Unveiling the Different Emission Behavior of Polytriazoles Constructed from Pyrazine-Based AIE Monomers by Click Polymerization

( E )- N ′-((2-Hydroxynaphthalen-1-yl)methylene)picolinohydrazide (H-PNAP) shows aggregation-induced emission (AIE) strictly in a 90% water/MeOH (v/v) mixture at 540 nm, and the solid-state emission is blue-shifted to 509 nm upon excitation at 400 nm. The AIE activity of H-PNAP is selectively quenched by 2,4,6-trinitrophenol (TNP) and 2,4-dinitrophenol (DNP) out of different nitroaromatic compounds with a limit of detection (LOD) of 7.79 × 10 –7 and 9.08 × 10 –7 M, respectively. The probe is nonemissive in aqueous medium (4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid, HEPES buffer, pH 7.2); however, it shows a strong emission to Al 3+ (λ em , 490 nm) in the presence of 17 other biological metal ions, and the LOD is 2.09 nM which is far below the WHO recommended value (7.41 mM). The emission of the [Al(PNAP)(NO 3 ) 2 ] complex is quenched by HF 2 – (F – and PO 4 3– are weak quencher), and the LOD is as low as 15 nM. The probable mechanism of the sensing feature of the probe has been authenticated by 1 H nuclear magnetic resonance titration, mass spectrometry, Fourier transform infrared spectroscopy, Benesi–Hildebrand plot, and Job’s plot in each case. The probe has some practical applications such as recovery of Al 3+ from the drinking water sample, construction of the INHIBIT logic gate, and detection kits for Al 3+ and TNP/DNP by simple paper test strips. The probe, H-PNAP, has successfully been applied to the detection of intracellular Al 3+ and HF 2 – ions in the human breast cancer cell, MDA-MB-468.

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“…The fluorescence properties in the aggregated state are recognized for the fabrication of organic light-emitting diode material. 38…”

Section: Results and Discussionmentioning

confidence: 99%

Aggregation-Induced Emission-Active Hydrazide-Based Probe: Selective Sensing of Al³⁺, HF₂^–, and Nitro Explosives

et al. 2019

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“…Thus, the luminescence behavior in the solid state is attributed to the fabrication of organic light-emitting diode as a suitable material. 12,48…”

Section: Resultsmentioning

confidence: 99%

Design of a Pyrene Scaffold Multifunctional Material: Real-Time Turn-On Chemosensor for Nitric Oxide, AIEE Behavior, and Detection of TNP Explosive

et al. 2018

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A dual-emission pyrene-based new fluorescent probe ( N -(4-nitro-phenyl)- N ′-pyren-1-ylmethyl-ene-ethane-1,2-diamine (PyDA-NP)) displays green fluorescence for nitric oxide (NO) sensing, whereas it exhibits blue emission in the aggregated state. The mechanism of nitric oxide (NO/NO + ) sensing is based on N-nitrosation of aromatic secondary amine, which was not interfered by reactive oxygen species and reactive nitrogen species. The aggregation-induced enhancement of emission (AIEE) behaviors of the PyDA-NP could be attributed to the restriction of intramolecular rotation and vibration, resulting in rigidity enhancement of the molecules. The AIEE behavior of the probe was well established from fluorescence, dynamic light scattering, scanning electron microscopy, transmission electron microscopy, X-ray diffraction, optical fluorescence microscopy, and time-resolved photoluminescence studies. In a H 2 O/CH 3 CN binary mixture (8:2 v/v), the probe showed maximum aggregation with extensive (833-fold) increases in fluorescence intensity and high quantum yield (0.79). The aggregated state of the probe was further applied for the detection of nitroexplosives. It displayed efficient sensing of 2,4,6-trinitrophenol (TNP), corroborating mainly the charge-transfer process from pyrene to a highly electron-deficient TNP moiety. Furthermore, for the on-site practical application of the proposed analytical system, a contact-mode analysis was performed.

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“…In addition, the planar conformations of traditional dyes are inherently linked to their conjugated electronic structures, allowing for better orbital overlap than twisted structures. While these planar structures often exhibit strong emission intensity in their 'single-molecule states' [10,11] , e.g., when dissolved, the luminescence becomes weaker or is quenched entirely in aggregated states. This property of many π-conjugated chromophores is problematic, as it prevents their use as materials for solid-state devices [12] .…”

Section: Introductionmentioning

confidence: 99%

Clusterization-triggered emission: Uncommon luminescence from common materials

et al. 2020

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Unveiling the Different Emission Behavior of Polytriazoles Constructed from Pyrazine-Based AIE Monomers by Click Polymerization

Cited by 41 publications

References 59 publications

Aggregation-Induced Emission-Active Hydrazide-Based Probe: Selective Sensing of Al³⁺, HF₂^–, and Nitro Explosives

Aggregation-Induced Emission-Active Hydrazide-Based Probe: Selective Sensing of Al³⁺, HF₂^–, and Nitro Explosives

Design of a Pyrene Scaffold Multifunctional Material: Real-Time Turn-On Chemosensor for Nitric Oxide, AIEE Behavior, and Detection of TNP Explosive

Clusterization-triggered emission: Uncommon luminescence from common materials

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Unveiling the Different Emission Behavior of Polytriazoles Constructed from Pyrazine-Based AIE Monomers by Click Polymerization

Cited by 41 publications

References 59 publications

Aggregation-Induced Emission-Active Hydrazide-Based Probe: Selective Sensing of Al3+, HF2–, and Nitro Explosives

Aggregation-Induced Emission-Active Hydrazide-Based Probe: Selective Sensing of Al3+, HF2–, and Nitro Explosives

Design of a Pyrene Scaffold Multifunctional Material: Real-Time Turn-On Chemosensor for Nitric Oxide, AIEE Behavior, and Detection of TNP Explosive

Clusterization-triggered emission: Uncommon luminescence from common materials

Contact Info

Product

Resources

About

Aggregation-Induced Emission-Active Hydrazide-Based Probe: Selective Sensing of Al³⁺, HF₂^–, and Nitro Explosives

Aggregation-Induced Emission-Active Hydrazide-Based Probe: Selective Sensing of Al³⁺, HF₂^–, and Nitro Explosives