Polyoxy-Derivatized Perylenediimide as Selective Fluorescent Ag (I) Chemosensor

Abstract

Recent investigations indicated that same concentrations of the ionic silver have harmful effects on aquatic life, bacteria and human cells. Herein we report chemosensory properties of N,N -Bis(4-{2-[2-(2-methoxyethoxy)ethoxy] eth- oxy}phenyl) -3,4:9,10-perylene tetracarboxydiimide (PERKAT) towards ionic silver. The dye doped sensing agents were prepared utilizing ethyl cellulose (EC) and poly (methylmethacrylate) (PMMA) and then forwarded to electrospinning to prepare sensing fibers or mats. The PERKAT exhibited bright emission in embedded forms in EC or in the solvents of N,N-Dimethylformamide (DMF), Dichloromethane (DCM), Tetrahydrofurane (THF) and in the mixture of DCM/ethanol. The PERKAT exhibited selective and linear response for ionic silver in the concentration range of 10 - 10 M Ag (I) at pH 5.5. Detection limits were found to be 2.6 × 10 and 4.3 × 10 M, in solution phase studies and PERKAT doped sensing films, respectively. Cross sensitivity of the PERKAT towards pH and some metal ions was also studied. There were no response for the Li, Na, K, Ca, Ba, Mg, NH, Ni, Co, Cu,Pb, Al, Cr,Mn, Sn, Hg, Hg, Fe and Fe in buffered solutions. To the best of our knowledge, this is the first study investigating silver sensing abilities of the PERKAT.

Synthesis and Structural Characterization of Azine Based Chemosensors for Ag+ Ion Detection and Their Theoretical Investigations.

“…The fluorescence of oligoesters and DPHMM are completely arrested respectively at 70 and 82 equivalents of Ag + ion. The electron or energy transfer process and formation of d–π interaction between the fluorophore and Ag + ion is responsible for quenching [19,20] . Oligoesters exhibit a spot response and become saturated with minimum equivalent of Ag + ion, indicating greater sensitive response than that of monomer.…”

“…Many probes have been reported for Ag + ion detection. Among them, azines (=N−N=) and azine derivatives have desirable ligand properties towards metal ions and are very potential probes, capable of detecting transition and post‐transition metal ions in the chemosensor study because of their =N−N= and −C=N−moieties [20–22] . Moreover, the design of higher conjugation with repeating unit of azine [23] and ester (−C(=O)−O−) moiety [24] in the backbone is enhancing the interaction of fluorophores with metal ions.…”

“…Among them, azines (=NÀ N=) and azine derivatives have desirable ligand properties towards metal ions and are very potential probes, capable of detecting transition and posttransition metal ions in the chemosensor study because of their =NÀ N= and À C=NÀ moieties. [20][21][22] Moreover, the design of higher conjugation with repeating unit of azine [23] and ester (À C(=O)À OÀ ) moiety [24] in the backbone is enhancing the interaction of fluorophores with metal ions. Especially, the bidentate ligands with this structural property can potentially generate sensors signal [25] with different sensing mechanisms, offering diverse possible responses to various metal ions.…”

Perylene Diimide‐Based Pseudo‐Crown Ether I: Supramolecular Aggregates for Sensing of Pb2+ and Diethanolamine

“…Zhang, Ziu and co‐workers reported PDI derivative containing tetrathiafulvalene (TTF) subunit at N‐imide position through pentaoxa‐heptadecane for detection of Ca 2+ ions in CH 2 Cl 2 [30] . Ertekin and Nadeem's group reported fluorescent fibrous membrane doped with PDI derivative containing bis(4‐{2‐[2‐methoxyethoxy]ethoxy}phenyl) for detection of Ag + ion [31] . Jin, Qi and co‐workers reported self‐assembly behaviour of PDI derivative containing benzo‐21‐crown ether at N‐imide positions [32] .…”

A reversible fluorescent probe for monitoring Ag(I) ions

“…Recent efforts to prepare fluorescent sensors for Ag(I) have included systems based on gold nanoparticles [26], carbon dots [27,28] and polyoxy-derivatized perylenediimide [29]. More traditional metal-sensing systems, involving a silver-selective receptor coupled to a fluorophore [30], have used a range of donor atoms for the soft Ag(I), from hard nitrogen and oxygen donors [31] to the very soft tellurium [32].…”