Synthesis of soluble oligo- and polymeric pentacene-based materials

Functionalization of pentacene at the 6- and 13-positions affords versatile building blocks for oligomer and polymer formation. Di- and trimeric materials are synthesized using unsymmetrical building block 18, while symmetrical diol monomer 17 allows for the synthesis of polymers. The materials reported herein are soluble in common organic solvents and air-stable. UV–vis and fluorescence spectroscopic properties have been investigated. Solid-state X-ray crystallography of building blocks 17 and 19 shows that these derivatives can π-stack with significant acene face-to-face interactions with spacing of less than 3.5 Å.