Browsing by Author "Hung, Chen-Hsiung"
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Item type:Item, A N-(2-Aminophenyl)-5-(dimethylamino)-1-naphthalenesulfonic Amide (Ds-DAB) Based Fluorescent Chemosensor for Peroxynitrite(2013-08-16) ;Lin, Ku-Kuei ;Wu, Shou-Cheng ;Hsu, Kuang-Mei ;Hung, Chen-HsiungLiaw, Wen-FengA dansyl derivative (Ds-DAB) was prepared and used as a fluorescent probe for peroxynitrite (ONOO-) detection. The results showed that the addition of peroxynitrite to the aqueous solution of Ds-DAB would result in obvious fluorescence enhancement. This probe is highly specific for peroxynitrite in aqueous solution, avoiding interference from other reactive oxygen species (ROS) and nitrogen species (RNS). The advantages of high selectivity, fast reaction rate, and peroxynitrite bioimaging render Ds-DAB suitable for peroxynitrite detection.Item type:Item, An organic hydrogel film with micron-sized pillar array for real-time and indicator-free detection of Zn(2+)(2011-11-01) ;Chao, Yu-Chiang ;Huang, Yi-Sa ;Wang, Hsin-Ping ;Fu, Ssu-MingHuang, Chien-HaoA hydrogel sensing film for a real-time and indicator-free detection of Zn(2+) is developed by embedding a fluorescent indicator 11,16-bis( phenyl)-6,6,21,21-tetramethyl-m-benzi-6,21-porphodimethene in a hydrogel host poly(2-hydroxyethyl methacrylate). The sensing film shows high stability and selectivity to Zn(2+). The sensitivity of the sensing film is increased by fabricating a micron-sized pillar array on the surface of the sensing film to increase the surface area. For Zn(2+) concentrations of 10 (4) and 10 (3) M, the response time is 30 and 3 s, respectively. (C) 2011 Elsevier B.V. All rights reserved.Item type:Item, An organic hydrogel film with micron-sized pillar array for real-time and indicator-free detection of Zn2+(2011-11-01) ;Chao, Yu-Chiang ;Huang, Yi-Sa ;Wang, Hsin-Ping ;Fu, Ssu-MingHuang, Chien-HaoA hydrogel sensing film for a real-time and indicator-free detection of Zn2+ is developed by embedding a fluorescent indicator 11,16-bis( phenyl)-6,6,21,21-tetramethyl-m-benzi-6,21-porphodimethene in a hydrogel host poly(2-hydroxyethyl methacrylate). The sensing film shows high stability and selectivity to Zn2+. The sensitivity of the sensing film is increased by fabricating a micron-sized pillar array on the surface of the sensing film to increase the surface area. For Zn2+ concentrations of 10 (4) and 10 (3) M, the response time is 30 and 3 s, respectively. (C) 2011 Elsevier B.V. All rights reserved.Item type:Item, Bioinorganic Chemistry of the Natural [Fe(NO)(2)] Motif: Evolution of a Functional Model for NO-Related Biomedical Application and Revolutionary Development of a Translational Model!(2018-10-15) ;Lu, Tsai-Te ;Wang, Yun-Ming ;Hung, Chen-Hsiung ;Chiou, Show-JenLiaw, Wen-FengIdentification of the distinctive electron paramagnetic resonance signal at g = 2.03 in the yeast cells and liver of mice treated with carcinogens opened the discovery and investigation of the natural [Fe(NO)(2)] motif in the form of dinitrosyliron complexes (DNICs). In this Viewpoint, a chronological collection of the benchmark for the study of DNIC demonstrates that the preceding study of its biological synthesis, storage, transport, transformation, and function related to NO physiology inspires the biomimetic study of structural and functional models supported by thiolate ligands to provide mechanistic insight at a molecular level. During the synthetic, spectroscopic, and theoretical investigations on the structure-to-reactivity relationship within DNICs, control of the Fe-NO bonding interaction and of the delivery of NO+/(NO)-N-center dot/HNO/NO- by the supporting ligands and nuclearity evolves