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1.
ACS Appl Mater Interfaces ; 13(38): 45214-45223, 2021 Sep 29.
Artigo em Inglês | MEDLINE | ID: mdl-34524789

RESUMO

Accurate and sensitive fluorescence imaging of intracellular miRNA is essential for understanding the mechanism underlying some physiological and pathological events, as well as the prevention and diagnosis of diseases. Herein, a highly sensitive ratiometric fluorescent nanoprobe for intracellular miRNA imaging was fabricated by integrating a Ru-SiO2@polydopamine (Ru-SiO2@PDA) nanoplatform with a near-infrared light (NIR)-assisted DNA strand displacement signal amplification strategy. The Ru-SiO2@PDA spheres have excellent biosafety, high photothermal effect, and unique photophysical properties that can both emit a stable red fluorescence and well quench the fluorophores getting closer to them. So, when the fuel DNA and carboxyfluorescein (FAM)-labeled signal DNA are co-assembled on their outer surfaces, the FAM's green fluorescence is quenched, and a low ratiometric signal is obtained. However, in the presence of miRNA, the target displaces the signal DNA from the capture DNA, releasing the signal DNA far away from the Ru-SiO2@PDA. Then, the green fluorescence recovers and leads to an enhanced Igreen/Ired value. Under NIR light irradiation, the Ru-SiO2@PDA increases the local temperature around the probe and triggers the release of fuel DNA, which thus recycles the target miRNA and effectively amplifies the ratiometric signal. Using A549 cells as a model, the nanoprobe realizes the highly sensitive ratiometric fluorescence imaging of miRNA let-7a, as well as its in vivo up- and down-regulation expressions. It provides a facile tool for highly sensitive and accurate intracellular miRNA detection through one-step incubation and may pave a new avenue for single-cell analysis.

2.
Artigo em Inglês | MEDLINE | ID: mdl-34435428

RESUMO

Metal-organic frameworks (MOFs) provide a platform to design new heterogeneous catalysts for catalytic CO2 reduction, but selective formation of C2 valuable liquid fuel products remains a challenge. Herein, we propose a strategy to synthesize composites by integrating MoS2 nanosheets into hierarchically porous defective UiO-66 (d-UiO-66) to form Mo-O-Zr bimetallic sites on the interfaces between UiO-66 and MoS2 . The active interfaces are favorable for the efficient transfer of photo-generated charge carriers and for promoting the activity, whereas, the synergy of the components at the interfaces achieves selectivity for C2 production. The d-UiO-66/MoS2 composite facilitates the photo-catalytic conversion of gas phase CO2 and H2 O to CH3 COOH under visible light irradiation without any other adducts. The evolution rate and selectivity of CH3 COOH reached 39.0 µmol g-1 h-1 and 94 %, respectively, without any C1 products, suggesting a new approach for the design of highly efficient photocatalysts of CO2 for C2 production. Theoretical calculations demonstrate the charge-polarized Zr-O-Mo aided the C-C coupling process with the largely reduced energy barrier.

3.
Nat Commun ; 12(1): 5092, 2021 08 24.
Artigo em Inglês | MEDLINE | ID: mdl-34429430

RESUMO

Development of a versatile, sustainable and efficient photosynthesis system that integrates intricate catalytic networks and energy modules at the same location is of considerable future value to energy transformation. In the present study, we develop a coenzyme-mediated supramolecular host-guest semibiological system that combines artificial and enzymatic catalysis for photocatalytic hydrogen evolution from alcohol dehydrogenation. This approach involves modification of the microenvironment of a dithiolene-embedded metal-organic cage to trap an organic dye and NADH molecule simultaneously, serving as a hydrogenase analogue to induce effective proton reduction inside the artificial host. This abiotic photocatalytic system is further embedded into the pocket of the alcohol dehydrogenase to couple enzymatic alcohol dehydrogenation. This host-guest approach allows in situ regeneration of NAD+/NADH couple to transfer protons and electrons between the two catalytic cycles, thereby paving a unique avenue for a synergic combination of abiotic and biotic synthetic sequences for photocatalytic fuel and chemical transformation.


