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

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., Dias, F. B., Skabara, P. J., Data, P., Clavier, G., & 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
• Public URL: https://durham-repository.worktribe.com/output/1272730