caa a22 4500 605513236 CHVBK 20210128100659.0 cr unu---uuuuu 210128e20150501xx s 000 0 eng 10.1007/s00894-015-2677-2 doi (NATIONALLICENCE)springer-10.1007/s00894-015-2677-2 Molecular stacking character and charge transport properties of tetrabenzoheptacenes derivatives: the effects of nitrogen doping and phenyl substitution [Elektronische Daten] [Lin Guan, Wenliang Wang, Rong Shao, Fengyi Liu, Shiwei Yin] 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. Graphical Abstract 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 Springer-Verlag Berlin Heidelberg, 2015 Charge transport nationallicence Density functional theory nationallicence Mobility nationallicence Tetrabenzoheptacene nationallicence Guan Lin Key Laboratory for Macromolecular Science of Shaanxi Province, School of Chemistry & Chemical Engineering, Shaanxi Normal University, 710062, Xi'an, Shaanxi, People's Republic of China aut Wang Wenliang Key Laboratory for Macromolecular Science of Shaanxi Province, School of Chemistry & Chemical Engineering, Shaanxi Normal University, 710062, Xi'an, Shaanxi, People's Republic of China aut Shao Rong Key Laboratory for Macromolecular Science of Shaanxi Province, School of Chemistry & Chemical Engineering, Shaanxi Normal University, 710062, Xi'an, Shaanxi, People's Republic of China aut Liu Fengyi Key Laboratory for Macromolecular Science of Shaanxi Province, School of Chemistry & Chemical Engineering, Shaanxi Normal University, 710062, Xi'an, Shaanxi, People's Republic of China aut Yin Shiwei Key Laboratory for Macromolecular Science of Shaanxi Province, School of Chemistry & Chemical Engineering, Shaanxi Normal University, 710062, Xi'an, Shaanxi, People's Republic of China aut Journal of Molecular Modeling Springer Berlin Heidelberg 21/5(2015-05-01), 1-9 1610-2940 21:5<1 2015 21 894 https://doi.org/10.1007/s00894-015-2677-2 text/html Onlinezugriff via DOI BK010053 XK010053 XK010000 Metadata rights reserved Springer special CC-BY-NC licence nationallicence 1 research-article jats NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE 856 40 https://doi.org/10.1007/s00894-015-2677-2 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Guan Lin Key Laboratory for Macromolecular Science of Shaanxi Province, School of Chemistry & Chemical Engineering, Shaanxi Normal University, 710062, Xi'an, Shaanxi, People's Republic of China aut NATIONALLICENCE 700 1- Wang Wenliang Key Laboratory for Macromolecular Science of Shaanxi Province, School of Chemistry & Chemical Engineering, Shaanxi Normal University, 710062, Xi'an, Shaanxi, People's Republic of China aut NATIONALLICENCE 700 1- Shao Rong Key Laboratory for Macromolecular Science of Shaanxi Province, School of Chemistry & Chemical Engineering, Shaanxi Normal University, 710062, Xi'an, Shaanxi, People's Republic of China aut NATIONALLICENCE 700 1- Liu Fengyi Key Laboratory for Macromolecular Science of Shaanxi Province, School of Chemistry & Chemical Engineering, Shaanxi Normal University, 710062, Xi'an, Shaanxi, People's Republic of China aut NATIONALLICENCE 700 1- Yin Shiwei Key Laboratory for Macromolecular Science of Shaanxi Province, School of Chemistry & Chemical Engineering, Shaanxi Normal University, 710062, Xi'an, Shaanxi, People's Republic of China aut NATIONALLICENCE 773 0- Journal of Molecular Modeling Springer Berlin Heidelberg 21/5(2015-05-01), 1-9 1610-2940 21:5<1 2015 21 894