Modulation of Chiroptical Properties in a Series of Helicene-like Compounds

Laure Guy (1) , Maëlle Mosser (1) , Delphine Pitrat (1) , Jean-Christophe Mulatier (1) , Mercedes Kukułka (2) , Monika Srebro-Hooper (2) , Erwann Jeanneau (3, 4) , Amina Bensalah-Ledoux (5) , Bruno Baguenard (5) , Stéphan Guy (5)

1 LC - Laboratoire de Chimie - UMR5182
2 Jagiellonian Univ, Fac Chem
3 LMI - Laboratoire des Multimatériaux et Interfaces
4 Centre de diffractométrie Henri Longchambon
5 iLM - MNP - iLM - Matériaux et nanostructures photoniques

We describe a large-scale synthesis of a series of helicene-like compounds based on a dibenzo[c]acridine fragment by the Friedlander reaction. The series includes targeted constrained (closed) derivatives comprising 11 rings that exhibit very intense circularly polarized luminescence (CPL) (g_lum = 8 × 10^–3) contrary to their nonconstrained (open) 10-ring precursors that are not CPL active. The relationship between structure and chiroptical properties in the series is discussed with the aid of quantum-chemical calculations.

Mots clés: Reaction products; Molecules; Circular dichroism spectroscopy; Aromatic compounds; Molecular structure

Domaines: Chimie organique; Cristallographie

Laure Guy, Maëlle Mosser, Delphine Pitrat, Jean-Christophe Mulatier, Mercedes Kukułka, et al.. Modulation of Chiroptical Properties in a Series of Helicene-like Compounds. Journal of Organic Chemistry, 2019, 84 (17), pp.10870-10876. ⟨10.1021/acs.joc.9b01465⟩. ⟨hal-02316017⟩