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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; Pander, Piotr Henryk; Vybornyi, Oleh; Vasylieva, Marharyta; Guillot, Régis; Miomandre, Fabien; Dias, Fernando B.; Skabara, Peter J.; Data, Przemyslaw; Clavier, Gilles; Audebert, Pierre

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 Thumbnail


Authors

Yangyang Qu

Oleh Vybornyi

Marharyta Vasylieva

Régis Guillot

Fabien Miomandre

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.

Citation

Qu, Y., Pander, P. H., Vybornyi, O., Vasylieva, M., Guillot, R., Miomandre, F., …Audebert, P. (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. Journal of Organic Chemistry, 85(5), 3407-3416. https://doi.org/10.1021/acs.joc.9b02817

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

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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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