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

Yangyang Qu (1) , Piotr Pander (2) , Oleh Vybornyi (3) , Marharyta Vasylieva (4) , Régis Guillot (5) , Fabien Miomandre (1) , Fernando B Dias (2) , Peter Skabara (3) , Przemyslaw Data (4) , Gilles Clavier (1) , Pierre Audebert (1)

1 PPSM - Photophysique et Photochimie Supramoléculaires et Macromoléculaires
2 Durham University
3 University of Glasgow
4 Silesian University of Technology
5 ICMMO - Institut de Chimie Moléculaire et des Matériaux d'Orsay

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.

Domaines: Chimie organique

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⟩