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1.
Di‐ and Triphosphate Recognition and Sensing with Mono‐ and Dinuclear Fluorescent Zinc(II) Complexes: Clues for the Design of Selective Chemosensors for Anions in Aqueous Media
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Dr. Francesco Bartoli Prof. Andrea Bencini Dr. Alessandra Garau Prof. Claudia Giorgi Prof. Vito Lippolis Dr. Alessandro Lunghi Prof. Federico Totti Prof. Barbara Valtancoli 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(42):14890-14901
The synthesis of a new ligand (L1) containing two 1,4,7‐triazacyclononane ([9]aneN3) moieties linked by a 4,5‐dimethylenacridine unit is reported. The binding and fluorescence sensing properties toward Cu2+, Zn2+, Cd2+, and Pb2+ of L1 and receptor L2, composed of two [9]aneN3 macrocycles bridged by a 6,6′′‐dimethylen‐2,2′:6′,2′′‐terpyridine unit, have been studied by coupling potentiometric, UV/Vis absorption, and emission measurements in aqueous media. Both receptors can selectively detect Zn2+ thanks to fluorescence emission enhancement upon metal binding. The analysis of the binding and sensing properties of the Zn2+ complexes toward inorganic anions revealed that the dinuclear Zn2+ complex of L1 selectively binds and senses the triphosphate anion (TP), whereas the mononuclear Zn2+ complex of L2 displays selective recognition of diphosphate (DP). Binding of TP or DP induces emission quenching of the Zn2+ complexes with L1 and L2, respectively. These results are exploited to discuss the role played by pH, number of coordinated metal cations, and binding ability of the bridging units in metal and/or anion coordination and sensing. 相似文献
2.
Qiu-Juan Ma Xiao-Bing Zhang Zhi-Xiang Han Bo Huang Qin Jiang Guo-Li Shen 《International journal of environmental analytical chemistry》2013,93(1):74-86
A ratiometric fluorescent zinc probe 1 of carboxamidoquinoline with a carboxylic acid group was designed and synthesised. Probe 1 exhibits high selectivity for sensing Zn2+; about a 13-fold increase in fluorescence emission intensity and an 82?nm red-shift of fluorescence emission are observed upon binding Zn2+ in EtOH/H2O (1?:?1, V/V) solution. The ratiometric fluorescence response is attributed to the 1?:?1 complex formation between probe 1 and Zn2+ which has been utilised as the basis for the selective detection of Zn2+. The analytical performance characteristics of the proposed Zn2+-sensitive probe were investigated. The linear response range covers a concentration range of Zn2+ from 2.0?×?10?6 to 5.0?×?10?5?mol?L?1 and the detection limit is 2.7?×?10?7?mol?L?1. The determination of Zn2+ in both tap and river water samples shows satisfactory results. 相似文献
3.
Highlights on the Road towards Highly Emitting Solid‐State Luminophores: Two Classes of Thiazole‐Based Organoboron Fluorophores with the AIEE/AIE Effect
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Kseniya I. Lugovik Alexander K. Eltyshev Polina O. Suntsova Dr. Pavel A. Slepukhin Dr. Enrico Benassi Prof. Nataliya P. Belskaya 《化学:亚洲杂志》2018,13(3):311-324
Developing a novel, small‐sized molecular building block that may be capable of emitting light in the solid state is a challenging task and has rarely been reported in the literature. BF2‐containing dyes seem to be promising candidates towards this aim. Two series of new N^NBF2 complexes showing aggregation‐induced emission (AIE) and aggregation‐induced emission enhancement (AIEE) were designed and synthesized by means of a new protocol, which improved on the traditional method by employing microwave irradiation. The optical and photophysical properties of the BF2 complexes were investigated in depth. The synthesized complexes showed fluorescence in both solution and the solid state and, in a mixture of tetrahydrofuran/water, may aggregate into fluorescent nanoparticles. The experimental investigation was supported by quantum mechanical calculations. Their availability, stability, large Stokes shifts, and aggregation capabilities, along with their solid‐state emission capability, render this new class of BF2 complexes promising AIEE/AIE fluorophores for further applications in the fields of fluorescence imaging and materials science. 相似文献
4.
