Synthesis, physical properties and field-effect transistors of novel thiazolothiazole–phenylene co-oligomers

Abstract

A series of thiazolothiazole-phenylene co-oligomers was synthesized and their properties, particularly as semiconductors for OFETs, were investigated. The naphthyl and biphenylsubstituted derivatives showed p-type semiconducting behavior with hole mobilities ranging from 10 22 to 10 21 cm 2 V 21 s 21 . The hole mobility and on/off ratio were enhanced to 0.12 cm 2 V 21 s 21 and 10 6 on the HMDS treated substrate. The introduction of phenyl groups as end substituents was found to be favorable for charge transport and air-stability.

Organic Chromophores Based on a Fused Bis‐Thiazole Core and Their Application in Dye‐Sensitized Solar Cells

“…[12,13] Thiazolo [5,4d]thiazoles were initially investigated for their potential biological activity, [14] but later they were especially used as spacer units in semiconducting organic materials for polymer light-emitting diodes (PLEDs) [15] and organic field-effect transistors (OFETs). [16] More recently, the thiazolothiazole unit has been incorporated in donor/acceptor polymers used as the photoactive components of organic bulk heterojunction (BHJ) solar cells. [17] In particular, thiazolothiazole-containing polymers showed remarkable charge carrier diffusion lengths, [17e,17g,17h] and power conversion efficiencies as high as 5.8 % were achieved.…”

Synthesis, 1H and 13C NMR assignment and electrochemical properties of novel thiophene–thiazolothiazole oligomers and polymers

“…[5] Secondly, the thiazolothiazole moiety has a rigid planar structure due to the fused ring system, which can lead to efficient intermolecular π -π interactions. [4,6,7] Finally, the 2,5-bissubstituted thiazolothiazole is quite straightforward to prepare, starting from the corresponding aldehyde and dithiooxamide. The interesting parent compound thiazolothiazole(5,4-d) has already been synthesized many years ago in moderate yield, by combining an aldehyde derivative with dithiooxamide at very high temperature.…”

One-pot microwave-assisted synthesis of 2,5-bis(pyrazol-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazoles from pyrazole-4-carbaldehydes and dithiooxamide

“…In addition there are short C-H … S contacts between methyl groups and sulfur atoms of neighboring molecules (Figure 1c). In contrast to pyridine or phenyl structures with thiazolo-thiazole fragment where pyridine 12 or phenyl 10,31 ring does not exceed 5.5°, angle between pyrazole and thiazolothiazole planes in compound 2c consists 16.83°.…”

“…A popular method for the preparation of diarylsubstituted thiazolo [5,4-d]thiazole, reported for the first time, 30 is based on the condensation of dithiooxamide with excess aromatic aldehydes (10-12-fold molar excess), which is used for oxidation of the initially formed products. This reaction is carried out in diverse solvents, 10,[31][32][33][34] or without solvent. 6,15,16,18 However, the harsh reaction conditions and duration of the process (24 h) lead to resinification and formation of the side products.…”