Three structural isomers of dinaphthothieno[3,2-b]thiophenes: Elucidation of physicochemical properties, crystal structures, and field-effect transistor characteristics

Tatsuya Yamamoto, Shoji Shinamura, Eigo Miyazaki, Kazuo Takimiya

Research output: Contribution to journalArticlepeer-review

47 Citations (Scopus)

Abstract

In order to gainan insight into the relationship between the molecular structure and the semiconductor characteristics of highly π-extended heteroarene-based organic semiconductors, three structural isomers of dinaphthothieno[3,2-b]thiophenes with C 2h symmetry were investigated. Of these, two isomers, dinaphtho[2,1-b:2′,1′- f]thieno[3,2-b] thiophene (2) and dinaphtho[1,2-b:1′,2′-f]thieno[3,2-b]thiophene (3), were newly synthesized, characterized, and utilized as active semiconducting layers in organic field-effect transistors (FETs). Detailed investigation of the physicochemical properties of 2 and 3, together with another isomer, dinaphtho[2,3-b:2′,3′-f]thieno[3,2-b]thiophene (1), indicated that the electronic structures of the three isomers are fairlydifferent from each other despite having the same molecular formula and the same aromatic constituents. Comparison of the molecular arrangements in the crystals elucidated by X-ray structural analysis implied that the molecular shape and the thus-induced favorable intermolecular interactions play important roles in determining the entire molecular arrangement. The characteristics of 2- and 3-based FETs with maximum field-effect mobilities (μ FETs) of 10-3-10-2 cm2 V-1 s-1 were inferior to those of 1-based FETs with μ FETs up to 3.0 cm2 V-1 s-1. The inferior characteristics of 2- and 3-based devices were due to film morphology as elucidated by atomic force microscopy (AFM) and supported by theoretical calculations of electronic structure in the solid state. Together, the results indicate that the molecular structure and shape, even for similar heteroarenes with the same molecular formula and symmetry, are important parameters to determine the solid-state properties of organic semiconductors.

Original languageEnglish
Pages (from-to)120-130
Number of pages11
JournalBulletin of the Chemical Society of Japan
Volume83
Issue number2
DOIs
Publication statusPublished - 2010
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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