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Double Click for Chirality: Chiral Dibenzo-cycloocta-bis-triazoles via Strain-Promoted Alkyne-Azide Cycloaddition

Lookup NU author(s): Aaron Campbell, Dr Michael HallORCiD, Dr Roly ArmstrongORCiD

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This work is licensed under a Creative Commons Attribution 4.0 International License (CC BY 4.0).

Abstract

The synthetically convenient strain promoted double azide cycloaddition of the Sondheimer-Wong diyne produces resolvable chiral dibenzo-cycloocta-bis-triazoles whose stereogenicity, to date, has gone unrecognised. Enantiomers were separable by chiral HPLC and showed no racemization at 100 °C. This unique method to produce chiral substrates was exploited for the synthesis and resolution of a chiral fluorescent BF₂-azadipyrromethene, with absorption and emission spanning the important spectral range of 600 to 700 nm. The fluorophore properties were studied utilising X-ray structural analysis, electronic circular dichroism spectra and DFT calculations.

Publication metadata

Author(s): O'Shea D, Pim S, Campbell ADG, Levshov D, Herrebout W, Durán-Sampedro D, Hall MJ, Armstrong R

Publication type: Article

Publication status: Published

Journal: ChemPhotoChem

Year: 2025

Pages: epub ahead of print

Online publication date: 14/03/2025

Acceptance date: 13/03/2025

Date deposited: 20/03/2025

ISSN (electronic): 2367-0932

Publisher: Wiley-VCH Verlag GmbH & Co. KGaA

URL: https://doi.org/10.1002/cptc.202500042

DOI: 10.1002/cptc.202500042

ePrints DOI: 10.57711/88mq-pe52

Data Access Statement: The data that support the findings of this study are available in the supplementary material of this article. All computational data can be obtained at the open access Zenodo repository at the DOI identifier: 10.5281/zenodo.14055785

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