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Synthesis and characterisation of homoleptic 2,9- diaryl-1,10-phenanthroline copper(I) complexes: influencing selectivity in photoredox-catalysed atom-transfer radical addition reactions

Citation

Nicholls, TP and Caporale, C and Massi, M and Gardiner, MG and Bissember, AC, Synthesis and characterisation of homoleptic 2,9- diaryl-1,10-phenanthroline copper(I) complexes: influencing selectivity in photoredox-catalysed atom-transfer radical addition reactions, Dalton Transactions, 48 pp. 7920-7301. ISSN 1477-9226 (2019) [Refereed Article]

Copyright Statement

Copyright 2019 The Royal Society of Chemistry

DOI: doi:10.1039/c8dt04116d

Abstract

This report details the synthesis and characterisation of eight homoleptic bis(2,9-diaryl-1,10-phenanthroline)copper(I) complexes, seven of which are previously unreported {aryl = p-CF3C6H4, p-FC6H4, m,p-(OMe)2C6H3, o,p-(OMe)2C6H3, p-OMe-m,m-Me2C6H2, p-OMe-m,m-(t-Bu)2C6H2, 9,9-dimethyl-9H-fluoren-2-yl, 4-(9H-carbazol-9-yl)phenyl)}. Where possible the solid state, photophysical and electrochemical properties of these complexes were studied. In order to obtain insights into the influence of the intrinsic features of these copper(I) complexes on their reactivity in visible light-mediated photoredox catalysis, their capacity to promote a known atom-transfer radical addition process was evaluated. This specific transformation was identified as a suitable model system as it is reported to proceed via a mechanism consistent with the inner-sphere reactivity enabled by coordinatively unsaturated phenanthroline-based copper(I) species.

Item Details

Item Type:Refereed Article
Keywords:photoredox catalysis, copper, atom-transfer radical addition
Research Division:Chemical Sciences
Research Group:Organic Chemistry
Research Field:Organic Chemical Synthesis
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
UTAS Author:Nicholls, TP (Mr Thomas Nicholls)
UTAS Author:Gardiner, MG (Associate Professor Michael Gardiner)
UTAS Author:Bissember, AC (Dr Alex Bissember)
ID Code:132960
Year Published:2019
Web of Science® Times Cited:4
Deposited By:Chemistry
Deposited On:2019-05-28
Last Modified:2019-06-12
Downloads:0

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