The new configurationally stable, unsymmetrical 2,12-diaza[6]helicene was synthesized as a racemate and the enantiomers were separated in an enantiopure state by semi-preparative HPLC on chiral stationary phase. Under selected alkylation conditions it was possible to obtain both the enantiopure 2-N-mono- and di-N-ethyl quaternary iodides. Metathesis with bis(trifluoromethanesulfonyl)imide anion gave low-melting salts which were tested as inherently chiral additives to achiral ionic liquids for the electrochemical enantiodiscrimination of chiral organic probes in voltammetric experiments. Remarkable differences in the oxidation potentials of the enantiomers of two probes, a chiral ferrocenyl amine and an aminoacid, were achieved; the differences increase with increasing additive concentration and number of alkylated nitrogen atoms.

Fontana, F., Bertolotti, B., Grecchi, S., Mussini, P.r., Micheli, L., Cirilli, R., et al. (2021). 2,12-diaza[6]helicene: An efficient non-conventional stereogenic scaffold for enantioselective electrochemical interphases. CHEMOSENSORS, 9(8) [10.3390/chemosensors9080216].

2,12-diaza[6]helicene: An efficient non-conventional stereogenic scaffold for enantioselective electrochemical interphases

Micheli L.;
2021-01-01

Abstract

The new configurationally stable, unsymmetrical 2,12-diaza[6]helicene was synthesized as a racemate and the enantiomers were separated in an enantiopure state by semi-preparative HPLC on chiral stationary phase. Under selected alkylation conditions it was possible to obtain both the enantiopure 2-N-mono- and di-N-ethyl quaternary iodides. Metathesis with bis(trifluoromethanesulfonyl)imide anion gave low-melting salts which were tested as inherently chiral additives to achiral ionic liquids for the electrochemical enantiodiscrimination of chiral organic probes in voltammetric experiments. Remarkable differences in the oxidation potentials of the enantiomers of two probes, a chiral ferrocenyl amine and an aminoacid, were achieved; the differences increase with increasing additive concentration and number of alkylated nitrogen atoms.
2021
Pubblicato
Rilevanza internazionale
Articolo
Esperti anonimi
Settore CHIM/01 - CHIMICA ANALITICA
English
azahelicenes
chiral voltammetry
enantiodiscrimination
ionic liquids
chiral additives
B.B. acknowledges funding from Università di Bergamo, Program STaRs Supporting Talented Researchers 2017–2018. P.R.M. and S.G. acknowledge financial support from the Università degli Studi di Milano. S.R. thanks Fondazione “Banca del Monte di Lombardia” for funding of the LCMS2020 mass spectrometer
Fontana, F., Bertolotti, B., Grecchi, S., Mussini, P.r., Micheli, L., Cirilli, R., et al. (2021). 2,12-diaza[6]helicene: An efficient non-conventional stereogenic scaffold for enantioselective electrochemical interphases. CHEMOSENSORS, 9(8) [10.3390/chemosensors9080216].
Fontana, F; Bertolotti, B; Grecchi, S; Mussini, Pr; Micheli, L; Cirilli, R; Tommasini, M; Rizzo, S
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2108/292143
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