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Journal Article

Complete charge separation provoked by full cation encapsulation in the radical mono- and di-anions of 5,6:11,12-di-o-phenylene-tetracene

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Goddard,  Richard
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Lehmann,  Christian W.
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Wombacher, T., Goddard, R., Lehmann, C. W., & Schneider, J. J. (2018). Complete charge separation provoked by full cation encapsulation in the radical mono- and di-anions of 5,6:11,12-di-o-phenylene-tetracene. Dalton Transactions, 47(32), 10874-10883. doi:10.1039/c8dt01285g.


Cite as: https://hdl.handle.net/21.11116/0000-0002-A043-D
Abstract
Herein, we report the synthesis and molecular structure of the mono- and dianionic aromatic molecules
[(B15C5-κ5O)2K+](L DOPT•−) (1) and [(B15C5-κ5
O)2K+]2(L DOPT2−)THFsolv (2) derived from the parent aromatic
polyhydrocarbon 5,6:11,12-di-o-phenylenetetracene (DOPT, L DOPT) by a controlled stepwise one and two
electron chemical reduction. The effect of single and double electron charge transfer to a polycondensed
aromatic hydrocarbon (PAH) without any disturbing influence of an associated metal cation has been
demonstrated. This was achieved by fully sandwiching the cationic K+ counterions between two benzo15-crown-5-ether
(B15C5) ligands resulting in a fully encapsulating (κ10O) geometry which ensures a
complete separation of the K+ counterions and the bare anionic PAH species [L DOPT•−] and [L DOPT2−]. The
structural changes accompanied by the stepwise reduction from L DOPT to [L DOPT•−] to [L DOPT2−] are discussed
and compared to earlier predictions based on density functional theory (DFT) as well as the results
of previous studies of alkaline metal cationic PAH anion interactions of DOPT in which only a partial metal
cation encapsulation has been achieved so far.