In recent years, the widely explored phenomenon “aggregation-induced emission (AIE)” has played a crucial role in the development of luminescent materials for light-emitting applications. In the same direction, the contribution of its sister concept “AIE switching” has been impressive. In comparison, the application of this concept in the field of biosensing or bioimaging is still in its infancy. Therefore, to shed light into the sensing of bioanalytes, we have developed a new perylenediimide (PDI)-based small fluorescent probe, benzoannulated PDI (Bp(Im)2MA), that selectively detects diamines and biogenic amines (BAs) in solution via an “AIE-switching” phenomenon. The synthesized probe containing the bay-annulated anhydride moiety exhibits strong cyan emission in solution. In the mechanism, we have shown that the terminal free amine group of BAs readily reacts with a highly reactive anhydride moiety, which opens the cyclic anhydride moiety. In the open conformation, the free amine group along with a carboxylate group modulates the polarity of the system strikingly. Because of this induced polarity, the monomer of Bp(Im)2MA-BAs conjugate aggregated in solution, thereby exhibiting a significant change in emission property in solution. This method may also be called a very simple and straightforward “naked eye” detection of BAs in solution, with a nanomolar detection limit. A detailed spectroscopic and microscopic investigation demonstrated the existence of the aggregated state. As the reporter dye also emits strongly in the solid state (yellowish orange), it therefore instantly made vapor-phase detection of BAs feasible. Finally, this vapor-phase detection of BAs by the probe was applied very effectively in the determination of spoilage of raw fish.
Perylene dyes have transcended their role as simple colorants and have been reinvigorated as functional dyes. Based on the substitution at the peri position by six-membered carboxylic imides, the perylene family is principally embellished with perylene diimides (PDIs) and perylene monoimides (PMIs). Perylene dyes are widely acclaimed and adorned on account of their phenomenal thermal, chemical, and photostability juxtaposed with their high absorption coefficient and near-unity fluorescence quantum yield. Although symmetric PDIs have always been in the limelight, its asymmetrical counterpart PMI is already rubbing shoulders, thanks to the consistent efforts of several scientific minds. Recently, there has been an upsurge in engendering PMI-based versatile organic architectures decked with intriguing photophysical properties and pertinent applications. In this review, the synthesis and photophysical features of various PMI-based derivatives along with their relevant applications in the arena of organic photovoltaics, photocatalysis, self-assembly, fluorescence sensing, and bioimaging are accrued and expounded, hoping to enlighten the less delved but engrossing realm of PMIs.
A regioselective synthetic protocol is developed via tetrabromination of perylenemonoimide (PMI) which leads to a series of PMI derivatives.
require the simultaneous emission from either three primary colored (red, green, and blue) or two complementary colored (such as blue and orange) emitters to span the visible spectrum (see Scheme 1). [4] Multi-component approach relies on energy transfer between complementary emissive chromophores to attain WL emission [4d,5] while in single-component approach, WL emission occurs from a single molecule. Single-component white light (SCWL) emitters have surpassed their multicomponent analogs from the viewpoint of superior stability, color reproducibility, less phase separation, negligible color aging issue, and easy device fabrication. [6] Kasha's rule clearly states that fluorophores always tend to attain the lowest vibrational states resulting in monochromatic emission. [7] So, realization of WL emission from a single molecular system is difficult and is therefore of great significance. SCWL emission obtained via covalent grafting of emissive units in a single-molecular backbone is often not efficient due to intramolecular FRET (Förster Resonance Energy Transfer) or TBET (Through Bond Energy Transfer). [8] Hence, several systems rely on mechanisms such as intramolecular energy transfer (IET), [4e] intramolecular electron transfer, [4g] excited-state intramolecular proton transfer (ESIPT), [4h,9] intramolecular charge transfer (ICT), [10] host-guest interaction, [11] and self-assembly, [4f,12] to attain SCWL emission (Scheme 1). Organic radical anions are open-shell molecular entities carrying a negative charge. They have found widespread applications in catalysis, magnetic materials, near-infrared photothermal effect, and optoelectronic materials. [13] For the development of efficient radical-based functional materials, stability is imperative. [14] To generate persistent ambient-stable radical anion, electron-deficient perylenediimide derivatives (PDI) are an obvious choice as they are inherently electron-deficient and offer ample opportunity to conjugate electron-withdrawing groups at different regions of the π-scaffold. In recent years, several reports related to chemical, electrochemical, and photochemical generation of stable PDI-based radical anion have surfaced. [13e,15] Stability of radicals can be modulated by resorting to either a covalent [15d,16] or non-covalent approach. [13d,17] Adoption of supramolecular strategies can tune the stability of radicals in a dynamic fashion. However, to the best of our knowledge, the potential of White light-emitting materials have attracted considerable attention in lighting devices and display media. This article reports the first-ever demonstration of a radical-based self-assembly for white light emission. Singlecomponent white light (SCWL) emitters are more advantageous than multicomponent ones due to better stability, color-reproducibility, and negligible color aging problem. The present study demonstrates SCWL emission arising out of the dynamic self-assembly of a photo-reduced perylene diimide derivative (PF-BPDI). Photo-reduction of PF-BPDI leads...
The colorimetric and ratiometric fluorogenic detection of harmful organic peroxides by using the S–S annulated perylene monoimide (PMISS) mediated emergence of a unique solid-state red-emitting perylene monoimide (PMI) derivative is demonstrated.
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