Yangyang Qu
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; Pander, Piotr Henryk; Vybornyi, Oleh; Vasylieva, Marharyta; Guillot, Régis; Miomandre, Fabien; Dias, Fernando B.; Skabara, Peter J.; Data, Przemyslaw; Clavier, Gilles; Audebert, Pierre
Authors
Piotr Pander piotr.h.pander@durham.ac.uk
Academic Visitor
Oleh Vybornyi
Marharyta Vasylieva
Régis Guillot
Fabien Miomandre
Dr Fernando Dias f.m.b.dias@durham.ac.uk
Associate Professor
Peter J. Skabara
Przemyslaw Data
Gilles Clavier
Pierre Audebert
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.
Journal Article Type | Article |
---|---|
Online Publication Date | Jan 24, 2020 |
Publication Date | Mar 6, 2020 |
Deposit Date | Jan 29, 2020 |
Publicly Available Date | Jan 24, 2021 |
Journal | Journal of Organic Chemistry |
Print ISSN | 0022-3263 |
Electronic ISSN | 1520-6904 |
Publisher | American Chemical Society |
Peer Reviewed | Peer Reviewed |
Volume | 85 |
Issue | 5 |
Pages | 3407-3416 |
DOI | https://doi.org/10.1021/acs.joc.9b02817 |
Public URL | https://durham-repository.worktribe.com/output/1272730 |
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Copyright 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
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