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.
J Org Chem
; 85(5): 3407-3416, 2020 Mar 06.
Article
em En
| MEDLINE
| ID: mdl-31975598
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 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.
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Base de dados:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2020
Tipo de documento:
Article
País de afiliação:
França