Novel pentacenediquinone and pentacene derivatives

Pentacenediquinones are of recent interest for their rigid, linear, conjugated molecular framework. These compounds in the reduced form display absorbance in the near infrared region between 800 and 1600 nm. They are also notoriously insoluble which makes characterization very difficult.; Starting from pentacenediquinone, a series of twelve pentacenediquinones containing electron-withdrawing and electron-donating substituents were prepared.; It is hypothesized in this work, that by appropriately choosing the number, position and type of substituents, the near infrared absorbance of these compounds could be tuned and the solubility could also be improved.; Halogenated pentacenediquinones are monomers for a novel class of polymers, poly(aryl ether quinone)s. These polymers are electrochromic and display a visible colour change when being reduced. They also show a near infrared absorbance in the reduced state, between 1300 and 1400 nm for the semiquinone and between 800 and 900 nm for the dianion. Poly(aryl ether quinone)s display interesting light attenuating properties, fatigue resistance to electrochemical switching, and good adhesion to the ITO (indium-doped tin oxide) electrode. The semiquinone of poly(arylether quinone)s also displays an electrical conductivity in the order of 10-5 S/cm.; Halogenated pentacenediquinones can also be reduced to produce halogenated pentacenes. Four pentacenes containing halogen substituents have been prepared and their electron mobilities investigated.; In conclusion, tuning the near infrared absorbtion of pentacenediquinone through appropriate substituents has been demonstrated. The substituted pentacenediquinones are proven to be useful precursors for making a novel class of poly(aryl ether)s and substituted pentacenes.