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Persistent Organic Room-Temperature Phosphorescence in Cyclohexane-Trans-1,2-Bisphthalimide Derivatives: The Dramatic Impact of Heterochiral vs. Homochiral Interactions

preprint
submitted on 10.06.2020, 11:14 and posted on 12.06.2020, 06:27 by Ludovic Favereau, Cassandre Quinton, Cyril Poriel, Thierry Roisnel, Denis Jacquemin, Jeanne Crassous
Persistent metal-free Room-Temperature Phosphorescence (RTP) materials attract significant interest owing to the production of long-lived triplet excited states. Although several organic designs show RTP, the impact of intermolecular interactions on the triplet excitons stabilization and migrations remains hardly understood because obtaining different ordered intermolecular interactions while conserving identical molecular electronic properties is very challenging. We propose here a new strategy to circumvent this problem by taking advantage of the distinct molecular packing that can be found between enantiomer and racemic forms of a chiral molecule. Structural, photophysical and chiroptical investigations of chiral cyclohexane bisphthalimide derivatives showed that heterochiral and homochiral dimer interactions play a crucial role on the triplet excited state stabilization, resulting in higher RTP efficiency for enantiopure systems than for racemic one. This study paves the way to the use of molecular chirality to rationalize supramolecular properties arising from subtle intermolecular interactions.

History

Email Address of Submitting Author

ludovic.favereau@univ-rennes1.fr

Institution

Univ Rennes, CNRS, ISCR-UMR 6226

Country

Rennes

ORCID For Submitting Author

0000-0001-7847-2911

Declaration of Conflict of Interest

no conflict interest

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