A new perylene bisimide-armed calix[4]-aza-crown as “turn on” fluorescent sensor for Hg2+ ion and its application to living cells

Perylene Diimide-Based Fluorescent and Colorimetric Sensors for Environmental Detection

“…Remarkably, PDI-14 sensor can be operated in pure water system without any assistance of organic solvents like DMF or THF that are often needed for optimal performance of aqueous fluorescence sensors. In 2015, Erdemir [22] reported on PDI-15 sensor Figure 6d) was reported by Chen [24]. Surprisingly, in phosphate buffer DMSO/H 2 O (1/1, v/v, pH = 7.0) solutions, PDI-17 showed both high sensitivity with much lower LDL of 0.01 µM, and selectivity towards Hg 2+ via dual-wavelength (ratiometric) fluorescence modulation.…”

“…The fluorescent sensing mechanism is often based on analyte-binding-induced assembly-disassembly of PDIs, taking advantage of the sensitive dependence of fluorescence of PDIs on the π-π stacking interaction [5,6,10,[18][19][20][21]49,[52][53][54]. Many other PDI sensors work through fluorescence turn-on or turn-off mechanism, which relies on an intramolecular PET process [7][8][9]13,[15][16][17][22][23][24][25][26][27][28][29][42][43][44][45], or intermolecular electron/proton transfer [51,58,61]. For the turn-on sensor, the original PDI sensor molecule is non-fluorescent or weakly fluorescent because of the efficient fluorescence quenching caused by the electron transfer from the side-binding group (e.g., amine) to the photoexcited state of PDI core.…”

“…Detection of toxic metal ions is particularly important for monitoring water pollution, food safety and disease diagnosis. In view of the strong tendency of aggregation PDIs molecules through stacking interactions between the π-conjugated skeletons in aqueous media, most studies of PDI-based chemosensors are in organic-aqueous composite systems to maintain the molecular dispersion of PDI sensors [7,8,[15][16][17][18][19][20][22][23][24][25][26][27][29][30][31]. There still remain challenges to study the sensing performances in pure water solutions [10,21,[32][33][34][35][36][37][38][39].…”

“…Remarkably, PDI-14 sensor can be operated in pure water system without any assistance of organic solvents like DMF or THF that are often needed for optimal performance of aqueous fluorescence sensors. In 2015, Erdemir [22] reported on PDI-15 sensor ( Figure 6b) by introducing two calix [4]arene units into the imide-positions of PDI. Under pH range of 5.5-7.5 in DMF/H2O (19/1, v/v) solutions, strong fluorescence turn-on (over 14-fold increase in intensity) was observed when PDI-15 forms a 1:2 complex with Hg 2+ ion.…”

Highly sensitive and selective Hg2+-chemosensor based on dithia-cyclic fluorescein for optical and visual-eye detections in aqueous buffer solution

“…All of these sensors utilized the ligands which responded and bound to Hg 2+ to serve as the ionophores. These ligands included hydroxyquinolines [17,18], cyclens [19,20], cyclams [21][22][23], dioxocyclams [24], diazatetrathia crown ethers [25], azines [26], and calixarenes [27][28][29].…”