A fluorescent bis-NBD derivative of calix[4]arene: Switchable response to Ag+ and HCHO in solution phase

Shaofei, Zhang; Yang, Hui; Ma, Ying; Fang, Yu

doi:10.1016/j.snb.2015.12.016

Cited by 24 publications

(10 citation statements)

References 49 publications

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“…The incorporation of a 1,2,3-triazole as both the linker and part of the receptor in the bis -nitrobenzoxadiazole (NBD) substituted calix[4]arene structure 16 ( Figure 9 ) has been reported to afford a sensor for Ag + and formaldehyde (HCHO) [ 89 ]. Alkylation of the precursor calixarene phenols with propargyl bromide followed by CuAAC to attach the NBD azide afforded sensor 16 , which was selective for Ag + over a variety of cations tested.…”

Section: Calixarene-based Sensorsmentioning

confidence: 99%

“… Benzoxadizole-functionalised calix[4]arene probe 16 responds selectively to Ag + , which triggers quenching of the free ligand emission at 527 nm and emergence of a new emission band at 576 nm; the resulting metal complex is then an effective probe for HCHO, which reduces the Ag + and regenerates the free probe 16 [ 89 ]. The anthraquinone-functionalised calix[4]arene 17 responds selectively to Ca 2+ with enhanced fluorescence emission at 510 nm, and the resulting 17 ·Ca 2+ complex then functions as a turn-off probe for fluoride [ 90 ].…”

Section: Figurementioning

confidence: 99%

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Recent Advances in Macrocyclic Fluorescent Probes for Ion Sensing

2017

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Small-molecule fluorescent probes play a myriad of important roles in chemical sensing. Many such systems incorporating a receptor component designed to recognise and bind a specific analyte, and a reporter or transducer component which signals the binding event with a change in fluorescence output have been developed. Fluorescent probes use a variety of mechanisms to transmit the binding event to the reporter unit, including photoinduced electron transfer (PET), charge transfer (CT), Förster resonance energy transfer (FRET), excimer formation, and aggregation induced emission (AIE) or aggregation caused quenching (ACQ). These systems respond to a wide array of potential analytes including protons, metal cations, anions, carbohydrates, and other biomolecules. This review surveys important new fluorescence-based probes for these and other analytes that have been reported over the past five years, focusing on the most widely exploited macrocyclic recognition components, those based on cyclam, calixarenes, cyclodextrins and crown ethers; other macrocyclic and non-macrocyclic receptors are also discussed.

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Section: Calixarene-based Sensorsmentioning

confidence: 99%

Section: Figurementioning

confidence: 99%

Recent Advances in Macrocyclic Fluorescent Probes for Ion Sensing

2017

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“…In detail, the combination of derivatives of organic fluorophores such as terthiophene, 58,59 perylenebisimide (PBI), 26,60,61 BPEB, 27,62 nitrobenzoxadiazole (NBD), 25,52,[63][64][65] or pyrene (Py) 47,53,66 together with cholesterol or glucose resulted in a variety of potential low-molecular-mass fluorescent gelators. Specially designed gelators are the basis of the construction of SA-3D fluorescent films via a molecular gel strategy.…”

Section: Sa-3d Fluorescent Sensing Filmsmentioning

confidence: 99%

“…Very recently, we designed and synthesized compounds 6-8, 27,63,64 in which the fluorophores are endowed with self-assembly properties. Chemical science is very helpful in socioeconomic development.…”

Section: Sa-3d Fluorescent Sensing Filmsmentioning

confidence: 99%

Recent advances in fluorescent film sensing from the perspective of both molecular design and film engineering

Miao

Peng

Fang

2016

Mol. Syst. Des. Eng.

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Fluorescence is now a dominant technology and is used extensively in many fields owing to its incomparable properties. On account of its advantages, scientists and engineers have been investigating novel and powerful fluorescent sensors and sensor arrays for real-life applications, in which the construction of highperformance fluorescent films plays a prominent role. The appropriate immobilization of suitable fluorescent sensing elements onto a given substrate is an efficient way to construct usable fluorescent films. Molecular design and film fabrication are two key issues in the development of films because they determine the sensing performance of the films. Via the careful design and selection of sensing fluorophores, the development of convenient film fabrication strategies and the study of the relevant sensing dynamics, a variety of fluorescent sensing films with desirable sensing performance have been developed over at least the last ten years. This review describes recent progress in this important area of science, which combines surface and interface chemistry, photophysics and materials science.High-performance sensing films are the key to real-life usable fluorescent sensors. Different strategies have been developed to fabricate fluorescent sensing films during the previous decades, which mainly include physical coating, doping, single-layer chemistry and molecular gel-based fabrication. The asdeveloped films can be divided into disordered and generally densely packed physical films, 2-dimensional chemical films and 3-dimensional networked physical films. To enhance sensing performance, the structures of films should be optimized both at a molecular level and on a microscopic scale. Therefore, more factors are involved in the design of sensing molecules; in particular, some functional structures need to be introduced to obtain films with favorable adlayer structures. A molecular gel strategy possesses advantages in the fabrication of fluorescent sensing films: 1) increased surface density and effectiveness of sensing sites; 2) increased speed and reversibility of response; and 3) ease of scale-up. However, this strategy is still open to improvement. For example, a general method is urgently needed to increase the adhesive and mechanical strength of gel-based films. Films that were fabricated using the newly developed strategy have found important applications in the sensitive and fast detection of hidden explosives and illegal drugs.

