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The small Stokes shift and weak emission in the solid state are two main shortcomings associated with the boron-dipyrromethene (BODIPY) family of dyes. This study presents the design, synthesis and luminescent properties of boron difluoro complexes of 2-aryl-5-alkylamino-4-alkylaminocarbonylthiazoles. These dyes display Stokes shifts (Delta lambda, 77-101 nm) with quantum yields (phi(FL)) up to 64.9 and 34.7 % in toluene solution and in solid state, respectively. Some of these compounds exhibit dual fluorescence and room-temperature phosphorescence (RTP) emission properties with modulable phosphorescence quantum yields (phi(PL)) and lifetime (tau(p) up to 251 mu s). The presence of intramolecular H-bonds and negligible pi-pi stacking revealed by X-ray crystal structure might account for the observed large Stokes shift and significant solid-state emission of these fluorophores, while the enhanced spin-orbit coupling (SOC) of iodine and the self-assembly driven by halogen bonding, pi-pi and C-H center dot center dot center dot pi interactions could be responsible for the observed RTP of iodine containing phosphors.
Christophe Marcel Georges Galland, Konstantin Malchow, Wen Chen, Sakthi Priya Amirtharaj
Christophe Ballif, Jonathan Emanuel Thomet, Janina Christine Isabelle Löffler, Samira Alexandra Frey, Mohamed Belhaj