into the "redesign of the natural [Fe(NO)(2)] motif" as a strategy to develop DNICs for NO-related biomedical application and therapeutic approach. The revolutionary transformation of covalent a [Fe(NO)(2)] motif into a translational model for hydrogenase, triggered by the discovery of redox interconversion among [{Fe(NO)(2)}(9)-L-center dot] <-> {Fe(NO)(2)}(9) <-> {Fe(NO)(2)}(10) <-> [{Fe(NO)(2)}(10)-L-center dot](-) echoes the preceding research journey on [Fe]/[NiFe]-hydrogenase and completes the development of an electrodeposited-film electrode for electrocatalytic water splitting. Through the 50-year journey, bioinorganic chemistry of DNIC containing the covalent [Fe(NO)(2)] motif and noninnocent/labile NO ligands highlights itself as a unique metallocofactor to join the longitudinal study between biology/chemistry/biomedical application and the lateral study toward multielectron (photo/electro)catalysis for industrial application. This Viewpoint discloses the potential [Fe(NO)(2)] motif awaiting continued contribution in order to emerge as a novel application in the next 50 years, whereas the parallel development of bioinorganic chemistry, guided by inspirational Nature, moves the science forward to the next stage in order to benefit the immediate needs for human activity.Item type:Item, Development of Hybrid Pseudohalide Tin Perovskites for Highly Stable Carbon-Electrode Solar Cells(2020-05-13) ;Rameez, Mohammad ;Lin, Eric Yan-Ru ;Raghunath, Putikam ;Narra, SudhakarSong, DonghoonTin-based perovskites degrade rapidly upon interaction with water and oxygen in air because Sn-I bonds are weak. To address this issue, we developed novel tin perovskites, FASnI((3-x))(SCN)(x) (x = 0, 1, 2, or 3), by employing a pseudohalide, thiocyanate (SCN-), as a replacement for halides and as an inhibitor to suppress the Sn2+/Sn4+ oxidation. The structural and electronic properties of pseudohalide tin perovskites in this series were explored with quantum-chemical calculations by employing the plane-wave density functional theory (DFT) method; the corresponding results are consistent with the experimental results. Carbon-based perovskite devices fabricated with tin perovskite FASnI(SCN)(2) showed about a threefold enhancement of the device efficiency (2.4%) relative to that of the best FASnI(3)-based device (0.9%), which we attribute to the improved suppression of the formation of Sn4+, retarded charge recombination, enhanced hydrophobicity, and stronger interactions between Sn and thiocyanate for FASnI(SCN)(2) than those for FASnI(3). After the incorporation of phenylethyleneammonium iodide (PEAI, 10%) and ethylenediammonium diiodide (EDAI(2), 5%) as coadditives, the FASnI(SCN)(2) device gave the best photovoltaic performance with J(SC) = 20.17 mA cm(-2), V-OC = 322 mV, fill factor (FF) = 0.574, and overall efficiency of power conversion PCE = 3.7%. Moreover, these pseudohalide-containing devices display negligible photocurrent-voltage hysteresis and great stability in ambient air conditions.Item type:Item, Different sensing modes of fluoride and acetate based on a calix[4]arene with 25,27-bistriazolylmethylpyrenylacetamides(2014) ;Hung, Hao-Chih ;Chang, Yung-Yu ;Luo, Liyang ;Hung, Chen-HsiungDiau, Eric Wei-Guang25,27-Bis{1'-N-(1-pyrenyl)-aminocarbonylmethyl-1H-[1',2',3']tri-azolyl-4'-methoxy}-26,28-dihydroxycalix-[4]arene, 4, is synthesized as a fluorescent chemosensor for the selective detection of both anions and ion pairs in MeCN. Sensor 4 uses bis-triazoles as ligands to bind a metal ion, bis-amides and bis-triazoles as the sites to recognize anions, and pyrenes as fluorophores. Among eight anions screened, chemosensor 4 showed a marked fluorescence change