Customizing photoredox properties of PXX-based dyes through energy level rigid shifts of frontier molecular orbitals

Sciutto, Andrea, Fermi, Andrea, Folli, Andrea ORCID: https://orcid.org/0000-0001-8913-6606, Battisti, Tommaso, Beames, Joseph ORCID: https://orcid.org/0000-0002-5508-8236, Murphy, Damien ORCID: https://orcid.org/0000-0002-5941-4879 and Bonifazi, Davide ORCID: https://orcid.org/0000-0001-5717-0121 2018. Customizing photoredox properties of PXX-based dyes through energy level rigid shifts of frontier molecular orbitals. Chemistry - a European Journal 24 (17) , pp. 4382-4389. 10.1002/chem.201705620

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Abstract

Here we describe the synthesis of electron-rich PXX derivatives in which the energy levels of the excited states have been tailored through the insertion of imide groups. This has allowed the development of a new series of oxygen-doped photoredox-active chromophores with improved oxidizing and reducing properties. Capitalizing on the dehalogenation of organic halides as a model reaction, we could investigate the photooxidative and photoreductive potential of these molecules in model chemical transformations. This prompted us to consider the first chemoselective transformation protocol, in which two different C-Br bonds could be chemoselectively reacted through the sequential photoactivation of two different colorants.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Publisher:	WileyBlackwell
ISSN:	0947-6539
Funders:	ERC and Marie Curie
Date of First Compliant Deposit:	19 December 2017
Date of Acceptance:	11 December 2017
Last Modified:	05 Nov 2024 18:00
URI:	https://orca.cardiff.ac.uk/id/eprint/107683

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