Novel functional sulfur-bridged neutral annulene: Structure, physical properties and progress on field-effect performance

•A novel sulfur-bridged neutral annulene has been synthesized.•This annulene is an important building block for organic electronic materials.•This annulene has been fully characterized.•Field-effect transistors based on this compound have been fabricated.•The highest mobility and on/off ratio recorded are the best amongst this series.

The novel aromatic heteromacrocycle, p-bromophenyl substituted tetrathia[22]annulene[2,1,2,1] was synthesized as a convenient derivable building block to obtain a variety of tetrathia[22]annulene[2,1,2,1] derivatives, which were recently found to be promising p-type semiconducting materials for OFETs with some unique properties. Furthermore the annulene itself was found to perform well as an active material in OFETs. A thin film transistor based on the annulene had the best hole mobility of 0.73 cm2V−1s−1 and the on/off ratio of 1.4 × 107, which are class leading amongst the macrocyclic field-effect materials.