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Issue 21, 2019
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Renewing accessible heptazine chemistry: 2,5,8-tris(3,5-diethyl-pyrazolyl)-heptazine, a new highly soluble heptazine derivative with exchangeable groups, and examples of newly derived heptazines and their physical chemistry

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Abstract

We have prepared 2,5,8-tris(3,5-diethyl-pyrazolyl)-heptazine, the first highly soluble heptazine derivative possessing easily exchangeable leaving groups. We present its original synthesis employing mechanochemistry, along with a few examples of its versatile reactivity. It is, in particular, demonstrated that the pyrazolyl leaving groups can be replaced by several secondary or primary amino substituents or by three aryl- or benzyl-thiol substituents. In addition to being a synthetic platform, 2,5,8-tris(3,5-diethyl-pyrazolyl)-heptazine is fluorescent and electroactive, and its attractive properties, as well as those of the derived heptazines, are briefly presented.

Graphical abstract: Renewing accessible heptazine chemistry: 2,5,8-tris(3,5-diethyl-pyrazolyl)-heptazine, a new highly soluble heptazine derivative with exchangeable groups, and examples of newly derived heptazines and their physical chemistry

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Supplementary files

Article information


Submitted
07 Feb 2019
Accepted
23 Apr 2019
First published
25 Apr 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 5513-5518
Article type
Edge Article

Renewing accessible heptazine chemistry: 2,5,8-tris(3,5-diethyl-pyrazolyl)-heptazine, a new highly soluble heptazine derivative with exchangeable groups, and examples of newly derived heptazines and their physical chemistry

L. Galmiche, C. Allain, T. Le, R. Guillot and P. Audebert, Chem. Sci., 2019, 10, 5513
DOI: 10.1039/C9SC00665F

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