Chemistry Reference
In-Depth Information
Fig. 33 Thermal ellipsoid plots for 70a (
top
), 70b (
center
), and 70c (
bottom
), and packing
diagrams (
right
). F
green
,Si
blue
. Alkyl groups and fluorine substituents omitted from packing
diagrams for clarity. Thermal ellipsoids set at 50% probability. Reprinted with permission from
[
61
]. Copyright 2011 John Wiley and Sons
4.3 Thioaryl Substituted Nonacenes
The Miller group also reported the synthesis of nonacene derivatives 75 and 76
using their thioaryl approach discussed above in the context of substituted
heptacenes [
62
]. The synthesis is reminiscent of that of heptacene derivatives
[
58
], with the key step being the Diels-Alder reaction between anthracenequinone
72 and the bis-ortho-quinodimethane precursor 73 (Fig.
35
). The persistence of the
less substituted derivative 76 is insufficient for characterization by solution phase
methods. Derivative 75, however, could be investigated by NMR, UV/vis-NIR, and
fluorescence spectroscopies as well as by LDI-TOF-MS [
62
].
