Development of Separation Methods for the Chiral Resolution of Hexahelicenes.

0472516 - ÚCHP 2017 RIV NL eng J - Journal Article
Storch, Jan - Kalíková, K. - Tesařová, E. - Maier, V. - Vacek, J.
Development of Separation Methods for the Chiral Resolution of Hexahelicenes.
Journal of Chromatography A. Roč. 1476, DEC 9 (2016), s. 130-134. ISSN 0021-9673. E-ISSN 1873-3778
R&D Projects: GA TA ČR TA04010082
Institutional support: RVO:67985858
Keywords : capillary electrophoresis * chirality * helicene
Subject RIV: CC - Organic Chemistry
Impact factor: 3.981, year: 2016

In this short communication we report optimized procedures for the chiral separation of non-charged [6]helicene (1) and cationic derivative 1-butyl-3-(2-methyl[6]helicenyl)-imidazolium bromide (2) using high-performance liquid chromatography (HPLC) and supercritical fluid chromatography (SFC) methods. The possibility of using capillary electrophoresis (CE) was also tested. The satisfactory results were obtained with SFC, where the highly selective resolution of four enantiopure 1 and 2 helicenes was achieved in a single run within 5 min. The semi-preparative procedure for the isolation of P and M enantiomers of compound 2, including circular dichroism data, is reported here for the first time. The results could be used in further separations and analytical applications targeting carbohelicenes vs. positively charged helicene derivatives.
Permanent Link: http://hdl.handle.net/11104/0269809