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“…However, the calixarene conjugates with bifunctional mode and with the NBD moiety have not been explored in the literature and hence the present study is of great relevance. Recently, the lower rim of calix[4]arene was modified by the NBD moiety, where the conjugate was used for the detection of either a cation, such as Ag + , or an anion, such as F – ions. , In another report, four folic acid units are appended at the upper rim and an NBD moiety at the lower rim of calix[4]arene, where the conjugate was demonstrated to be internalized by the cancer cells . Because of the requirement of special features for selective sensing of mercury, a bifunctional calix[4]arene conjugate ( L ) was designed (Figure ) to have a binding core within a fluorophore at the lower rim while having −SMe terminals at the upper rim.…”

Section: Introductionmentioning

confidence: 99%

Physicochemical and Ion-Sensing Properties of Benzofurazan-Appended Calix[4]arene in Solution and on Gold Nanoparticles: Spectroscopy, Microscopy, and DFT Computations in Support of the Species of Recognition

et al. 2018

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A calix[4]arene conjugate ( L ) functionalized at the lower rim with a benzofurazan fluorophore (NBD) and at the upper rim with a thioether moiety has been synthesized and characterized by 1 H NMR, 13 C NMR, and mass spectrometry techniques. Both the absorption and emission spectral data for L in different solvents exhibited progressive changes with an increase in polarity. Ion recognition studies were performed by absorption and fluorescence spectroscopy using 10 different metal ions. Among these, Hg 2+ exhibited greater changes in these spectra, whereas Cu 2+ showed only significant changes and all other ions showed no change in the spectral features. Although the Hg 2+ has dominant influence on the spectral features and provides a detection limit of 56.0 ± 0.6 ppb, the selectivity was hampered because of the presence of the derivatizations present on both the rims of L for ion interaction in solution. Therefore, L was immobilized onto gold nanoparticles (AuNP L ’s) so that the upper rim derivatizations anchor onto the gold surface through Au–S interactions, and this leaves out only the lower rim NBD derivatization for interaction with ions selectively. The AuNP L ’s were characterized by transmission electron microscopy, scanning electron microscopy, energy-dispersive X-ray spectroscopy, and X-ray photoelectron spectroscopy (XPS) analyses. The surface characteristics were analyzed by contact angle measurements. The AuNP L ’s exhibit greater selectivity and enhanced sensitivity for Hg 2+ ions with a lowest detection limit of 48.0 ± 0.8 ppb. The immobilization of L onto AuNPs was reflected in the corresponding fluorescence lifetime values, and the addition of Hg 2+ to either L or AuNP L showed fluorescence quenching. The reversible recognition of Hg 2+ by L was demonstrated by titrating L or AuNP L with Hg 2+ followed by tetra-butyl ammonium iodide for several cycles. The structural features of Hg 2+ -bound species were demonstrated by density functional theory computations and were supported by the XPS data. The Hg 2+ induces aggregated fibrillar morphology into supramolecular L , as demonstrated by microscopy when Hg 2+ was added either to L or to AuNP L , supporting aggregation-caused quenching.

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A fluorescent bis-NBD derivative of calix[4]arene: Switchable response to Ag+ and HCHO in solution phase

Cited by 24 publications

References 49 publications

Recent Advances in Macrocyclic Fluorescent Probes for Ion Sensing

Recent Advances in Macrocyclic Fluorescent Probes for Ion Sensing

Recent advances in fluorescent film sensing from the perspective of both molecular design and film engineering

Physicochemical and Ion-Sensing Properties of Benzofurazan-Appended Calix[4]arene in Solution and on Gold Nanoparticles: Spectroscopy, Microscopy, and DFT Computations in Support of the Species of Recognition

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