Effect of import of additional functional groups on the photocurrent produced by small-molecule organic semiconductors

Abstract

The reaction of acenaphthenequinone – a low-cost commercial product with an insulator's behavior – with an active methylene (malononitrile CNCH 2CN) was carried out. This is a simple, one-pot reaction with satisfactory efficiency. Setting the experimental procedure, the introduction of one or two nitrile groups in the original molecule was made possible. In fact, a new product was synthesized, in the second case. Afterwards, the photoconductivity of the as-prepared materials was measured. Thanks to the development of extended π-conjugated systems, as proved, the products show a remarkable photosensitivity. This synthesis can be also applied even to other active methylene compounds, such as ethyl cyanoacetate (NCCH 2COOEt) [I. Mhaidat, S. Hamilakis, C. Kollia, A. Tsolomitis, Z. Loizos, Mater Lett 2007;61:321–325] and generally to nucleophilic reagents, such as p-anisidine ( p-NH 2C 6H 4OMe) [I. Mhaidat, S. Hamilakis, C. Kollia, A. Tsolomitis, Z. Loizos, Mater Lett 2005;60:147–149].