Halogenated Phenazinothiadiazoles: Electron‐Transporting Materials

Abstract

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.

Stabilizing Azaheptacenes

“…It is oxidized to DAH2 by MnO 2 (85%). The synthesis of TAH-H 2 and HAH-H 2 exploits ortho -quinone 4 , obtained from dibromo­diiodoveratrole by demethylation and oxidation; 4 dimerizes spontaneously , and was immediately combined with 2a or 2b into 5a,b . 5a reacted with 5 equiv of TIPS-acetylene under Sonogashira conditions (50 °C) into multiply ethynylated N,N ′-dihydro-intermediates, with 6a isolated in 39% yield.…”