Article Dans Une Revue Journal of Organic Chemistry Année : 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

Résumé

A facile efficient synthetic tool, Buchwald-Hartwig cross-coupling reaction, for the functionalization of 1,2,4,5tetrazines 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.

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hal-03024473 , version 1 (25-11-2020)

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Yangyang Qu, Piotr Pander, Oleh Vybornyi, Marharyta Vasylieva, Régis Guillot, et al.. 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, 2020, 85 (5), pp.3407-3416. ⟨10.1021/acs.joc.9b02817⟩. ⟨hal-03024473⟩
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