Tetrachloro-substituted perylene bisimide dyes as promising n-type organic semiconductors: studies on structural, electrochemical and charge transport properties.

Experimental Section Solvents and reagents were purchased from Merck and used as received. 1,6,7,12Tetrachloroperylene-3,4:9,10-tetracarboxylic acid bisanhydride was obtained from BASF. N,N'-Didodecylperylene-3,4:9,10-tetracarboxylic acid bisimide 2 was synthesized according to the literature. NMR spectra were recorded on a Bruker DRX 400 spectrometer using the proton signal of TMS as internal standard. Matrix-assisted laser desorption ionization time-offlight (MALDI-TOF) mass spectra were performed with a Bruker Franzen Reflex III spectrometer. UV/Vis spectra were measured at 298 K on a Perkin Elmer Lambda 40P spectrometer equipped with a Perkin Elmer PTP-1 Peltier System as the temperature controller.