A highly efficient solution and solid state ESIPT fluorophore and its OLED application

Abstract

Readily accessible and functionalized ESIPT dyes with high fluorescence quantum yield in solution, including water, and in crystalline state are presented.

Synthesis and Optical Properties of Excited-State Intramolecular Proton Transfer (ESIPT) Emitters with Sulfobetaine Fragments

“…4. The absorption and emission of [8][9][10]12,13,15 and 16 in PBS with 10% DMSO or pure PBS can be seen on Fig. 5.…”

“…11 Recent trends include the search for dual-state emission (DSE) 12 based on ESIPT fluorescence by introduction of molecular rigidification 13 or stabilization of excited species by resonance effects. 14 There is currently a rich database of molecular scaffolds displaying ESIPT including 2,2′-bipyridine-diol, 15 2,5-dithienylpyrrole 16 or imidazo[1,2- f ]phenanthridine 17 examples. 2-(2′-Hydroxyphenyl)benzazole (HBX) dyes 18 and their benzofuran-extended 2-(2′-hydroxybenzofuranyl)benzazole (HBBX) 19 analogs have also been widely used as model ESIPT dyes for molecular engineering studies due to their synthetic availability, stability and possibility to fine-tune the optical properties by introduction of small molecular inputs.…”

N-Hydroxy–N-oxide photoinduced tautomerization and excitation wavelength dependent luminescence of ESIPT-capable zinc(ii) complexes with a rationally designed 1-hydroxy-2,4-di(pyridin-2-yl)-1H-imidazole ESIPT-ligand

“…As a result of the excited state tautomerization, the ESIPT-fluorophores tend to exhibit large Stokes shifts which reduce the inner filter effect and are not achievable for most conventional fluorophores. 1–15…”

Excited-State Intramolecular Proton Transfer in 2-(2′-Hydroxyphenyl)pyrimidines: Synthesis, Optical Properties, and Theoretical Studies

“… 11 , 12 Because of the major structural reorganization, the fluorescence properties are highly sensitive to the microenvironment. Thus, the dual emission of the ESIPT molecules is finely tunable and has found numerous applications in fields such as UV photostabilizers, 13 , 14 fluorescent probes and imaging agents, 15 − 19 and organic optoelectronic devices, 20 − 25 among others.…”