Solution-Processable Quinoidal Dithioalkylterthiophene-Based Small Molecules Pseudo-Pentathienoacenes via an Intramolecular S···S Lock for High-Performance n-Type Organic Field-Effect Transistors

Sureshraju Vegiraju, Alfonsina Abat Amelenan Torimtubun, Po Shen Lin, Hsin Chia Tsai, Wei Chieh Lien, Cheng Shiun Chen, Guan Yu He, Chih Yu Lin, Ding Zheng, Yi Fan Huang, Yi Ching Wu, Shueh Lin Yau, Gene Hsiang Lee, Shih Huang Tung, Chien Lung Wang, Cheng Liang Liu*, Ming Chou Chen, Antonio Facchetti

*Corresponding author for this work

Research output: Contribution to journalArticle

1 Scopus citations

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 languageEnglish
Pages (from-to)25081-25091
Number of pages11
JournalACS Applied Materials and Interfaces
Volume12
Issue number22
DOIs
StatePublished - 3 Jun 2020

Keywords

  • dithioalkylterthiophene
  • organic field-effect transistors
  • pseudo-pentathienoacenes
  • quinoidal
  • tetracyanoquinodimethane

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    Vegiraju, S., Amelenan Torimtubun, A. A., Lin, P. S., Tsai, H. C., Lien, W. C., Chen, C. S., He, G. Y., Lin, C. Y., Zheng, D., Huang, Y. F., Wu, Y. C., Yau, S. L., Lee, G. H., Tung, S. H., Wang, C. L., Liu, C. L., Chen, M. C., & Facchetti, A. (2020). Solution-Processable Quinoidal Dithioalkylterthiophene-Based Small Molecules Pseudo-Pentathienoacenes via an Intramolecular S···S Lock for High-Performance n-Type Organic Field-Effect Transistors. ACS Applied Materials and Interfaces, 12(22), 25081-25091. https://doi.org/10.1021/acsami.0c03477