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Room-temperature discotic liquid-crystalline coronene diimides exhibiting high charge-carrier mobility in air†
Zesheng An,Junsheng Yu,Benoit Domercq,Simon C. Jones,Stephen Barlow,Bernard Kippelen,Seth R. Marder
Journal of Materials Chemistry Pub Date : 08/18/2009 00:00:00 , DOI:10.1039/B910898J
Abstract

Six N,N′,5,11-tetrasubstituted coronene-2,3,8,9-tetracarboxydiimides have been synthesised incorporating 3,4,5-tri(n-dodecyloxy)phenyl or 2-(n-decyl)-n-tetradecyl groups in various positions. Differential scanning calorimetry, polarised optical microscopy, and X-ray diffraction indicate that all form columnar discotic mesophases from around room temperature to around 200 °C. Charge-carrier mobility values, which energetic considerations suggest are electron mobility values, have been determined in non-aligned samples cooled from the isotropic melt using the space-charge-limited current technique. The highest mobility, 6.7 cm2V−1 s−1, was found in N,N′-bis(n-2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecylfluorooctyl)-5,11-bis(3-[{3,4,5-tri(n-dodecyloxy)phenyl}carbonyloxy]-n-propyl)coronene-2,3,8,9-tetracarboxydiimide, which X-ray diffraction suggests is the most highly ordered of the materials examined.

Graphical abstract: Room-temperature discotic liquid-crystalline coronene diimides exhibiting high charge-carrier mobility in air
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