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Accueil du site > À la une > Controlling the canonical/zwitterionic balance through intramolecular proton transfer : a strategy for vapochromism

Controlling the canonical/zwitterionic balance through intramolecular proton transfer : a strategy for vapochromism

Simon Pascal, Lucien Lavaud, Cloé Azarias, Gabriel Canard, Michel Giorgi, Denis Jacquemin and Olivier Siri Material Chemistry Frontiers 2018, 2, 1618-1625 (DOI : 10.1039/C8QM00171E)

The detection of volatile organic compounds (VOC) is of particular interest for the protection against harmful chemical species. In the context of optical gas detection, vapochromic materials are highly sought and so far mainly represented by organometallic and coordination complexes.

In this publication we report the design of a new family of organic compounds derived from diamino-benzoquinone diimines which display an unprecedented equilibrium between (uncharged) canonical and zwitterionic ground states, enabled by an intramolecular proton transfer.

For the first time, the subtle variation of electronic richness of the quinone allows to control the canonical vs zwitterionic equilibrium through the tuning of the intramolecular proton transfer and generate colorful species. Such a color change is advantageously used for the rapid and naked-eye detection of N,N-dimethylformamide using the quinone as an efficient vapochromic material.

This work is issued from a collaboration between Dr. Denis Jacquemin at the University of Nantes (CEISAM), Dr. Simon Pascal and Dr. Olivier Siri from at the CNRS/Aix-Marseille University (CINaM).

Ref : S. Pascal, L. Lavaud, C. Azarias, G. Canard, M. Giorgi, D. Jacquemin and O. Siri, Mater. Chem. Front., 2018, 2, 10186 (DOI : 10.1039/C8QM00171E)

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