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New types of organic semiconductors based on diketopyrrolopyrroles and 2,1,3-benzochalcogenadiazoles: a computational study

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Abstract

A comprehensive computational study is performed on model compounds based on 2,1,3-benzochalcogenadiazoles and diketopyrrolopyrroles of A-π-A′-π-A architecture (A and A′ represent 2,1,3-benzochalcogenadiazoles and diketopyrrolopyrroles, respectively, and π is the bridging unit between them including thiophene, furan, and selenophene) for their utility as organic semiconductors. The compounds were found to possess planar geometry, which is a desired property for organic semiconductors. The electronic properties, including adiabatic and vertical electron affinity (EA), adiabatic and vertical ionization potential (IP), reorganization energy (λ), hole injection barrier and electron injection barrier, transfer integral, and charge mobility, were calculated. The electron affinity is higher in the case of thiophene/selenophene as the linker for a given terminal benzochalcogenadiazole than the corresponding compounds with furan as a linker, while the ionization potential is lowest for compounds having selenophene as the linker with a given terminal benzochalcogenadiazole moiety than the compounds having furan or thiophene as a linker. The hole injection barrier in these compounds is lower than the electron injection barrier, which facilitates the hole injection from the metal electrode, while hole reorganization energy is found to be larger than the electron reorganization energy. The compounds possess hole mobilities in the range of 2.50–4.91 cm2/Vs and electron mobilities in a similar range of 4.58–9.68 cm2/Vs. This study reveals that compounds based on a combination of diketopyrrolopyrrole and 2,1,3-benzochalcogenadiazole units would exhibit hole transporting properties and act as potential ambipolar materials.

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Acknowledgments

Sagar Sharma would like to thank the Department of Science and Technology, Govt. of India for the INSPIRE faculty grant.

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  1. Sagar Sharma

    Present address: Department of Chemistry, School of Fundamental and Applied Sciences, Assam Don Bosco University, Tapesia Gardens, Guwahati, Assam, 782402, India

Authors and Affiliations

  1. Physical Sciences Division, Institute of Advanced Study in Science and Technology, Vigyan Path, Paschim Boragaon, Guwahati, Assam, 781035, India

    Gautomi Gogoi, Neelotpal Sen Sarma & Sagar Sharma

  2. High Performance Computing Lab, Department of Applied Physics, Indian Institute of Technology (ISM), Dhanbad, Jharkhand, 826004, India

    Smruti R. Sahoo & Sridhar Sahu

  3. Cotton University, College Hostel Road, Pan Bazaar, Guwahati, Assam, 781001, India

    Basanta Kumar Rajbongshi

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In the supporting information, additional data including (a) the optimized geometries (b) geometrical parameters (c) the frontier molecular orbitals, (d) density of states plot, and (e) electrostatic potential isosurface plot of the compounds have been provided.

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Gogoi, G., Sahoo, S.R., Rajbongshi, B.K. et al. New types of organic semiconductors based on diketopyrrolopyrroles and 2,1,3-benzochalcogenadiazoles: a computational study. J Mol Model 25, 42 (2019). https://doi.org/10.1007/s00894-019-3922-x

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