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Issue 17, 2008
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The influence of side chains on the structures and properties of functionalized pentacenes

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Abstract

We investigated substituent-induced variations in microstructure and physical properties of a family of functionalized pentacenes, materials currently of intensive interest for making organic electronic devices such as thin film transistors, to shed light on the complex relationships between functionalization, film formation, stability, and microstructure. In this study, the pentacenes were modified with alkyl acetylene or alkylsilylethynyl groups with systematic variations in the alkyl chain length. With a proper side chain, this modification can effectively disrupt the herringbone packing seen in neat pentacene, promoting face-to-face arrangements between the acene rings and providing solubility in a variety of convenient solvents. Thin films can be readily formed by solution casting from THF, bromobenzene, toluene and other organic solvents. We have investigated the structure and properties of the functionalized pentacenes using UV-vis spectroscopy, hot stage optical microscopy, differential scanning calorimetry, transmission electron microscopy, X-ray and electron diffraction. The materials show regular variations in their thermal behavior, crystal packing and macroscopic properties as the chemistry of the side-group substituent changes.

Graphical abstract: The influence of side chains on the structures and properties of functionalized pentacenes

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Publication details

The article was received on 05 Nov 2007, accepted on 15 Jan 2008 and first published on 12 Feb 2008


Article type: Paper
DOI: 10.1039/B717082C
Citation: J. Mater. Chem., 2008,18, 1961-1969
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    The influence of side chains on the structures and properties of functionalized pentacenes

    J. Chen, S. Subramanian, S. R. Parkin, M. Siegler, K. Gallup, C. Haughn, D. C. Martin and J. E. Anthony, J. Mater. Chem., 2008, 18, 1961
    DOI: 10.1039/B717082C

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