Pentacene

Pentacene is a polycyclic aromatic hydrocarbon consisting of five linearly-fused benzene rings. This highly conjugated compound is an organic semiconductor. The compound generates excitons upon absorption of ultra-violet (UV) or visible light; this makes it very sensitive to oxidation. For this reason, this compound, which is a purple powder, slowly degrades upon exposure to air and light. Pentacene is a polycyclic aromatic hydrocarbon consisting of five linearly-fused benzene rings. This highly conjugated compound is an organic semiconductor. The compound generates excitons upon absorption of ultra-violet (UV) or visible light; this makes it very sensitive to oxidation. For this reason, this compound, which is a purple powder, slowly degrades upon exposure to air and light. Structurally, pentacene is one of the linear acenes, the previous one being tetracene (four fused benzene rings) and the next one being hexacene (six fused benzene rings). In August 2009, a group of researchers from IBM published experimental results of imaging a single molecule of pentacene using an atomic force microscope. In July 2011, they used a modification of scanning tunneling microscopy to experimentally determine the shapes of the highest occupied and lowest unoccupied molecular orbitals. In 2012, pentacene-doped p-terphenyl was shown to be effective as the amplifier medium for a room-temperature maser. Pentacene was first synthesized in 1912 by British chemists William Hobson Mills and Mildred May Gostling. A classic method for pentacene synthesis is by the Elbs reaction. Pentacenes can also be prepared by extrusion of a small volatile component (carbon monoxide) from a suitable precursor at 150 °C. The precursor itself is prepared in three steps from two molecules of α,α,α',α'-tetrabromo-o-xylene with a 7-tert-butoxybicyclohepta-2,5-diene by first heating with sodium iodide in dimethylformamide to undergo a series of elimination and Diels–Alder reactions to form the ring system, then hydrolysing the tert-butoxy group to an alcohol and followed by its oxidation to the ketone. The product is reported to have some solubility in chloroform and is therefore amenable to spin coating. Pentacene is soluble in hot chlorinated benzenes, such as 1,2,4-trichlorobenzene, from which it can be recrystallized to form platelets. 6,13-Substituted pentacenes are accessible through pentacenequinone by reaction with an aryl or alkynyl nucleophile (for example Grignard or organolithium reagents) followed by reductive aromatization. Another method is based on homologization of diynes by transition metals (through zirconacyclopentadienes) Functionalization of pentacene has allowed for control of the solid-state packing of this chromophore. The choice of the substituents (both size and location of substitution on the pentacene) influences the solid-state packing and can be used to control whether the compound adopts 1-dimensional or 2-dimensional cofacial pi-stacking in the solid-state, as opposed to the herringbone packing observed for pentacene. Although pentacene's structure resembles that of other aromatic compounds like anthracene, its aromatic properties are poorly defined; as such, pentacene and its derivatives are the subject of much research.