TY - JOUR
T1 - π-Extended Zigzag-Shaped Diphenanthrene-Based p-Type Semiconductors Exhibiting Small Effective Masses
AU - Mitani, Masato
AU - Kumagai, Shohei
AU - Yu, Craig P.
AU - Oi, Ayako
AU - Yamagishi, Masakazu
AU - Nishinaga, Shuhei
AU - Mori, Hiroki
AU - Nishihara, Yasushi
AU - Hashizume, Daisuke
AU - Kurosawa, Tadanori
AU - Ishii, Hiroyuki
AU - Kobayashi, Nobuhiko
AU - Takeya, Jun
AU - Okamoto, Toshihiro
N1 - Funding Information:
This work was supported by the JST‐PRESTO and JST‐CREST programs, “Molecular Technology and Creation of New Functions” (grant JPMJPR13K5 and JPMJPR12K2), “Scientific Innovation for Energy Harvesting Technology” (JPMJPR17R2 and JPMJCR21Q1), “Exploring Innovative Materials in Unknown Search Space” (JPMJCR21O3), and KAKENHI. T.O. and H.I. thank JSPS for a Grant‐in‐Aid for Scientific Research B (KAKENHI grant number JP17H03104 and JP18H01856). T.O., H.M. and Y.N. thank JSPS for a Grant‐in‐Aid for Scientific Research B (KAKENHI grant number JP21H02014). M. Y. thank JSPS for a Grant‐in‐Aid for Scientific Research C (KAKENHI grant number 19K05336 and 22K05261). This work was performed under the Cooperative Research Program of the Network Joint Research Center for Materials and Devices. The X‐ray single‐crystal structural analysis of DPT was performed at BL02B1 of SPring‐8 with the approval of the Japan Synchrotron Radiation Research Institute (JASRI) (Proposal 2018A1523).
Publisher Copyright:
© 2022 Wiley-VCH GmbH.
PY - 2022
Y1 - 2022
N2 - Molecular design strategy of the π-electron core is of importance to enhance the organic semiconducting performance. In this study, diphenanthro[1,2-b:2′,1′-d]thiophene (DPT) as a new zigzag-shaped sulfur-bridged π-electron core and its phenyl-substituted derivative (Ph–DPT) exhibiting unique orbital configurations are reported. The DPT derivatives are readily synthesized through a versatile synthetic scheme in five steps from the commercially available dibenzothiophene. Their single-crystal structural analyses and band calculations revealed that both DPTs form typical herringbone packing structures, which are favorable for 2D charge carrier transport, along with small effective masses. Single-crystal-based field-effect transistors (FETs) of both DPT and Ph–DPT exhibit p-type behaviors and charge-carrier mobility up to 5.5 cm2 V–1 s–1. These results provide information that can broaden the molecular design approaches toward high-performance organic semiconductors.
AB - Molecular design strategy of the π-electron core is of importance to enhance the organic semiconducting performance. In this study, diphenanthro[1,2-b:2′,1′-d]thiophene (DPT) as a new zigzag-shaped sulfur-bridged π-electron core and its phenyl-substituted derivative (Ph–DPT) exhibiting unique orbital configurations are reported. The DPT derivatives are readily synthesized through a versatile synthetic scheme in five steps from the commercially available dibenzothiophene. Their single-crystal structural analyses and band calculations revealed that both DPTs form typical herringbone packing structures, which are favorable for 2D charge carrier transport, along with small effective masses. Single-crystal-based field-effect transistors (FETs) of both DPT and Ph–DPT exhibit p-type behaviors and charge-carrier mobility up to 5.5 cm2 V–1 s–1. These results provide information that can broaden the molecular design approaches toward high-performance organic semiconductors.
KW - molecular orbitals
KW - organic field-effect transistors
KW - organic semiconductors
KW - zigzag-shaped π-conjugated molecules
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U2 - 10.1002/aelm.202200452
DO - 10.1002/aelm.202200452
M3 - Article
AN - SCOPUS:85135093218
SN - 2199-160X
JO - Advanced Electronic Materials
JF - Advanced Electronic Materials
ER -