Abstract
A series of five excited-state intramolecular proton transfer (ESIPT) emitters based on a 2-(2′-hydroxyphenyl) benzoxazole (HBO) scaffold, functionalized with a mono-or bis-(trialkylsilyl) acetylene extended spacer are presented. Investigation of their photophysical properties in solution and in the solid-state in different matrix, along with ab initio calculations gave useful insights into their optical behavior. Random lasing studies were conducted on a series of PMMA doped thin films, showing the presence of stimulated emission above the threshold of pumping energy density (ρth ≈ 0.5–2.6 mJ cm−2). In this work, the similarity of four level laser systems is discussed in light of the ESIPT photocycle.
Highlights
Excited-state intramolecular proton transfer (ESIPT) single or dual emitters serve as efficient fluorophores owing to their attractive optical properties, including large Stokes’ shifts, strong solid-state luminescence efficiency and environment-sensitive emission bands ratio [1,2,3,4,5]
Optimized ESIPT dyes have been successfully applied in a wide array of fields, spanning from optoelectronics [6,7] to cellular fluorescence mapping [8,9], multiple stimuli sensing [10] and polymer science [11]
Several families of ESIPT dyes have been developed, including compounds derived from imidazole [12,13], pyrazole [14], hydroxytriazine [15] or 2,2 -bipyridine-diol [16] cores, ESIPT fluorophores incorporating a 2-(2 -hydroxyphenyl) benzazole (HBX) scaffold remain one of the most interesting families due to their versatile π-conjugated structure, expedite synthesis and overall beneficial modularity [17,18,19,20]
Summary
Excited-state intramolecular proton transfer (ESIPT) single or dual emitters serve as efficient fluorophores owing to their attractive optical properties, including large Stokes’ shifts, strong solid-state luminescence efficiency and environment-sensitive emission bands ratio [1,2,3,4,5]. Several groups have successfully developed ESIPT emitters displaying good photoluminescent quantum yield in solution and in the solid-state, enlarging the potential fields of applications for these innovative dyes [22,23,24].
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