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

2019; American Chemical Society; Volume: 84; Issue: 17 Linguagem: Inglês

10.1021/acs.joc.9b01465

1520-6904

Laure Guy, Maëlle Mosser, Delphine Pitrat, Jean‐Christophe Mulatier, Mercedes Kukułka, Monika Srebro‐Hooper, Erwann Jeanneau, Amina Bensalah‐Ledoux, Bruno Baguenard, Stéphan Guy,

Photoreceptor and optogenetics research

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) (glum = 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.