Halogenated Phenazinothiadiazoles: Electron‐Transporting Materials

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 cm2 V−1 s−1 and 0.76 cm2 V−1 s−1. Triisopropylsilyl‐alkynylated phenazinothiadiazoles substituted with different halogen atoms were synthesized. The compounds pack in brickwall motif of head‐to‐head dimers induced by intermolecular S−N contacts. In bottom gate / top contact field effect transistors the materials showed electron mobilities μmax ranging from 0.14 to 0.76 cm2 V−1 s−1 were. The charge carrying species, the radical anions, were synthesized and characterized via UV‐Vis.