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Charge transport and electronic properties of N-heteroquinones: quadruple weak hydrogen bonds and strong π–π stacking interactions

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Abstract

The charge transport and photophysical properties of N-heteroquinones, which can function as n-type organic semiconductors in organic field-effect transistors (OFETs) with high electron mobility, were systematically investigated using hopping model, band theory, and time-dependent density functional theory (TDDFT). The calculated absorption spectra and electron mobility are in good agreement with experimental results. To the studied compounds, subtle structural modifications can greatly reduce the reorganization energy. There are two main kinds of intermolecular interaction forces of the studied compounds in the crystal, which result from intermolecular π–π and hydrogen bonds interactions, respectively. The results of hopping model show that the electron transport properties are mainly determined by pathways containing intermolecular π–π interactions, and hole transport properties are mainly determined by pathways containing intermolecular hydrogen bonds from the standpoint of transfer integral. Moreover, electronic transfer integral value increases with the enhancement of intermolecular overlap corresponding to the overlap extent of π–π packing. Hole transfer integral value decreases with decreasing the number of hydrogen bonds. This means that charge transport properties can be efficiently tuned by controlling the relative positions of the molecules and the number of hydrogen bonds. The analysis of band structure also supports the conclusion of hopping model.

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Acknowledgments

The authors gratefully acknowledge the financial support from the National Natural Science Foundation of China (Project No. 20903020; 20703008), Chang Jiang Scholars Program (2006), Program for Changjiang Scholars and Innovative Research Team in University (IRT0714), National Basic Research Program of China (973 Program—2009CB623605), the Science and Technology Development Project Foundation of Jilin Province (20090146), the Training Fund of NENU’s Scientific Innovation Project (NENU-STC08005 and -STC08012), The Project-sponsored by SRF for ROCS, SEM and Open Project Program of State Key Laboratory of Supramolecular Structure and Materials, Jilin University. And we also thank Patrik Callis (MSU) for supplying the Bozesuite program. Science Foundation for Young Teachers of Jilin Agricultural University.

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Authors and Affiliations

  1. Institute of Functional Material Chemistry, Faculty of Chemistry, Northeast Normal University, 130024, Changchun, Jilin, People’s Republic of China

    Guochun Yang, Yanling Si, Yun Geng, Fei Yu, Qingxiu Wu & Zhongmin Su

  2. College of Resource and Environmental Science, Jilin Agricultural University, 130118, Changchun, Jilin, People’s Republic of China

    Yanling Si

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  1. Guochun Yang
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Correspondence to Zhongmin Su.

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Yang, G., Si, Y., Geng, Y. et al. Charge transport and electronic properties of N-heteroquinones: quadruple weak hydrogen bonds and strong π–π stacking interactions. Theor Chem Acc 128, 257–264 (2011). https://doi.org/10.1007/s00214-010-0841-4

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