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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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Hauptverfasser: Caronna, Tullio (VerfasserIn) , Mele, Andrea (VerfasserIn) , Famulari, Antonino (VerfasserIn) , Mendola, Daniele (VerfasserIn) , Fontana, Francesca (VerfasserIn) , Juza, Markus (VerfasserIn) , Kamuf, Matthias (VerfasserIn) , Zawatzky, Kerstin (VerfasserIn) , Trapp, Oliver (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 13 August 2015
In: Chemistry - a European journal
Year: 2015, Jahrgang: 21, Heft: 40, Pages: 13919-13924
ISSN:1521-3765
DOI:10.1002/chem.201502288
Online-Zugang: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
Volltext
Verfasserangaben:Tullio Caronna, Andrea Mele, Antonino Famulari, Daniele Mendola, Francesca Fontana, Markus Juza, Matthias Kamuf, Kerstin Zawatzky, and Oliver Trapp
Beschreibung
Zusammenfassung: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.
Beschreibung:Gesehen am 04.11.2020
Beschreibung:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.201502288

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