TY - JOUR
T1 - Bis[1]benzothieno[5,4-d:5¤,4¤-d¤]benzo[1,2-b:4,5-b¤]dithiophene Derivatives
T2 - Synthesis and effect of sulfur positions on their transistor properties
AU - Nishinaga, Shuhei
AU - Mitani, Masato
AU - Mori, Hiroki
AU - Okamoto, Toshihiro
AU - Takeya, Jun
AU - Nishihara, Yasushi
N1 - Funding Information:
This work was partly supported by ACT-C, JST, Grant JPMJCR12YW, Japan, and a Grant-in-Aid for Scientific Research on Innovative Areas, MEXT, Grant 15H00751, Japan, and JSPS KAKENHI Grant JP16J02003. The GIWAXS experiments were performed at BL46XU of SPring-8 with the approval of the Japan Synchrotron Radiation Research Institute (JASRI) (Proposal 2017A1771). The X-ray powder diffraction experiments were performed at BL44B2 of SPring-8 (Proposal 20180049). We gratefully thank Prof. Itaru Osaka (Hiroshima University) and Dr. Tomoyuki Koganezawa (JASRI) for the measurements of GIWAXS images, Dr. Daisuke Hashizume (RIKEN) for the X-ray powder diffraction experiments, Prof. Koichi Mitsudo and Prof. Seiji Suga (Okayama University) for the CV measurements, Prof. Naoshi Ikeda (Okayama University) for the AFM images, and Ms. Megumi Kosaka and Mr. Motonari Kobayashi at the Department of Instrumental Analysis, Advanced Science Research Center, Okayama University, for the elemental analyses, and the SC-NMR Laboratory of Okayama University for the NMR spectral measurements.
Publisher Copyright:
© 2019 The Chemical Society of Japan.
PY - 2019
Y1 - 2019
N2 - Bis[1]benzothieno[5,4-d:5¤,4¤-d¤]benzo[1,2-b:4,5-b¤]dithiophene (BBTBDT-2) and its phenyl-substituted derivative were successfully synthesized and characterized. From DFT calculations, highest occupied molecular orbitals (HOMOs) of both compounds are well delocalized and large orbital coefficients exist on sulfur atoms. Single-crystal X-ray analysis revealed that BBTBDT-2 derivatives formed herringbone structures in the solid state. In particular, BBTBDT-2 formed a layer-by-layer structure with effective 2D charge-carrier transporting capability. The fabricated OFETs based on BBTBDT-2 gave mobility up to 0.49 cm2 V11 s11 in the vacuum-deposited thin films, which is the highest value among BBTBDT derivatives including our previously reported syn-counterparts. We have also clarified a detailed structureproperty relationship of sulfur positions and phenyl substituents as indicated by theoretical calculation, GIWAXS, and AFM analyses.
AB - Bis[1]benzothieno[5,4-d:5¤,4¤-d¤]benzo[1,2-b:4,5-b¤]dithiophene (BBTBDT-2) and its phenyl-substituted derivative were successfully synthesized and characterized. From DFT calculations, highest occupied molecular orbitals (HOMOs) of both compounds are well delocalized and large orbital coefficients exist on sulfur atoms. Single-crystal X-ray analysis revealed that BBTBDT-2 derivatives formed herringbone structures in the solid state. In particular, BBTBDT-2 formed a layer-by-layer structure with effective 2D charge-carrier transporting capability. The fabricated OFETs based on BBTBDT-2 gave mobility up to 0.49 cm2 V11 s11 in the vacuum-deposited thin films, which is the highest value among BBTBDT derivatives including our previously reported syn-counterparts. We have also clarified a detailed structureproperty relationship of sulfur positions and phenyl substituents as indicated by theoretical calculation, GIWAXS, and AFM analyses.
KW - Organic field-effect transistor
KW - Polycyclic aromatic compounds
KW - Structural isomers of thienoacene
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U2 - 10.1246/bcsj.20180358
DO - 10.1246/bcsj.20180358
M3 - Article
AN - SCOPUS:85069512370
SN - 0009-2673
VL - 92
SP - 1107
EP - 1116
JO - Bulletin of the Chemical Society of Japan
JF - Bulletin of the Chemical Society of Japan
IS - 6
ER -