Modular Synthesis, Orthogonal Post-Functionalization, Absorption, and Chiroptical Properties of Cationic [6]Helicenes

Torricelli, Franck; Bosson, Johann; Besnard, Céline; Chekini, Mahshid; Buergi, Thomas; Lacour, Jérôme

doi:10.1002/anie.201208926

Scientific article

English

Modular Synthesis, Orthogonal Post-Functionalization, Absorption, and Chiroptical Properties of Cationic [6]Helicenes

ContributorsTorricelli, Franck; Bosson, Johann; Besnard, Céline; Chekini, Mahshid; Buergi, Thomas; Lacour, Jérôme

Published inAngewandte Chemie, vol. 52, no. 6, p. 1796-1800

Publication date2013

Abstract

Pick and choose: Novel cationic diaza-, azaoxo-, and dioxo[6]helicenes are readily prepared and functionalized selectively by orthogonal aromatic electrophilic and vicarious nucleophilic substitutions (see scheme). Reductions, cross-coupling, or condensation reactions introduce additional diversity and allow tuning of the absorption properties up to the near-infrared region. The diaza salts can be resolved into single enantiomers.

Keywords

Arenes
Helical structures
Synthetic methods
UV/Vis spectroscopy
Vicarious nucleophilic substitution

Affiliation entities

Citation (ISO format)

TORRICELLI, Franck et al. Modular Synthesis, Orthogonal Post-Functionalization, Absorption, and Chiroptical Properties of Cationic [6]Helicenes. In: Angewandte Chemie, 2013, vol. 52, n° 6, p. 1796–1800. doi: 10.1002/anie.201208926

Article (Published version)

Identifiers

PID : unige:26214
DOI : 10.1002/anie.201208926

Journal ISSN1433-7851

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Modular Synthesis, Orthogonal Post-Functionalization, Absorption, and Chiroptical Properties of Cationic [6]Helicenes

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