Assuntos
Etanol/química , Fotossíntese/fisiologia , Luz Solar , Catálise , Corantes , Elétrons , Hidrogênio/química , Hidrogenase/química , Cinética , Ligantes , Simulação de Acoplamento Molecular
4.
Anal Sci ; 37(8): 1081-1085, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34373415

RESUMO

Simple, accurate and real-time analytical methods are required for the detection of metal ions in a complex environment. In the present work, a fluorescent probe CPB based on coumarin was designed for recognizing Cu2+ ions. The fluorescence of CPB gradually quenched with increasing concentration of Cu2+ ions, due to the interactions between CPB and Cu2+ ions. With the addition of Cu2+ ions, the emission changes of CPB exhibited a good liner relationship toward the Cu2+ ions content in solution. Additionally, CPB could highly selective recognize Cu2+ ions among other metal ions in solution. Bearing the selectivity and fluorescence property toward Cu2+ ions, CPB was successfully applied to monitoring Cu2+ ions in Hela cells and zebrafish.

5.
Artigo em Inglês | MEDLINE | ID: mdl-34347334

RESUMO

Organic self-assembled co-crystals have garnered considerable attention due to their facile synthesis and intriguing properties, but supramolecular interactions restrict their stability in aqueous solution, which is especially important for biological applications. Herein, we report on the first biological application of aqueous dispersible self-assembled organic co-crystals via the construction of metal-organic framework (MOF) -stabilized co-crystals. In particular, we built an electron-deficient MOF with naphthalene diimide (NDI) as the ligand and biocompatible Ca2+ as the metal nodes. An electron donor molecule, pyrene, was encapsulated to form the host-guest MOF self-assembled co-crystal. We observed that such MOF structure leads to uniquely high-density ordered arrangement and the close intermolecular distance (3.47 Å) of the charge transfer pairs. Hence, the concomitant superior charge transfer interaction between pyrene/NDI can be attained and the resultant photothermal conversion efficiency of Py@Ca-NDI in aqueous solution can thus reach up to 41.8 %, which, to the best of our knowledge, is the highest value among the reported organic co-crystal materials; it is also much higher than that of the FDA approved photothermal agent ICG as well as most of the reported MOFs. Based on this realization, as a proof of concept, we demonstrated that such a self-assembled organic co-crystal platform can be used in biological applications that are exemplified via highly effective long wavelength light photothermal therapy.

6.
Molecules ; 26(11)2021 Jun 02.
Artigo em Inglês | MEDLINE | ID: mdl-34199465

RESUMO

Hydrogen peroxide (H2O2) plays an important role in the human body and monitoring its level is meaningful due to the relationship between its level and diseases. A fluorescent sensor (CMB) based on coumarin was designed and its ability for detecting hydrogen peroxide by fluorescence signals was also studied. The CMB showed an approximate 25-fold fluorescence enhancement after adding H2O2 due to the interaction between the CMB and H2O2 and had the potential for detecting physiological H2O2. It also showed good biocompatibility and permeability, allowing it to penetrate cell membranes and zebrafish tissues, thus it can perform fluorescence imaging of H2O2 in living cells and zebrafish. This probe is a promising tool for monitoring the level of H2O2 in related physiological and pathological research.


Assuntos
Cumarínicos/química , Corantes Fluorescentes/química , Peróxido de Hidrogênio/análise , Animais , Membrana Celular , Humanos , Células MCF-7 , Imagem Óptica , Peixe-Zebra
7.
Chem Sci ; 12(24): 8512-8520, 2021 May 18.
Artigo em Inglês | MEDLINE | ID: mdl-34221332

RESUMO

Direct functionalization of C(sp3)-H bonds in a predictable, selective and recyclable manner has become a central challenge in modern organic chemistry. Through incorporating different triarylamine-containing ligands into one coordination polymer, we present herein a heterogeneous approach to the combination of hydrogen atom transfer (HAT) and photoredox catalysis for regioselective C-H arylation of benzylamines. The different molecular sizes and coordination modes of the ligands, tricarboxytriphenylamine (H3 TCA) and tris(4-(pyridinyl)phenyl)amine (NPy3), in one coordination polymer consolidate the triarylamine (Ar3N) moiety into a special structural intermediate, which enhances the chemical and thermal stability of the polymers and diminishes structural relaxation during the catalytic process. The inherent redox potentials of Ar3N moieties prohibit the in situ formed Ar3N˙+ to earn an electron from C(sp3)-H nucleophiles, but allow the abstraction of a hydrogen atom from C(sp3)-H nucleophiles, enabling the formation of the C(sp3)˙ radical and the cross-coupling reaction to proceed at the most electron-rich sites with excellent regioselectivity. The new heterogeneous photoredox HAT approach skips several interactions between transient species during the typical synergistic SET/HAT cycles, demonstrating a promising redox-economical and reagent-economical heterogeneous platform that has not been reported for α-amino C-H arylation to form benzylamine derivatives. Control experiments based on monoligand coordination polymers suggested that the mixed-ligand approach improved the photochemical and photophysical properties, providing important insight into rational design and optimization of recyclable photocatalysts for rapid access to complex bioactive molecules and late-stage functionalized pharmaceuticals.

