Turning ESIPT-Based triazine fluorophores into dual emitters: From theory to experiment. (April 2019)

• Record Type: Journal Article
• Authors: Jacquemin, Denis; Khelladi, Mustapha; De Nicola, Antoinette; Ulrich, Gilles
• Is Part Of: Dyes and pigments. Volume 163(2019)
• Page Start: 475
• Page End: 482
• Publication Date: 2019-04
• Subjects: Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2018.12.023
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: In an effort to design new dyes presenting multiple fluorescence bands, we use theoretical chemistry to guide the synthesis of new triazine structures undergoing excited-state intramolecular proton transfer (ESIPT). Starting with experimentally-known compounds showing emission from the keto tautomer only, we model several chemically-achievable substitutions aiming to sufficiently frustrate the ESIPT process by stabilising the enol structure in the electronic excited state. In a second step, some of the proposed dyes are synthesised. It turns out that the emergence of an emission band due to the enol confirms the theoretical prediction, though the observed quantum yields in solution are small most probably due to the selection of methoxy substituents. The quantum yields are strongly improved when going to the solid-state as a result of the impeded rotations. Graphical abstract: Highlights: New ESIPT-based dual emitters are conceived with the help of theory. The acceptor (rather than the donor) side is modified. Emission yields are low in solution and moderate in the the solid state.