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Thiophene oligomers end-capped with phenyl-1H-pyrrole were used as active layers of organic field-effect transistors. Two types of cores that vary in size and shape of α-linked thiophenes and fused-ring thiophenes were chosen to study the structure-property relationship. The crystal structures, optical, electrochemical and electronic properties were investigated, and the heterocyclic compounds exhibited clear p-type semiconducting behavior. A new series of phenyl-1H-pyrrole end-capped thiophene oligomers has been synthesized, and the relationships between the molecular structures and electronic properties were investigated. As the semiconductors are in organic thin-film transistors, they all show good p-type organic thin-film transistor properties. [ABSTRACT FROM AUTHOR]