8.
ACS Appl Mater Interfaces ; 13(22): 25898-25905, 2021 Jun 09.
Artigo em Inglês | MEDLINE | ID: mdl-34043310

RESUMO

Hydrogen atom transfer (HAT) has become an attractive strategy for the activation of hydrocarbon feedstocks. Alcohols, as inexpensive and efficient hydrogen transfer reagents, have limited application in C-H functionalization due to the difficulty in the alkoxy radical acquisition. 9-Fluorenone moieties were incorporated into the metal-organic framework (MOF) as a photocatalyst; through the formation of hydrogen bonds between the carbonyl group of a ligand and alcohol, alkoxy radicals could be obtained by the visible-light-driven oxidation of 2,2,2-trichloroethanol via proton-coupled electron transfer (PCET). Effectively photocatalyzed intermolecular coupling reactions between phenyl vinyl sulfone and aldehyde or cyclic ether were realized through the HAT pathway. Compared to homogeneous catalysts, the heterogeneous MOF photocatalyst improved the catalytic efficiency and could be recycled at least five times. The microenvironment of the Zn-OFDC channel was beneficial for the formation of hydrogen bonds and stability of alkoxy radicals.

9.
ACS Appl Mater Interfaces ; 13(16): 18619-18626, 2021 Apr 28.
Artigo em Inglês | MEDLINE | ID: mdl-33848135

RESUMO

Safe storage and transportation of H2 is a fundamental requirement for its wide applications in the future. Controllable release of high-purity H2 from a stable storage medium such as CH3OH before use offers an efficient way of achieving this purpose. In our case, Cu nanoclusters uniformly dispersed onto (001) surfaces of TiO2 nanosheets (TiO2/Cu) are selectively prepared by thermal treatment of HKUST-1 loaded TiO2 nanosheets. One of the TiO2/Cu composites, TiO2/Cu_50, exhibits remarkably high activity toward the selective dehydrogenation of CH3OH to HCHO with a H2 evolution rate of 17.8 mmol h-1 per gram of catalyst within a 16-h photocatalytic reaction (quantum efficiency at 365 nm: 16.4%). Theoretical calculations reveal that interactions of Cu nanoclusters with TiO2 could affect their electronic structures, leading to higher adsorption energy of CH3OH at Ti sites and a lower barrier for the dehydrogenation of CH3OH by the synergistic effect of Cu nanoclusters and TiO2, and lower Gibbs free energy for desorption HCHO and H2 as well.

10.
Chem Asian J ; 16(10): 1237-1244, 2021 May 17.
Artigo em Inglês | MEDLINE | ID: mdl-33769702

RESUMO

Visible-light-driven hydrogen production coupled with selective organic oxidation has attracted increasing attention, as it not only provides clean and renewable energy, but also utilizes the other half reaction to achieve some value-added organic chemicals. Metal-organic frameworks based on metal clusters and organic ligands self-assembly give a perspective on the formation of multifunctional heterogeneous photocatalyst to significantly boost visible-light photocatalytic activities under mild conditions. By incorporating two types of photoactive units, tricarboxytriphenylamine (H3 TCA) and tris(4-(pyridinyl)phenyl)amine (NPy3 ), into a single metal-organic frameworks, a multi-component MOF Co-MIX was obtained. With the redox active metal centers enabling the photoexcitation reduction of protons into hydrogen and the photogenerated holes promoting considerable oxidation of substrates, the resulting Co-MIX exhibits high catalytic activity for the photocatalytic hydrogen production coupled with selective oxidation of benzylamine or 1,2,3,4-tetrahydroisoquinoline. Importantly, the photocatalytic experiments of single-component Co-TCA and Co-NPy3 verified the positive synergistic effects on stability and photocatalytic ability of the two ligands (H3 TCA and NPy3 ) in one single MOF, revealing that the multi-component strategy is very important for the efficient charge separation and excellent photocatalytic activity of the catalyst.

