Synthesis and characterization of tetracene derivatives as high performance organic semiconductors

Organic semiconductors are leading their way towards making thin, flexible, and inexpensive and energy efficient displays. Charge carrier mobility is an important property of organic semiconductors in making devices. According to the theoretical prediction, the mobility of organic semiconductor can be improved by strong intermolecular electronic coupling, which can be achieved by stacking of π-electron systems from p-orbitals. I have synthesized a series of tetracene derivatives that may form pi-stacking pattern in the solids, hence, having higher mobilities. My research is to synthesize amino-substituted tetracene derivatives, in particular, tetracene with methyl amine and ethylene diamine substituted at 5,6,11 and 12 positions. The synthesis began with the preparation of 6,11-dihydroxy-5,12-tetracenedione with Friedel Crafts Acylation reaction, which was then methylated using dimethyl sulfate. The methylated compound was then aminated using ethylene diamine or methyl amine by stirring overnight or by refluxing to get the corresponding amino derivatives. The products were confirmed by NMR and mass spectroscopy. There are some confusions of the ethylene diamine compound, which were also discussed