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Donor-acceptor 1,2,4,5-tetrazines prepared by Buchwald-Hartwig cross-coupling reaction and their photoluminescence turn-on property by inverse electron demand Diels-Alder reaction.

Qu, Yangyang and Pander, Piotr Henryk and Vybornyi, Oleh and Vasylieva, Marharyta and Guillot, Régis and Miomandre, Fabien and Dias, Fernando B. and Skabara, Peter J. and Data, Przemyslaw and Clavier, Gilles and Audebert, Pierre (2020) 'Donor-acceptor 1,2,4,5-tetrazines prepared by Buchwald-Hartwig cross-coupling reaction and their photoluminescence turn-on property by inverse electron demand Diels-Alder reaction.', The journal of organic chemistry., 85 (5). pp. 3407-3416.

Abstract

A facile efficient synthetic tool, Buchwald-Hartwig cross-coupling reaction, for the functionalization of 1,2,4,5-tetrazines is presented. Important factors affecting the Buchwald-Hartwig cross-coupling reaction have been optimized. Seven new donor-acceptor tetrazine molecules (TA1-TA7) were conveniently prepared in good to high yields (61%-72%). They have been subsequently engaged in inverse Electron Demand Diels-Alder (iEDDA) reaction with cyclooctyne. The photophysical and electrochemical properties of the new pyridazines have been studied. Some are fluorescent acting as turn-on probes. More importantly two pyridazines (DA3 and DA6) exhibit room temperature phosphorescence (RTP) properties.

Item Type:Article
Full text:(AM) Accepted Manuscript
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Status:Peer-reviewed
Publisher Web site:https://doi.org/10.1021/acs.joc.9b02817
Publisher statement:This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.9b02817
Date accepted:No date available
Date deposited:29 January 2020
Date of first online publication:24 January 2020
Date first made open access:24 January 2021

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