Large‐Scale Synthesis of Helicene‐Like Molecules for the Design of Enantiopure Thin Films with Strong Chiroptical Activity

Abstract

Helicenes are fascinating molecules owing to their unusual properties and applications in many fields from catalysis to organic electronics. Herein, we report a straightforward pathway for the synthesis of helicene-like molecules on a gram scale in an enantiopure form. Thin-film materials with good propagating optical properties and very high chiroptical responses have been grown by using pulsed laser ablation without altering the structure or the enantiopurity of the molecules. Moreover, electronic and vibrational circular dichroism spectroscopies coupled with theoretical calculations enabled some dependences of the chiroptical properties with the structure to be highlighted, for example, effects of rigidification, aromatization, or the state of matter (liquid versus solid).

Light-inducedin situchemical activation of a fluorescent probe for monitoring intracellular G-quadruplex structures

“…The water-soluble bisquinoline 1 is obtained in one step by Opegylation of its previously described phenol precursor 14 according to the Scheme 1 (SI for full synthetic procedure, NMR spectra Fig. S1-S3).…”

“…10,12 In a recent series of papers, we have described a low-cost and high-yielding, gram-scale synthetic procedure that afforded enantiopure binaphthol-like compounds featuring extended quinoline moieties, a motif quite commonly found in bioactive molecules. [14][15][16] In the present paper, we describe how, upon UV light irradiation of 1, selective conversion to a new emissive photoproduct 2 is achieved where the intramolecular macrocyclization of the individual quinoline moieties occur with significant extension of the aromatic skeleton of the molecule (Scheme 1 and Fig. 1A).…”

Au10(SG)10: A Chiral Gold Catenane Nanocluster with Zero Confined Electrons. Optical Properties and First-Principles Theoretical Analysis

“…Fluorescence excitation and emission spectra were obtained using a Fluoromax-4 Horiba fluorimeter. CD spectra were recorded using a homemade setup based on a photoelastic modulator and a lock-in amplifier detection device previously described in ref .…”

“…Fluorescence excitation and emission spectra were obtained using a Fluoromax-4 Horiba fluorimeter.CD spectra were recorded using a home-made setup based on a Photo Elastic Modulator and a lock-in amplifier detection device previously described in ref. [40] Nonlinear optical measurements. The set-up for Hyper-Rayleigh Scattering (HRS) and twophoton fluorescence emission (TPEF) has been described in details in previous works [11][12][13].…”

Effect of the Metal–Ligand Interface on the Chiroptical Activity of Cysteine‐Protected Nanoparticles

“…These g factor values are relatively high and comparable to helicene‐like molecules that have been classified as strong chiroptical systems. [ 64 ]…”