Halogenated Phenazinothiadiazoles: Electron Transporting Materials [data]

Triisopropylsilyl-(TIPS)-alkynylated phenazinothiadiazoles were prepared by the condensation of halogenated ortho-quinones and TIPS-alkynylated 5,6-diamino-2,1,3-benzothiadiazole with different combinations of halogen substituents. The compounds pack in brickwall motif of head-to-head dimers featuring intermolecular S-N contacts and short π-π distances, suggesting their suitability as n-channel materials in organic thin film transistors. The halogenated phenazinothiadiazoles show electron mobilities μmax ranging between 0.14 cm2V-1 s-1 and 0.76 cm2 V-1 s-1.