Azaarene Dimers

Binaphthyl‐3,3′,4,4′‐tetraone was prepared and coupled to different bis(TIPS‐ethynyl)‐substituted (TIPS=triisopropyl silane) aromatic diamines, resulting in the formation of dimeric benzo‐fused azaacenes, centrally connected by a single bond. The two halves of the molecules are highly twisted with r...

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Bibliographic Details
Published in:Chemistry : a European journal 2019-05, Vol.25 (30), p.7285-7291
Main Authors: Hahn, Sebastian, Butscher, Julian, An, Qingzhi, Jocic, Angelina, Tverskoy, Olena, Richter, Marcus, Feng, Xinliang, Rominger, Frank, Vaynzof, Yana, Bunz, Uwe H. F.
Format: Article
Language:English
Subjects:
Absorption spectra
acceptor materials
aromatic dimers
azaarenes
Chemistry
Diamines
Dimers
Fluorescence
Monomers
organic electronics
organic photovoltaics
Photovoltaics
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Summary:Binaphthyl‐3,3′,4,4′‐tetraone was prepared and coupled to different bis(TIPS‐ethynyl)‐substituted (TIPS=triisopropyl silane) aromatic diamines, resulting in the formation of dimeric benzo‐fused azaacenes, centrally connected by a single bond. The two halves of the molecules are highly twisted with respect to each other and showed limited electronic interaction in the ground state because their absorption spectra remained very similar to those of the constituting monomers. The dimers displayed greatly reduced fluorescence when compared to the monomers, suggesting that there is a significant interaction of the two azarene units in the excited state. Preliminary investigations showed that the dimers are attractive for application as acceptors in organic photovoltaic because they significantly outperform their monomeric counterparts. Dimer doubles efficiency in an organic photovoltaic (OPV) cell. Substituted bent azaarene dimers with quenched fluorescence that significantly outperform their monomeric counterparts when applied as acceptors in OPV cells are reported.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201901139