Coronenohelicenes with Dynamic Chirality

Weiß C, Sharapa DI, Hirsch A (2020)

Publication Type: Journal article

Publication year: 2020

Journal

DOI: 10.1002/chem.202001703

Abstract

The synthesis of a new type of chiral and dynamic nonplanar aromatics containing a combination of fused perylene-based coronenes and helicenes is reported. Either one or two helicene moieties were fused to the bay regions of an extended perylene core. The target compounds contain either identical or two different helicene building blocks. The combination with two helicene units leads to six different isomers, including two pairs of enantiomers and two meso forms. The experimental determination of the isomerization barriers the corresponding double [5]-helicenes revealed activation energies of Ea=24.81 and 25.38 kcal mol⁻¹, which is slightly above the barrier of the parent [5]-helicene. Resolution of all possible regio- and stereoisomers allowed for the systematic investigation of the chiroptical properties. They revealed remarkable dissymmetry factors IgabsI of up to 1.2×10⁻², which mirror the synergy between the strong absorbing perylenes and the inherent chirality of helicenes.

Authors with CRIS profile

Corinna Weiß Lehrstuhl für Organische Chemie II Andreas Hirsch Lehrstuhl für Organische Chemie II

Involved external institutions

Karlsruhe Institute of Technology (KIT)

Germany (DE)

How to cite

APA:

Weiß, C., Sharapa, D.I., & Hirsch, A. (2020). Coronenohelicenes with Dynamic Chirality. Chemistry - A European Journal. https://dx.doi.org/10.1002/chem.202001703

MLA:

Weiß, Corinna, Dmitry I. Sharapa, and Andreas Hirsch. "Coronenohelicenes with Dynamic Chirality." Chemistry - A European Journal (2020).

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