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Synthesis, Resolution, Configurational Stability, and Properties of Cationic Functionalized [5]Helicenes

Published inJournal of Organic Chemistry, vol. 85, no. 18, p. 11908-11923
Publication date2020
Abstract

A straightforward approach to the synthesis of two different series of cationic [5]helicenes has been achieved including, in dioxa series, the possibility to introduce aromatic functional groups at the periphery of the helical structure. While photophysical study highlights that the introduction of aryl substituents at position 23 of the helical moieties has a negligible impact on the optical properties, styryl substituents allow a welcoming extension of the conjugation pathways. Finally, a red shift of the optical properties was evidenced upon introduction of nitrogen atoms in the helicene scaffold, leading to particularly good fluorescence efficiencies in the red domain for a helicenic dye. Detailed information on racemization kinetics was collected for the most stable species upon direct high-performance liquid chromatography (HPLC) resolution or, when configurational lability was too high, through VT-HPLC analysis on the chiral stationary phase (ΔG‡ values ranging from 85.0 to 137.1 kJ·mol–1 and above).

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Citation (ISO format)
MARINOVA, Maya Krasimirova et al. Synthesis, Resolution, Configurational Stability, and Properties of Cationic Functionalized [5]Helicenes. In: Journal of Organic Chemistry, 2020, vol. 85, n° 18, p. 11908–11923. doi: 10.1021/acs.joc.0c01716
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ISSN of the journal0022-3263
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Creation09/18/2020 6:13:00 PM
First validation09/18/2020 6:13:00 PM
Update time03/15/2023 10:37:55 PM
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