A Chiral Dicationic [8]Circulenoid: Photochemical Origin and Facile Thermal Conversion into a Helicene Congener

0385590 - ÚOCHB 2013 RIV DE eng J - Journal Article
Severa, Lukáš - Ončák, M. - Koval, Dušan - Pohl, Radek - Šaman, David - Císařová, I. - Reyes Gutierrez, Paul Eduardo - Sázelová, Petra - Kašička, Václav - Teplý, Filip - Slavíček, P.
A Chiral Dicationic [8]Circulenoid: Photochemical Origin and Facile Thermal Conversion into a Helicene Congener.
Angewandte Chemie - International Edition. Roč. 51, č. 48 (2012), s. 11972-11976. ISSN 1433-7851. E-ISSN 1521-3773
R&D Projects: GA ČR GA203/09/1614; GA ČR GAP207/10/2391; GA ČR(CZ) GA203/08/1428
Grant - others:GA ČR(CZ) GA203/09/0422; GA MŠk(CZ) ME08086
Program: GA
Institutional support: RVO:61388963
Keywords : capillary electrophoresis * cationic circulenes * closed helicenoids * isomerization * photochemistry
Subject RIV: CC - Organic Chemistry
Impact factor: 13.734, year: 2012

Circulene-like species has been transformed, for the first time, into its helical counterpart by exclusive application of heat. Synthesis, structure, and properties of the chiral dicationic [8]circulenoid are reported. The presented results are significant from several further perspectives: 1) no nitrogen-based cationic circulene compound has been reported before; 2) a rare saddle-shaped circulene system with order higher than [7] is presented; 3) the synthetic sequence leading to the chiral [8]circulenoid 1 based on the key [6+6] photocycloaddition is particularly succinct as it requires only five synthetic steps and no chromatographic purification. In this context, it is notable that photochemical strategies towards circulenes have remained overlooked so far.
Permanent Link: http://hdl.handle.net/11104/0007312