Synthesis and Characterization of 6,13-Diamino-Substituted Pentacenes.

A series of 6,13-diamino-substituted pentacenes 1 a-d has been prepared and characterized as a new class of pentacene derivatives with strong donor ability and enhanced solubility in common organic solvents. The spectroelectrochemical and DFT studies revealed that the two-electron oxidation process was accompanied by the substantial structural change into a butterfly-like conformation of the pentacene moiety. More importantly, the extent of deformation from the planar pentacene moiety in the dications of 6,13-diaminopentacene is tunable by varying the N-substituents.