10.1002/chem.201701139
Chemistry - A European Journal
FULL PAPER
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In conclusion, we have developed efficient gold- and platinum-
catalyzed domino reactions to synthesize 3-alkynylated
benzofurans and benzothiophenes based on the use of EBX
hypervalent iodine reagents. Heterotetracenes containing two O,
two S, or one O and one S heteroatoms were accessed in only
four steps. Subsequent proof-of-principle computations suggest
that some of the synthesized compounds and other
heterotetracenes can potentially afford hole mobilities,
comparable or superior to current state-of-the-art organic
materials, provided they are not hampered by the crystal
packing and disorder effects. The results confirmed that both the
identity and position of the heteroatom in the conjugated system
strongly affect the hole mobility. Our study combining improved
synthetic methodologies and in silico analysis of the electronic
structure leads to a better understanding of the relationships
between the structure and charge transport properties of the
heteroacenes. Further effort can now be focused on other
factors (e.g. crystallization techniques, substitution patterns) that
influence both the solid-state structure and the material
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Acknowledgements
EPFL is acknowledged for financial support. J.W. thanks the
European Research Council (ERC Grant 334840, iTools4MC)
for financial support. C.C. acknowledges funding from the
European Research Council (ERC Grant 306528, COMPOREL).
K.S. and X.A.J. thank the European Research Commission
(Project No. 336506, CEMOS) for financial support, and Dr. M.
Johnson is acknowledged for assistance with thin film XRD
results.
Keywords: Acenes • Domino Reactions • Hole Mobility
Computation• Organic Materials • Hypervalent Iodine
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[23] Crystal data of 12h has been deposited at the Cambridge
Crystallographic Data Centre (CCDC 1420341).
[24] Unfortunately, the deprotection-cyclization of multi-domino reaction
products was unsuccessful due to the poor solubility and/or instability of
the deprotected alkynes.
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