scholarly journals 2,12-Diaza[6]helicene: An Efficient Non-Conventional Stereogenic Scaffold for Enantioselective Electrochemical Interphases

Chemosensors ◽  
2021 ◽  
Vol 9 (8) ◽  
pp. 216
Author(s):  
Francesca Fontana ◽  
Benedetta Bertolotti ◽  
Sara Grecchi ◽  
Patrizia Romana Mussini ◽  
Laura Micheli ◽  
...  
Keyword(s):  
Ionic Liquids ◽  
Stationary Phase ◽  
Chiral Stationary Phase ◽  
Preparative Hplc ◽  
Additive Concentration ◽  
Oxidation Potentials ◽  
Inherently Chiral

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.

scholarly journals Helicity: A Non-Conventional Stereogenic Element for Designing Inherently Chiral Ionic Liquids for Electrochemical Enantiodifferentiation

Molecules ◽  
2021 ◽  
Vol 26 (2) ◽  
pp. 311
Author(s):  
Francesca Fontana ◽  
Greta Carminati ◽  
Benedetta Bertolotti ◽  
Patrizia Romana Mussini ◽  
Serena Arnaboldi ◽  
...  
Keyword(s):  
Ionic Liquids ◽  
Stationary Phase ◽  
Chiral Stationary Phase ◽  
Bioactive Molecules ◽  
Organic Salt ◽  
Preparative Hplc ◽  
Enantiomerically Pure ◽  
Chiral Ionic Liquids ◽  
Quaternary Salts ◽  
Inherently Chiral

Configurationally stable 5-aza[6]helicene (1) was envisaged as a promising scaffold for non-conventional ionic liquids (IL)s. It was prepared, purified, and separated into enantiomers by preparative HPLC on a chiral stationary phase. Enantiomerically pure quaternary salts of 1 with appropriate counterions were prepared and fully characterized. N-octyl-5-aza[6]helicenium bis triflimidate (2) was tested in very small quantities as a selector in achiral IL media to perform preliminary electrochemical enantiodifferentiation experiments on the antipodes of two different chiral probes. The new organic salt exhibited outstanding enantioselection performance with respect to these probes, thus opening the way to applications in the enantioselective electroanalysis of relevant bioactive molecules.

Chiral drugs separation by a new antibiotics-based chiral stationary phase

2014 ◽  
Author(s):  
Chunye Liu ◽  
Yanqing Miao ◽  
Yihui Guo ◽  
Yinjuan An ◽  
Yunfang Li ◽  
...  
Keyword(s):  
Stationary Phase ◽  
Chiral Stationary Phase ◽  
Chiral Drugs ◽  
New Antibiotics

Advances in polymer materials as chiral stationary phase

2016 ◽  
Vol 34 (1) ◽  
pp. 34 ◽  
Author(s):  
Rongji DAI ◽  
Huiting WANG ◽  
Weiwei SUN ◽  
Yulin DENG ◽  
Fang LV ◽  
...  
Keyword(s):  
Stationary Phase ◽  
Chiral Stationary Phase ◽  
Polymer Materials

Immobilized cellulase (CBH I) as a chiral stationary phase for direct resolution of enantiomers

1990 ◽  
Vol 112 (11) ◽  
pp. 4573-4574 ◽  
Author(s):  
Per Erlandsson ◽  
Ingrid Marle ◽  
Lennart Hansson ◽  
Roland Isaksson ◽  
Goeran Pettersson ◽  
...  
Keyword(s):  
Stationary Phase ◽  
Chiral Stationary Phase ◽  
Resolution Of Enantiomers ◽  
Immobilized Cellulase

scholarly journals A Novel Method for the Preparation of a Chiral Stationary Phase Containing an Enantiopure Acridino-18-Crown-6 Ether Selector

2014 ◽  
Vol 53 (3) ◽  
pp. 431-435 ◽  
Author(s):  
T. Nemeth ◽  
S. Levai ◽  
T. F di ◽  
J. Kupai ◽  
G. Turos ◽  
...  
Keyword(s):  
Stationary Phase ◽  
Chiral Stationary Phase ◽  
Novel Method

Enantioseparation of novel chiral tetrahedral clusters on an amylose tris-(3,5-dimethylphenylcarbamate) chiral stationary phase by normal phase HPLC

2010 ◽  
Vol 22 (10) ◽  
pp. 1070-1074 ◽  
Author(s):  
Wen-Zhi Li ◽  
Xia Wang ◽  
Wei-Qiang Zhang ◽  
Chen Li-Ren ◽  
Yong-Min Li ◽  
...  
Keyword(s):  
Stationary Phase ◽  
Chiral Stationary Phase ◽  
Normal Phase ◽  
Normal Phase Hplc
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