Abstract
To achieve enantioselective electroanalysis either chiral electrodes or chiral media are needed. High enantiodiscrimination properties can be granted by the “inherent chirality” strategy of developing molecular materials in which the stereogenic element responsible for chirality coincides with the molecular portion responsible for their specific properties, an approach recently yielding outstanding performances as electrode surfaces. Inherently chiral ionic liquids (ICILs) have now been prepared starting from atropisomeric 3,3′-bicollidine, synthesized from inexpensive reagents, resolved into antipodes without need of chiral HPLC and converted into long-chain dialkyl salts with melting points below room temperature. Both the new ICILs and shorter family terms, solid at room temperature, employed as low-concentration additives in achiral ILs, afford impressive enantioselection for the enantiomers of different probes on achiral electrodes, regularly increasing with additive concentration.
| Original language | English |
|---|---|
| Pages (from-to) | 2079-2082 |
| Number of pages | 4 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 56 |
| Issue number | 8 |
| DOIs | |
| Publication status | Published - Jan 1 2017 |
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Keywords
- bicollidinium salts
- chiral electroanalysis
- chiral ionic liquids
- enantiodiscrimination
- inherent chirality
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
Cite this
“Inherently Chiral” Ionic-Liquid Media : Effective Chiral Electroanalysis on Achiral Electrodes. / Rizzo, Simona; Arnaboldi, Serena; Mihali, Voichita; Cirilli, Roberto; Forni, Alessandra; Gennaro, Armando; Isse, Abdirisak Ahmed; Pierini, Marco; Mussini, Patrizia Romana; Sannicolò, Francesco.
In: Angewandte Chemie - International Edition, Vol. 56, No. 8, 01.01.2017, p. 2079-2082.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - “Inherently Chiral” Ionic-Liquid Media
T2 - Effective Chiral Electroanalysis on Achiral Electrodes
AU - Rizzo, Simona
AU - Arnaboldi, Serena
AU - Mihali, Voichita
AU - Cirilli, Roberto
AU - Forni, Alessandra
AU - Gennaro, Armando
AU - Isse, Abdirisak Ahmed
AU - Pierini, Marco
AU - Mussini, Patrizia Romana
AU - Sannicolò, Francesco
PY - 2017/1/1
Y1 - 2017/1/1
N2 - To achieve enantioselective electroanalysis either chiral electrodes or chiral media are needed. High enantiodiscrimination properties can be granted by the “inherent chirality” strategy of developing molecular materials in which the stereogenic element responsible for chirality coincides with the molecular portion responsible for their specific properties, an approach recently yielding outstanding performances as electrode surfaces. Inherently chiral ionic liquids (ICILs) have now been prepared starting from atropisomeric 3,3′-bicollidine, synthesized from inexpensive reagents, resolved into antipodes without need of chiral HPLC and converted into long-chain dialkyl salts with melting points below room temperature. Both the new ICILs and shorter family terms, solid at room temperature, employed as low-concentration additives in achiral ILs, afford impressive enantioselection for the enantiomers of different probes on achiral electrodes, regularly increasing with additive concentration.
AB - To achieve enantioselective electroanalysis either chiral electrodes or chiral media are needed. High enantiodiscrimination properties can be granted by the “inherent chirality” strategy of developing molecular materials in which the stereogenic element responsible for chirality coincides with the molecular portion responsible for their specific properties, an approach recently yielding outstanding performances as electrode surfaces. Inherently chiral ionic liquids (ICILs) have now been prepared starting from atropisomeric 3,3′-bicollidine, synthesized from inexpensive reagents, resolved into antipodes without need of chiral HPLC and converted into long-chain dialkyl salts with melting points below room temperature. Both the new ICILs and shorter family terms, solid at room temperature, employed as low-concentration additives in achiral ILs, afford impressive enantioselection for the enantiomers of different probes on achiral electrodes, regularly increasing with additive concentration.
KW - bicollidinium salts
KW - chiral electroanalysis
KW - chiral ionic liquids
KW - enantiodiscrimination
KW - inherent chirality
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U2 - 10.1002/anie.201607344
DO - 10.1002/anie.201607344
M3 - Article
VL - 56
SP - 2079
EP - 2082
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 8
ER -