11.
ACS Appl Mater Interfaces ; 13(9): 10925-10932, 2021 Mar 10.
Artigo em Inglês | MEDLINE | ID: mdl-33625823

RESUMO

The activation and transformation of inert alkyl C(sp3)-H bonds to obtain high-value fine chemicals by sustainable solar energy are of great significance. Herein, by incorporating IrIII-porphyrin into metal-organic frameworks (MOFs) to stabilize the highly active carbene, we reported a new approach to combining metallo- and photocatalysis to efficiently accelerate carbene migratory insertion and C-H bond activation via the radical coupling pathway for inert alkane functionalization. The in situ-formed carbene was restricted into the pores of MOFs to produce IrIII-carbene, allowing the first-time isolation and structural characterization of the IrIII-carbene intermediate which are not stabilized by a heteroatom. The product of the reaction, especially the cyclic ethers as substrates, suggested that the functionalization of the α position of the alkoxy group was favored. Additionally, the new approach could be extended to stabilize the metal carbene intermediates to realize C(sp3)-H bond alkylation and arylation.

12.
Angew Chem Int Ed Engl ; 60(3): 1561-1566, 2021 Jan 18.
Artigo em Inglês | MEDLINE | ID: mdl-33009696

RESUMO

The addition of π-allylmetal complexes to carbonyls is the most important route to homoallylic alcohols. This study reports the first photocatalytic generation of π-allyltitanium complexes by a radical strategy. This novel strategy enables the three-component allylation of carbonyls with 1,3-butadiene, providing rapid access to valuable homoallylic alcohols (over 60 examples). The exceptional regio- and diastereoselectivity provided by dual photoredox/Ti catalysis is comparable to that of the Cr-catalyzed Nozaki-Hiyama-Kishi allylation reaction.

13.
Anal Chem ; 92(24): 15908-15915, 2020 12 15.
Artigo em Inglês | MEDLINE | ID: mdl-33237720

RESUMO

Fluorescence ratiometric biosensors are valuable tools for the accurate and sensitive prediction and diagnosis of diseases. However, seldom have fluorescence ratiometric biosensors for protein and DNA been reported because of the shortage of suitable nanoscale scaffolds. Herein, a tripyridinyl RuII complex-encapsulated SiO2@polydopamine (Ru-SiO2@PDA) nanocomposite was designed as a universal platform for fluorescence ratiometric detection of DNA and protein in serum samples. The Ru-SiO2@PDA nanocomposites have a narrow size distribution, exhibit good biosafety, and are convenient for the postmodification of biorecognition elements. Under irradiation, they can emit a stable and strong luminescence at 650 nm and simultaneously quench the fluorescence emitted from the fluorophores getting close to them. Once the capture probes such as single-stranded DNA and aptamer are assembled, the fluorophores labeled on them are then brought close to their PDA shell and quenched. However, the biorecognition behaviors change the probe's configuration and take the fluorophore far away from the PDA shell. Correspondingly, the fluorescence recovers and its ratio to the constant fluorescence reference is linear to the targets' concentration. Using a D-catalyst and thrombin as model analytes, the Ru-SiO2@PDA-based nanoplatform shows high sensitivity and good accuracy in the serum sample analysis. Regarding these attractive properties, the Ru-SiO2@PDA nanoplatform provides a new avenue for the accurate and sensitive fluorescence assay of a wide range of targets in complex systems.


