Solution-Processable Quinoidal Dithioalkylterthiophene-Based Small Molecules Pseudo-Pentathienoacenes via an Intramolecular S···S Lock for High-Performance n-Type Organic Field-Effect Transistors

Vegiraju, S.S.VegirajuAmelenan Torimtubun, A.A.A.A.Amelenan TorimtubunLin, P.-S.P.-S.LinTsai, H.-C.H.-C.TsaiLien, W.-C.W.-C.LienChen, C.-S.C.-S.ChenHe, G.-Y.G.-Y.HeLin, C.-Y.C.-Y.LinZheng, D.D.ZhengHuang, Y.-F.Y.-F.HuangWu, Y.-C.Y.-C.WuYau, S.-L.S.-L.YauLee, G.-H.G.-H.LeeTung, S.-H.S.-H.TungWang, C.-L.C.-L.WangLiu, C.-L.C.-L.LiuChen, M.-C.M.-C.ChenFacchetti, A.A.FacchettiSHIH-HUANG TUNGCHENG-LIANG LIU2021-02-042021-02-042020https://www.scopus.com/inward/record.url?eid=2-s2.0-85085687190&partnerID=40&md5=09b3b0db9a6f61317de7ddab466a2cfehttps://scholars.lib.ntu.edu.tw/handle/123456789/547049A new organic small-molecule family comprising tetracyanoquinodimethane-substituted quinoidal dithioalky(SR)terthiophenes (DSTQs) (DSTQ-6 (1); SR = SC6H13, DSTQ-10 (2); SR = SC10H21, DSTQ-14 (3); SR = SC10H21) was synthesized and contrasted with a nonthioalkylated analogue (DRTQ-14 (4); R = C14H29). The physical, electrochemical, and electrical properties of these new compounds are thoroughly investigated. Optimized geometries obtained from density functional theory calculations and single-crystal X-ray diffraction reveal the planarity of the SR-containing DSTQ core. DSTQs pack in a slipped π-πstacked two-dimensional arrangement, with a short intermolecular stacking distance of 3.55 Å and short intermolecular S···N contacts of 3.56 Å. Thin-film morphological analysis by grazing incident X-ray diffraction reveals that all DSTQ molecules are packed in an edge-on fashion on the substrate. The favorable molecular packing, the high core planarity, and very low lowest unoccupied molecular orbital (LUMO) energy level (-4.2 eV) suggest that DSTQs could be electron-transporting semiconductors. Organic field-effect transistors based on solution-sheared DSTQ-14 exhibit the highest electron mobility of 0.77 cm2 V-1 s-1 with good ambient stability, which is the highest value reported to date for such a solution process terthiophene-based small molecular semiconductor. These results demonstrate that the device performance of solution-sheared DSTQs can be improved by side chain engineering.[SDGs]SDG7Solution-Processable Quinoidal Dithioalkylterthiophene-Based Small Molecules Pseudo-Pentathienoacenes via an Intramolecular S···S Lock for High-Performance n-Type Organic Field-Effect Transistorsjournal article10.1021/acsami.0c03477323404392-s2.0-85085687190WOS:000538515700060