Aryl substitution of pentacenes

作者：Waterloo Andreas R; Sale Anna Chiara; Lehnherr Dan; Hampel Frank; Tykwinski Rik R^*

来源：Beilstein Journal of Organic Chemistry, 2014, 10: 1692-1705.

DOI：10.3762/bjoc.10.178

• carbon-nanomaterials
• organic semiconductor
• pentacene
• Pi-stacking
• polycyclic aromatic hydrocarbon
• solid-state structure

A series of 11 new pentacene derivatives has been synthesized, with unsymmetrical substitution based on a trialkylsilylethynyl group at the 6-position and various aryl groups appended to the 13-position. The electronic and physical properties of the new pentacene chromophores have been analyzed by UV-vis spectroscopy (solution and thin films), thermoanalytical methods (DSC and TGA), cyclic voltammetry, as well as X-ray crystallography (for 8 derivatives). X-ray crystallography has been specifically used to study the influence of unsymmetrical substitution on the solid-state packing of the pentacene derivatives. The obtained results add to our ability to better predict substitution patterns that might be helpful for designing new semiconductors for use in solid-state devices.

• 出版日期2014-7-28