toward F-, H2PO4- and AcO-, but 4 responded to each anion in a distinct way. In the presence of F- at low concentrations, the dynamic excimer emission of compound 4 at lambda(max) 482 nm was quenched, but an emission at lambda(max) 472 nm appeared at large doses of F-. A control compound 6 showed very similar red shifts in the UV-vis and excitation spectra as 4 did, and its 472 nm emission band grew as the fluoride doses increased. Thus, the growth of the 472 nm emission of 4 and 6 in the presence of excess F- may be because strong H-bonding interactions of amido protons with F- favoured the formation of pyrene dimers in the ground state with charge transfer characteristics. The addition of H2PO4-, unlike F-, to a solution of 4 showed an enhanced monomer emission but a decreased excimer emission (lambda(max) 482 nm). Adding AcO- to 4 produced a systematic change from a dynamic excimer (lambda(max) 482 nm) to lambda(max) 472 nm but with very little change in the UV-vis spectrum. Time-resolved fluorescence measurements on compound 6 with F- and AcO- confirmed that the 472 nm emission band mainly came from static excimers for the former, but was partly from a dynamic excimer for the latter because it contained a growth component in the fluorescence decay traces. Without pre-treatment with an anion, chemosensor 4 showed recognition of only metal ions Cu2+, Hg2+ and Cr3+, but it became sensitive to Ag+ when it was pretreated with fluoride.Item type:Item, Effects of Core-modification on Porphyrin Sensitizers to the Efficiencies of Dye-sensitized Solar Cells(2014-05-01) ;Mane, Sandeep B. ;Luo, Liyang ;Chang, Gao-Fong ;Diau, Eric Wei-GuangHung, Chen-HsiungTo study dye-sensitized solar cells (DSSCs) with core-modified porphyrins as the sensitizing dyes, three porphyrins with an ethynyl benzoic acid as an anchoring group are prepared. The properties of free-base regular porphyrin (N4), thiaporphyrin (N3S) and oxaporphyrin (N3O) were thoroughly studied by spectroscopic methods, DFT calculations, and photovoltaic measurements. Replacing one of the porphyrinic core nitrogen atoms by oxygen or sulfur considerably changes the absorption spectra. The Soret band of the N3O and N3S observed bathochromic shifts of 3-9 nm while the Q band reaches 700 nm to the near-infrared region. The overall conversion efficiencies of the DSSCs based on these porphyrins are in the order N4 (3.66%) >> N3S (0.22%) > N3O (0.01%). The time-correlated single photon counting observed short fluorescence lifetimes for N3O adsorbed both on TiO2 and Al2O3 which explicates the poor efficiency of DSSC using N3O as the photosensitizer.Item type:Item, Effects of Porphyrinic meso-Substituents on the Photovoltaic Performance of Dye-Sensitized Solar Cells: Number and Position of p-Carboxyphenyl and Thienyl Groups on Zinc Porphyrins(2012-06-07) ;Ambre, Ram ;Chen, Kwan-Bo ;Yao, Ching-Fa ;Luo, LiyangDiau, Eric Wei-GuangIn order to understand the effects of meso-substituents of the zinc porphyrins on optical, electrochemical, and photovoltaic properties, a series of porphyrins with different combinations of thienyl (S) and p-carboxyphenyl (A) groups as the meso substituents have been systematically synthesized and studied. The properties of zinc complexes 3S1A, trans-2S2A, cis-2S2A, and 1S3A were fully investigated by absorption and emission spectra, attenuated total reflectance-Fourier transform infrared (ATR-FTIR) spectra, density functional theory (DFT) calculations, electrochemical, photophysical, and photovoltaic measurements. With the increasing number of meso-thienyl groups, slight red-shifts of Soret and Q bands were observed in both absorption and emission spectra. All of the absorption spectra