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 | |
| Publication status | Published - Jan 1 2017 |
Fingerprint
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 journal › Article
}
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 -