A Novel L-Shaped Fluorescent Probe for AIE Sensing of Zinc (II) Ion by a DR/NIR Response

Diana, Rosita; Caruso, Ugo; Gentile, Francesco Silvio; Costanzo, Luigi Di; Panunzi, Barbara

doi:10.3390/molecules26237347

Cited by 7 publications

(3 citation statements)

References 103 publications

(137 reference statements)

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“…The model compound ZnNB is a red crystalline material with an absorbance maximum at 530 nm in the solid state. The narrow bandgap drives the deep-red emission of the ligand [ 30 , 44 ]; the maximum of the emission band of the NB molecule redshifts by 10 nm upon zinc coordination. The ZnNB molecule in its crystalline state is a DR/NIR emitter, with an appreciable amount of NIR emission (see the hump above 700 nm, Figure 2 , CIE (Commission Internationale de l’Éclairage) (0.44; 0.27) when excited at its λ abs maximum.…”

Section: Resultsmentioning

confidence: 99%

“…Therefore, we did not proceed further with refinement. Nonetheless, the unit cell parameters of the ligand crystals grown in the presence of Zn acetate were isomorphic with the monomeric form of the ligand itself, grown in the absence of metal and previously determined, and provided insights into the equimolar ratio between the NB ligand and zinc [ 44 ].…”

Section: Methodsmentioning

confidence: 99%

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A DR/NIR Hybrid Polymeric Tool for Functional Bio-Coatings: Theoretical Study, Cytotoxicity, and Antimicrobial Activity

et al. 2023

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Among modern biomaterials, hybrid tools containing an organic component and a metal cation are recognized as added value, and, for many advanced biomedical applications, synthetic polymers are used as thin protective/functional coatings for medical or prosthetic devices and implants. These materials require specific non-degradability, biocompatibility, antimicrobial, and antiproliferative properties to address safety aspects concerning their use in medicine. Moreover, bioimaging monitoring of the biomedical device and/or implant through biological tissues is a desirable ability. This article reports a novel hybrid metallopolymer obtained by grafting zinc-coordinated fragments to an organic polymeric matrix. This hybrid polymer, owing to its relevant emission in the deep red to near-infrared (DR/NIR) region, is monitorable; therefore, it represents a potential material for biomedical coating. Furthermore, it shows good biocompatibility and adhesion properties and excellent stability in slightly acidic/basic water solutions. Finally, in contact with the superficial layers of human skin, it shows antimicrobial properties against Staphylococcus aureus bacterial strains.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

A DR/NIR Hybrid Polymeric Tool for Functional Bio-Coatings: Theoretical Study, Cytotoxicity, and Antimicrobial Activity

et al. 2023

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“…In recent years, the solid-state luminescence of organic materials has drawn much attention due to the rapid development of optoelectronic devices and applications such as organic light emitting diodes (OLEDs) [ 1 , 2 , 3 ], optical sensors [ 4 ], stimuli responses, and anti-counterfeit printing [ 5 ]. However, many organic materials exhibit intense fluorescence emission in dilute solutions, while the emission is severely quenched in the aggregate state.…”

Section: Introductionmentioning

confidence: 99%

Tuning Photophysical Properties via Positional Isomerization of the Pyridine Ring in Donor–Acceptor-Structured Aggregation-Induced Emission Luminogens Based on Phenylmethylene Pyridineacetonitrile Derivatives

et al. 2023

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A series of aggregation-induced emission (AIE)-featured phenylmethylene pyridineacetonitrile derivatives named o-DBCNPy ((Z)-3-(4-(di-p-tolylamino)phenyl)-2-(pyridin-2-yl)acrylonitrile), m-DBCNPy ((Z)-3-(4-(di-p-tolylamino)phenyl)-2-(pyridin-3-yl)acrylonitrile), and p-DBCNPy ((Z)-3-(4-(di-p-tolylamino)phenyl)-2-(pyridin-4-yl)acrylonitrile) have been synthesized by tuning the substitution position of the pyridine ring. The linkage manner of the pyridine ring had influences on the molecular configuration and conjugation, thus leading to different photophysical properties. The absorption and fluorescence emission peak showed a bathochromic shift when the linking position of the pyridine ring changed from the meta to the ortho and para position. Meanwhile, o-DBCNPy exhibited the highest fluorescence quantum yield of 0.81 and the longest fluorescence lifetime of 7.96 ns as a neat film among all three isomers. Moreover, non-doped organic light-emitting diodes (OLEDs) were assembled in which the molecules acted as the light-emitting layer. Due to the relatively prominent emission properties, the electroluminescence (EL) performance of the o-DBCNPy-based OLED was superior to those of the devices based on the other two isomers with an external quantum efficiency (EQE) of 4.31%. The results indicate that delicate molecular modulation of AIE molecules could endow them with improved photophysical properties, making them potential candidates for organic photoelectronic devices.

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A New ‘Off–On’ System Based on Core‐Substituted Naphthalene Diimide with Dimethylamine for Reversible Acid–Base Sensing

Nadimetla

Zalmi

et al. 2022

ChemistryOpen

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A new ‘Off–On’ system designed and synthesised by functionalisation of a naphthalene diimide (NDI) core with dimethylamine produces 4,9‐bis(dimethylamino)‐2,7‐dioctylbenzo[ lmn ][3,8]‐phenanthroline‐1,3,6,8‐(2 H ,7 H )‐tetraone, abbreviated as DDPT ( 1 ). DDPT 1 was synthesised using a simple strategy, namely aromatic nucleophilic substitution using Br 2 ‐NDI with dimethylamine at 110 °C. DDPT was characterized by 1 H and 13 C NMR spectroscopy, ESI mass spectrometry and elemental analysis. DDPT 1 was then used for optical studies through protonation of its dimethylamine core with trifluoroacetic acid (TFA), blue‐shifting the absorption band from 600 nm to 545 nm in solution. Interestingly, the fluorescence of DDPT 1 is weak in solution with a quantum yield Φ=0.09, which is significantly enhanced to Φ=0.78 upon addition of TFA. The limit of detection (LOD) was determined to 2.77 n m . Furthermore, DDPT 1 can be used for naked eyed detection not only under UV light (365 nm) but also using visible light, as clear changes can be clearly seen upon addition of TFA. The binding constant of DDPT was calculated to 2.1×10 −3 m −1 . Importantly, DDPT 1 showed reversible switching by alternative addition of acid (TFA) and base (triethylamine) without loss of activity. Immobilised on paper, DDPT 1 can be used for strip‐test sensing in which the colour changes from blue to reddish when expose to TFA vapours and reverse in the presence of triethylamine vapours.

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A Novel L-Shaped Fluorescent Probe for AIE Sensing of Zinc (II) Ion by a DR/NIR Response

Cited by 7 publications

References 103 publications

A DR/NIR Hybrid Polymeric Tool for Functional Bio-Coatings: Theoretical Study, Cytotoxicity, and Antimicrobial Activity

A DR/NIR Hybrid Polymeric Tool for Functional Bio-Coatings: Theoretical Study, Cytotoxicity, and Antimicrobial Activity

Tuning Photophysical Properties via Positional Isomerization of the Pyridine Ring in Donor–Acceptor-Structured Aggregation-Induced Emission Luminogens Based on Phenylmethylene Pyridineacetonitrile Derivatives

A New ‘Off–On’ System Based on Core‐Substituted Naphthalene Diimide with Dimethylamine for Reversible Acid–Base Sensing

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