Resolution of 9,10-Diketo[7]helicene and Its Use in One-Step Preparation of Helicene-Based D-A-D Push-Pull Systems

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2024 May 28

PMID 38804645

Authors

Martin Kos

Tomas Beranek

Ivana Cisarova

Petra Curinova

Jaroslav Zadny

Jan Storch

Vladimir Cirkva

Martin Jakubec

Affiliations

Soon will be listed here.

Abstract

Racemic 9,10-diketo[7]helicene was successfully separated into enantiomers using a reversible and stereoselective reaction with 2,2'-diamino-1,1'-binaphthalene with moderate yields but with remarkable purity (>99% de). The enantiomerically pure diketone was used as a convenient starting material for the preparation of helicene-based push-pull molecules, which incorporated aza-aryl acceptors and diarylaminophenylene donor groups in a single step. A series of six push-pull systems, along with three reference molecules without donors, were prepared and studied using UV/vis and fluorescence measurements, circular dichroism, and DFT calculations.

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