Dianthra[2,3-b:2′,3′-f]thieno[3,2-b]thiophene (DATT): Synthesis, Characterization, and FET Characteristics of New π-Extended Heteroarene with Eight Fused Aromatic Rings

Abstract

A novel highly π-extended heteroarene with eight fused aromatic rings, dianthra[2,3-b:2',3'-f]thieno[3,2-b]thiophene (DATT), was selectively synthesized via a newly developed synthetic strategy, fully characterized by means of single crystal X-ray structural analysis, and examined as an organic semiconductor in thin film transistors. Even with its highly extended acene-like π-system, DATT is a fairly air-stable compound with IP of 5.1 eV. Single crystal X-ray structural analysis revealed its planar molecular structure and the lamella-like layered structure with typical herringbone packing. Theoretical calculations of the solid state electronic structure based on the bulk single crystal structure suggest that DATT affords almost comparable intermolecular orbital couplings between HOMOs (t(HOMO)) with those of dinaphtho[2,3-b:2',3'-f]thieno[3,2-b]thiophene (DNTT), implying its good potential as an organic semiconductor for organic field-effect transistors. In fact, field-effect mobilities as high as 3.0 cm(2) V(-1) s(-1) were achieved with vapor-processed DATT-based devices, which is comparable with that of DNTT-based devices. The molecular ordering of DATT in the thin film state, however, turned out to be not completely uniform; as elucidated by in-plane and out-of-plane XRD measurements, the face-on molecular orientation was contaminated in the edge-on orientation, the former of which is not optimal for efficient carrier transport and thus could limit the mobility.

Recent advances in organic field effect transistors

“…[66]. Vacuum deposited films of asymmetrically substituted C [87]. In a demonstration of the effectiveness of end substitution of the conjugated core in enhancing charge transport performance, the mobility of vacuum deposited films of alkyl end-substituted C 10 -DNTT was increased to 8.0 cm 2 V −1 s −1 [68], and that of solution processed films of the same molecule reached a value of 11.0 cm 2 V −1 s −1 [69].…”

Thienoacene‐Based Organic Semiconductors

“…The fi nal ring-closing reaction promoted by excess iodine successfully proceeded to afford 34 . [ 93 ] It should be emphasized that DAcTTs are substantially stabilized by the incorporation of the thienothiophene moiety. Even for 34 , which has eight aromatic rings fused in a linear manner, the molecule itself is quite stable in air.…”

“…[ 92 ] Further π -extension has been achieved very recently, giving dianthra[2,3-b:2 ′ ,3 ′ -f ]thieno [3,2-b]thiophene (DATT, 34 ) with eight fused aromatic rings. [ 93 ] In this section, we will fi rst overview the synthetic chemistry of DAcTTs, which features versatile methods for the construction of a thienothiophene moiety between two aromatic hydrocarbon rings, followed by the FET characteristics and the solid-state packing structures of a range of DAcTTs.…”

Adsorption and thermal decomposition of 2-octylthieno[3,4-b]thiophene on Au(1 1 1)

“…Meanwhile, thiophene based materials have shown strong intermolecular interactions originating from the high polarizability of sulfur atoms in the thiophene rings, but they easily twist from planarity, thus disrupting conjugation and potentially affecting the band gap in the solid state [11][12][13]. To circumvent these disadvantages, highly stable materials based on fused thiophenes have been proposed as alternative organic semiconductors [14][15][16][17][18]. Among them, thieno-thiophene derivatives have demonstrated high potential due to their high stability and hole mobility [16][17][18].…”

“…To circumvent these disadvantages, highly stable materials based on fused thiophenes have been proposed as alternative organic semiconductors [14][15][16][17][18]. Among them, thieno-thiophene derivatives have demonstrated high potential due to their high stability and hole mobility [16][17][18].…”