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Diquats with Robust Chirality: Facile Resolution, Synthesis of Chiral Dyes, and Application as Selectors in Chiral Analysis
Author(s) -
Talele Harish R.,
Koval Dušan,
Severa Lukáš,
ReyesGutiérrez Paul E.,
Císařová Ivana,
Sázelová Petra,
Šaman David,
Bednárová Lucie,
Kašička Václav,
Teplý Filip
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201800369
Subject(s) - racemization , chirality (physics) , chemistry , derivatization , diquat , molecule , combinatorial chemistry , computational chemistry , stereochemistry , organic chemistry , chiral perturbation theory , pion , paraquat , physics , high performance liquid chromatography , particle physics , nambu–jona lasinio model
Diquats with extremely high racemization barriers with Δ G ≠ theor of 233 kJ mol −1 at 180 °C are described. Reported configurational robustness is due to a combination of two structural features: the rigid o ‐xylylene tether connecting the nitrogen atoms and the presence of two substituents in the bay region of the bipyridinium scaffold. The straightforward synthesis of diquats, plus facile resolution and derivatization make them attractive for chiral application studies. This is demonstrated by: 1) synthesis of the first non‐racemic diquat dyes with pronounced chiroptical properties, and 2) capability of diquats to interact stereospecifically with chiral molecules. This suggests potential for diquat derivatives to be used as chiral selectors in separation methods.