Imidazole octasubstituted novel mono and double-decker phthalocyanines: Synthesis, characterization, electrical and gas sensing properties

Imidazole disubstituted phthalonitrile (1) was prepared by the reaction of 4,5-dichlorophthalonitrile with 4,5-diphenyl-1H-imidazolethiole. Imidazole octasubstituted metal free (2), zinc(II) (3), cobalt(II) (4) monophthalocyanines and lutetium(III) (5) and europium(III) (6) double-decker phthalocyanines were prepared by cyclotetramerization of compound 1. The new compounds were characterized by 1H NMR, 13C NMR, UV–vis, IR, MALDI-TOF mass, ESR spectra and elemental analysis. Dc and ac conductivity and gas sensing properties (at room temperature) of the compounds of 2–6 were studied between the temperatures of 295–523 K. Ac conductivity values of the films were measured in the frequency region of 40 Hz–100 kHz. The films were tested for the vapors of toluene, ethanol, THF, n-hexane, chloroform and xylene. DC conductivity results revealed that the compounds 2–6 show a semiconductor behavior. Results of ac measurements show dominant conduction mechanism can be modeled depending on temperature and frequency. The best sensitivity values were obtained for the xylene vapors. The sensor 3 showed best sensitivity among the other sensors for xylene vapor. Response times of the sensors were also determined.