Abstract
A new organic small-molecule family comprising tetracyanoquinodimethane-substituted quinoidal dithioalky(SR)terthiophenes (DSTQs) (DSTQ-6 (1); SR = SC6H13, DSTQ-10 (2); SR = SC10H21, DSTQ-14 (3); SR = SC10H21) was synthesized and contrasted with a nonthioalkylated analogue (DRTQ-14 (4); R = C14H29). The physical, electrochemical, and electrical properties of these new compounds are thoroughly investigated. Optimized geometries obtained from density functional theory calculations and single-crystal X-ray diffraction reveal the planarity of the SR-containing DSTQ core. DSTQs pack in a slipped π-πstacked two-dimensional arrangement, with a short intermolecular stacking distance of 3.55 Å and short intermolecular S···N contacts of 3.56 Å. Thin-film morphological analysis by grazing incident X-ray diffraction reveals that all DSTQ molecules are packed in an edge-on fashion on the substrate. The favorable molecular packing, the high core planarity, and very low lowest unoccupied molecular orbital (LUMO) energy level (-4.2 eV) suggest that DSTQs could be electron-transporting semiconductors. Organic field-effect transistors based on solution-sheared DSTQ-14 exhibit the highest electron mobility of 0.77 cm2 V-1 s-1 with good ambient stability, which is the highest value reported to date for such a solution process terthiophene-based small molecular semiconductor. These results demonstrate that the device performance of solution-sheared DSTQs can be improved by side chain engineering.
Original language | English (US) |
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Pages (from-to) | 25081-25091 |
Number of pages | 11 |
Journal | ACS Applied Materials and Interfaces |
Volume | 12 |
Issue number | 22 |
DOIs | |
State | Published - Jun 3 2020 |
Keywords
- dithioalkylterthiophene
- organic field-effect transistors
- pseudo-pentathienoacenes
- quinoidal
- tetracyanoquinodimethane
ASJC Scopus subject areas
- Materials Science(all)
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Dive into the research topics of 'Solution-Processable Quinoidal Dithioalkylterthiophene-Based Small Molecules Pseudo-Pentathienoacenes via an Intramolecular S···S Lock for High-Performance n-Type Organic Field-Effect Transistors'. Together they form a unique fingerprint.Datasets
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CCDC 1916105: Experimental Crystal Structure Determination
Vegiraju, S. (Contributor), Amelenan Torimtubun, A. A. (Contributor), Lin, P. (Contributor), Tsai, H. (Contributor), Lien, W. (Contributor), Chen, C. (Contributor), He, G. (Contributor), Lin, C. (Contributor), Zheng, D. (Contributor), Huang, Y. (Contributor), Wu, Y. (Contributor), Yau, S. (Contributor), Lee, G. (Contributor), Tung, S. (Contributor), Wang, C. (Contributor), Liu, C. (Contributor), Chen, M. (Contributor) & Facchetti, A. F. (Contributor), Cambridge Crystallographic Data Centre, 2020
DOI: 10.5517/ccdc.csd.cc229vv3, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc229vv3&sid=DataCite
Dataset
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CCDC 1916104: Experimental Crystal Structure Determination
Vegiraju, S. (Contributor), Amelenan Torimtubun, A. A. (Contributor), Lin, P. (Contributor), Tsai, H. (Contributor), Lien, W. (Contributor), Chen, C. (Contributor), He, G. (Contributor), Lin, C. (Contributor), Zheng, D. (Contributor), Huang, Y. (Contributor), Wu, Y. (Contributor), Yau, S. (Contributor), Lee, G. (Contributor), Tung, S. (Contributor), Wang, C. (Contributor), Liu, C. (Contributor), Chen, M. (Contributor) & Facchetti, A. F. (Contributor), Cambridge Crystallographic Data Centre, 2020
DOI: 10.5517/ccdc.csd.cc229vt2, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc229vt2&sid=DataCite
Dataset