Synthesis, Properties, Crystal Structures, and Semiconductor Characteristics of Naphtho[1,2-b:5,6-b′]dithiophene and -diselenophene Derivatives

• Published in: Journal of organic chemistry Vol. 75; no. 4; pp. 1228 - 1234
• Main Authors: Shinamura, Shoji, Miyazaki, Eigo, Takimiya, Kazuo
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 19.02.2010; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Condensed benzenic and aromatic compounds; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; CHARGE-TRANSFER COMPLEXES; FUNCTIONALIZED ACENES; FACILE SYNTHESIS; MOLECULAR MODIFICATION; THIN-FILM TRANSISTORS; HIGH-PERFORMANCE SEMICONDUCTORS; BENT ACENEDITHIOPHENES; ORGANIC SEMICONDUCTORS; LOW-TEMPERATURE; FIELD-EFFECT TRANSISTORS; Semiconductor materials; Molecular structure; Organic chalcogenide; Selenium heterocycle; Sodium compound; Naphthalene derivatives; Field effect transistor; Sulfur heterocycle; Electronic structure; Chlorine Organic compounds; Soluble compound; Aromatic compound; Chemical synthesis; Structural analysis; Crystalline structure
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo902545a

In this paper we present the synthesis, structures, characterization, and applications to field-effect transistors (FETs) of naphtho[1,2-b:5,6-b′]dithiophene (NDT) and -diselenophene (NDS) derivatives. Treatment of 1,5-dichloro-2,6-diethynylnaphthalenes, easily derived from commercially available 2,6-dihydroxynaphthalene, with sodium chalcogenide afforded a straightforward access to NDTs and NDSs including the parent and dioctyl and diphenyl derivatives. Physicochemical evaluations of NDT and NDS derivatives showed that these heteroarenes have a similar electronic structure with isomeric [1]benzothieno[2,3-b][1]benzothiophene (BTBT) and [1]benzoselenopheneno[2,3-b][1]benzoselenophene (BSBS) derivatives, respectively. Although attempts to fabricate solution-processed field-effect transistors (FETs) with soluble dioctyl-NDT (C8-NDT) and -NDS (C8-NDS) failed, diphenyl derivatives (DPh-NDT and DPh-NDS) afforded vapor-processed FETs showing field-effect mobility as high as 0.7 cm2 V−1 s−1. These results indicated that NDT and NDS are new potential heteroarene core structures for organic semiconducting materials.