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

Qu, Y. et al. (2020) 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. Journal of Organic Chemistry, 85(5), pp. 3407-3416. (doi: 10.1021/acs.joc.9b02817) (PMID:31975598)

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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.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Vybornyi, Mr Oleh and Skabara, Professor Peter
Authors: Qu, Y., Pander, P., Vybornyi, O., Vasylieva, M., Guillot, R., Miomandre, F., Dias, F. B., Skabara, P., Data, P., Clavier, G., and Audebert, P.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Journal of Organic Chemistry
Publisher:American Chemical Society
ISSN:0022-3263
ISSN (Online):1520-6904
Published Online:24 January 2020
Copyright Holders:Copyright © 2020 American Chemical Society
First Published:First published in Journal of Organic Chemistry 85(5): 3407-3416
Publisher Policy:Reproduced in accordance with the publisher copyright policy

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
303468EXCILIGHTPeter SkabaraEuropean Commission (EC)674994Chemistry