of zinc porphyrins on TiO2 film show broadening and splitting of Soret bands because of excitonic coupling of porphyrins. ATR-FTIR spectra revealed likely modes to determine either a single arm (in 3S1A and trans-2S2A) or double arms (in 1S3A and cis-2S2A) attached on TiO2. Two factors of p-carboxyphenyl and thienyl groups affecting the devices performance-heavy atom effect and the amount of dye loading on TiO2-are concluded. Overall, the power conversion efficiencies (eta) of the devices exhibit the following order: 1S3A (3.0%) > cis-2S2A (2.5%) > trans-2S2A (1.8%) >> 3S1A (0.2%).Item type:Item, Effects of Position and Electronic Nature of Substituents on Cobalt-Porphyrin-Catalyzed Hydrogen Evolution Reaction(2017-11-13) ;Beyene, Belete B. ;Mane, Sandeep B. ;Leonardus, Mario ;Hung, Chen-Hsiung交大名義發表Cobalt(II) porphyrins bearing ortho/para-amino and ortho-nitro groups at meso-phenyl rings have been prepared and employed for catalytic hydrogen generation. Electrochemical and catalytic studies show that position and electronic nature of the substituents strongly affect catalytic activity and overpotential of catalysis. Our study reveals that the complex with ortho-aminophenyl substituents on porphyrin core displays higher activity toward H-2 evolution with rate constant of 1.1 x 10(5) M-1 s(-1) at onset potential close to thermodynamic reduction potential of trifluoroacetic acid (TFA), and 89% efficiency. On the other hand, the reactions involving cobalt porphyrins with para-aminophenyl or ortho-nitrophenyl groups showed lower or no activity under the same experimental conditions, implying the significant role of pendant ortho-amino groups in accelerating the intramolecular proton transfer and the proton-hydride interactions to thermodynamically favor H-2 evolution.Item type:Item, Electrospun Fibers as a Solid-State Real-Time Zinc Ion Sensor with High Sensitivity and Cell Medium Compatibility(2013-03-25) ;Syu, Jia-Hao ;Cheng, Yi-Kai ;Hong, Wun-Yan ;Wang, Hsing-PingLin, Yu-Chaomeso-2,6-Dichlorophenyltripyrrinone (TPN-Cl2), a probe molecule for zinc II ions, is dispersed in a polymer host. The red fluorescence peak at 620 nm appears when the molecule forms a complex with zinc at its center. TPN-Cl2 has a high selectivity for zinc II and tolerates many common metal ions present in the human body. The probe molecules are blended with a hydrogel polymer, poly(2-hydroxyethyl methacrylate) (poly HEMA), with 30 wt% dimethylformamide (DMF). The fiber structure with 1 m diameter is made by electrospinning in DMF solution of the probe and poly HEMA mixture. The fibrous film detects zinc ions with concentrations as low as 106 M in real-time both in water and in the commonly used cell culture liquid media Dulbecco's modified Eagle medium (DMEM) and fetal bovine serum (FBS), which contain many metal ions and proteins. The time-resolution is 5 min for 106 M and 1 min for 105 M. This sensitivity and response speed satisfy the requirements for non-invasive biomedical studies.Item type:Item, Formation of Stable Tin Perovskites Co-crystallized with Three Halides for Carbon-Based Mesoscopic Lead-Free Perovskite Solar Cells(2017-10-23) ;Tsai, Cheng-Min ;Mohanta, Nayantara ;Wang, Chi-Yung ;Lin, Yu-PeiYang, Yaw-WenWe synthesized and characterized methylammonium (MA) mixed tri-halide tin perovskites (MASnIBr(2-x)Cl(x)) for carbon-based mesoscopic solar cells free of lead and holetransporting layers. Varied SnCl2/SnBr2 ratios yielded tin perovskites with three halides (I, Br, and Cl) co-crystallized inside the tin-perovskite. When the SnCl2 proportion was >= 50% (x >= 1), phase separation occurred to give MAS-nI(3-y)Br(y) and MASnCl(3-z)Br(z) in the stoichiometric proportions