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2a and 3 were synthesized by phenylation of the corresponding pentacene quinones followed by reduction in acidic conditions, similar to ret 2a.
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26
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31944451321
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note
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The crystallographic information files for 1-5 are available in the Supporting Information.
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27
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0032474156
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All the crystals were grown by vapor transport crystallization except that of 6-phenylpentacene (1), which was grown by sublimation under vacuum. See Supporting Information for preparation of the crystals. For vapor transport crystallization, see: Laudise, R. A.; Kloc, C.; Simpkins, P. G.; Siegrist, T. J. Cryst. Growth 1998, 187, 449-454.
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28
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31944435112
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note
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All density functional theory calculations were performed using Jaguar 6.0, Schrödinger, L.L.C., Portland OR, 1991-2004. The geometries were optimized in each case assuming no a priori molecular symmetry. The calculations used the B3LYP hybrid functional and 6-31G** basis sets throughout. Calculated molecular geometries for 1-5 can be found in the Supporting Information.
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29
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31944434216
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note
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See Supporting Information for the crystal structure of the tetraphenyl pentacene 3.
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30
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31944442544
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note
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See ref 6b.
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31
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31944449065
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note
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2. See ref 6d for the OTS substrate preparation.
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32
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31944452067
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note
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2.
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33
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31944447844
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note
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2 (100 nm)/Si substrate held at 80 °C.
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34
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