The spectroelectrochemical, magnetic, and structural characterization of reduced hexaazatriphenylenehexacarbonitrile, HAT(CN)6

The cyanoazacarbon, hexaazatriphenylenehexacarbonitrile, or HAT(CN)6, is readily reduced and the spectroelectrochemical properties associated with the multiple reductions are described. The singly reduced radical monoanion forms stable salts and we report the crystal structure and magnetic properties for the tetrabutylammonium salt. [Tetra-n-butylammonium] [HAT(CN)6] behaves ferromagnetically below 3 K and follows Curie Law behavior at higher temperatures after correction for Pauli-type susceptibility. The room temperature conductivity of the powdered salt is 3.8 × 10−8 S/cm. The crystal structure shows closely bound pairs of radical anions with slip-stacking of these pairs to form a staircase, features that elucidate the observed properties. Thin films of HAT(CN)6 were found to support negative charge transport by electron time-of-flight measurements, yielding electron mobilities of 10−4 cm2/Vs at room temperature.