Hayriye Genç Bilgiçli Ahmet T. Bilgiçli Armağan Günsel Burak Tüzün Derya Ergön M. Nilüfer Yarasir Mustafa Zengin 《应用有机金属化学》2020,34(6):e5624
In this study, simple on–off fluorescent/UV–visible (UV–Vis) probes were easily prepared using 2-(2-hydroxyphenyl)thiazolidine-4-carboxylic acid ( Sen-1 ) and/or 2-(2-hydroxy-5-nitrophenyl)thiazolidine-4-carboxylic acid ( Sen-2 ) for fast detection of Zn2+ ions. Their sensing properties towards common metal ions were investigated using UV–Vis and fluorescence spectroscopies. Sen-1 and Sen-2 displayed a significant change with the addition of Zn2+ ions in the UV–Vis spectra. The addition of Zn2+ ions induced a 104 nm bathochromic shift for Sen-1 . The binding ratio towards Zn2+ metal ions was determined to be 1:1 by using Job plot analysis and fluorescence spectroscopy. The association constant and free energy (ΔG) of Sen-1 and Sen-2 towards Zn2+ ions were calculated by the Benesi–Hildebrand equation. The limit of detection of Sen-1 towards Zn2+ ions is 3.73 × 10−8 M, which is about 1/100 of the value recommended by the World Health Organization for drinking water. Sen-1 was successfully applied to detect Zn2+ ions in water samples and the fluorescence test strip was prepared for visual detection of Zn2+ ions. Finally, the quantum chemical parameters of Sen-1 and Sen-2 , such as highest occupied molecular orbital, lowest unoccupied molecular orbital, and chemical hardness, were investigated by the Becke, three-parameter, Lee–Yang–Parr, Hartree–Fock, and M062x methods. 相似文献
5.
《Polyhedron》2002,21(14-15):1397-1404
The new open-chain polyazaalkanes ligands L1, L2, L3 and L4 functionalised with one or two pyrene groups were synthesised and characterised and their potential use as selective cation and anion sensing chemosensors studied. Solution studies by potentiometric methods were carried out in the presence of the metal cations Cu2+ and Zn2+ in acetonitrile–water (70:30 v/v, 0.1 mol dm−3 tetrabutylammonium perchlorate, 25 °C) The results are compared with those reported for the analogous non-functionalised ligand triethylentetraamine (tta). The fluorescence behaviour of the ligands L1–L4 has been studied as a function of the pH in the presence of the metal cations Ni2+, Cu2+, Zn2+, Cd2+, Hg2+ and Pb2+ in acetonitrile–water 70:30 v/v mixtures. The Zn2+ and Cd2+ cations enhance the fluorescence emission of the L1–L4 chemosensors at basic pH, whereas Cu2+ induce quenching of the fluorescence emission at acid pH. The fluorescence behaviour of L1–L4 receptors was also studied as a function of the pH in acetonitrile–water 70:30 v/v in the presence of anions. 相似文献
6.
A series of novel (oligo)thienyl-imidazo-benzocrown ethers were synthesised through a simple method and evaluated as fluorimetric chemosensors for transition metal cations. Interaction with Ni2+, Pd2+, and Hg2+ in ACN/DMSO solution (99:1) was studied by absorption and emission spectroscopy. Chemoselectivity studies in the presence of Na+ were also carried out and a fluorescence enhancement upon chelation (CHEF) effect was observed following Hg2+ complexation. Considering that most systems using fluorescence spectroscopy for detecting Hg2+ are based on the complexation enhancement of the fluorescence quenching (CHEQ) effect, the present work represents one of the few examples for sensing of Hg2+ based on a CHEF effect. 相似文献
7.
