Solution-Processed Isoindigo- and Thienoisoindigo-Based Donor-Acceptor-Donor π-Conjugated Small Molecules: Synthesis, Morphology, Molecular Packing, and Field-Effect Transistor Characterization

Liao, Yu TingYu TingLiaoHsiao, Yi ChunYi ChunHsiaoLo, Yuan ChihYuan ChihLoCHIA-CHI LINLin, Po ShenPo ShenLinSHIH-HUANG TUNGKEN-TSUNG WONGCHENG-LIANG LIU2023-04-122023-04-122022-12-2119448244https://scholars.lib.ntu.edu.tw/handle/123456789/630152Molecular design and precise control of thin-film morphology and crystallinity of solution-processed small molecules are important for enhancing charge transport mobility of organic field-effect transistors and gaining more insight into the structure-property relationship. Here, two donor-acceptor-donor (D-A-D) architecture small molecules TRA-IID-TRA and TRA-TIID-TRA comprising an electron-donating triarylamine (TRA) and two different electron-withdrawing cores, isoindigo (IID) and thienoisoindigo (TIID), respectively, were synthesized and characterized. Replacing the phenylene rings of central IID A with thiophene gives a TIID core, which reduces the optical band gap and upshifts the energy levels of frontier molecular orbitals. The single-crystal structures and grazing-incidence wide-angle X-ray scattering (GIWAXS) analysis revealed that TRA-TIID-TRA exhibits the relatively tighter π-πstacking packing with preferential edge-on orientation, larger coherence length, and higher crystallinity due to the noncovalent S···O/S···πintermolecular interactions. The distinctly oriented and connected ribbon-like TRA-TIID-TRA crystalline film by the solution-shearing process achieved a superior hole mobility of 0.89 cm2V-1s-1in the organic field-effect transistor (OFET) device, which is at least five times higher than that (0.17 cm2V-1s-1) of TRA-IID-TRA with clear cracks. Eventually, rational modulation of fused core in the π-conjugated D-A-D small molecule provides a new understanding of structural design for enhancing the performance of solution-processed organic semiconductors.endonor-acceptor-donor | isoindigo | organic transistor | thienoisoindigo | triarylamine[SDGs]SDG7Solution-Processed Isoindigo- and Thienoisoindigo-Based Donor-Acceptor-Donor π-Conjugated Small Molecules: Synthesis, Morphology, Molecular Packing, and Field-Effect Transistor Characterizationjournal article10.1021/acsami.2c18049365082792-s2.0-85143981465WOS:000896752300001https://api.elsevier.com/content/abstract/scopus_id/85143981465