of their precursors, confirmed by XRD. A device with MASnIBr(1.8)Cl(0.2) (SnCl2= 10%) showed the best photovoltaic performance: J(SC)= 14.0 mAcm(-2), V-OC= 380 mV, FF= 0.573, and PCE= 3.1%, and long-term stability. Electrochemical impedance spectra (EIS) show superior charge recombination and dielectric relaxation properties for the MASnIBr(1.8)Cl(0.2) cell. Transient PL decays showed the intrinsic problem of tinbased perovskites with average lifetimes less than 100 ps.Item type:Item, Hydro gel light-guiding conjunction for absorptive type multi-ions detection(2016-10-05) ;Lin, Hung-Cheng ;Yang, Sean Tsungyeh ;Ng, Sock Hoon ;Zan, Hsiao-WenMeng, Hsin-FeiWe present a novel miniaturized solid state sensor produced by embedding two optical fibers in a sensing hydro gel conjunction. The conjunction is a poly (2-hydroxyethyl methacrylate) (poly HEMA) hydro gel mixed with two kinds of selective fluorescent probes. Meso-2,6-Dichlorophenyltripyrrinone (TPN-Cl2) is used to react with zinc ion (Zn2+) and the synthesized "Chemosensor 1" is used to detect ferric ion (Fe3+). This hydro gel conjunction can serve as a light-guiding waveguide that allows light signals to transfer between two fibers. By using a multi-wavelength excitation light, a mixed solution that contains Zn2+ and Fe3+ can be detected in real-time. This miniaturized sensor develops an image for real-time monitoring of Zn2+ and Fe3+ ions in vivo. (C) 2016 Elsevier B.V. All rights reserved.Item type:Item, Hydrogel-based zinc ion sensor on optical fiber with high resolution and application to neural cells(2020-08-15) ;Tsai, May-Jywan ;Cheng, Henrich ;Ho, Hsin-Hsien ;Lin, Peng-WeiLiou, Dann-YingSolid-state zinc ion sensor is developed with high enough resolution and reproducibility for the potential application in brain injury monitoring. An optical diffuser is incorporated into the zinc ion sensor based on optical fiber and hydrogel doped with the fluorescent zinc ion probe molecule meso-2,6-Dichlomphenyltripyrrinone (TPN-Cl-2). The diffuser transforms the high-peak-intensity excitation light near the fiber end into a broad light with moderate local intensity to reduce the degradation of the probe molecule. Reversible detection can be reached for 1, 2, and 5 mu m (10(-6) Molar), with slopes 0.3, 0.6, and 0.8 respectively. This is the pathophysiological concentration range after brain injury. The sensor is applied to neuron-glial cultures and macrophage under the stimulation of lipopolysaccharide (LPS), KCl and oxygen/glucose deprivation (OGD) that reflect inflammation, depolarization and ischemia respectively, mimicking events after brain injury. The zinc ion level is raised to 4-5 mu m after LPS treatment, and then reduced to <3 mu m after the co-treatment with the herbal drug silymarin. The results suggest the conditions of the neural cells under stress can be monitored.Item type:Item, Integrated semiconductor optoelectronic devices for real-time and indicator-free detection of aqueous nitric oxide(2011-05-01) ;Chao, Yu-Chiang ;Yeh, Shih-De ;Zan, Hsiao-Wen ;Chang, Gao-FongMeng, Hsin-FeiA real-time and indicator-free sensor specific to nitric oxide (NO) is realized for the first time by integrating a sensing hydrogel film, a top-emitting polymer light-emitting diode (PLED), and a silicon photodetector. The top-emitting PLED is utilized to excite the sensing film specific to NO, and the photoluminescence of the sensing film is transformed into electric signal by the photodetector. The influence of the excitation light on the out-put photocurrent of the photodetector is diminished by two delicately selected organic filters based on their absorption spectra. Lead phthalocyanine is deposited on a