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For examples of unsymmetrical pentacenes, see: (a) Clar, E.; Wright, J. W. Nature 1949, 163, 921-922.
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(p) For a recent report of unsymmetrical tetracenes, see: Lin, Y.-C.; Lin, C-H. Org. Lett. 2007, 9, 2075-2078.
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A related approach has been used by Dehaen and co-workers to form an unsymmetrical, 6,13-diarylpentacene (ref 2f).
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A related approach has been used by Dehaen and co-workers to form an unsymmetrical, 6,13-diarylpentacene (ref 2f).
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(a) Boudebous, A.; Constable, E. C.; Housecraft, C. E.; Neuburger, M.; Schaffner, S. Acta Crystallogr. Sect. C 2006, 62, o243-o245.
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See also
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(b) See also: Ried, W.; Danken, G. Chem. Ber. 1959, 92, 1223-1236.
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0035955152
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(a) Anthony, J. E.; Brooks, J. S.; Eaton, D. L.; Parkin, S. R. J. Am. Chem. Soc. 2001, 123, 9482-9483.
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J. Am. Chem. Soc
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Anthony, J.E.1
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0009784459
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(b) Anthony, J. E.; Eaton, D. L.; Parkin, S. R. Org. Lett. 2002, 4, 15-18.
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Anthony, J.E.1
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2 or -CN) have not been successful.
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2 or -CN) have not been successful.
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32
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84868912261
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max of ca. 643 nm is typical for 6,13- bis(trialkylsilylethynyl) pentacenes. See: (a) ref 9a and
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max of ca. 643 nm is typical for 6,13- bis(trialkylsilylethynyl) pentacenes. See: (a) ref 9a and
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(b) Chen, J.; Subramanian, S.; Parkin, S. R.; Siegler, M.; Gallup, K.; Haughn, C.; Martin, D. C.; Anthony, J. E. J. Mater. Chem. 2008, 18, 1961-1969.
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Chen, J.1
Subramanian, S.2
Parkin, S.R.3
Siegler, M.4
Gallup, K.5
Haughn, C.6
Martin, D.C.7
Anthony, J.E.8
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This is analogous to the behavior of related pentacenes. See, for example, refs 8 and 11b
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This is analogous to the behavior of related pentacenes. See, for example, refs 8 and 11b.
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See Supporting Information for details
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See Supporting Information for details.
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X-ray crystallographic data for 2e: C42H 40Si, M, 572.83; triclinic space group P1̄ (No. 2, ρcalcd, 1.153 g cm-3; a, 12.0801 (14) Å, b, 13.1806 (15) Å, c, 13.6258 (16) Å; α, 95.3146 (18)°, β, 115.2970 (16)°, γ, 116.2079 (16)°; ν, 1650.6 (3) Å3; Ζ, 2; μ, 0.099 mm-1. Final R1(F, 0.0553 (4807 observations [Fo2 > 2σ(Fo 2), wR2(F2, 0.1529 for 386 variables and 6264 data with [Fo2 ≥ -3σ(Fo2, CCDC 692481. X-ray data have been deposited at the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax:, 44)-122-333-6033
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2)]; CCDC 692481. X-ray data have been deposited at the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: (+44)-122-333-6033.
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The interplanar distance was measured by calculating the distance between the least-squares plane of each pentacene moiety as defined by the 22 carbon atoms of the acene framework
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The interplanar distance was measured by calculating the distance between the least-squares plane of each pentacene moiety as defined by the 22 carbon atoms of the acene framework.
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