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 journalArticle

2 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 languageEnglish
Pages (from-to)963-967
Number of pages5
JournalTetrahedron Letters
Volume58
Issue number10
DOIs
Publication statusPublished - Jan 1 2017

Fingerprint

Thiophenes
Field effect transistors
Crystal structure
Aromatization
Acylation
Equipment and Supplies
Anhydrides
Cyclization
Spin coating
Solubility
Organic solvents
Thin films
Acids
heparinized hydrophilic polymer

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Synthesis, crystal structure, and FET characteristics of thieno[2,3-b]thiophene-based bent-thienoacenes. / Ogawa, Yuta; Takiguchi, Erika; Mamada, Masashi; Kumaki, Daisuke; Tokito, Shizuo; Katagiri, Hiroshi.

In: Tetrahedron Letters, Vol. 58, No. 10, 01.01.2017, p. 963-967.

Research output: Contribution to journalArticle

Ogawa, Yuta ; Takiguchi, Erika ; Mamada, Masashi ; Kumaki, Daisuke ; Tokito, Shizuo ; Katagiri, Hiroshi. / Synthesis, crystal structure, and FET characteristics of thieno[2,3-b]thiophene-based bent-thienoacenes. In: Tetrahedron Letters. 2017 ; Vol. 58, No. 10. pp. 963-967.
@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",
month = "1",
day = "1",
doi = "10.1016/j.tetlet.2017.01.074",
language = "English",
volume = "58",
pages = "963--967",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "10",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=85011319956&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85011319956&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2017.01.074

DO - 10.1016/j.tetlet.2017.01.074

M3 - Article

AN - SCOPUS:85011319956

VL - 58

SP - 963

EP - 967

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 10

ER -