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 |
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| Authors: | Prof Dr Tullio Caronna Prof Dr Andrea Mele Prof Dr Antonino Famulari Dr Daniele Mendola Prof Dr Francesca Fontana Dr Markus Juza Dr Matthias Kamuf Dr Kerstin Zawatzky Prof Dr Oliver Trapp |
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| Affiliation: | 1. Università di Bergamo, INSTM R.U. and Dipartimento di Ingegneria e Scienze Applicate Viale Marconi 5, 24044 Dalmine (Bergamo) (Italy);2. Politecnico di Milano, Department of Chemistry, Materials and Chemical Engineering “G. Natta”, Piazza L. da Vinci 32, 20132 Milano (Italy);3. Corden Pharma Switzerland LLC, Eichenweg 1, 4410 Liestal (Switzerland);4. Ruprecht‐Karls Universit?t Heidelberg, Organisch‐Chemisches Institut, Im Neuenheimer Feld 270, 69120 Heidelberg (Germany) www.trapp.uni‐hd.de |
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| Abstract: | 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 monoaza5]helicenes is shown by enantioselective dynamic HPLC and DFT calculations. At variance with previous theoretical calculations, 1‐aza5]helicene shows a surprisingly high enantiomerization barrier, which is triggered by specific solvent interactions. |
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| Keywords: | chiral separation DFT calculations dynamic chromatography helical structures heterocycles |
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