Novel Mg-responsive fluorescent chemosensor based on benzo-15-crown-5 possessing 1-naphthaleneacetamide moiety

A new fluorescent ionophore for Mg²⁺, 4′-(1-naphthaleneacetamido)benzo-15-crown-5 (1), was synthesized, and its complexation behavior in acetonitrile was investigated by means of UV and fluorescence spectrometry. In the absence of a metal ion, the naphthalene moiety showed quite weak fluorescence emission (fluorescence ‘Off’ state). On the other hand, after the addition of Mg²⁺, fluorescence emission from the naphthalene moiety increased (fluorescence ‘On’ state).     

Two novel rhodamine-perylenediimide fluorescent probes: Synthesis,photophysical properties,and cell imaging

In this study, two novel dual-switch fluorescent chemosensors based on rhodamine-peryleneiimide have been designed and synthesized. The dual-switching behaviors of the sensors were based on the structural transformations of rhodamine and an intramolecular photoinduced electron transfer (PET) process from rhodamine to perylenediimide. These probes exhibited excellent sensitivity to protons with enhanced fluorescence emission from 500 nm to 580 nm. The fluorescence changes of probes were reversible within a wide range of pH values from 2.0 to 11.0. Moreover, the sensors exhibited high selectivity, short response time, and long lifetime toward protons. The possible mechanism was investigated by the DFT calculation and 1 H NMR. According to the experiment of confocal laser scanning microscopy, these probes could be used to detect the acidic pH variations in living cells.     

Naphthalene-derived Al3+-selective fluorescent chemosensor based on PET and ESIPT in aqueous solution

A simple fluorescent chemosensor HL based on naphthalene with high selectivity and sensitivity towards Al³⁺ over other commonly coexisting metal cations in fully aqueous solution to enhance the potential applications of the fluorescent chemosensor was developed. HL exhibited a significant fluorescence enhancement at 475?nm in the presence of Al³⁺ over other competitive metal ions with a low detection limit of 0.43?μM due to the inhibition of the photo induced electron transfer (PET) and the excited-state intramolecular proton transfer (ESIPT). The 1:1 binding stoichiometry between HL and Al³⁺ was corroborated by the Job plot and the ESI-MS spectrum. Importantly, the reversible recognition process of HL to Al³⁺ will make HL could be used circularly and repeatedly in practical applications by addition of Na₂EDTA. In addition, the binding behavior and sensing mechanism of HL to Al³⁺ were illustrated in detail by the ¹H NMR titration experiment.     

A fluorescent PET chemosensor for Zn2+ cations based on 4-methoxy-1,8-naphthalimide derivative containing salicylideneamino receptor group

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A ratiometric chemosensor for fluorescent determination of Hg based on a new porphyrin-quinoline dyad

Quinolin-8-ol p-[10′,15′,20′-triphenyl-5′-porphyrinyl]benzoate (1) was synthesized for the first time and developed as a ratiometric fluorescent chemosensor for recognition of Hg²⁺ ions in aqueous ethanol with high selectivity. The 1–Hg²⁺ complexation quenches the fluorescence of porphyrin at 646 nm and induces a new fluorescent enhancement at 603 nm. The fluorescent response of 1 towards Hg²⁺ seems to be caused by the binding of Hg²⁺ ion with the quinoline moiety, which was confirmed by the absorption spectra and ¹H NMR spectrum. The fluorescence response fits a Hill coefficient of 1 (1.0308), indicating the formation of a 1:1 stoichiometry for the 1–Hg²⁺ complex. The analytical performance characteristics of the chemosensor were investigated. The sensor shows a linear response toward Hg²⁺ in the concentration range of 3 × 10⁻⁷ to 2 × 10⁻⁵ M with a limit of detection of 2.2 × 10⁻⁸ M. Chemosensor 1 shows excellent selectivity to Hg²⁺ over transition metal cations except Cu²⁺, which quenches the fluorescence of 1 to some extent when it exists at equal molar concentration. Moreover, the chemosensor are pH-independent in 5.0–9.0 and show excellent selectivity for Hg²⁺ over transition metal cations.     

A GSH-responsive PET-based fluorescent probe for cancer cells imaging

An efficient PET-based probe, in which the ferrocene quencher and the naphthalimide fluorophore are linked by a disulfide bond, has been developed. This probe can be activated by GSH with fluorescence a turn-on response for blocking the PET process. In addition, it was successfully applied for distinguishing cancer cells from normal cells     

