Design, synthesis, and characterization of a persistent nonacene derivative.

A significant technical barrier (i.e., facile oxidative degradation) that has prevented the preparation of large acenes has now been breached.

Exploiting substituent effects for the synthesis of a photooxidatively resistant heptacene derivative.

Substituent effects have been exploited to produce an unusually persistent heptacene derivative. In total, four new heptacene derivatives with varying levels of photooxidative resistance (1 < 2 < 3 < 4) have been synthesized. A combination of p-(t-butyl)thiophenyl substituents at positions 7 and 16 (i.

Substituent effects in pentacenes: gaining control over HOMO-LUMO gaps and photooxidative resistances.

A combined experimental and computational study of a series of substituted pentacenes including halogenated, phenylated, silylethynylated and thiolated derivatives is presented. Experimental studies include the synthesis and characterization of six new and six known pentacene derivatives and a kinetic study of each derivative under identical photooxidative conditions. Structures, HOMO-LUMO energies and associated gaps were calculated at the B3LYP/6-311+G**//PM3 level while optical and electrochemical HOMO-LUMO gaps were measured experimentally.