Synthesis and Physicochemical Properties of Dibenzo[2,3- d:2′,3′- d′]anthra[1,2- b:5,6- b′]dithiophene (DBADT) and Its Derivatives: Effect of Substituents on Their Molecular Orientation and Transistor Properties

Keita Hyodo, Shuhei Nishinaga, Yuta Sawanaka, Takumi Ishida, Hiroki Mori, Yasushi Nishihara

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Abstract

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 cm2 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.

Original languageEnglish
Pages (from-to)698-709
Number of pages12
JournalJournal of Organic Chemistry
Volume84
Issue number2
DOIs
Publication statusPublished - Jan 18 2019

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Organic field effect transistors
Molecular orientation
Transistors
Bearings (structural)
Derivatives
Thin films
Molecular orbitals
Field effect transistors
Electrochemical properties
Surface morphology
Atomic force microscopy
Optical properties
X ray diffraction
heparinized hydrophilic polymer
diphenyl

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Synthesis and Physicochemical Properties of Dibenzo[2,3- d:2′,3′- d′]anthra[1,2- b:5,6- b′]dithiophene (DBADT) and Its Derivatives: Effect of Substituents on Their Molecular Orientation and Transistor Properties",
abstract = "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 cm2 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.",
author = "Keita Hyodo and Shuhei Nishinaga and Yuta Sawanaka and Takumi Ishida and Hiroki Mori and Yasushi Nishihara",
year = "2019",
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doi = "10.1021/acs.joc.8b02557",
language = "English",
volume = "84",
pages = "698--709",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
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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

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 cm2 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 cm2 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

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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