Organocatalytic Hydrogen Bond Donor/Lewis Base (HBD/LB) Synthesis and Chiroptical Properties of Thiabridged [5]helicenes

Overview

Journal Org Biomol Chem

Publisher Royal Society of Chemistry

Specialties Biochemistry
Chemistry

Date 2024 Jul 23

PMID 39040026

Authors

Michela Lupi

Mose Fabbri

Giuseppe Mazzeo

Giovanna Longhi

Sergio Abbate

Caterina Viglianisi

Stefano Menichetti

Affiliations

Soon will be listed here.

Abstract

Thiabridged [5]helicenes are obtained from thioaryl--phthalimido benzo[]phenothiazines using a hydrogen bond donor/Lewis base organocatalytic approach. Resolution of [5]helicenes using either (1)-(-)-camphanic acid as a chiral auxiliary or CSP-HPLC is reported. Thiabridged [5]helicenes show an exceptional configurational stability with racemization energy barriers higher than 40 kcal mol. Electronic circular dichroism and TD-DFT calculations permit the assignment of the absolute configuration, demonstrating that the sign of optical rotation is not easily related to the or structure. Separated enantiomers show circularly polarized luminescence with high dissymmetry ratio.

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