TY - JOUR
T1 - Synthesis and Physicochemical Properties of Dibenzo[2,3- d:2′,3′- d′]anthra[1,2- b:5,6- b′]dithiophene (DBADT) and Its Derivatives
T2 - Effect of Substituents on Their Molecular Orientation and Transistor Properties
AU - Hyodo, Keita
AU - Nishinaga, Shuhei
AU - Sawanaka, Yuta
AU - Ishida, Takumi
AU - Mori, Hiroki
AU - Nishihara, Yasushi
N1 - Funding Information:
This work was partly supported by ACT-C, JST Grant Number JPMJCR12YW, Japan, and a Grant-in-Aid for Scientific Research (KAKENHI) (No. 15J07968) from JSPS. The 2D-GIXD measurements were performed at BL46XU of SPring-8 with the approval of the Japan Synchrotron Radiation Research Institute (JASRI) (Proposal 2016A1542, 2016A1768, 2016B1875). The authors gratefully thank Prof. Itaru Osaka (Hiroshima University) and Dr. Tomoyuki Koganezawa (JASRI) for providing the 2D-GIXD images, Profs. Koichi Mitsudo and Seiji Suga (Okayama University) for the measurement of CV, Prof. Naoshi Ikeda (Okayama University) for providing the AFM images, and Ms. M. Kosaka and Mr. M. Kobayashi at the Department of Instrumental Analysis, Advanced Science Research Center, Okayama University, for the elemental analyses. The help of the SC-NMR Laboratory of Okayama University in obtaining the NMR spectral measurements is gratefully acknowledged.
Publisher Copyright:
© 2018 American Chemical Society.
PY - 2019/1/18
Y1 - 2019/1/18
N2 - We have synthesized dibenzo[2,3-d:2′,3′-d′]anthra[1,2-b:5,6-b′]dithiophene (DBADT) and several derivatives bearing alkyl and phenyl groups at various positions. The optical and electrochemical properties of the synthesized compounds were investigated. All the fabricated OFET devices exhibited typical p-type behavior under ambient conditions, and diphenyl-substituted analogue-based OFET devices showed excellent mobility, as high as 0.66 cm 2 V -1 s -1 . The surface morphology and molecular orientation in thin films were also investigated using atomic force microscopy (AFM) and two-dimensional grazing incidence X-ray diffraction (2D-GIXD). It was found that the substituents and their positions affect the molecular orbitals, molecular orientation, and morphology of the thin films, producing different FET performance.
AB - We have synthesized dibenzo[2,3-d:2′,3′-d′]anthra[1,2-b:5,6-b′]dithiophene (DBADT) and several derivatives bearing alkyl and phenyl groups at various positions. The optical and electrochemical properties of the synthesized compounds were investigated. All the fabricated OFET devices exhibited typical p-type behavior under ambient conditions, and diphenyl-substituted analogue-based OFET devices showed excellent mobility, as high as 0.66 cm 2 V -1 s -1 . The surface morphology and molecular orientation in thin films were also investigated using atomic force microscopy (AFM) and two-dimensional grazing incidence X-ray diffraction (2D-GIXD). It was found that the substituents and their positions affect the molecular orbitals, molecular orientation, and morphology of the thin films, producing different FET performance.
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U2 - 10.1021/acs.joc.8b02557
DO - 10.1021/acs.joc.8b02557
M3 - Article
C2 - 30562469
AN - SCOPUS:85059618069
SN - 0022-3263
VL - 84
SP - 698
EP - 709
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 2
ER -