Theoretical investigations into the charge transfer properties of thiophene α-substituted naphthodithiophene diimides: excellent n-channel and ambipolar organic semiconductors

Physical Chemistry Chemical Physics : PCCP
Li-Fei JiAi-Min Ren

Abstract

A theoretical study was carried out to investigate the electronic structures and the charge transport properties of a series of naphthodithiophene diimide (NDTI) thiophene α-substituted derivatives NDTI-X using density functional theory and classical Marcus charge transfer theory. This study deeply revealed the structure-property relationships by analyzing the intermolecular interactions in crystal structures of C8-NDTI and C8-NDTI-Cl thoroughly by using the Hirshfeld surface, QTAIM theories and symmetry-adapted perturbation theory (SAPT). Our results suggested that a 2-D brick-like π-stacking structure makes C8-NDTI-Cl a more excellent n-type semiconducting material with μmax-e of 2.554 cm2 V-1 s-1 than C8-NDTI with a herringbone-like slipped π-stacking motif. In addition, the calculated results showed that by modifying the thiophene α-positions of NDTI with electron-withdrawing substituents, -F, -Cl and -CN, low-lying LUMO energy levels and a high adiabatic electron affinity EA(a) can be obtained; while introducing electron-donating groups, benzene (-B), thiophene (-T), benzo[b]thiophene (-BT) and naphtha[2,3-b]thiophene (-NT), expanded the molecular π-conjugated backbone, and narrow band gaps, high EA(a) and small reorganiza...Continue Reading

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Citations

Feb 1, 2019·Physical Chemistry Chemical Physics : PCCP·Maebienne Anjelica B Gapol, Dong Hee Kim
Jul 2, 2020·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Rui JiangZe-Sheng Li
Dec 15, 2020·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Ahmed M El-MahalawyAhmed R Wassel
Jul 25, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Gaetano RicciFabrizia Negri
Nov 6, 2018·Journal of the American Chemical Society·Ganna Gryn'ovaClémence Corminboeuf

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