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Fluorescent pH Probes based on PET Quenching of Long Fluorescence Lifetime Triangulenium Dyes Martin Rosenberg, Anne Kathrine R. Junker, Thomas Just S?rensen, and Bo W. Laursen*[a]
摘要： Azaoxatriangulenium dyes with long fluorescence lifetimes offer advantages in fluorescence lifetime imaging (FLIM), time-gated detection and polarization assays. However, the long excited state lifetimes are also expected to increase sensitivity to photoinduced electron transfer (PET) quenching, potentially increasing the on-off ratio of PET probes. We report the synthesis and investigation of the optical properties of azaoxatriangulenium salts substituted with phenol substituents for pH sensing. Two series of pH probes with the phenol hydroxy group placed in the ortho, meta, or para positions to azadioxatriangulenium (ADOTA) and diazaoxatriangulenium (DAOTA) chromophores are investigated. All the phenol substituted dyes possess pH responsive fluorescence signals in the biological relevant pH window (pH 6-9) due to efficient intramolecular PET from the phenolate form of the pendant arm. While the PET mechanism is partly suppressed in the phenol form the ADOTA derivatives, it is completely suppressed in the DAOTA derivatives. The long excited state lifetimes of the triangulenium dyes ensure efficient PET quenching leading to very high on-off ratios of the pH probes. The study clearly demonstrates effects of the position of the phenol/phenolate group relative to the chromophore on both PET quenching rates and pKa values.
关键词： PET probes,triangulenium,pH probes,photoinduced electron transfer,Fluorescent probes
更新于2025-10-22 19:40:53
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Background-free fluorescence decay time sensing and imaging of pH with highly photostable diazaoxotriangulenium dyes
摘要： Novel fluorescent diazaoxatriangulenium (DAOTA) pH indicators for lifetime-based self-referenced pH sensing are reported. The DAOTA dyes were decorated with phenolic receptor groups inducing fluorescence quenching via photoinduced electron transfer mechanism. Electron-withdrawing chlorine substituents ensure response in the most relevant pH range (apparent pK’a values ~5 and 7.5 for the p,p-dichlorophenol- and the p-chlorophenol-substituted dyes, respectively). The dyes feature long fluorescence lifetime (17-20 ns), high quantum yield (~60%) and high photostability. Planar optodes are prepared upon immobilization of the dyes into polyurethane hydrogel D4. Apart from the response in the fluorescence intensity, the optodes show pH-dependent lifetime behaviour which makes them suitable for studying 2D pH distribution with help of fluorescence lifetime imaging technique. The lifetime response is particularly pronounced for the sensors with high dye concentration (0.5-1% wt. in respect to the polymer) and is attributed to efficient homo-FRET mechanism.
关键词： pH sensor,photoinduced electron transfer,Decay time,triangulenium,Frequency Domain FLIM,FRET
更新于2025-09-09 09:28:46