top-emitting PLED as a filter for generating an excitation light without overlapping the emission maximum of the sensing hydrogel film. Poly(3-hexylthiophene) is placed in front of the photodetector as another filter to remove the excitation light. This sensor demonstrated a fast photocurrent response to NO with response time within 5 min. (C) 2011 Elsevier B.V. All rights reserved.Item type:Item, Integrated semiconductor optoelectronic devices for real-time and indicator-free detection of aqueous nitric oxide(2011-01-01) ;Wang, Shin-Ping ;Cheng, Yi-Kai ;Chao, Yu-Chiang ;Zan, Hsiao-WenChang, Gao-FongSensing films specific to nitric oxide and zinc were fabricated by embedding respectively indicator 1,2-diaminoanthraquinone (DAQ) and 11,16-Bis(phenyl)-6,6,21,21-tetramethyl-m-benzi-6,21-porphodimethene (BPDM-H) in hydrogel host poly(2-hydroxyethyl methacrylate). The sensing film contains DAQ, which responses to nitric oxide, shows stability in acid environment. The sensing film contains BPDM-H responses to zinc. The electrospinning technique was also utilized to fabricate the fibrous film.Item type:Item, Intrinsic Ultralow-Threshold Laser Action from Rationally Molecular Design of Metal-Organic Framework Materials(2020-08-12) ;Bera, Krishna Prasad ;Kamal, Saqib ;Inamdar, Arif I. ;Sainbileg, BatjargalLin, Hung-, IMetal-organic frameworks (MOFs) are superior for multiple applications including drug delivery, sensing, and gas storage because of their tunable physiochemical properties and fascinating architectures. Optoelectronic application of MOFs is difficult because of their porous geometry and conductivity issues. Recently, a few optoelectronic devices have been fabricated by a suitable design of integrating MOFs with other materials. However, demonstration of laser action arising from MOFs as intrinsic gain media still remains challenging, even though some studies endeavor on encapsulating luminescence organic laser dyes into the porous skeleton of MOFs to achieve laser action. Unfortunately, the aggregation of such unstable laser dyes causes photoluminescence quenching and energy loss, which limits their practical application. In this research, unprecedently, we demonstrated ultralow-threshold (similar to 13 nJ/cm(2)) MOF laser action by a judicious choice of metal nodes and organic linkers during synthesis of MOFs. Importantly, we also demonstrated that the white random lasing from the beautiful microflowers of organic linkers possesses a porous network, which is utilized to synthesize the MOFs. The highly luminescent broad-band organic linker 1,4-NDC, which itself exhibits a strong white random laser, is used not only to achieve the stimulated emission in MOFs but also to reduce the lasing threshold. Such white lasing has multiple applications from bioimaging to the recently developed versatile Li-Fi technology. In addition, we showed that the smooth facets of MOF microcrystals can show Fabry-Perot resonant cavities having a high quality factor of similar to 10(3) with excellent photostability. Our unique discovery of stable, nontoxic, high-performance MOF laser action will open up a new route for the development of new optoelectronic devices.Item type:Item, m-Benziporphodimethene: a new porphyrin analogue fluorescence zinc(II) sensor(2008) ;Hung, Chen-Hsiung ;Chang, Gao-Fong ;Kumar, Anil ;Lin, Geng-FongLuo, Li-Yangm-Benziporphodimethene is presented here as a long-wavelength Zn2+ specific chemosensor; this sensor shows fluorescence switch-on upon Zn2+ binding with no apparent background fluorescence.Item type:Item, New Dual Donor-Acceptor (2D--2A) Porphyrin Sensitizers for Stable and Cost-Effective Dye-Sensitized Solar Cells(2013-09-01) ;Ambre, Ram