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A combined experimental and theoretical study on the stereodynamics of monoaza[5]helicenes: solvent-induced Increase of the enantiomerization barrier in 1-Aza-[5]helicene

Helicenes and heterohelicenes are attractive compounds with great potential in materials sciences to be used in optoelectronics as ligand backbones in enantioselective catalysis and as chiral sensors. The properties of these materials are related to the stereodynamics of these helical chiral compoun...

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Main Authors: Caronna, Tullio (Author) , Mele, Andrea (Author) , Famulari, Antonino (Author) , Mendola, Daniele (Author) , Fontana, Francesca (Author) , Juza, Markus (Author) , Kamuf, Matthias (Author) , Zawatzky, Kerstin (Author) , Trapp, Oliver (Author)
Format: Article (Journal)
Language:English
Published: 13 August 2015
In: Chemistry - a European journal
Year: 2015, Volume: 21, Issue: 40, Pages: 13919-13924
ISSN:1521-3765
DOI:10.1002/chem.201502288
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/chem.201502288
Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/chem.201502288
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Author Notes:Tullio Caronna, Andrea Mele, Antonino Famulari, Daniele Mendola, Francesca Fontana, Markus Juza, Matthias Kamuf, Kerstin Zawatzky, and Oliver Trapp
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Summary:Helicenes and heterohelicenes are attractive compounds with great potential in materials sciences to be used in optoelectronics as ligand backbones in enantioselective catalysis and as chiral sensors. The properties of these materials are related to the stereodynamics of these helical chiral compounds. However, little is known about features controlling stereodynamics in helicenes; in particular, for heterohelicenes the position of the heteroatom could be relevant in this respect. Herein the complete stereodynamic characterization of monoaza[5]helicenes is shown by enantioselective dynamic HPLC and DFT calculations. At variance with previous theoretical calculations, 1-aza[5]helicene shows a surprisingly high enantiomerization barrier, which is triggered by specific solvent interactions.
Item Description:Gesehen am 04.11.2020
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.201502288

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