Diquats with Robust Chirality: Facile Resolution, Synthesis of Chiral Dyes, and Application as Selectors in Chiral Analysis

0490986 - ÚOCHB 2019 RIV DE eng J - Journal Article
Talele, Harish Ramesh - Koval, Dušan - Severa, Lukáš - Reyes Gutierrez, Paul Eduardo - Císařová, I. - Sázelová, Petra - Šaman, David - Bednárová, Lucie - Kašička, Václav - Teplý, Filip
Diquats with Robust Chirality: Facile Resolution, Synthesis of Chiral Dyes, and Application as Selectors in Chiral Analysis.
Chemistry - A European Journal. Roč. 24, č. 30 (2018), s. 7601-7604. ISSN 0947-6539. E-ISSN 1521-3765
R&D Projects: GA ČR(CZ) GA17-12648S; GA ČR(CZ) GA17-04393S; GA ČR(CZ) GA17-10832S
Institutional support: RVO:61388963
Keywords : capillary electrophoresis * chiral selector * helical chirality * N-heterocyclic cations * racemization barrier
OECD category: Organic chemistry
Impact factor: 5.160, year: 2018

Diquats with extremely high racemization barriers with G(theor) of 233kJmol(-1) at 180 degrees 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.
Permanent Link: http://hdl.handle.net/11104/0285085