Asymmetrical [1]Benzothieno[3,2-b][1]benzothiophene (BTBT) derivatives for organic thin-film and single-crystal transistors

Packing structures of (trialkylsilyl)ethynyl-substituted dinaphtho[2,3-b:2′,3′-f]thieno[3,2-b]thiophenes (DNTTs): effects of substituents on crystal structures and transport properties

“…To the best of our knowledge, the experimental mobility of 3 -based OFETs (0.19 cm 2 V −1 s −1 ) is among the highest reported for thin-film OFETs with a sandwich herringbone structure. 44–47…”

Architecting Layered Crystalline Organic Semiconductors Based on Unsymmetric π-Extended Thienoacenes

“…Single-crystal X-ray analysis revealed that the molecules formed a typical b -LHB packing motif; the packing was composed of multiple side-by-side interactions between the BTBTT cores, decyl chains, and phenyl groups, respectively, as seen in Figure b. This feature is in sharp contrast to the antiparallel dimerized packing of the unsubstituted BTBTT . This result indicates that the BTBTT cores are “forced” to form a unidirectionally aligned layer structure by both-end-cap substitutions with the phenyl and decyl groups.…”

“…Benzothieno­[6,5- b ]­benzothieno­[3,2- b ]­thiophene (BTBTT) is an unsymmetric five-fused-ring thienoacene, an isoelectronic analogue of BTNT, as depicted in Chart . The unsubstituted BTBTT involves structural isomers, and it was reported that both form an antiparallel dimerized packing motif in the crystals . It was also shown that hexyl-substituted BTBTT forms a b -LHB-like packing with high carrier mobility, although the packing motif involves incomplete alkyl chain ordering .…”

“…To date, development has focused mainly on molecules based on centrosymmetric π-cores, such as diacene-fused thieno­[3,2- b ]­thiophenes and others, − while few unsymmetric thienoacenes were shown to provide high-performance organic semiconductors (OSCs). − Most unsymmetric π-cores are unfavorable for OSCs as they tend to form molecular layers composed of antiparallel long-axis alignment or pairs of neighboring molecules that are only partially overlapped with each other along the molecular long axis, , which eventually inhibits efficient carrier transport. Crystal engineering would be necessary to fully utilize the unsymmetric π-cores, which is a significant issue for exploring the further potential of molecular materials.…”

Dinaphthotetrathienoacenes: Synthesis, Characterization, and Applications in Organic Field‐Effect Transistors

“…central thieno [3,2-b]thienyl core of DN4T was introduced by a Stille coupling involving 2 equivalents of 2 with one equivalent of commercial 2,5-bis-trimethylstannylthieno[3,2-b]thiophene 3 to afford 4. The formation of the two last thienyl rings was performed by oxidation of the two thiomethyl groups into sulfoxides using m-CPBA in a quantitative yield followed by subsequent cyclization in triflic acid containing 0.5 equivalent of phosphorus pentoxide and demethylation of the resulting triflate salt in refluxed pyridine according to the procedure of Dong et al [23] to give DN4T with an overall yield of 32%. The synthesis of isoDN4T takes a somewhat similar pathway.…”