Anthracene−Pentacene Dyads: Synthesis and OFET Characterization

Abstract

The synthesis of a series of unsymmetrical derivatives of pentacene appended with functionalized anthracene moieties is reported. These anthraceneÀ pentacene dyads have been characterized by UV-vis spectroscopy and cyclic voltammetry to examine their electronic properties. X-ray crystallographic analysis was used to examine the solid-state features of anthraceneÀ pentacene dyads 1 a-d with HÀ , FÀ , ClÀ , and BrÀ substituents on the 9-position of anthracene, and shows that the packing arrangement of anthraceneÀ pentacene derivatives 1 b,d,e are remarkably similar irrespective of the presence of fluoride, bromide or methyl substituents. The pentaceneÀ anthracene dyads have been incorporated into OTFTs to evaluate their semiconducting properties. The pentacene derivative 1 b shows ambipolar behavior using AlO x C 14 PA as the gate dielectric (electron and hole mobilities of 7.6 · 10 À 3 and 1.6 · 10 À 1 cm 2 V À 1 s À 1 ), while performance of all derivatives was poor using p-doped Silicon as the substrate. These studies highlight the importance of thin-film formation over molecular structure.

Photophysical Properties of Anthracene Derivatives

“…However, the addition metal ions such as Cu (II) and Hg (II) led to the increase in the emission, indicating that the nitrogen atom of aniline and the sulfur atom in thiourea are the binding sites for the metal ion coordination in 65 (Figure 55). Further, an anthracene-based dyad was published by Tykwinski et al [130], this time combined with a pentacene unit 66. The anthracene core was modified at position 9 with different substituents, e.g., H, F, Cl, Br, and CH 3 (Figure 56).…”

“…The anthracene core was modified at position 9 with different substituents, e.g., H, F, Cl, Br, and CH 3 (Figure 56). Further, an anthracene-based dyad was published by Tykwinski et al [130], this time combined with a pentacene unit 66. The anthracene core was modified at position 9 with different substituents, e.g., H, F, Cl, Br, and CH3 (Figure 56).…”