C. Lakshmi 《Tetrahedron》2004,60(49):11307-11315
A series of Zn2+-2,2′-dipicolylamine (Zn2+-DPA) coordination complexes with an attached NBD fluorophore are synthesized and evaluated as fluorescent sensors. The sensors do not respond to vesicles composed of zwitterionic phosphatidylcholine, but the NBD fluorescence emission is enhanced in the presence of anionic vesicles. A sensor with two Zn2+-DPA units and a hydrophilic tris(ethyleneoxy) linker produced a larger emission enhancement than an analogue with a butyl linker, and titration with 1:1 POPC:POPS vesicles lead to an apparent phospholipid association constant of 5.3×104 M−1. The sensor can detect the presence of vesicles containing as little as 5% phosphatidylserine. The sensing effect apparently requires a membrane surface because the sensors do not respond to a phosphatidylserine derivative that is monodispersed in aqueous solution. 相似文献
8.
A New 3,5‐Bisporphyrinylpyridine Derivative as a Fluorescent Ratiometric Probe for Zinc Ions
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Dr. Nuno M. M. Moura Dr. Cristina Núñez Dr. Sérgio M. Santos Prof. M. Amparo F. Faustino Prof. José A. S. Cavaleiro Dr. Filipe A. Almeida Paz Prof. M. Graça P. M. S. Neves Prof. José Luis Capelo Prof. Carlos Lodeiro 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(22):6684-6692
A new 3,5‐disubstituted pyridine with two porphyrin moieties was prepared through an efficient synthetic approach involving 2‐formyl‐5,10,15,20‐tetraphenylporphyrin ( 1 ), piperidine, and catalytic amounts of [La(OTf)3]. 3,5‐Bis(5,10,15,20‐tetraphenylporphyrin‐2‐ylmethyl)pyridine ( 2 ) was fully characterized and its sensing ability towards Zn2+, Cu2+, Hg2+, Cd2+, and Ag+ was evaluated in solution by absorption and fluorescence spectroscopy and in gas phase by using matrix‐assisted laser desorption/ionization (MALDI)‐TOF mass spectrometry. Strong changes in the ground and excited state were detected in the case of the soft metal ions Zn2+, Cd2+, Hg2+, and Cu2+. A three‐metal‐per‐ligand molar ratio was obtained in all cases and a significant ratiometric behavior was observed in the presence of Zn2+ with the appearance of a new band at 608 nm, which can be assigned to a metal‐to‐ligand charge transfer. The system was able to quantify 79 ppb of Zn2+ and the theoretical calculations are in accordance with the stoichiometry observed in solution. The gas‐phase sensorial ability of compound 2 towards all metal ions was confirmed by using MALDI‐TOF MS and in solid state by using polymeric films of polymethylmethacrylate (PMMA) doped with ligand 2 . The results showed that compound 2 can be analytically used to develop new colorimetric molecular devices that are able to discriminate between Hg2+ and Zn2+ in solid phase. The crystal structure of ZnII complex of 3,5‐bisporphyrinylpyridine was unequivocally elucidated by using single‐crystal X‐ray diffraction studies. 相似文献
9.
A novel diarylethene containing a 3-(4-methylphenyl)-1H-pyrazol-5-amine was synthesized. Its multi-responsive properties induced by UV/Vis lights and metal ions were studied in detail by absorption and fluorescence emission spectroscopy. It showed excellent fluorescence sensing ability for Al3+ and Zn2+ with very low detection limit. In addition, based on the multi-responsive characteristics, a logic circuit was constructed by using both UV/Vis lights and chemical species stimuli as inputs and fluorescence intensity as outputs. Moreover, the diarylethene was successfully applied to effectively detect Al3+ and Zn2+ in actual water samples. 相似文献
10.