CdTe量子点作为荧光探针测定水环境中微量镉离子

利用CdTe量子点(QDs)和乙二胺四乙酸(EDTA)构建的纳米探针,建立了一种能快速灵敏检测Cd2+的新方法。利用EDTA溶液与Cd2+的络合作用对QDs的表面进行化学蚀刻,在QDs表面形成了Cd2+的空腔,这些表面缺陷使得QDs荧光猝灭,而继续加入Cd2+后,新加入的Cd2+能够迅速补位空腔修复表面缺陷,使得QDs的荧光恢复。在最佳的实验条件下,当Cd2+浓度在3.3×10-9~6.7×10-6mol/L范围时,QDs恢复的荧光强度与Cd2+浓度之间呈良好的线性关系,检出限为1.0×10-9mol/L(S/N=3)。此外,相对于其他金属离子,该荧光探针对Cd2+具有高选择性,并且将其用于实际水样中Cd2+含量的检测,结果令人满意。     

Rational design of novel photoinduced electron transfer type fluorescent probes for sodium cation

We have developed novel fluorescence probes for sodium cation based on photoinduced electron transfer (PeT). In this study, we rationally designed new probes and succeeded in achieving fluorescence enhancement upon sodium ion binding by reducing the HOMO energy level of the chelator group within the probe molecule. Our new probes show low pH dependency, possibly because of their simple structures. Our results confirm the value of rational probe design based on PeT.     

Silole‐Infiltrated Photonic Crystal Films as Effective Fluorescence Sensor for Fe3+ and Hg2+

We develop a highly effective silole‐infiltrated photonic crystal (PC) film fluorescence sensor with high sensitivity, good selectivity and excellent reproducibility for Fe³⁺ and Hg²⁺ ions. Hexaphenylsilole (HPS) infiltrated PCs show amplified fluorescence due to the slow photon effect of PC because the emission wavelength of HPS is at the blue band edge of the selected PC’s stopband. The fluorescence can be quenched significantly by Fe³⁺/Hg²⁺ ions owing to electron transfer between HPS and metal ions. The amplified fluorescence enhances the sensitivity of detection, with a detection limit of 5 nM for Fe³⁺/Hg²⁺ ions. The sensor is negligibly responsive to other metal ions and can easily be reproduced by rinsing with pure water due to the special surface wettability of PC. As a result, a highly effective Fe³⁺/Hg²⁺ ions sensor based on HPS‐infiltrated PC film has been achieved, which will be important for effective and practical detection of heavy metal ions.     

Synthesis and structural studies of some fluorescent group XII metal complexes with a terpyridine based ligand

Three 4′-(2-thienyl) substituted terpyridine (thioterpy) complexes of cadmium(II) and mercury(II) have been synthesized and fully characterized by spectroscopies. According to the crystallographic studies, the packing of these complexes was stabilized by several intermolecular interactions such as hydrogen bonding, C-H?π and π?π. Finally, the florescent properties of the prepared complexes have been investigated.     

Synthesis of a sugar-aza-crown ether-based cavitand as a selective fluorescent chemosensor for Cu ion

A chemosensor based upon the sugar-aza-crown ether 7 with one anthracenetriazolymethyl moiety was prepared and its fluoroionophoric properties toward transition metal ions were investigated. Chemosensor 7 exhibits highly selective recognition toward Cu²⁺ ion among a series of tested metal ions in MeOH solution. The association constant for 7∗Cu²⁺ in MeOH solution was calculated to be 2.5 × 10⁴ M⁻¹.     

Synthesis of new benzimidazolium salts with tunable emission intensities and their application as fluorescent probes for Fe in pure aqueous media

A series of novel, water-soluble benzimidazolium salts with common ‘fluorophore–spacer–receptor’ PET design has been synthesized. Despite the common PET scaffold these benzimidazolium salts displayed diverse emission intensities in pure aqueous solutions. The observed emission intensities were found to be influenced by the functionalized alkyl side arms present on the benzimidazolium ring. These benzimidazolium salts were also found to act as selective sensors for Fe³⁺ ions over other metal ions like Na⁺, K⁺, Ca²⁺, Mg²⁺, Ba²⁺, Al³⁺, Cr³⁺, Co²⁺, Ni²⁺, Mn²⁺, Zn²⁺, Pb²⁺, Ag⁺, Cu²⁺ and Hg²⁺ in pure aqueous media.     

A tetra-sulfonamide derivative bearing two dansyl groups designed as a new fluoride selective fluorescent chemosensor

A new fluorescent chemosensor based on an acyclic tetra-sulfonamide derivative linked to two dansyl groups has been conveniently synthesized. Its high selective binding ability to fluoride ions over other halide ions was demonstrated by using fluorescence as well as ¹H NMR spectra.     

Chiral 6-phenyl-2,3-bismethylenemethoxycarbonyl-[1,4]-dioxane as a designer synthon for an efficient and short synthesis of optically pure 2,6-dioxabicyclo[3.3.0]octane-3,7-dione

Chiral 6-phenyl-2,3-bismethylenemethoxycarbonyl-[1,4]-dioxane, synthesized by the PET cyclization of 8, has been used as a designer synthon for an efficient and short synthesis of optically pure 2,6-dioxabicyclo[3.3.0]octane-3,7-dione.     

