Solution-Processable Dicycloheptatrienerubicenes With Two Trialkylsilylethynyl Groups.

Introduction of trialkylsilylethynyl groups to polycyclic aromatic hydrocarbon (PAH) is one effective strategy to improve the solubility and tune the packing modes. Based on our previously reported non-benzenoid PAH, dicycloheptatrienerubicene (DHR), we developed a bromination/borylation/oxidation/ alkynylation sequence to successfully introduce two trialkylsilylethynyl groups to the 2, 2'-positions of it. The resulting DHR derivatives, DHR-TES and DHR-TIPS with triethylsilylethynyl and triisopropylethynyl groups, respectively, can be solution-processable, and their packing modes were tuned to be herringbone and 1D column, respectively. DHR-TES shows higher mobility than DHR-TIPS, reaching 0.012 and 0.094 cm2V- 1s- 1, respectively, for solution-processable thin films and microcrystals of DHR-TES.