Assuntos
Técnicas Biossensoriais , DNA/análise , Corantes Fluorescentes/química , Nanopartículas/química , Compostos Organometálicos/química , Dióxido de Silício/química , Trombina/análise , Humanos , Indóis/química , Tamanho da Partícula , Polímeros/química , Rutênio/química , Propriedades de Superfície , Trombina/metabolismo
14.
Nat Commun ; 11(1): 5384, 2020 10 23.
Artigo em Inglês | MEDLINE | ID: mdl-33097706

RESUMO

Synergistic photoredox and copper catalysis confers new synthetic possibilities in the pharmaceutical field, but is seriously affected by the consumptive fluorescence quenching of Cu(II). By decorating bulky auxiliaries into a photoreductive triphenylamine-based ligand to twist the conjugation between the triphenylamine-based ligand and the polar Cu(II)-carboxylate node in the coordination polymer, we report a heterogeneous approach to directly confront this inherent problem. The twisted and polar Cu(II)-dye conjunction endows the coordination polymer with diode-like photoelectronic behaviours, which hampers the inter- and intramolecular photoinduced electron transfer from the triphenylamine-moiety to the Cu(II) site and permits reversed-directional ground-state electronic conductivity, rectifying the productive loop circuit for synergising photoredox and copper catalysis in pharmaceutically valuable decarboxylative C(sp3)-heteroatom couplings. The well-retained Cu(II) sites during photoirradiation exhibit unique inner-spheric modulation effects, which endow the couplings with adaptability to different types of nucleophiles and radical precursors under concise reaction conditions, and distinguish the multi-olefinic moieties of biointeresting steride derivatives in their late-stage trifluoromethylation-chloration difunctionalisation.

15.
Chem Soc Rev ; 49(15): 5561-5600, 2020 Aug 07.
Artigo em Inglês | MEDLINE | ID: mdl-32643720

RESUMO

The incorporation of electron transfer pairs in both ground and excited states (including electron transfer pairs in excited states and hydrogen or oxygen transfer pairs in ground states) into redox-active hosts with electronic acceptor or donor guests has led to development of a novel method of mimicking the photophysical properties and redox reactions of naturally occurring enzymatic systems. This occurs within the confined microenvironments of metal-organic capsules and metal-organic frameworks. These two types of coordination supramolecular host-guest systems can dock and separate electronic donor-acceptor pairs via closed through-space separation. Electron transfer within confined cavities, which is mainly controlled by spatial and kinetic effects, does not utilize a through-bond electron transfer pathway. In this review, we provide an overview of significant progress in the photophysical and catalytic applications of supramolecular host-guest systems with electron-transfer processes in confined environments. Special emphasis is placed on the action modes and regulatory factors that affect electron transfer between different components to produce enhanced photophysical or redox catalytic performance. Finally, the prospects for confined-environment electron transfer, its application to photophysics and catalysis, and the remaining challenges in this field are highlighted.

16.
Chem Commun (Camb) ; 56(55): 7537-7548, 2020 Jul 14.
Artigo em Inglês | MEDLINE | ID: mdl-32573609

RESUMO

The design of novel agents that specifically target DNA and interrupt its normal biological processes is an attractive goal in drug design. Among the promising metallodrugs, metal-directed self-assembled metallohelices with defined three-dimensional stereochemical structures display unique structure-inherent and unprecedented noncovalent targeting abilities towards DNA, resulting in excellent anticancer or antibiotic activities. A newly burgeoning hotspot is focusing on lighting them up by embedding luminescent metal ions as the vertices. The photoactive metallohelices that combine strong interactions toward DNA targets and efficient 1O2 quantum yield may provide new motivation in diagnostic and photodynamic therapy (PDT) areas. This perspective focuses on research progress on metallohelices as DNA binders and chemotherapeutic agents, and highlights recent advances in fabricating luminescent examples for PDT. The relative assembly strategies are also discussed and compared. Finally, perspectives on the future development of the lit-up metallohelices are presented.


Assuntos
Antineoplásicos/uso terapêutico , Complexos de Coordenação/uso terapêutico , DNA/química , Substâncias Luminescentes/uso terapêutico , Fármacos Fotossensibilizantes/uso terapêutico , Animais , Antineoplásicos/química , Linhagem Celular Tumoral , Complexos de Coordenação/química , Humanos , Substâncias Luminescentes/química , Metais Pesados/química , Fotoquimioterapia/métodos , Fármacos Fotossensibilizantes/química
17.
Nat Commun ; 11(1): 2903, 2020 06 09.
Artigo em Inglês | MEDLINE | ID: mdl-32518257