Dipodal fluorescent chemosensor for Cu and resultant complex as a chemosensor for iodide

A dipodal receptor was synthesized by condensation of isophthalaldehyde and p-toluenesulfonylhydrazide. The receptor was found to be selective for Cu²⁺ recognition in CH₃CN. The resultant Cu²⁺ receptor complex selectively recognized iodide through cation displacement assay in a CH₃CN/H₂O (8:2, v/v) solvent system.     

A fluorescent chemosensor for Hg based on naphthalimide derivative by fluorescence enhancement in aqueous solution

Naphthalimide derivative (compound 1) containing hydrophilic hexanoic acid group was synthesized and used to recognize Hg²⁺ in aqueous solution. The fluorescence enhancement of 1 is attributed to the formation of a complex between 1 and Hg²⁺ by 1:1 complex ratio (K = 2.08 × 10⁵), which has been utilized as the basis of fabrication of the Hg²⁺-sensitive fluorescent chemosensor. The comparison of this method with some other fluorescence methods for the determination of Hg²⁺ indicated that the method can be applied in aqueous solution rather than organic solution. The analytical performance characteristics of the proposed Hg²⁺-sensitive chemosensor were investigated. The chemosensor can be applied to the quantification of Hg²⁺ with a linear range covering from 2.57 × 10⁻⁷ to 9.27 × 10⁻⁵ M and a detection limit of 4.93 × 10⁻⁸ M. The experiment results show that the response behavior of 1 toward Hg²⁺ is pH independent in medium condition (pH 4.0–8.0). Most importantly, the fluorescence changes of the chemosensor are remarkably specific for Hg²⁺ in the presence of other metal ions, which meet the selective requirements for practical application. Moreover, the response of the chemosensor toward Hg²⁺ is fast (response time less than 1 min). In addition, the chemosensor has been used for determination of Hg²⁺ in hair samples with satisfactory results, which further demonstrates its value of practical applications.     

Calix[4]arene based selective fluorescent chemosensor for organic acid recognition

A novel calix[4]arene-based fluorescent chemosensor bearing a 2-aminopyridine moiety and a naphthalenic fluorophore was synthesized The chemical structure of the product was elucidated by FT-IR, MS-FAB, NMR and elemental analyses. Then, the properties and identification mechanism of the synthesized chemosensor were investigated. The results show that the chemosensor exhibits selective fluorescent quenching in the presence of aromatic organic acid in acetonitrile solution, and that the binding ability of the chemosensor with organic acid is in the order of p-cyanic-benzyl acid > p-chloric-benzyl acid > p-methoxyl-benzyl acid > benzyl acid. __________ Translated from Journal of South China University of Technology (Natural Science Edition), 2007, 35(4): 20–24 [译自: 华南理工大学学报(自然科学版)]     

Novel side‐chain naphthalimide polyphenylacetylene as a ratiometric fluorescent chemosensor for fluoride ion

Novel polyphenylacetylene ( P1 ) containing naphthalimides units in the side chain was designed and synthesized. The structure and properties of the polymer were characterized and evaluated by IR, NMR, UV, and PL. The measurements of sensing behavior to various halide anions, that is, F^?, Cl^?, Br^?, and I^?, reveal that the polymer is a ratiometric fluorescent chemosensors for fluoride ion. The polymer sensor shows spectral shifts and intensity changes in the presence of fluoride, in a wavelength‐ratiometric and ‐colorimetric manner, which can detect fluoride concentrations in range of 10–100 μM at visible wavelengths. The obvious colorless‐to‐yellow color change and blue‐to‐orange emission color change on the addition of fluoride ion are easily observed by naked eyes. It provides a feasible way to construct a ratiometric fluorescent chemosensors for fluoride ion. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 1544–1552, 2009     

Tunable design strategy for fluorescence probes based on 4-substituted BODIPY chromophore: improvement of highly sensitive fluorescence probe for nitric oxide

4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) is a well-known fluorophore, with a high molar extinction coefficient and high fluorescence quantum efficiency (Phi(fl)). Furthermore, its structure can be modified to change its excitation and emission wavelengths. However, little work has been done on the structural modification of fluorines at the B-4 position with other functional groups. We synthesized 4-methoxy-substituted BODIPY derivatives in satisfactory yields, and found that they exhibited improved solubility in aqueous solution. Moreover, their oxidation and reduction potentials were greatly decreased without any change in their absorbance and fluorescence properties. These features of 4-substituted BODIPYs may be useful for developing novel fluorescence probes based on the intramolecular photoinduced electron transfer (PeT) mechanism, because it is possible to optimize the PeT process precisely by modulating the electrochemical properties of the fluorophore. The value of this approach is exemplified by its application to the development of a highly sensitive and pH-independent fluorescence probe for nitric oxide.