2,7-diphenyl[1]benzoselenopheno[3,2-b][1]benzoselenophene as a stable organic semiconductor for a high-performance field-effect transistor.

[1]Benzoselenopheno[3,2-b][1]benzoselenophene (BSBS) and its 2,7-diphenyl derivative (DPh-BSBS) were readily synthesized from diphenylacetylene and bis(biphenyl-4-yl)acetylene, respectively, with a newly developed straightforward selenocyclization protocol. In contrast to the parent BSBS that has poor film-forming properties, the diphenyl derivative DPh-BSBS formed a good thin film on the Si/SiO(2) substrate by vapor deposition. X-ray diffraction examination revealed that this film consists of highly ordered molecules that are nearly perpendicular to the substrate, making it suitable for use in the fabrication of organic field-effect transistors (OFETs).

Facile synthesis, structure, and properties of benzo[1,2-b:4,5-b']dichalcogenophenes.

[reaction, structures: see text] A general and convenient synthesis of benzo[1,2-b:4,5-b']dichalcogenophenes including the thiophene (BDT, 1), selenophene (BDS, 2), and tellurophene (BDTe, 3) homologues is developed. Thus synthesized heterocycles are structurally characterized by single-crystal X-ray analysis, and all three homologues are isostructural with one another. They all have completely planar molecular structures packed in a herringbone arrangement.

2,6-Diphenylbenzo[1,2-b:4,5-b']dichalcogenophenes: a new class of high-performance semiconductors for organic field-effect transistors.

2,6-Diphenylbenzo[1,2-b:4,5-b']dichalcogenophenes including thiophene, selenophene, and tellurophene analogues as organic semiconductors for field-effect transistors were effectively synthesized in three steps from commercially available 1,4-dibromobenzene. All three benzodichalcogenophenes acted as good p-type semiconductors, and particularly the selenophene analogue, 2,6-diphenylbenzo[1,2-b:4,5-b']diselenophene, showed high FET mobility of 0.17 cm2 V-1 s-1.