Donor–Acceptor 1,2,4,5-Tetrazines Prepared by the Buchwald–Hartwig Cross-Coupling Reaction and Their Photoluminescence Turn-On Property by Inverse Electron Demand Diels–Alder Reaction
dataset
posted on 2020-02-12, 18:08 authored by Yangyang Qu, Piotr Pander, Oleh Vybornyi, Marharyta Vasylieva, Régis Guillot, Fabien Miomandre, Fernando B. Dias, Peter Skabara, Przemyslaw Data, Gilles Clavier, Pierre AudebertA 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 the 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.
