Convergent and Practical Synthesis of Fluorescent Triphenylamine Derivatives and Their Localization in Living Cells

Romain Mougeot (1) , Samuel Oger (1) , Marie Auvray (2) , Thibault Gallavardin (1) , Stéphane Leleu (1) , Florence Mahuteau-Betzer (2) , Xavier Franck (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
2 CMBC - Chimie et modélisation pour la biologie du cancer

In the search for new fluorescent triphenylamine (TP) derivatives, we studied the influence of the position and substitution of diverse heterocyclic substituents. A library of 10 fluorescent triphenylamines bearing either oxazoles or thiazoles and pyridiniums, substituted at different positions has been developed. The approach is based on a convergent C-H activation reaction between pyridineoxazoles or pyridine-thiazoles and di-iodo triphenylamine. We showed that the nature and substitution pattern of the 5-membered-(oxazole, thiazole) or 6-membered heterocycle (pyridine) has a strong influence on their fluorescence properties and on their localization in living cells as they stain either the nucleus or mitochondria.

Domaines: Chimie organique; Chimie théorique et/ou physique; Imagerie

Romain Mougeot, Samuel Oger, Marie Auvray, Thibault Gallavardin, Stéphane Leleu, et al.. Convergent and Practical Synthesis of Fluorescent Triphenylamine Derivatives and Their Localization in Living Cells. European Journal of Organic Chemistry, 2022, 2, ⟨10.1002/ejoc.202101397⟩. ⟨hal-03487097⟩