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Crystal structure and modeled charge carrier mobility of benzobis(thiadiazole) derivatives
The crystal structures of benzobis(thiadiazole) (BBT)-based organic semiconductors with high electron mobilities were revealed using single-crystal X-ray analyses, followed by density functional theory and hopping modeling to estimate the charge carrier mobility levels. The crystal packings and inte...
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Published in: | New journal of chemistry 2016-01, Vol.4 (2), p.143-1411 |
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Main Authors: | , , , , , , |
Format: | Article |
Language: | English |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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Summary: | The crystal structures of benzobis(thiadiazole) (BBT)-based organic semiconductors with high electron mobilities were revealed using single-crystal X-ray analyses, followed by density functional theory and hopping modeling to estimate the charge carrier mobility levels. The crystal packings and intermolecular interactions were found to be similar regardless of trifluoromethyl and trifluoromethoxy groups for the corresponding
para
-substituted or
meta
-substituted derivatives. Although a compound with
ortho
-trifluoromethyl groups showed a molecule with a twisted conformation, the
ortho
-trifluoromethoxy derivative had nearly planar conformation. Since the
ortho
-trifluoromethyl groups prevent effective intermolecular interactions through short heteroatom contacts between BBT rings, molecules have a one-dimensional charge carrier transport path, resulting in lower overall charge carrier mobility in transistor devices. On the other hand, the
ortho
-trifluoromethoxy derivative exhibits a herringbone packing with large diffusion coefficients. The
para
and
meta
-derivatives showed an unusually large diffusion coefficient between the molecules located in the co-planar and the standard π-π stacking directions. The formation of a two-dimensional structure afforded high electron mobilities in actual organic thin-film transistor (OTFT) devices using these BBT-based materials.
Benzobis(thiadiazole) derivatives showed a large diffusion coefficient between the molecules located in the co-planar and the standard π-π stacking directions. |
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ISSN: | 1144-0546 1369-9261 |
DOI: | 10.1039/c5nj02302e |