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Diquats with Robust Chirality: Facile Resolution, Synthesis of Chiral Dyes, and Application as Selectors in Chiral Analysis.
Talele, Harish R; Koval, Dusan; Severa, Lukás; Reyes-Gutiérrez, Paul E; Císarová, Ivana; Sázelová, Petra; Saman, David; Bednárová, Lucie; Kasicka, Václav; Teplý, Filip.
Afiliação
  • Talele HR; Institute of Organic Chemistry and Biochemistry of the, Czech Academy of Sciences, Flemingovo nam. 542/2, 166 10, Prague 6, Czech Republic.
  • Koval D; Institute of Organic Chemistry and Biochemistry of the, Czech Academy of Sciences, Flemingovo nam. 542/2, 166 10, Prague 6, Czech Republic.
  • Severa L; Institute of Organic Chemistry and Biochemistry of the, Czech Academy of Sciences, Flemingovo nam. 542/2, 166 10, Prague 6, Czech Republic.
  • Reyes-Gutiérrez PE; Institute of Organic Chemistry and Biochemistry of the, Czech Academy of Sciences, Flemingovo nam. 542/2, 166 10, Prague 6, Czech Republic.
  • Císarová I; Department of Inorganic Chemistry, Charles University, Hlavova 2030/8, 128 43, Prague 2, Czech Republic.
  • Sázelová P; Institute of Organic Chemistry and Biochemistry of the, Czech Academy of Sciences, Flemingovo nam. 542/2, 166 10, Prague 6, Czech Republic.
  • Saman D; Institute of Organic Chemistry and Biochemistry of the, Czech Academy of Sciences, Flemingovo nam. 542/2, 166 10, Prague 6, Czech Republic.
  • Bednárová L; Institute of Organic Chemistry and Biochemistry of the, Czech Academy of Sciences, Flemingovo nam. 542/2, 166 10, Prague 6, Czech Republic.
  • Kasicka V; Institute of Organic Chemistry and Biochemistry of the, Czech Academy of Sciences, Flemingovo nam. 542/2, 166 10, Prague 6, Czech Republic.
  • Teplý F; Institute of Organic Chemistry and Biochemistry of the, Czech Academy of Sciences, Flemingovo nam. 542/2, 166 10, Prague 6, Czech Republic.
Chemistry ; 24(30): 7601-7604, 2018 May 28.
Article em En | MEDLINE | ID: mdl-29575285
Diquats with extremely high racemization barriers with ΔG≠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.
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Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2018 Tipo de documento: Article

Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2018 Tipo de documento: Article