A water‐soluble benzenesulfonamidoquinolino‐β‐cyclodextrin has been successfully synthesized in 30 % yield by incorporating a N‐(8‐quinolyl)‐p‐aminobenzenesulfonamide (HQAS) group to β‐cyclodextrin through a flexible linker. This compound exhibits a good fluorescence response in the presence of Zn2+ in water but gives poor fluorescence responses with other metal ions commonly present in a physiological environment under similar conditions. Fluorescence microscopic and two‐dimensional NMR experiments showed that benzenesulfonamidoquinolino‐β‐cyclodextrin could bind to the loose bilayer membranes. As a result, benzenesulfonamidoquinolino‐β‐cyclodextrin was found to act as an efficient cell‐impermeable Zn2+ probe, showing a specific fluorescent sensing ability to Zn2+‐containing damaged cells whilst exhibiting no response in the presence of healthy cells. 相似文献
11.
A novel fluorescent probe 5‐(diethylamino)‐2‐(((2‐(hydroxymethyl)quinolin‐8‐yl)imino)methyl)phenol ( QS) was synthesized by condensation reaction of 8‐aminoquinoline derivative and 4‐(diethylamino)salicylaldehyde. It was found that the probe QS was capable of high selectivity and sensitivity about specific color and fluorescence changes towards Zn2+ ion in EtOH‐H2O (v/v = 4/1, 0.01 M, Tris–HCl buffer, pH = 7.30) solution. The interaction of QS with Zn2+ ion illustrated a “turn‐on” fluorescence response at 550 nm (λex: 458 nm), moreover, after the subsequent addition of inorganic phosphate (Pi) into the solution above, a “turn‐off” fluorescence response was observed. The sensing ability of the probe QS towards Zn2+ was confirmed by fluorescence titration, UV–Vis titration and HRMS analysis. Besides, the intracellular sensing behavior of QS with Zn2+ and Pi were captured in living PC12 cells. The limit of detection (LOD) for Zn2+ and Pi sensing was found to be 0.03 μM and 0.08 μM, respectively. 相似文献
12.
Lijun Qian Bin Tong Shu Sun Jianbing Shi Junge Zhi Yuping Dong 《Frontiers of Chemistry in China》2011,6(1):15-20
Transition metal ions (Pb2+, Zn2+, Cd2+, Co2+, Mn2+, Cu2+, Ni2+, Hg2+, Ag+, Fe3+) in water are used to quench emission of 2-(6-oxido-6H-dibenz 〈c,e〉 〈1,2〉 oxaphosphorin-6-yl)-1,4-phenylene-bis(p-pentyloxylbenzoate)s
(MD5) with aggregation-induced emission enhancement (AIEE) in water-acetonitrile (AN) mixture (80:20 by volume). Among all
metal ions, Fe3+ exhibits the highest quenching efficiency on AIEE of MD5 even when the concentration of Fe3+ is lower than 1×10−6 mol/L. The quenching efficiency of Hg2+ is lower than that of Fe3+ at the same concentration, though MD5 is used to detect Hg2+ efficiently, too. To other metal ions, low quenching efficiency has few relations with a wider concentration range. The UV
absorbance spectra show only red shift of absorbance wavelength in the presence of Hg2+ and Fe3+, which indicates a salt-induced Jaggregation. SEM photos reveal larger aggregation and morphological change of nanoparticles
of MD5 in water containing Hg2+ and Fe3+, which reduce the surface area of MD5 emission for further aggregation. The selective quenching effect of transition metal
ions to emission of MD5 has a potential application in chemical sensors of some metal ions. 相似文献
13.
