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Theoretical study on the charge transport properties of three series dicyanomethylene quinoidal thiophene derivatives

Abstract

It is very important to analyse the most advantageous connection style for quinoidal thiophene derivatives, which are used in n-type organic semiconductor transport materials. In the present work, the charge transport properties of three series of quinoidal thiophene derivatives, oligothiophene (series A), thienothiophene (series B) and benzothiophene (series C), are systematically investigated by employing the full quantum charge transfer theory combined with kinetic Monte-Carlo simulation. The single crystal structures of the molecules we constructed were predicted using the USPEX program combined with density functional theory (DFT) and considering the dispersion corrected. Our theoretical results expounded that how the different connection styles, including oligo-, thieno-, benzo- thiophene in the quinoidal thiophenes derivatives, effectively tune their electronic structures, and revealed that how their intermolecular interactions affect the molecular packing patterns and hence their charge transport properties by symmetry-adapted perturbation theory (SAPT). In the meanwhile we also elucidated the role of end-cyano groups in noncovalent interactions. Furthermore, it is clarified that the quinoidal thiophene derivatives show excellent carrier transport properties due to their optimal molecular stacking motifs and larger electronic couplings besides low energy gap. In addition, our theoretical results demonstrate that quinoidal oligothiophene derivatives (n=3~5) with more thiophene rings will have ambipolar transport properties, quinoidal thienothiophene and benzothiophene derivatives should be promising alternatives as n-type OSC. When we focused only on the electronic transport properties in the three series of molecules, quinoidal benzothiophene derivatives are slightly better than quinoidal oligothiophene and thienothiophene derivatives.

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Publication details

The article was received on 13 Nov 2018, accepted on 07 Jan 2019 and first published on 09 Jan 2019


Article type: Paper
DOI: 10.1039/C8CP06871B
Citation: Phys. Chem. Chem. Phys., 2019, Accepted Manuscript
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    Theoretical study on the charge transport properties of three series dicyanomethylene quinoidal thiophene derivatives

    P. Lin, S. Zhang, N. Zhang, J. Fan, L. F. Ji, J. F. Guo and A. Ren, Phys. Chem. Chem. Phys., 2019, Accepted Manuscript , DOI: 10.1039/C8CP06871B

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