Pentacene Fused Porphyrin Dimer Exhibiting High Stability and Solubility

Abstract

Acenes have the potential to be used in the next gengeration of electronic devices due to their unique electronic properties. Pentacene is one of the most widely utilized organic compounds for organic-filed effect transistor (OFET) because of its high charge mobility. However, solubility and stability are two critical factors that limit their use in practical application. Ethynylation has shown to be one of the best strategies to stabilize pentacene. Our group is interested in linearly fusing another aromatic chromophore such as porphyrin with alkynyl-substituted pentacene to further increase its stability and solubility. In this work, a new pentacene fused porphyrin dimer with high stability and solubility was prepared and characterized. The new pentacene fused porphyrin dimer exhibits a narrow energy gap up to 1.4 eV. Photodegradation studies using UV-Vis and 1H NMR reveal that the new pentacene derivative exhibits an increased solubility and stability up to 16 times compared to 6,13-bis(phenyethynyl)pentacene. Figure 1