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Si
O
1. TIPS-C 2 Li
2. SnCl 2 ,AcOH
Br
Br
LiTMP
Br
Br
Ph
41
42
O
O
Si
Ph
Si
Si
Zn
O
O
S i
S i
43
44
Fig. 21 Synthesis of stabilized heptacene 44 [ 56 ]
Fig. 22 Left : crystal packing of heptacene 40. Right : molecular structure of heptacene 40.
Reprinted with permission from [ 56 ]. Copyright 2008 John Wiley and Sons
the smaller TIPS-ethynyl groups (that were unable to stabilize the heptacene [ 37 ])
with four phenyl groups provides sufficient protection of the heptacene core.
Chun et al. also investigated the electronic structure of their heptacene 44 by
UV/vis-NIR spectroscopy and cyclic voltammetry [ 56 ]. The heptacene shows one
reversible reduction and one reversible oxidation step. The electrochemically
derived HOMO-LUMO gap is 1.38 eV, in good agreement with the gap derived
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