B. ;Chang, Gao-Fong ;Zanwar, Manoj R. ;Yao, Ching-FaDiau, Eric Wei-GuangA series of porphyrin sensitizers that featured two electron-donating groups and dual anchoring groups that were connected through a porphine -bridging unit have been synthesized and successfully applied in dye-sensitized solar cells (DSSCs). The presence of electron-donating groups had a significant influence on their spectroscopic, electrochemical, and photovoltaic properties. Overall, the dual anchoring groups gave tunable electronic properties and stronger attachment to TiO2. These new dyes were readily synthesized in a minimum number of steps in gram-scale quantities. Optical and electrochemical data confirmed the advantages of these dyes for use as sensitizers in DSSCs. Porphyrins with electron-donating amino moieties provided improved charge separation and better charge-injection efficiencies for the studied dual-push-pull dyes. Attenuated total reflectance-Fourier-transform infrared (ATR-FTIR) and X-ray photoelectron spectroscopy of the porphyrin dyes on TiO2 suggest that both p-carboxyphenyl groups are attached onto TiO2, thereby resulting in strong attachment. Among these dyes, cis-Zn2BC2A, with two electron-donating 3,6-ditertbutyl-phenyl-carbazole groups and dual-anchoring p-carboxyphenyl groups, showed the highest efficiency of 4.07%, with JSC=9.81mAcm-2, VOC=0.63V, and FF=66%. Our results also indicated a better photostability of the studied dual-anchored sensitizers compared to their mono-anchored analogues under identical conditions. These results provide insight into the developments of a new generation of high-efficiency and thermally stable porphyrin sensitizers.Item type:Item, Ni and Pd N-confused porphyrin complexes as catalysts for the synthesis of cyclic carbonates from epoxides and CO2(2019-06-14) ;dela Cruz, Jay-ar B. ;Ruamps, Mirko ;Arco, Susan ;Hung, Chen-Hsiung應用化學系We have demonstrated the design of a novel bifunctional catalyst that is based on an N-confused tetraphenylporphyrin (NCTPP) motif for the cycloaddition of an epoxide to carbon dioxide via cooperative activation of the epoxide through a Pd(II) or Ni(II) metal center and a peripheral benzoate moiety with percent conversions of up to 99% and TON = 7000.Item type:Item, Nitric Oxide Turn-on Fluorescent Probe Based on Deamination of Aromatic Primary Monoamines(2012-05-07) ;Shiue, Tsun-Wei ;Chen, Yen-Hao ;Wu, Chi-Ming ;Singh, GyanChen, Hsing-YinThe stable, water-soluble, and nonfluorescent FA-OMe can sense nitric oxide (NO) and form the intensely fluorescent product dA-FA-OMe via reductive deamination of the aromatic primary amine. The reaction is accompanied by a notable increase of the fluorescent quantum yield from 1.5 to 88.8%. The deamination mechanism of FA-OMe with NO was proposed in this study. The turn-on fluorescence signals were performed by suppression of photoinduced electron transfer (PeT), which was demonstrated by density functional theory (DFT) calculations of the components forming FA-OMe and dA-FA-OMe. Furthermore, FA-OMe showed water solubility and good stability at physiological pHs. Moreover, the selectivity study indicated that FA-OMe had high specificity for NO over other reactive oxygen/nitrogen species. In an endogenously generated NO detection study, increasing the incubation time of FA-OMe with lipopolysaccharide (LPS) pretreated Raw 264.7 murine macrophages could cause an enhanced fluorescence intensity image. In addition, a diffusion/localization cell imaging study showed that FA-OMe could be trapped in Raw 264.7 cells. These cell imaging results demonstrated that FA-OMe could be used as a turn-on fluorescent sensor for the detection of endogenously generated NO.