Abstract

Organic semiconductors are key components of numerous electronic and optoelectronic devices for a wide range of applications such as light-emitting diodes, photovoltaic cells and organic thin-film transistors (TFTs). Thus the search for new organic materials which serve this purpose is of considerable current interest. Several years ago, we developed an efficient metal-induced synthesis of 4,9-diamino-3,10-perylenequinone diimine (DPDI) by oxidative coupling of two 1,8-diaminonaphthalene units. This functionalized perylene may be converted to tetraazaperopyrene (TAPP) as well as a range of derivatives which have proved to possess considerable potential as organic n-channel semiconductors.

Water soluble TAPP derivatives have also been found to possess considerable potential as biological fluorescence markers, with relatively low cytotoxicity, specifically targeting chromatides.

Finally, these heteropolycycles have proved to display an interesting surface chemistry when deposited on well defined faces of coinage metal single crystals. The formation of stable porous surface networks (and their exciting physical properties), including the covalent coupling of the polycycles to give oligomers or polymers, have been investigated in a series of studies.