution (Ph-TTBH) at the 6,8,15,17 positions adopts a non-planar conformation, adverse to close packing and therefore leads to smaller electron/hole transport mobility (μ) than those of TTBH and TTH. The calculations suggest TTBH and TTH are promising candidates for excellent ambipolar OFET materials.

In comparison with parent tetrabenzoheptacenes compound, the C-H···N hydrogen bonds interaction caused by nitrogen doping gives rise to different relative in-plane displacement of the dimer with shortest centroid distance in crystal structure. Such distinguish leads to the significantly different frontier molecular orbital interaction of monomers in the dimer, which explains the different nature of the charge transfer

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Acknowledgments

This work is supported by the National Nature Science Foundation of China (21173139, 21173138, 21473108), the Fundamental Research Funds for the Central Universities (No: GK201101004, GK201303004), and the Shaanxi Innovative Team of Key Science and Technology (2013KCT-17).

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Authors and Affiliations

  1. Key Laboratory for Macromolecular Science of Shaanxi Province, School of Chemistry & Chemical Engineering, Shaanxi Normal University, Xi’an, Shaanxi, 710062, People’s Republic of China

    Lin Guan, Wenliang Wang, Rong Shao, Fengyi Liu & Shiwei Yin

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  1. Lin Guan
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  2. Wenliang Wang
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  3. Rong Shao
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Correspondence to Wenliang Wang.

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Guan, L., Wang, W., Shao, R. et al. Molecular stacking character and charge transport properties of tetrabenzoheptacenes derivatives: the effects of nitrogen doping and phenyl substitution. J Mol Model 21, 126 (2015). https://doi.org/10.1007/s00894-015-2677-2

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