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 | Zendy

Yangyang Qu | Zendy; Piotr Pander | Zendy; Oleh Vybornyi | Zendy; Marharyta Vasylieva | Zendy; Régis Guillot | Zendy; Fabien Miomandre | Zendy; Fernando B. Dias | Zendy; Peter J. Skabara | Zendy; Przemysław Data | Zendy; Gilles Clavier | Zendy; Pierre Audebert | Zendy

Open Access

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

Author(s) -

Yangyang Qu,

Piotr Pander,

Oleh Vybornyi,

Marharyta Vasylieva,

Régis Guillot,

Fabien Miomandre,

Fernando B. Dias,

Peter J. Skabara,

Przemysław Data,

Gilles Clavier,

Pierre Audebert

Publication year - 2020

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.9b02817

Subject(s) - chemistry , coupling reaction , photoluminescence , diels–alder reaction , acceptor , cross reactions , electron acceptor , coupling (piping) , photochemistry , inverse , organic chemistry , catalysis , physics , condensed matter physics , mechanical engineering , geometry , mathematics , engineering , antibody , optics , immunology , biology

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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