Synthesis, crystal structure, and FET characteristics of thieno[2,3-b]thiophene-based bent-thienoacenes

Yuta Ogawa; Erika Takiguchi; Masashi Mamada; Daisuke Kumaki; Shizuo Tokito; Hiroshi Katagiri

doi:10.1016/j.tetlet.2017.01.074

Synthesis, crystal structure, and FET characteristics of thieno[2,3-b]thiophene-based bent-thienoacenes

Yuta Ogawa, Erika Takiguchi, Masashi Mamada, Daisuke Kumaki, Shizuo Tokito, Hiroshi Katagiri

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

Abstract

Two novel bent-shaped thienoacenes, naphtho[2,3-b]naphtho[2′,3′:4,5]thieno[3,2-d]thiophene (bent-DNTT) and anthra[2,3-b]anthra[2′,3′:4,5]thieno[3,2-d]thiophene (bent-DATT) were synthesized from thieno[2,3-b]thiophene and their corresponding aromatic anhydrides by three steps: Friedel–Crafts acylation, acid-promoted cyclization, and reductive aromatization. The structural curvature improved the solubility of these thienoacenes in organic solvents. The bent-DNTT based FET device was fabricated by the spin-coating method. The device exhibited p-type characteristics with a mobility of 5.1 × 10⁻⁵ cm² V⁻¹ s⁻¹. Its thin-film structure was fully characterized as an edge-on orientation with large intermolecular orbital coupling.

Original language	English
Pages (from-to)	963-967
Number of pages	5
Journal	Tetrahedron Letters
Volume	58
Issue number	10
DOIs	https://doi.org/10.1016/j.tetlet.2017.01.074
Publication status	Published - Jan 1 2017

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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@article{129604822dcc465fa14c4c5228bc3a6d,

title = "Synthesis, crystal structure, and FET characteristics of thieno[2,3-b]thiophene-based bent-thienoacenes",

abstract = "Two novel bent-shaped thienoacenes, naphtho[2,3-b]naphtho[2′,3′:4,5]thieno[3,2-d]thiophene (bent-DNTT) and anthra[2,3-b]anthra[2′,3′:4,5]thieno[3,2-d]thiophene (bent-DATT) were synthesized from thieno[2,3-b]thiophene and their corresponding aromatic anhydrides by three steps: Friedel–Crafts acylation, acid-promoted cyclization, and reductive aromatization. The structural curvature improved the solubility of these thienoacenes in organic solvents. The bent-DNTT based FET device was fabricated by the spin-coating method. The device exhibited p-type characteristics with a mobility of 5.1 × 10−5 cm2 V−1 s−1. Its thin-film structure was fully characterized as an edge-on orientation with large intermolecular orbital coupling.",

author = "Yuta Ogawa and Erika Takiguchi and Masashi Mamada and Daisuke Kumaki and Shizuo Tokito and Hiroshi Katagiri",

year = "2017",

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T1 - Synthesis, crystal structure, and FET characteristics of thieno[2,3-b]thiophene-based bent-thienoacenes

AU - Ogawa, Yuta

AU - Takiguchi, Erika

AU - Mamada, Masashi

AU - Kumaki, Daisuke

AU - Tokito, Shizuo

AU - Katagiri, Hiroshi

PY - 2017/1/1

Y1 - 2017/1/1

N2 - Two novel bent-shaped thienoacenes, naphtho[2,3-b]naphtho[2′,3′:4,5]thieno[3,2-d]thiophene (bent-DNTT) and anthra[2,3-b]anthra[2′,3′:4,5]thieno[3,2-d]thiophene (bent-DATT) were synthesized from thieno[2,3-b]thiophene and their corresponding aromatic anhydrides by three steps: Friedel–Crafts acylation, acid-promoted cyclization, and reductive aromatization. The structural curvature improved the solubility of these thienoacenes in organic solvents. The bent-DNTT based FET device was fabricated by the spin-coating method. The device exhibited p-type characteristics with a mobility of 5.1 × 10−5 cm2 V−1 s−1. Its thin-film structure was fully characterized as an edge-on orientation with large intermolecular orbital coupling.

AB - Two novel bent-shaped thienoacenes, naphtho[2,3-b]naphtho[2′,3′:4,5]thieno[3,2-d]thiophene (bent-DNTT) and anthra[2,3-b]anthra[2′,3′:4,5]thieno[3,2-d]thiophene (bent-DATT) were synthesized from thieno[2,3-b]thiophene and their corresponding aromatic anhydrides by three steps: Friedel–Crafts acylation, acid-promoted cyclization, and reductive aromatization. The structural curvature improved the solubility of these thienoacenes in organic solvents. The bent-DNTT based FET device was fabricated by the spin-coating method. The device exhibited p-type characteristics with a mobility of 5.1 × 10−5 cm2 V−1 s−1. Its thin-film structure was fully characterized as an edge-on orientation with large intermolecular orbital coupling.

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