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

Ludovic Favereau (1, 2) , Cassandre Quinton (2, 1) , Cyril Poriel (2, 1) , Thierry Roisnel (2, 1) , Denis Jacquemin (3) , Jeanne Crassous (2, 1)

1 ScanMAT - Synthèse Caractérisation Analyse de la Matière
2 ISCR - Institut des Sciences Chimiques de Rennes
3 CEISAM - Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation

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.

Domains: Chemical Sciences; Organic chemistry

Ludovic Favereau, Cassandre Quinton, Cyril Poriel, Thierry Roisnel, Denis Jacquemin, et al.. Persistent Organic Room-Temperature Phosphorescence in Cyclohexane-trans-1,2- Bisphthalimide Derivatives: The Dramatic Impact of Heterochiral vs. Homochiral interactions. Journal of Physical Chemistry Letters, 2020, 11 (15), pp.6426-6434. ⟨10.1021/acs.jpclett.0c01816⟩. ⟨hal-02999452⟩