Perylene diimides: will they flourish as reaction-based probes?

Perylene diimides (PDI) are a well-studied class of functional organic dyes, and in recent years, they have been accepted as promising scaffolds for the design of small molecule/polymer-based chromogenic and fluorogenic reaction-based-probes because of their strong absorption combined with high fluorescence quantum yield in organic solvents, low reduction potential, good electron-acceptor properties, and broad color range properties. Undoubtedly, the intrinsically poor solubility of PDI-based derivatives in water greatly hampers their exploitation as reaction-based probes; however, a vast array of functionalizations now offer design strategies that have resulted in >50% solubility of PDI derivatives in water. A chemodosimeter, wherein chemical transformation is achieved by specific reactions, affords naked-eye visibility, fast response time, sensitivity, ratiometric response, and low cost.

Multifunctional metallo-supramolecular interlocked hexagonal microstructures for the detection of lead and thiols in water.

We report Pb2+-mediated interlocked hexagonal self-assembly associated with the near-IR (660 nm) 'turn-on' detection of Pb2+ ions (LOD = 25 nM) in water using a perylene diimide derivative (PDI-HQ). The PDI-HQ-Pb2+ complex was further used to develop a fluorescent NIR ensemble for the detection of thiols.

Ionic Self-Assembled Platform of Perylenediimide-Sodium Dodecylsulfate for Detection of Spermine in Clinical Samples.

The detection and quantification of spermine in clinical practice is important for early diagnosis of many diseases. Chromatographic and immunoassay-based methods are commonly used. However, a fluorescence-based assay could provide real-time detection.

Self-assembled vesicle and rod-like aggregates of functionalized perylene diimide: reaction-based near-IR intracellular fluorescent probe for selective detection of palladium.

Herein, we report design, synthesis, and self-assembly of perylene diimide (PDI) based near-IR intracellular probe (PS-PDI). PS-PDI molecules undergo aggregation to form self-assembled nanospheres and nanorods morphology in THF : HO (1 : 1) and DMSO : HO (1 : 9), respectively. The nanospheres have an open hole on surface reminiscent of vesicle structure (with a diameter of internal void in the range of 20-25 nm) whereas lengths of the nanorods extended up to few μm range.

Bay functionalized perylenediimide as a deaggregation based intracellular fluorescent probe for perchlorate.

The aggregates of perylenediimide based chemosensor (PDI 1) undergo de-aggregation induced fluorescence quenching selectively with ClO4(-) ions both in the solution and in the solid phase and can detect ClO4(-) ions in drinking water and fireworks. PDI 1 is permeable to C6 glioma cells, and ClO4(-) can be detected using confocal microscopy.

Perylene diimide appended with 8-hydroxyquinoline for ratiometric detection of Cu2+ ions and metal displacement driven "turn on" cyanide sensing.

Perylene diimide (PDI) 3 and 4 appended with 8-hydroxyquinoline derivatives have been synthesized and their photophysical and spectroscopic properties have been experimentally determined. Moreover, PDIs 3 and 4 show ratiometric behavior to detect Cu(2+) colorimetrically with visible color change from coral red to light pink, whereas 3 and 4 show "turn-off" behavior in fluorescence with lowest limit of detection 5 × 10(-7) M. The PDI 3 could be further utilized for ratiometric CN(-) detection colorimetrically and as "turn-on" sensor for CN(-) detection fluorometrically with lowest limit of detection 8 × 10(-6) M.