Machine Learning‐Inspired Molecular Design, Divergent Syntheses, and X‐Ray Analyses of Dithienobenzothiazole‐Based Semiconductors Controlled by S⋅⋅⋅N and S⋅⋅⋅S Interactions

Abstract Inspired by the previous machine‐learning study that the number of hydrogen‐bonding acceptor ( N HBA ) is important index for the hole mobility of organic semiconductors, seven dithienobenzothiazole (DBT) derivatives 1 a – g ( N HBA =5) were designed and synthesized by one‐step functionalization from a common precursor. X‐ray single‐crystal structural analyses confirmed that the molecular arrangements of 1b (the diethyl and ethylthienyl derivative) and 1c (the di( n ‐propyl) and n ‐propylthienyl derivative) in the crystal are classified into brickwork structures with multidirectional intermolecular charge‐transfer integrals, as a result of incorporation of multiple hydrogen‐bond acceptors. The solution‐processed top‐gate bottom‐contact devices of 1b and 1c had hole mobilities of 0.16 and 0.029 cm 2 V −1 s −1 , respectively.