RESUMO

Direct transfer of protons and electrons between two tandem reactions is still a great challenge, because overall reaction kinetics is seriously affected by diffusion rate of the proton and electron carriers. We herein report a host-guest supramolecular strategy based on the incorporation of NADH mimics onto the surface of a metal-organic capsule to encapsulate flavin analogues for catalytic biomimetic monooxygenations in conjunction with enzymes. Coupling an artificial catalysis and a natural enzymatic catalysis in the pocket of an enzyme, this host-guest catalyst-enzyme system allows direct proton and electron transport between two catalytic processes via NADH mimics for the monooxygenation of both cyclobutanones and thioethers. This host-guest approach, which involves the direct coupling of abiotic and biotic catalysts via a NADH-containing host, is quite promising compared to normal catalyst-enzyme systems, as it offers the key advantages of supramolecular catalysis in integrated chemical and biological synthetic sequences.


Assuntos
Biomimética , Oxigênio/química , Catálise , Domínio Catalítico , Cristalografia por Raios X , Transporte de Elétrons , Enzimas/química , Ligação de Hidrogênio , Íons , Cinética , Ligantes , NAD/química , Solventes/química , Zinco/química
18.
Artigo em Inglês | MEDLINE | ID: mdl-32164043

RESUMO

Boron dipyrromethene (BODIPY), as a traditional fluorescent dye, has drawn increasing attention because of its excellent photophysical properties like adjustable spectra and outstanding photostability. BODIPY dyes could be assembled into nanoparticles for cancer imaging and therapy via rational design. In this review, the bio-applications of BODIPY-containing nanoparticles are introduced in detail, such as cellular imaging, near-infrared fluorescence imaging, computed tomography imaging, photoacoustic imaging, phototherapy, and theranostics. The construction strategies of BODIPY-containing nanoparticles are emphasized so the review has three sections-self-assembly of small molecules, chemical conjugation with hydrophilic compounds, and physical encapsulation. This review not only summarizes various and colorific bio-applications of BODIPY-containing nanoparticles, but also provides reasonable design methods of BODIPY-containing nanoparticles for cancer theranostics. This article is categorized under: Diagnostic Tools > in vivo Nanodiagnostics and Imaging.


Assuntos
Boro/química , Diagnóstico por Imagem , Nanopartículas/química , Neoplasias/diagnóstico por imagem , Neoplasias/terapia , Porfobilinogênio/análogos & derivados , Animais , Composição de Medicamentos , Humanos , Porfobilinogênio/química
19.
Org Biomol Chem ; 18(10): 1933-1939, 2020 03 14.
Artigo em Inglês | MEDLINE | ID: mdl-32101242

RESUMO

A novel and convenient photo-mediated halogenated spirocyclization of N-(p-methoxyaryl)propiolamides has been developed. The photolysis of phenyliodine bis(trifluoroacetate) (PIFA) as an iodination reagent led to iodinated ipso-cyclization under the irradiation of a xenon lamp, while brominated ipso-cyclization or chlorinated ipso-cyclization was achieved by irradiating a mixture of PIFA and KBr/KCl under a blue LED. The present protocol simply utilizes light as the safe and clean energy source and doesn't require any external photocatalyst providing various 3-halospiro[4,5]trienones in good to excellent yields (up to 93%).

20.
ACS Appl Mater Interfaces ; 12(10): 12043-12053, 2020 Mar 11.
Artigo em Inglês | MEDLINE | ID: mdl-32069396

RESUMO

Multiemissive sensors are being actively pursued, because of their ratiometric luminescent detection capabilities, which demonstrates better sensitivity and selectivity than conventional single-emission sensors. Herein, we present a trichromatic white-light-emitting metal-organic framework (MOF) composite (Z3) by simultaneously incorporating red/green-emitting Pt/Ru complex cations into porous blue-emitting bio-MOF-1 through post-synthetic modification. With the help of a three-dimensional (3-D) dual-ratiometric luminescence recognition method, and unique turn-on responses of the red emission toward amine compounds (ACs), including NH3 and aliphatic amines, via confinement-induced luminescence enhancement effect, Z3 can work as a dual-ratiometric luminescent sensor for discrimination of 7 out of 11 AC vapors. This work not only provides a new AC sensing mechanism (confinement effect) that can induce a "turn-on" response but also proves that the accuracy and selectivity of composite sensor can be greatly improved through the combination of 3-D recognition method and the confinement effect. Thus, it open up fresh opportunities to develop composite sensors with excellent sensing and differentiating ability.

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