V.V. Sreenivasu Mummidivarapu Rakesh Kumar Pathak Vijaya Kumar Hinge Jayaraman Dessingou 《Supramolecular chemistry》2014,26(7-8):538-546
A triethylene glycol di-imine locked triazole linked bis-calix[4]arene conjugate L has been synthesised and characterised. Conjugate L exhibits high fluorescence enhancement towards Zn2+ among the 13 metal ions studied down to a lower detection limit of ~12 ppb. The absorption and visual colour change experiments differentiated the Zn2+ from the other metal ions studied. The isolated zinc complex, [Zn2L] has been used as a chemo-sensing ensemble for the recognition of anions based on their binding affinities towards Zn2+. [Zn2L] was found to be sensitive and selective towards phosphate-bearing species and in particular to adenosine triphosphate (ATP2 ? ) among the other 20 anions studied as observed based on the changes occurred in the fluorescence intensity. The selectivity of the ATP2 ? has been shown on the basis of the changes observed in the emission and absorption spectral studies. The lowest detectable concentration for ATP2 ? with the chemo-sensing ensemble [Zn2L] is 348 ppb in methanol. The fluorescence quenching by the phosphate-based anions has been modelled by molecular mechanics studies and found that the anions possessing two or more phosphate moieties can only bridge between the two zinc centres, and hence those possessing only one phosphate moiety (H2PO4? and AMP2 ? ) are ineffective. 相似文献
14.
Sutapa Sahu Yeasin Sikdar Riya Bag Javier Cerezo Jos P. Cern-Carrasco Sanchita Goswami 《Molecules (Basel, Switzerland)》2022,27(9)
Optical chemosensors caused a revolution in the field of sensing due to their high specificity, sensitivity, and fast detection features. Imidazole derivatives have offered promising features in the literature as they bear suitable donor/acceptor groups for the selective analytes in the skeleton. In this work, an isoindole-imidazole containing a Schiff base chemosensor (1-{3-[(2-Diethylamino-ethylimino)-methyl]-2-hydroxy-5-methyl-phenyl}-2H-imidazo[5,1-a]isoindole-3,5-dione) was designed and synthesized. The complete sensing phenomena have been investigated by means of UV-Vis, fluorescence, lifetime measurement, FT-IR, NMR and ESI-MS spectroscopic techniques. The optical properties of the synthesized ligand were investigated in 3:7 HEPES buffer:DMSO medium and found to be highly selective and sensitive toward Zn2+ ion through a fluorescence turn-on response with detection limit of 0.073 μm. Furthermore, this response is effective in gel form also. The competition studies reveal that the response of the probe for Zn2+ ion is unaffected by other relevant metal ions. The stoichiometric binding study was performed utilizing Job’s method which indicated a 1:1 sensor–Zn2+ ensemble. Computational calculations were performed to pinpoint the mechanism of sensing. 相似文献
15.
AbstractA triethylene glycol di-imine locked triazole linked bis-calix[4]arene conjugate (L) and its Zn2+ complex [Zn2L], were synthesised, characterised and the three-dimentional (3-D) structure of the complex was established by single crystal XRD. In this complex, the Zn2+ centre exhibits distorted tetrahedral geometry with N2O2 binding core. The complex showed selectivity towards cysteine (Cys) with greater sensitivity followed by histidine (His) among the naturally occurring amino acids studied based on fluorescence and absorption spectroscopy. The fluorescence quenching of the complex is much greater with Cys as compared to that of His. The detection limit of Cys is 650 ppb. Release of Zn2+ from its complex [Zn2L] followed by its capture by –SH containing molecules was shown based on absorption and emission spectroscopy. This was also shown in one case by 1H NMR spectroscopy. 相似文献
16.
Xing Zhang Ling-Yi Shen Qi-Long Zhang Xian-Jiong Yang Ya-Li Huang Carl Redshaw Hong Xu 《Molecules (Basel, Switzerland)》2021,26(5)
An aniline-functionalized naphthalene dialdehyde Schiff base fluorescent probe L with aggregation-induced enhanced emission (AIEE) characteristics was synthesized via a simple one-step condensation reaction and exhibited excellent sensitivity and selectivity towards copper(II) ions in aqueous media with a fluorescence “ turn-off ” phenomenon. The detection limit of the probe is 1.64 × 10−8 mol·L−1. Furthermore, according to the results of the UV-vis/fluorescence titrations, Job’s plot method and 1H-NMR titrations, a 1:2 stoichiometry was identified. The binding constant between L and Cu2+ was calculated to be Ka = 1.222 × 103. In addition, the AIEE fluorescent probe L could be applied to detection in real water samples with satisfactory recoveries in the range 99.10–102.90% in lake water and 98.49–102.37% in tap water. 相似文献
17.
Sabir H. Mashraqui Rupesh Betkar Mukesh Chandiramani Kiran Poonia David Quinonero Antonio Frontera 《Supramolecular chemistry》2013,25(9):524-531
Newly synthesised 1,8-naphthyridine-based molecular probes, NAP-1 and NAP-2, exhibit highly selective fluorescence responses towards the toxic cadmium over coordinatively competing Zn2+ and several other metal ions examined. On the one hand, NAP-1 (MeOH:H2O, v/v 80:20, pH 7.4) exhibits ca. 1.5 order of magnitude higher stability constant for Cd2+ over Zn2+; on the other hand, NAP-2 in MeOH offers unique selectivity only towards Cd2+, exhibiting both absorbance and emission red shifts as well as fluorescence enhancement. By 1H NMR analysis, the tetra-coordinated binding is indicated at least for the NAP-1+Cd2+ complex and theoretical calculations reveal relatively stronger binding of Cd2+ over Zn2+. 相似文献
18.
Dr. Vandana Bhalla Varun Vij Abhimanew Dhir Dr. Manoj Kumar 《Chemistry (Weinheim an der Bergstrasse, Germany)》2012,18(12):3765-3772
New hetero‐oligophenylene derivative ( 2 ) was synthesized which exhibits aggregation‐induced emission enhancement (AIEE) in H2O/THF (80:20). The aggregates serve as a biological probe for three different proteins, that is bovine serum albumin (BSA), cytochrome c, and lysozyme, and DNA in contrasting modes. Further, among 29 metal ions tested, the contrasting fluorescence behavior of aggregates of 2 is observed with only Pb2+ and Pd2+ ions. Multiple output logic circuits based upon the fluorescence behavior between BSA and cytochrome c and between Pb2+ and Pd2+ ions are constructed. 相似文献
19.
5-amino-l,10-phenanthroline (5-AP), as a tautomeric heterocyclic aromatic chelating fluorophore (THACF), can sense Zn^2+ selectively by shifting emission from 495 to 564 nm upon Zn^2+ addition in ethanol. The ratiometric fluorescent sensing behavior has been correlated to the tautomerization of 5-AP affected by solvents and metal chelation. The strategy using THACF as ratiometric fluorescent sensor for Zn^2+ not only simplifies the synthetic procedure but also gives a promising alternative for Zn^2+ ratiometric fluorescent sensor design. 相似文献
20.
《中国化学快报》2023,34(6):107686
Herein we report a covalent cage TPE-Zn4 based on a tetraphenylethylene molecule via subcomponent self-assembly, which is templated by zinc ions. TPE-Zn4 features a quadrangular prismatic cage structure, which is characterized by NMR, mass spectrum, and single-crystal X-ray diffractions. TPE-Zn4 emitted orange fluorescence (λem = 620 nm) in DMSO solution under the irradiation of UV light (λex = 395 nm) and can be applied as a fluorescence sensor for selectively detecting Pd2+. The fluorescence of TPE-Zn4 was quenched by Pd2+ in DMSO solution, and a very low detection limit of 62.3 nM was achieved. Mechanism studies reveal that the Pd2+ can replace the Zn2+, and the heavy atom effect and chelation-enhanced quenching effect between the Pd2+ and the cage probably cause the fluorescence quenching. 相似文献